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October | octobre 2011

Canadian Chemical News | L’Actualité chimique canadienne A Magazine of the Chemical Institute of Canada and its Constituent Societies | Une magazine de l’institut de chimie du canada et ses sociétés constituantes



The debate over chemicals in cosmetics

Detox for tailIngs ponds recoding dna

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Chemical


Table of Contents

Features Chemical Engineering

Business

14

October | octobre Vol.63, No./No 9

Lipstick Jungle

Chemists and consumer advocates come out swinging in the debate over ­chemicals in household products. By Tim Lougheed

20

Tailings Termination

Murray Gray is working to speed up the reclamation of land from oil sands ­tailings ponds. By Tyler Irving Pour obtenir la version française de cet article, écrivez-nous à magazine@accn.ca

Chemistry

24

Departments

DNA Artisan

Hanadi Sleiman tinkers with DNA to create smart delivery systems for ­therapeutics. By Melora Koepke

5

From the Editor

7

Guest Column By John C. Polanyi

8

 hemical News C By Tyler Irving

28

Society News

30

ChemFusion By Joe Schwarcz

october 2011 CAnadian Chemical News   3


3rd Canadian Science Policy Conference

Building BRIDGES for the Future of Science Policy in Canada

THEMES Science, Politics and Culture in Canada Enabling Private Sector Innovation Exploring the True North, Reflections on Northern Science Policy Special Focus: International Year of Chemistry Major Issues In Canadian Science Policy Workshop on Nuts and Bolts of Science Policy 5 themes, 16 panels, 1 workshop, more than 60 invited speakers, 2 receptions, & 2 surprise events.

2011

Ottawa Convention Centre Ottawa, ON November 16-18

For more information or to register go to www.CSPC2011.ca Or write to us: info@sciencepolicy.ca

www.CSPC2011.ca


FRom the editor

Executive Director

Roland Andersson, MCIC

ACTING EDITOR

Roberta Staley

M

any accolades have been bestowed upon John C. Polanyi over the years: Nobel Prize in chemistry, Companion of the Order of Canada, member of the Queen’s Privy Council for Canada. There is even a grant given out in his name: the NSERC John C. Polanyi Award, recognizing advances in the natural sciences or ­engineering. The latest honour for this University of Toronto professor comes from Canada Post, which commissioned Tejashri Kapure of Toronto design group q30 to create a stamp that would recognize Polanyi’s contributions to chemistry. Polanyi reacted with typical humility and modesty to the news his visage would grace a stamp, which is on Page 29. And that is one of the best things about Polanyi, in addition to his prodigious talents and intellect, he is, quite simply, a nice person, generous with his time and genuinely interested in people — a true scholar and gentleman. ACCN is chock full of news. We present the final installment of our special five-part Women in Chemistry series, recognizing the International Year of Chemistry as well the 100th anniversary of Madam Curie’s Nobel Prize in Chemistry. Our featured researcher is Hanadi Sleiman, who is doing marvelous things with DNA in her laboratory at McGill University. Her work highlights the fact that Canadian scholars are — following in Polanyi’s ­footsteps — committed to world-class research. ACCN also delves into the murky world of bitumen waste tailings ponds and the efforts being made by researchers like Alberta’s Murray Gray to clean up this dirty by-product of the oil sands industry, which has given Canada’s ­international reputation such a shiner. Finally, a shout-out to participants at this month’s 61st Canadian Chemical Engineering conference in London, Ont. Make sure to say “hello” and pass along any story ideas you may have.

Editor (on leave)

Jodi Di Menna

news editor

Tyler Irving, MCIC

contributing editor

Tim Lougheed

art direction & Graphic Design

Krista Leroux Kelly Turner

Society NEws

Bobbijo Sawchyn, MCIC Gale Thirlwall

Marketing Manager

Bernadette Dacey

Marketing Coordinator

Luke Andersson

Circulation

Michelle Moulton

Finance and Administration Director

Joan Kingston

Membership Services Coordinator

Angie Moulton

Editorial Board

Joe Schwarcz, MCIC, chair Milena Sejnoha, MCIC Bernard West, MCIC

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Subscription Rates Go to www.accn.ca to subscribe or to purchase single ­issues. The individual non-CIC member s­ ubscription price for 2011 is $100 CDN. The institutional subscription price for 2011 is $150 CDN. Single copies can be ­purchased for $10. ACCN (Canadian Chemical News/ L’Actualité chimique canadienne) is published 10 times a year by the ­Chemical Institute of Canada, www.cheminst.ca Recommended by the Chemical Institute of Canada (CIC), the Canadian Society for Chemistry (CSC), the Canadian Society for Chemical Engineering (CSChE), and the Canadian Society for Chemical Technology (CSCT). Views expressed do not necessarily represent the official position of the Institute or of the Societies that recommend the magazine.

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 Continuing

Education for Chemical Professionals

Laboratory Safety course October 24–25, 2011 London, ON

For → Chemists and chemical technologists whose responsibilities include managing, conducting safety audits or improving the operational safety of chemical laboratories, chemical plants and research facilities.

Registration Fees* CIC Members $550 Non-members $750 Student Members $150

*includes Laboratory Health and Safety Guidelines 4th ed.

For more information, visit www.cheminst.ca/profdev


guestcolumn

The science versus public policy paradox By John C. Polanyi

n common with other scientific explorers, chemists need the freedom to be opportunistic. What is anticipated is seldom what is most worth discovering. This has profound implications for public policy in regard to basic science. Loath though we are admit it, it is the scientist free to pilot his or her own vessel across hidden shoals into the unknown sea who gives the best value for money spent. It is the chemist’s daunting task to figure out why some atoms attract and others don’t. This is a field extending from biology to geology; from the living to the dead. No individual chemist roams so far. We move a few tentative ant-footsteps from where our teachers left us. After that, we communicate with one another. Communication depends on questioning the best people and getting answers. This is as vital as is getting your calls returned in the wider world. And that depends entirely on who is calling. No organizing power can command it. This personal element is why communication, collaboration and the formation of teams in science are best left to the initiative of the scientist. Governments hamper scientific progress when they attempt to manage university science, rather than facilitating the business of exploiting discoveries once made. It is an oddity that governments, which for good reason hesitate to manage the traffic in goods, are so keen to plan the traffic in ideas. The fault lies with scientists, who have failed to explain what they do. Communication, on which the scientific enterprise so much depends, is a high art. What is being communicated is

seldom ‘fact’ — it is opinion. That is why it needs the skill of the scientist, operating in a self-governing society. The society of scientists, more complex than that of ants, balances the need for freedom against order. Freedom is vital so that imagination can take flight. But to achieve order, scientists subject themselves to rules. These rules, ­amazingly, are un-codified and enforced without police. Publication is censored by anonymous scientific juries, so as to protect the community from ill-founded reports. Such censorship is hazardous, hence is itself subject to constant scrutiny by the same community. This intricate structure underlies the functioning of science. Its purpose is to flag what is important, set aside what is pedestrian and abjure what is fraudulent. That is a tall order, but the health of science depends on it. Yet in many countries, Canada among them, public policy encroaches on this system. That the encroachment will do damage can be seen from the fact that it embodies the following paradox. We know that scientific talent is unevenly distributed. Consequently we require the scientific community to identify those whose work shows signs of excellence. These, the best of the best, are the rare commodity we seek for success in the nation’s science. But then, paradoxically, governments cause us to do an about-face, treating excellence as a resource so abundant that we can select from among the most excellent those deemed by policymakers to be the most ‘relevant.’ We thereby confuse a professional judgment with a seat-of-the-pants one.

