SOUTHWEST RETORT
SEVENTY-SIXTH YEAR
November 2023
Published for the advancement of Chemists, Chemical Engineers and Chemistry in this area published by The Dallas-Fort Worth Section, with the cooperation of five other local sections of the American Chemical Society in the Southwest Region.
Vol. 76(3) November 2023 Editorial and Business Offices: Contact the Editor for subscription and advertisement information. Editor: Connie Hendrickson: retort@acsdfw.org Copy and Layout Editor: Lance Hughes: hugla64@gmail.com Business Manager: Martha Gilchrist: Martha.Gilchrist@tccd.edu The Southwest Retort is published monthly, September through May, by the Dallas-Ft. Worth Section of the American Chemical Society, Inc., for the ACS Sections of the Southwest Region.
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TABLE OF