For how good are we, scientists or non-scientists, at extrapolating from as yet unmade scientific discoveries to distant technologies? Not good at all. The reason we fail is that it is in the nature of discovery to surprise, while it is in the nature of bureaucracy to oppose surprise. What is a ‘plan’ if it is not to diminish the element of surprise? Nonetheless, we prescribe the dubious medicine of perceived relevance in ever-increasing doses. If we should come to the conclusion that the current governmental management of university science is not making our industries more innovative, what should we do? Increase the required dose of ‘relevance’ as judged by some central authority? That is what is being done in other parts of the world. As a result, university science suffers from shrinking horizons that trivialize it. There is an opportunity here for Canada to do something far-sighted. Toss out the medicine. No longer tell the scientist what to discover. Instead, insist they make the biggest possible discoveries at the least possible cost, in the shortest possible time. Demand that they surprise us, recognizing that there is nothing in the world to beat the best science for the highest degree of relevance. John C. Polanyi,HFCIC, is a chemistry professor at the University of Toronto and the 1986 recipient of the Nobel Prize in chemistry. He has written extensively on science policy, the control of armaments and peacekeeping.

october 2011 CAnadian Chemical News   7


Chemical News Policy and Law

Ottawa ­announces new oil sands ­monitoring plan In late 2010, several scientific panels condemned the Alberta oil sands mining monitoring system, calling it inadequate. This past summer, Environment Canada released its plan for a revamped system, but questions remain over how it will be implemented and who will pay for it. The new plan standardizes methods for measuring and reporting indicators of environmental health and improves integration of the various components, such as water quality, air emissions and monitoring of biodiversity. As well, it includes mechanisms whereby ­abnormal measurements trigger additional studies and increased scrutiny.

At a news conference announcing the plan, Environment Minister Peter Kent estimated that implementation of the plan would cost $50  million per year, which he characterized as small compared to the $80 billion generated annually by oil companies. However, Canadian Association of Petroleum Producers spokesperson Travis Davies says that industry has had no formal consultation with the federal government over how the system will be funded. “We’re going to be more than constructive participants, but we need to wait until all the stakeholders can sit down around the table and hammer that out. We haven’t had those discussions yet,” Davies says. Regardless of how the plan is implemented and paid for, the real proof of its effectiveness will be increased enforcement, according to Marc Huot, a policy analyst with the Pembina Institute. “If it shows that there are problems, and we know there already are some, will they commit to actually addressing those issues with the same effort that they’ve committed to addressing the monitoring system?” Huot asks. “That remains to be seen.”

Nanotechnology

Artificial molecules ­harvest light energy

Cadmium ­telluride quantum dots (red, yellow and green spheres) ­connected by short strands of DNA can gather and transfer light energy from multiple wavelengths. This could lead to advanced materials for solar cells and other ­optical ­devices.

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Bill Baker

Molecules are often compared to children’s construction sets, where ­atoms of different sizes are connected by chemical bonds. Now the same principle has been applied to quantum dots and the result could lead to advances in solar cells and optical devices. Quantum dots are crystalline nanoparticles that can absorb and ­reflect light at very specific frequencies based on their size. A team led by Shana Kelley and Ted Sargent at the University of Toronto has ­managed to connect cadmium telluride quantum dots of different sizes to each other using DNA as a linker. “DNA is inherently a very ­programmable material and you can define what other molecule that sequence will bind to,” says Kelley. “That allows us to build up pretty complex ­structures.” The team builds up the dots using a one-pot process, where ­cadmium salts, tellurium salts, and DNA oligomers are all mixed ­together and heated to just below boiling. After a few minutes, ­cadmium telluride crystals begin to grow. The size of these quantum dots is controlled by terminating the reaction at the desired time. Meanwhile, the short DNA sequences start to bind to the surface. By changing the length of these sequences, the team can control how many of them attach; if the sequences are longer, there is less room and fewer of them bind. By mixing dots of different sizes and valencies the team was able to create complex structures similar to the way atoms assemble to build molecules. The complexes absorb light at multiple wavelengths and transfer them to a single point, a feature that could be very useful in the solar harvesting or optical detection. “We have lots of ideas for interesting devices, so we're in a phase of trying to get creative with what we can build and what the assemblies should be able to do,” says Kelley. The work is published in Nature Nanotechnology.


Canada's top stories in the chemical sciences and engineering By Tyler Irving Biotechnology

Fatemeh Nazly Pirmoradi

Magnetic implant could halt vision loss Tens of thousands of Canadians suffer from diabetic retinopathy, where unwanted blood vessels permeate the retina and cause vision loss. Currently, these vessels can only be removed with lasers or surgery. But an implantable, magnetic drug delivery device designed at the University of British Columbia could offer a new way of treating this pervasive condition. Recent PhD graduate Fatemeh Nazly Pirmoradi designed the device, which looks like a tiny contact lens. It’s actually a disc-shaped polydimethylsiloxane (PDMS) chamber filled with docetaxel, a chemotherapy drug that inhibits cell division. The top of the chamber is a membrane made of PDMS impregnated with magnetic iron oxide particles, with a tiny laser-drilled hole in it. When fluid fills the chamber, a small amount of the relatively insoluble docetaxel is dissolved. When exposed to a magnetic field, the membrane

A new ­implantable ­device ­deforms in the presence of a magnetic field and could allow for ­targeted drug ­deli­very without the need for ­multiple ­injections.

deforms, squeezing out the docetaxel solution like toothpaste from a tube. The chamber then refills and more docetaxel dissolves for the next dose. “It worked really well,” says ­Pirmoradi. “I was activating it every day for five weeks and it was a constant dose.” A second test, where the device was ­activated after sitting unused for seven months, again showed the same dose. So far, the experiments have used permanent magnets to actuate devices

in test tubes; more data on biocompatibility is needed before the device can be tested in vivo. Still, Pirmoradi is optimistic. “It’s very simple. It doesn’t have a battery, wires or electronics, which allows for a smaller device. And by providing the drug locally, we avoid systemic toxicity,” she says. This means the device may be useful not only for diabetic retinopathy but other applications such as cancer treatments. The work is published in Lab on a Chip.

health

Sweetly healthy maple syrup Canadians love maple syrup, but the associated sugar rush can be hazardous to one’s health, especially for those living with diabetes or other metabolic disorders. But thanks to some clever chemical engineering, a new maple syrup product may soon alleviate those concerns. The project is a collaboration between the National ­Research Council, the University of Guelph Kemptville ­Campus and ­Natunola Health Inc., an Ottawa-based supplier of ­botanical ingredients for both cosmetics and food. The idea was to use natural enzymes to convert sucrose - the main sugar ­component of maple syrup - to its structural isomer, isomaltulose. Because it has a different shape than sucrose, isomaltulose is not as readily digested by human enzymes, leading to a slower release of sugar into the blood stream and eliminating spikes in blood glucose. In order to convert the sugars, Wie Zou and his team at the NRC relied on two species of bacteria, Erwinia rhapontici and Protaminobacter rubrum. These plant pathogens, harm-

less to humans, produce enzymes that convert sucrose into ­isomaltulose. The team immobilized these species in gels made of calcium alginate or carageenan and placed them in a bioreactor with concentrated maple sap from the sugar bush at Kemptville Campus. The enzymes did the conversion ­efficiently and worked even when the bacteria themselves were killed before inoculation. The altered sap was then boiled into syrup in the traditional way. Zou says the new product tastes great. “We made some ­cookies, butter, maple candy, all kinds of things. If you didn’t know, you wouldn’t be able to tell the difference.” There are still a few hurdles to jump, including approval from the ­Canadian Food ­Inspection Agency and tests to determine the glycemic index (GI), a measure of how fast the body metabolizes the sugars in a given food. This past May, Natunola received a grant from the ­Ontario Ministry of Agriculture, Food and Rural Affairs to help with this process and Zou is hopeful that consumers can be ­enjoying new, low-GI maple products by 2012.

october 2011 CAnadian Chemical News   9


Chemical News Fundamentals

Colour-changing crystals ­detect O2 and CO

Rhodium complexes of ­N-heterocyclic carbenes form macroscopic ­crystals that are able to bind to gases like oxygen and carbon monoxide without changing their internal structure or oxidation state. The distinct colour change could be used in sensors to detect these gases.

Environment

Persistent organic ­pollutants released in the Arctic For years, scientists have speculated that warming temperatures in Canada’s Arctic could lead to the release of persistent organic pollutants (POPs) currently trapped in ice and frozen ­tundra. Now, a team from Environment Canada has provided some of the first evidence that this is ­indeed happening. POPs are a broad class of organic chemicals that are bioaccumulative, resistant to degradation and toxic to organisms. They arrive in the Arctic in vapour form or attached to air-borne particles, travelling on air currents from further south. Once they deposit, the cold temperatures make it difficult for them to evaporate once more. “We know that these chemicals are stored in the ­Arctic,” says Environment Canada’s Hayley Hung, one of the co-authors of the study. “What we don't know is how much,” Hung says. In general, the concentration of POPs in Arctic air has been decreasing since the early 1990s when measurements first began, because most Western countries have banned the use of these chemicals. Against that overall trend, a release of POPs due to rising temperatures

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Olena Zenkina/Eric Keske

When a molecule binds with oxygen, it usually ends up behaving quite differently than it did before. So when Cathleen Crudden and her team at Queen’s University found a complex of rhodium that binds oxygen and ­changes colour while leaving its crystal structure intact, they knew they were on to something unique. The original discovery was made by accident two years ago while studying the bonding properties of rhodium complexes of N-heterocyclic carbenes (NHCs). When solutions of these compounds were exposed to oxygen in a fumehood, they changed from yellow to green, which prompted further investigations into their structure. “We were able to show that it binds oxygen, but it doesn’t actually oxidize,” says Crudden. “It stays as rhodium (I), which was really unusual.” Building on this work, post-doctoral researcher Olena Zenkina and PhD candidate Eric ­Keske prepared Rh complexes featuring different NHCs. They were able to generate macroscopic crystals which change from ­yellow to blue on exposure to oxygen, and then to brown on exposure to carbon monoxide. Remarkably, they do this without any change in their crystal structure. “One gas diffuses in, the ­other diffuses out and all the other atoms stay basically in the same place,” says Crudden. Such colour-changing compounds could be used in ­sensors to detect oxygen (for ­example to see if food has been ­contaminated by exposure to air) or carbon ­monoxide. The work is ­published in ­Angewandte ­Chemie.


Canada's top stories in the chemical sciences and engineering By Tyler Irving biochemistry

Patrick Gunning

Protein-membrane anchors ­offer new cancer strategy Protein-membrane anchors have two domains; a ’key’ domain which binds to some part of the target molecule, and an ’anchor’ domain which is attracted to the non-polar cell membrane. A team from the ­University of ­Toronto ­Mississauga is using this strategy to block the STAT3 signalling pathway, which is implicated in c­ertain cancers.

would likely be small and hard to spot. The team solved this problem by using statistical methods to remove the general declining trend from the POP concentrations measured in the Arctic each year, leaving only the residual. This value showed a gradual ­increase over time since 2000, evidence that these chemicals are in fact being released. Showing that the process is underway is one thing, but predicting the potential ­impacts on human health is much more ­complicated. For one thing, nobody ­really knows how much of each POP is ­currently sequestered in the Arctic. Moreover, ­climate change will affect human health in other ways. “It might change the food web, which would subsequently affect the ­bioaccumulation of POPs,” Hung says. “The remobilization  of POPs is only one factor out of many. This is the beginning of a story, rather than the end.” The work is published in Nature ­Climate Change.

In order to block the action of an enzyme, it’s usually necessary to create a molecule that binds to its active site. But a group of researchers at the University of Toronto Mississauga (UTM) have come up with a different strategy — they simply throw out an anchor. STAT3 (from Signal Transduction and Activation of ­Transcription) is a protein that activates certain genes involved in cell ­differentiation, proliferation and survival. In cancer cells, this protein’s pathway is permanently turned on and turning it off is a big goal for drug makers. “Despite its clinical relevance to cancer, there is no easily targetable site on the surface of the protein and no STAT3 drug in the clinic,” says Patrick Gunning, professor in the ­Department of Chemical and Physical Sciences at UTM. The team reasoned that because STAT3 is a macromolecular ­signalling protein that shuttles between the cytoplasm and the ­nucleus, preventing it from moving freely throughout the cell would be enough to block its action. They made the anchor by attaching a peptide sequence known to bind to STAT3 to various ­hydrophobic molecules, which are attracted to the non-polar environment of the cell membrane. The hydrophobic molecule that worked best turned out to be cholesterol. “We were quite amazed by the images that we got. We see complete anchorage of the protein to the ­cytosolic membrane,” Gunning says. The team is now working on replacing the peptide binding ­sequence with a more robust molecule that will not degrade in the body. Gunning notes that the new strategy could work on other ­enzymes as well. “If we can inhibit any protein’s movement within the cell using a protein-membrane anchor, then we have the potential to stop its function and reverse its aberrant role.” The work is published in Angewandte Chemie.

october 2011 CAnadian Chemical News   11


Ichikizaki Fund for Young Chemists The Ichikizaki Fund for Young Chemists provides financial­assistance to young chemists who show unique achievements­in basic research by facilitating their participation­in international conferences or symposia.

Eligibility: • be a member of the Canadian Society for Chemistry or the Chemical Society of Japan; • not have passed his/her 34th birthday as of December 31 of the year in which the application is submitted; • have a research specialty in synthetic organic chemistry; • be scheduled to attend, within one year, an international conference or symposium directly related to synthetic organic­ chemistry. Conferences taking place in January to March of each year should be applied for a year in advance­in order to receive funding in time for the conference.

Deadline: December 31, 2011 For more details:

www.chemistry.ca/awards

Canadian Society for Chemical Engineering

Nominations are now open for the

Canadian Society for Chemical Engineering

2012AWARDS

Do you know an outstanding person who deserves to be recognized?

Act now!

Deadlines Bantrel Award in Design and Industrial Practice D. G. Fisher Award Process Safety Management Award R. S. Jane Memorial Award The Syncrude Canada Innovation Award

The deadline for all CIC awards is December 1, 2011 for the 2012 selection.

Nomination Procedure Submit your nominations electronically to: awards@cheminst.ca Nomination forms and the full terms of reference for these awards are available at www.chemeng.ca/awards.


Consumer advocates slam what they call a lack of ­government r­ egulations pertaining to chemicals in cosmetics. Some call this fear mongering, pointing to a lack of data indicating that the chemicals in makeup, body lotion or sunscreen pose a threat to human health. By Tim Lougheed

n a world populated with highly processed chemical consumer products, each of us encounters a variety of unknown or questionable chemicals on a daily basis. Those encounters can be especially intimate when it comes to cosmetics. Every day millions of people apply these agents to delicate body parts such as eyelids or lips, raising the possibility of interactions through the skin that could continue over an extended period. The implications of these interactions have come under intense scrutiny over the past decade. The widespread popularity of products such as eye shadow or lipstick makes it easy to regard them as chemically benign. However, that does not mean they are chemically inert, as ­individuals who respond to them with an allergic reaction can testify. Such overt responses tend to be relatively rare, but some observers want to consider the prospect of broader, more subtle and significantly more hazardous effects. Entire books have dwelt on this theme, emblazoned with provocative titles announcing their intentions. In 2007, former reporter and newspaper publisher Stacy Malkan of San Francisco published Not Just a Pretty Face: The Ugly Side of the Beauty Industry. In the book, Malkan details the launch of the Campaign for Safe Cosmetics in the United States, a grassroots consumer movement to persuade the leading companies in the industry to reduce or eliminate some of the ingredients in their products. A similar initiative was subsequently taken up in Canada by former Discovery Channel presenter Gillian Deacon, who wrote There’s Lead in Your Lipstick. After exploring the gamut of identifiable toxins that are linked to cosmetics and personal hygiene products, Deacon highlights lesser-known alternatives that feature much shorter and

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business | consumer safety

simpler ingredient lists, in contrast to the offerings that currently ­dominate the cosmetics marketplace. The tone of these books is blunt and occasionally strident. They portray a manufacturing sector that has been graced with a light burden of regulation, despite the fact that its member firms deal in arcane, multi-syllabic chemicals that are known to do harm to human health. Moreover, this aspect of the industry tends to be eclipsed by the accompanying aura of glamour and sophistication. “It’s not that consumers don’t value safe cosmetics, judging by the number of beauty ads that emphasize the words healthy, clean, pure and natural,” writes Malkan. “But with no standards in the industry, the commercial advantage goes to companies that spend the most money on ads to convince consumers their products are pure — regardless of what’s actually in them.” Deacon, for her part, underscores the physical damage that could be wrought by cosmetics. Referring to the use of under-eye night creams, for example, she explains that the thin, porous skin around the eyes sits directly atop blood vessels that can serve as conduits to the body’s vital organs. In this way she casts a pall over what should be one of life’s happier moments, the venerable ritual that sees mothers introduce their daughters to the use of such products. “And yet without being selective about cosmetic ingredients,” writes Deacon, “they inadvertently begin a process of loading their precious daughters with toxins that do the very thing no mother would ever want done to her child — make her unwell.” Both authors are eager to link the intricate chemical cocktails found in cosmetics to known ailments, especially cancer. Readily accessible cosmetic ingredient databases offer up hundreds of candidates to consider, such as triethanolamine (TEA), which is found in three distinct types of commonly used products: sunscreen, body lotion and liquid makeup. “I delve deeper in the database and find that the chemical (spelled 32 different ways on product labels) forms carcinogenic nitrosamine compounds if mixed with other ingredients that act as nitrosating agents,” writes Malkan. “It is also a skin sensitizer and possibly toxic to the lungs and brain.” Malkan concedes that the amount of this agent found in any given batch of cosmetics can be all but undetectable. But she adds that the cumulative exposure — and thus the risk — from multiple sources could wind up being far greater. “Triethanolamine, I learned in my research, is also used in floor polish, pool cleaners, rug cleaners, laundry detergent, toilet bowl cleaners and other products I have been exposed to on the day I used the three beauty products. The risk assessment didn’t account for that. It also can’t tell me what happens when TEA is mixed in combination with the 16 other potential carcinogens, two dozen endocrine disruptors and other toxic substances in my daily routine. Few if any of the ­chemicals in my cosmetics have been tested in mixtures to understand the ­long-term health impacts of chronic use over time.” Joe Schwarcz, for his part, rejects this depiction as fear mongering. The McGill University chemist has made a second career out of soothing public panic over the chemicals around us. Schwarcz regularly harkens back to the Renaissance scientist Paracelsus, who is regarded as one of the founders of modern medicine. Among the

october 2011 CAnadian Chemical News   15


Government makeup tips Health Canada’s current regulations for cosmetics have deep legislative roots. They date from the Adulteration Act of 1906, which subsequently became the Food and Drugs Act in 1920. As the use of chemical processing burgeoned in the decades after the Second World War, the legislation diversified to deal more specifically with particular industries. This process extended to personal care products in 1977, when the existing Cosmetics Regulations emerged. This legislation has been amended many times since then, most recently in 2004. The latest change imposed a requirement on manufacturers to label all of the ingredients in their products according to a common code known as the International Nomenclature for Cosmetic Ingredients. This standard system is intended to make it easier for consumers and scientific ­investigators to identify agents that might be of concern, wherever in the world those agents might be found. Among the most significant distinctions of Health Canada’s approach to chemical-based risks is a consideration of exposure. While the European Union’s regulatory framework simply labels any compound with ­negative health effects as a hazard, Canadian ­authorities will consider how likely people are to encounter these compounds and how much of that compound they will encounter. If these interactions are sufficiently low, as they tend to be in the case of many cosmetics ingredients, then even the deadliest carcinogen can be deemed to pose little or no risk. While that approach may not satisfy observers who would prefer to banish all traces of such chemicals from their lives, Health Canada does nevertheless publish all potentially hazardous materials in its Cosmetic Ingredient Hotlist. This database, which is updated several times a year, ensures that both companies and consumers are aware of the substances that could be problematic, if individual exposure becomes sufficient.

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most important precepts established by Paracelsus was the principle that there are no inherent poisons; instead, it is the dosage of any particular agent that makes it poisonous. That principle is crucial to the way Schwarcz approaches prominent concerns about chemicals found in everyday products such as cosmetics. “Without a doubt, the scariest allegation is that cosmetics may contain carcinogens,” he acknowledges. “Indeed, some do. It is important to realize, though, that the definition of a carcinogen is a substance that is capable of causing cancer in some animal at some dose. Dioxane, for example, is found as an impurity in some cosmetics and is listed as a carcinogen because it triggers the disease when fed to rodents. Amounts in cosmetics, however, are vanishingly small, known to be present only because of the availability of extremely sensitive detection techniques.” Those same techniques can reveal the carcinogenic qualities of even the healthiest foods. Malkan confronts this apparent paradox as she recounts a presentation by University of California professor of biochemistry and molecular biology Bruce Ames, who pointed to assessments that indicate the extremely limited, but still measurable, cancer-causing potential of extremely low levels of synthetic chemical residues found in staples such as carrots or apples. Even so, Malkan and others remain adamant that cosmetic manufacturers should be forced to account for the content of their products. In fact, that disclosure does take place, although the particular regulatory regime can vary from one country to another. The European Union has erected one of the world’s most comprehensive legislative structures to deal with cosmetics, resulting in outright bans on some constituent chemicals, as well as products that might be commercially available elsewhere. In the U.S., this responsibility generally falls under the federal purview of the Food and Drug Administration, but in 2005 the state of California highlighted weaknesses in this oversight by imposing its own separate set of more stringent stipulations to inform the public of any hazardous materials found in cosmetics. California’s move subsequently prompted a revision of the federal regulations that are currently working their way into revised legislation that specifically deals with the safety of cosmetics. In this country, such questions of safety fall to Health Canada, which demands specific background information before a cosmetic product can be sold in this country. Elizabeth Nielsen, who used to work for that department but has since become an independent consultant and representative of the Consumers Council of Canada, points out that this information does not pertain to the safety of the product. Under Section 30 of Health Canada’s Cosmetic Regulations, manufacturers are only asked for the purpose of a product, its physical form, its ­ingredients and the concentration of those ingredients. “Health Canada does not require the manufacturers to provide it with the results of toxicological and other safety tests prior to bringing a product to the market,” she says.


Even more significant to Nielsen is the paucity of scientific data on exposure and long-term health effects of the various ingredients that appear at extremely low levels. Some enforced limits do exist, especially in the case of the metals lead, arsenic, cadmium, mercury and antimony, which are restricted to set measures of parts per million. In the absence of direct evidence to justify their elimination, agents like TEA or dioxane continue to appear in marketed goods, although Health Canada does publish this fact on a Cosmetic Ingredient Hotlist. “As far as I am aware, very little or no research has been carried out to determine the effect of persistent low doses of substances in products like cosmetics,” says Nielsen. That shortcoming was revealed in a report on metals in cosmetics, which drew a great deal of media attention early in 2011. Issued by an interest group called Environmental Defence, the report offered up case studies of the amount of particular metals that particular individuals would find in their daily cosmetic regime. A comprehensive bibliography was intended to support the assertion that these ingredients posed a clear health hazard. However, more than one-third of the 71 entries on this list consist of links to American and Canadian government websites, while others refer to mass media reports. Even where references to peer-reviewed scientific journal articles occur, many of them only describe analytical techniques that might be used to study low-level exposure to cosmetic ingredients, rather than documenting any cases of such exposure. In fact, no more than a handful of articles actually deal with such cases, and even these may not be immediately applicable to the circumstances of cosmetics users in North America. For instance, several articles deal exclusively with the use of surma, an antimony-based eye shadow that is traditionally used on children in North Africa and the Middle East. Schwarcz, for his part, insists that cosmetic firms have a vested interest in ensuring that their wares do not harm the health of customers. Despite a popular perception that leaving industries to police their own standards is the equivalent of letting the fox guard the henhouse, he maintains that companies are sensitive to the concerns voiced by observers like Malkan and Deacon. In the U.S., for example, members of an industry trade association known as the Personal Care Products Council have been conducting this kind of research since 1976, using procedures developed with the Food and Drug Administration and the Consumer Federation of America. The results of this collaboration, known as the Cosmetic Ingredient Review, include safety assessments that are published in the International Journal of Toxicology. Nevertheless, industry critics could well remain unsatisfied by this organization’s track record. By the time California was introducing its legislation in 2006, for example, one account of this development noted that the Cosmetics Ingredient Review had considered 1,286 agents over the previous 30 years and just nine of them had been formally removed from use in products. In the meantime, even more tantalizing aspects of this debate are emerging. Schwarcz puts forward a proposition that is likely to prove to be even more unsatisfactory to critics of the cosmetics industry: small quantities of toxic agents might actually benefit human health. Dubbed hormesis, this idea has been championed in the peer-reviewed scientific literature by University of Massachusetts toxicologist Edward Calabrese. Not surprisingly, his work has generated some lively

debate. “It does make biological sense,” observes Schwarcz. “When an organism is attacked by poisons, it responds by unleashing a variety of molecules, mostly enzymes, which attempt to repair the damage. If the amount of toxin is minute, there may be an overreaction, with more defense chemicals being churned out than needed, leaving an excess to deal with the molecular insults of everyday life. It may yet turn out that the apocalyptics who warn us of the perils of exposure to parts per trillion of toxic chemicals are on the wrong track.” Along with the emergence of this new perspective on chemical exposures, Nielsen sees the very definition of “lowlevel” moving to an entirely different plane. She suggests that a host of new problems could be posed by the growing use of agents that are being manipulated at the nanometre scale. And if little has been revealed about the impact of conventional chemical use over the past few decades, even less is known about the health effects that might ensue from recently launched nanotechnological methods. Nielsen has conducted surveys on consumers’ knowledge and concerns about nanotechnology. The results of these surveys reveal the public’s suspicion and skepticism toward the use of nano-scale materials in cosmetics. For her, this attitude is an extension of the disappointment she has heard individuals express when they learn about the limitations of Canada’s regulations on cosmetics. “Most consumers believe that the government looks at every product before it is sold,” she explains. “Most believe that their interests are being looked after. They will react with disbelief, however, when told that no safety assessment is carried out on cosmetics before they are allowed to be sold.”

october 2011 CAnadian Chemical News   17


Assistant Professor, Inorganic Chemistry The Department of Chemistry at the University of Alberta invites applications for a tenure-track faculty position in Inorganic or Materials Chemistry. The starting date is July 1, 2012. The rank for this position is directed at the Assistant or Associate Professor level. Outstanding individuals with research interests in areas related to Inorganic Chemistry that complement current expertise in the department are encouraged to apply. The Department has vibrant research programs encompassing most areas of modern chemistry including structure, dynamics, spectroscopy, synthesis, materials, instrumentation and analysis (www.chem.ualberta. ca). An outstanding research environment is offered with access

to excellent support facilities. The candidate will have a demonstrated potential for excellence in research and teaching and must hold a PhD. Interested individuals should submit a curriculum vitae, a detailed research proposal, a statement of teaching interests, and arrange to have three confidential letters of reference sent on their behalf. The application deadline is October 27, 2011. Applications should be sent to: Professor D. Jed Harrison, Chair; (chair@chem.ualberta. ca) Depart. of Chemistry, UofA E3-38 Gunning / Lemieux Chemistry Centre, Edmonton, AB, Canada T6G 2G2 Competition No.: A104915091 Closing Date: Oct 27, 2011

All qualified candidates are encouraged to apply; however, Canadians and permanent residents will be given priority. The University of Alberta hires on the basis of merit. We are committed to the principle of equity in employment. We welcome diversity and encourage applications from all qualified women and men, including persons with disabilities, members of visible minorities, and Aboriginal persons.

FINAL Date 08.05.11

University of Alberta

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Q A &

Tailings Termination

Murray Gray is leading a research network that seeks to eliminate ­tailings ponds of bitumen waste from the Northern Alberta landscape. By Tyler Irving

C

an research, innovation and clever chemical ­engineering overcome the environmental challenges facing Alberta’s oil sands industry? Murray Gray believes they can. Gray is the scientific director of the Centre for Oil Sands Innovation (COSI), a multi-million dollar network dedicated to funding breakthrough research that will eliminate oil sands tailings ponds and greatly speed up the reclamation of land disturbed by mining operations. Based at the University of Alberta, COSI celebrated its fifth anniversary of operation this year. ACCN spoke with Gray to find out more about his vision for­ ­sustainable oil sands.

ACCN Is there such a thing as sustainable oil sands development? MG If you look at the most widely accepted definition

of sustainability from the United Nations’ Brundtland Commission, it talks about sustaining communities and maintaining a long-term natural environment for local people. It doesn’t preclude use of fossil fuels. From that perspective, what you’re looking at is not to make the oil sands renewable, but to minimize the impact on the local environment. One of the biggest problems that the industry faces right now is with tailings. The current practice is to accumulate wet tailings materials until the mine is played out and then put that material back into the mine site. That gives a very long delay time between when the mine first starts operation and when serious reclamation work can begin. Our biggest single research program is focused on trying to extract the bitumen without using water. It would essentially eliminate this problem; you still have the sand and the clay, but if it’s dry it can go back in the mine immediately. ACCN How do tailings form in the first place? MG Bitumen is a naturally occurring, highly biodegraded

crude oil. The current mining operations extract this from

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the oil sands by digging up the sand and mixing it with warm water. The bitumen is melted as it warms up, then it releases from the sand and attaches to air bubbles. That material is collected as a froth, which is then cleaned up to remove the water and mineral particles and sent for upgrading. When you mix the oilsand ore with water you get sand, which is no problem, but you also take any clay that’s in the ore and disperse it. Those fine clay solids do not easily release water, so they form a huge volume of water-rich sludge which does not re-compact nicely. You can’t just put sludgy paste back into the mine so it accumulates in ­tailings ponds over the mine’s life span. As well, some of the components of bitumen dissolve in water at low concentrations and those are toxic to aquatic organisms. At present, the water is intensively recycled. In the future, some of that water will have to be released and so there’s an interest in technology for treating it. ACCN What kind of research are you focusing on to deal with this problem? MG Most of our work is on the fundamental properties of the

oil and how it interacts with clays. One major problem is that high molecular weight molecules in the bitumen bind to each other, forming aggregates. This aggregation is very important in terms of how the oil dissolves and how it releases from minerals. We’re working on understanding the basic ­molecular structure, how these molecules aggregate and how they stick to surfaces. On the non-aqueous extraction side we have several projects looking at using different solvents to extract material instead of using water. It’s a two-step problem: you want to get the bitumen away from the mineral material and then you have to clean up the bitumen to remove any suspended solids. We’re looking at a whole range of solvents but whatever ones we use, we have to be very sure of what happens if they go back into the environment.


Chemical Engineering | Oil sands ACCN People have been working­ with bitumen for more than 60 years, why do we still need fundamental­research?

University of Alberta, Faculty of Engineering

MG Bitumen is an extraordinarily

complex mixture that defies proper analysis. It contains millions of different components and that’s a conservative estimate. The molecular weight isn’t all that high, in the range of 1,000 to 3,000 daltons, but the aggregation makes measuring properties and doing chemical analysis very challenging. We’re making progress: we have new tools that we can use to probe interfacial behaviour and we can use techniques from nanotechnology to better understand what’s happening with these molecules at interfaces. But we’re still not there and, as it stands, nobody in the world has the capability of completely analyzing one of these mixtures. Another factor is a big change that has come from the industry side. When the oil sands mining industry started, nobody was too worried about wet ­tailings. Now, the companies understand that there’s a huge cost associated with that practice. When you change the ground rules, you open up a lot of possibilities for new approaches. So techniques that were rejected in the past as too expensive now have tremendous potential. ACCN What prompted the ­creation of the Centre for Oil

Sands ­Innovation? MG The centre was initially started in partnership with

Imperial Oil, which wanted new technologies because the current practices of the industry were not sustainable enough. They committed $10 million over a period of five years. They’ve subsequently renewed that commitment for the next five years, so they’ve committed $20 million in total. After that, we were able to get two provincial agencies on board: Alberta Ingenuity and the Alberta Energy Research Institute, which has since been restructured as Alberta Innovates, Energy and Environmental Solutions. The commitment from Alberta Ingenuity was in the range

Murray Gray, ­scientific director of the ­Centre for Oil Sands Innovation, holds up a sample of cracked bitumen that is being prepared for injection into a gas chromatograph. Understanding the fundamental ­properties of ­bitumen and its interactions with sand and clay could help ­industry deal with the problem of wet tailings.

of $7  million over five years and the commitment from Alberta Energy and Research Institute was in the range of $10 million over five years. ACCN How has the centre evolved over the past five years? MG As we expanded the program and developed major

initiatives looking at non-aqueous extraction and new technologies for upgrading, we quickly realized that we couldn’t just focus on one group of people at one university. So we started organizing projects with collaborating universities. One example is Keng Chou at the University of British Columbia, who’s using unique spectroscopic techniques to understand the structure of water, solvents and bitumen at the interfaces with solids like silicon dioxide, which mimics some of the minerals of the oil sands. By using non-linear spectroscopic techniques, he can cancel out the signals from the bulk liquid and look only at the material that’s

october 2011 CAnadian Chemical News   21


pembina institute

immediately at the interface. Given that our major objective in recovering bitumen is to get it off of clay and sand surfaces, that kind of scientific insight is very important. Another is Juliana Ramsay’s group at Queen’s University. They’re using microorganisms to degrade some of the soluble components that go into the water in the oil sands. A tiny fraction of the bitumen will dissolve in water and those components that dissolve are toxic to aquatic organisms. But they’re also biodegradable, so the team is trying to develop novel bioreactors and active bacterial cultures that will rapidly degrade those components. ACCN How do you expect your industrial and ­government partnerships will change? MG The big change over the past number of years has been a growing realization of just how big an issue the tailings ponds are for the oil sands industry. Earlier this year, all of the oil sands companies signed an accord in which they agreed to share all of their technology, data and research and development on trying to deal with wet tailings. As a result, one of the new initiatives that we’re starting is a theme on aqueous tailings in partnership with Imperial Oil and all the other oil sands companies. That’s a new initiative and it’s part of our proposal to the government of Alberta to renew funding for our centre for another five years.

never visited a mine in their life see the oil sands they’re horrified at all the destruction, but they’re not paying attention to the efforts being made. Companies are being successful in reclamation, the problem is the time lag. Last fall, Suncor successfully reclaimed its first tailings pond, which was first put into service in 1967, so that’s the timeline that I’m concerned about. The industry clearly needs to step up and reclaim much more quickly.

ACCN What do you say to skeptics who doubt the ­industry’s ability to make good on sustainability?

ACCN When you look back at the past five years, what are you most proud of?

MG The environmental groups typically don’t like big

MG My biggest source of pride is in developing a multi-

industry so there’s a political component there. But there are also a number of misconceptions, for example, the issue of acid mine drainage. In other mines, the extraction and milling of the ore pulverizes minerals that contain sulphur. The sulphur oxidizes and is released into ground water as acid, which then leaches out heavy metals. That whole cycle is irrelevant in the oil sands; the kinds of components in the tailings are radically different from what you get in any other mining operation. Yet people have written a number of times about the toxicity of acid tailings in the oil sands when in fact the pH is 8.5. Then you have to look at what has been proposed in terms of the time frame. These mines are planned on a 20-to 30-year cycle, so you can’t go in after five years and say, “You’ve made a big mess, why isn’t it all reclaimed?” When people who have

university, multi-disciplinary network of people who are committed to making a difference. Canada has a wonderful resource opportunity but has to use it wisely. Clearly we need to do research and understand the fundamentals in order to create a foundation to have much more sustainable oil sands technology. The experience of recruiting interested scientists and engineers from across Canada has been very exciting and I think that’s probably the single biggest satisfaction.

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ACCN How will you measure success? MG I’d like to see two or three major technologies rolled out.

It obviously takes time to go from the laboratory to practice but I think we will be in a situation with several technologies being piloted and tested in industry in three to five years. I think that would be a fair measure of success.


DNA

artisaN McGill University's Hanadi Sleiman looks to DNA as a template to pattern ­materials like nanotubes that act as smart delivery systems for therapeutics. By Melora Koepke

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Special Report for the International Year of Chemistry

H

anadi Sleiman’s tastefully decorated office at McGill University’s Department of Chemistry is dominated by a large picture window revealing the spires and rooftops of the 190-year-old Montreal institution. Displayed on the windowsill are several DNA knick-knacks: Francis Crick and James Watson bobble head dolls and a model of the iconic double helix. “This model of DNA is accurate down to the structure of nucleotides and bases,” Sleiman says, contemplating the intricate model. DNA — its mystery, its still-untapped potential for scientific innovation — has long fascinated Sleiman who, as a post-doctoral student, studied under French chemist Jean-Marie Lehn, winner of the 1987 Nobel Prize for his pioneering work in supramolecular chemistry. Sleiman and her research team, which works out of a bright, airy new laboratory in McGill’s Otto Maass Chemistry Building, is expanding upon Lehn’s work, focusing on the supramolecular chemistry of DNA. Backed by a number of funding agencies, including NSERC, the Sleiman Research Group uses the unique chemistry of DNA to design new nanomaterials for drug delivery, diagnostic tools and anti-tumour therapeutics. “It’s not just the molecule of life — now we


Tristan Brand

Chemistry | Nanotechnology

can do something with it. It’s the difference between studying what’s there and making your own versions of it,” Sleiman says. Sleiman was at Stanford University in the late 1980s completing her PhD in organic chemistry when she attended a lecture by Lehn on supramolecular chemistry — a discipline that examines the noncovalent interactions between molecules, from molecular self-assembly to molecular recognition. At the time, Sleiman had the idea that she would focus on the synthesis of small molecules for her post-doctoral work. Lehn, ever the visionary, articulated a challenge to his audience, which included Sleiman,

to “learn how to control the interactions between molecules the way nature controls them,” she recalls. Soon, Lehn predicted, scientists could combine supramolecular “components to make something: a machine, a functional molecule, a device, whose function is greater than the sum of its parts.” Lehn’s talk changed the course of Sleiman’s studies, propelling her along a journey of scientific discovery to her current position as one of Canada’s foremost researchers in supramolecular chemistry and DNA nanotechnology. Although nanotechnology is still considered an emerging field, nature itself already builds on this scale; a double strand of DNA is about two nanometres wide. Moreover, DNA is wonderfully programmable; sequences can be created that bind only to each other in certain ways. Combine that with excellent structural properties and DNA becomes one of the most promising templates to pattern materials with nanoscale precision. Sleiman and her team have used it to create one-,  two-  and three-dimensional nanostructures, including DNA  ­nanotubes, which have a variety of possible applications. For example, they could act as templates for the growth of nanowires, aid in the structural determination of proteins, or even provide new platforms for genomics applications. Nanotubes could also act as “smart” delivery systems for therapeutics, or become implantable ­nanoelectronic devices to sense, predict and diagnose disease. “We’re hoping this will be a whole new generation of molecules,” Sleiman says. One of Sleiman’s major innovations has been the incorporation of synthetic organic or metal-based linking molecules into the DNA structure. These act as the junctions, or corners, of the supermolecules and allow many short DNA sequences to be linked together in a modular way. Using this strategy, the team recently developed nanotubes that can selectively encapsulate molecular “cargo,” in this case gold nanoparticles, along the DNA nanotube length. This cargo can then be released by the nanotubes in response to specific external stimuli. The innovation could be used to deliver cancer drug molecules directly to tumours thus reducing the toxic effects on the body and enhancing efficacy.

october 2011 CAnadian Chemical News   25


Special Report for the International Year of Chemistry

The research is at a crucial juncture, Sleiman says. “This is the time for the field of DNA nanoscience to start producing useful things.” Easier said than done. For example, while DNA structures hold promise for biological applications, their ability to resist enzymes, to penetrate into cells and their safety in organisms all need to be examined and optimized. “There is a bright future and a lot of possibilities in DNA assembly, but there is still a lot of work to be done,” says Sleiman. Sleiman isn’t focusing solely upon DNA nanoscience. Other areas of research relate to her background synthesizing small molecules and polymers. Her team also works on designing and synthesizing biomimetic materials. Among some of the group’s research highlights, their work on the creation of hybrid polymer-DNA and gold nanoparticle DNA structures were selected as editor’s choices in Science and Nature. Sleiman’s science may be complex, but behind it is the simple but lofty goal of contributing to society in a meaningful way. This passionate sense of purpose grew out of the most dire of circumstances — war. The eldest of two children, Sleiman grew up in a family that emphasized achievement. Born in Beirut in 1965, Sleiman’s mother, Leila El-Horr, was a journalist, her professor father, Farouk Sleiman, chair of the biology department at Lebanese University Beirut. A happy home life was interrupted on Sleiman’s 10th birthday by the thud of falling bombs — malevolent heralds of the 15-year Lebanese Civil war. But the fear and ­devastation of that protracted conflict entrenched a sense of resolve in the ­precocious young girl. “If you’re going to school and there’s snipers and there’s bombs, it gives you a resilience,” Sleiman says. “You internalize the fact that no matter what happens around you, you’re going to get that education.” As the war worsened, Sleiman became determined to leave her beleaguered nation. “When I was in university, it was really tough, because the war got worse,” she recalls. “At that point, I said to myself, ‘I’m going to get really great grades so I can go to a really good graduate school and make it out of here.’ ” Sleiman received a B.Sc. in chemistry with high distinction and was accepted to Stanford University when she was only 20 to do a PhD in organic chemistry. It was at Stanford that Sleiman met her future husband, Bruce Arndtsen, who also became a chemistry professor at McGill. The couple has two children, Ryan, 12, and Maya, 7, both born while Sleiman’s career as an academic and researcher was in its early stages. By becoming the first female faculty member to have a child in the chemistry department in 1999, Sleiman broke through a glass ceiling of sorts — embracing her role as academic researcher and mother. McGill was supportive of their star researcher’s dual demands and, as it turns out, the children adapted well to their mother’s career. “I remember when Maya was two months old; I was invited to a conference to give a speech that was very important for my career. I held her in my arms as I paced back and forth, practicing my speech. She lay in my arms happily while I practiced.”

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It is a lesson that Sleiman hopes to pass on to her female students: motherhood and a career in science is not a contradiction in terms. Many female students have “internalized societal pressures” telling them that they can’t be both mothers and researchers, says Sleiman. “I tell them if they follow their dreams, they’ll be happier people as a result. And they’ll be passing on this happiness to their children; I really do think it’s a gift to my boy that he is growing up knowing that women are active contributors to society.” Sleiman has always shown such support and empathy for students, which is one of the reasons she was recognized several years ago with McGill’s Leo Yaffe Award and Principal’s Prize for excellence in teaching. She has also been recognized for academic achievement, winning, most recently, the Strem Award for Pure or Applied Inorganic Chemistry from the Canadian Society for Chemistry and McGill’s William Dawson Scholar Award (McGill’s equivalent to a Canada Research Chair Tier II). Research and teaching in tandem has given Sleiman the means to “try to transform the world.” As a researcher, orchestrating and manipulating nature’s tiniest particles, she seeks positive changes for humankind. As a teacher, the change is more immediate, but no less lofty because of it. “As a teacher, you really see your impact, it’s a person who’s changed by you.”


In Memoriam

Simon Fraser University mourns chemistry professor

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ian robertson

A special endowment fund has been created to honour the memory of Simon Fraser University chemistry professor Melanie O’Neill, 37, who was found slain in her home by Vancouver Police Department officers the evening of July 26, 2011. The Melanie O’Neill Chemistry Undergraduate Research Endowment Fund, established by SFU’s chemistry department as well as friends, family and colleagues, will be granted annually to a chemistry undergraduate student who demonstrates research excellence. Zuo-Guang Ye, chair of the chemistry department, gave a eulogy celebrating O’Neill’s many academic achievements at SFU at a packed memorial service Aug. 8. Born and raised in Halifax, O’Neill attended Dalhousie University for her ­undergraduate and graduate studies, receiving a PhD in physical organic chemistry in 2001. Afterwards, O’Neill attended California Institute of Technology as an NSERC postdoctoral fellow. After her postdoctoral work, O’Neill was hired by SFU, where she established an active and diverse research program in the interdisciplinary area of biophysical chemistry and chemical biology. O’Neill, MCIC, was a gifted researcher. In addition to setting up a molecular biology laboratory, O’Neill also established a first-class biophysical chemistry lab where she studied protein and other nucleic acid dynamics. She was considered a pioneer — one of only a handful of scientists around the globe who researched how humans use light to synchronize their metabolic and behavioural patterns with the outside world. Her most recent work attempted to correlate structural dynamics in the RNA editing process with primate evolution. O’Neill’s work netted accolades; in 2005 she won the Career Investigator Award, Scholar, from the Michael Smith Foundation for Health Research, the provincial support agency for health research in British Columbia. The foundation cited

O’Neill’s work in describing the mechanism of action of cryptochromes as circadian photoreceptors at the molecular and cellular level. The research enabled an understanding and potential manipulation of biological timing that had the potential to aid in the treatment of sleeping disorders and diseases like depression and cancer. A devoted instructor and mentor as well as researcher, O’Neill taught lowerand upper-division undergraduate and graduate chemistry courses. Described as a force of nature who lived life with passion in her professional and personal life, O’Neill especially loved the ocean and spent much of her free time boating, camping, hiking and bird watching. One of her favourite quotations was from 17th century French mathematician Blaise Pascal, whose own high-minded outlook on life resonated with O’Neill’s contemplative nature. In response to a Pascal quotation, O’Neill penned: “These are some of the most wise words I have known: ‘Beauty is a harmonious relation between something in our nature and the quality of the object which delights me.’ ” O’Neill is survived by her brother, Andrew O’Neill, and many aunts and uncles and their families. Donations to the Melanie O’Neill Chemistry Undergraduate Research Endowment Fund can be made online at www.sfu.ca/advancement. By deadline, no one had been arrested in connection with O’Neill’s murder and police weren’t releasing a cause of death.


Society news

ACHIEVEMENTS

CSChE and Green winners announced The 2011 winners of the annual CSChE awards are:

INTERNATIONAL YEAR OF CHEMISTRY

John Polanyi gets stamp of approval

Choon Jim Lim, University of British Columbia: Bantrel Award in Design and Industrial Practice, sponsored by Bantrel, for his research on the fundamentals of spouting and ­fluidization phenomena and the application of these technologies to environmentally friendly processes and clean energy production. David Shook, KemeX Ltd.: D. G. Fisher Award, sponsored by the Chemical Education Fund, for designing control schemes for new SAGD processes in the oil sands. Della Wong, MCIC, Shell Energy Canada: Process Safety Management Award, sponsored

by AON Reed Stenhouse. Wong has been a leader in the development of PSM programs such as inherently safe designs, process hazard analysis, risk assessments, operational risk studies, incident investigations and audits. Charles Xu, MCIC, University of Western Ontario: Syncrude Canada Innovation Award, sponsored by Syncrude Canada Ltd., for his work on developing forest biorefineries. John F. MacGregor, MCIC, McMaster University: R. S. Jane Memorial Award, ­sponsored by the CSChE, for research in the application of statistical methods to chemical ­engineering systems.

The 2011 winners of the Canadian Green Chemistry and Engineering Network awards are: EcoSynthetix Inc.: Ontario Green Chemistry and Engineering Award (Organization), s­ ponsored by the Ontario Ministry of the Environment. EcoSynthetix’s flagship product line represents a breakthrough in clean technology products that resulted in the ­production of the world’s first and only waterborne biopolymer latex derived from ­renewable raw material feed stocks such as corn or potato starches. Franco Berruti, University of Western Ontario: Ontario Green Chemistry and Engineering Award (Individual), sponsored by the Ontario Ministry of the Environment, for his research on particle technologies, gas-solid fluidization, heavy oil upgrading technologies and biomass conversion into biochemicals and biofuels.

In honour of the International Year of Chemistry, Canada Post has issued a stamp celebrating the work of John Charles Polanyi, HFCIC, who was awarded the Nobel Prize for chemistry in 1986. In giving the prize, the Royal Swedish Academy stated that Polanyi’s groundbreaking research in reaction dynamics forged a new field of research in chemistry. Polanyi, of the University of Toronto, was also cited for developing infrared chemiluminescence, where the extremely weak infrared emission from a newly formed molecule is measured and analyzed. This method provides a detailed understanding of how chemical reactions take place. “I am surprised and honoured to find myself a part of this intriguing stamp,” says Polanyi.

Order of Canada for Bandrauk

Award (Individual), sponsored by GreenCentre Canada, for research into ‘green’ routes to hydrofluorocarbons, base metal complex catalysts for selective, oxidative C-C bond cleavage for lignocellulose disassembly and mechanistic studies of metal ­complex-­catalyzed ­amine-borane dehydrogenation.

University of Sherbrooke professor of theoretical chemistry André Bandrauk, FCIC, was appointed Officer of the Order of Canada June 30 in Ottawa in recognition of his pioneering work in attosecond chemistry.

STUDENTS

In Memoriam

Turkish Delight for Canucks at Chemistry Olympiad

The Chemical Institute of Canada wishes to extend its condolences to the family of Saul Wolfe, FCIC, who died at age 78 in Vancouver. Wolfe was professor emeritus in the chemistry department at Simon Fraser University.

R. Tom Baker, MCIC, University of Ottawa: Canadian Green Chemistry and Engineering

Canada scored its best results in 26 years in Ankara, Turkey July 9-18 at the 43 rd annual International Chemistry Olympiad for high school students. Steven Song of Semiahmoo Secondary School in Vancouver won a gold medal, coming in 22nd overall out of 273 students from 70 countries. Silver medals were won by Shuoli Liu of Glebe Collegiate Institute in Ottawa and Melody Guan and Richard Liu, both of University of Toronto School in Toronto.

october 2011 CAnadian Chemical News   29


Chemfusion

The quirky and ­convoluted history of cocaine ocaine may have an infamous and well-deserved reputation as a dangerous drug when it is abused, but its contribution to the discovery of local anesthesia was spectacular. We have here another classic case of a chemical that can be beneficial or detrimental depending on how it is used. Long before the arrival of European explorers to South America, the Incas had discovered that chewing a concoction made by mixing coca leaves with lime had a stimulating effect and warded off hunger. They also noted that applying coca-laced saliva to skin injuries numbed the pain. This effect was eventually documented by Albert Niemann, a chemistry graduate student working in the laboratory of Friedrich Wohler, one of the fathers of organic chemistry. Wohler had been given some coca leaves brought back by an Austrian expedition and asked his student to undertake a chemical analysis. In 1860, Niemann managed to isolate a pure white powder he christened cocaine. As was common practice in those days, he tasted the newly isolated substance. The powder, he reported, left a peculiar numbness, followed by a sense of cold when applied to the tongue. Not much was made of this observation until Karl Koller came along. Koller began his career as a surgeon at the Vienna General Hospital where he collaborated with Sigmund Freud, who at the time was exploring the effects of cocaine on the central nervous system. Confronted with a young colleague who had become addicted to morphine after the amputation of a thumb, Freud treated him with cocaine to try to break the morphine habit. It worked, but it turned the unfortunate patient into the world’s first cocaine addict.

30   L’Actualité chimique canadienne

Freud became intrigued by cocaine and, when he went on leave to Germany, asked Koller to continue the experiments. Koller collaborated with another colleague, Dr. Engel. It was Engel’s tongue that would become pivotal in the discovery of local anesthesia. One day, after tasting a little cocaine from the end of a pen knife, Engel remarked, “How that numbs the tongue!” It was at that moment that the scales fell from Koller’s eyes. He had already become interested in eye surgery and had experimented with anesthetizing the eye with morphine, ether spray, chloral hydrate and potassium bromide, all of which were known to have effects on the nervous system. None of these was effective and general anesthesia with chloroform or ether, already widely practiced at the time, was not suitable for eye surgery because it failed to stop involuntary eye reflexes. Interestingly, Koller had been aware of the numbing effect of cocaine, but had never made the connection to his eye research until Engel’s comment. A classic experiment quickly followed. A solution of cocaine was placed into the protruding eye of a frog. Koller was then able to touch the eye with a needle without any reflex action occurring. The frog’s other eye responded in the usual fashion. Koller then bravely trickled a solution into his own eye, and using a mirror, touched his cornea with the head of a pin. There wasn’t the slightest unpleasant sensation or reaction! Local anesthesia was born! Before long, cocaine found wide acceptance in eye surgery, although it wasn’t problem-free. It dilated the pupils and caused other undesirable central nervous system effects. Eventually, it was replaced by synthetic compounds that retained the essential features

octobre 2011

By Joe Schwarcz

of the cocaine molecule but eliminated most of the undesirable effects. The most successful turned out to be procaine, familiar under the trade name Novocaine. It was followed by lidocaine, benzocaine and a host of others. All because Engel noted that his tongue became numb and Koller capitalized on this observation. Such a discovery should have secured a position for Koller as an ophthalmologist in the Vienna hospital. But fate intervened. After being called an impudent Jew by a colleague, Koller responded with a punch. This led to a duel with sabers. It seems Koller was as good with a saber as with a scalpel because he managed to inflict two gashes on his opponent without being harmed himself. But duels were illegal and when news of the confrontation reached hospital administrators, Koller’s hopes of a position were dashed. Koller immigrated to the United States where he worked as an ophthalmologist in private practice in New York until his death in 1944. To what extent he used cocaine is unknown, but the drug is still occasionally used for eye and nasal surgery. It is available from the Mallinckrodt Company, the only one licensed to produce purified cocaine for medical use. The raw material is purchased from the Stepan Chemical Company in New Jersey which has government approval for the importation of coca leaves from Peru. After the cocaine is extracted, the leaves are sold to cola manufacturers for use as a flavouring agent. But don’t look for any cocaine in cola beverages. The extraction process is very efficient. Joe Schwarcz is the director of McGill University’s Office for Science and Society. Read his blog at chemicallyspeaking.com.



ACCN, the Canadian Chemical News: October 2011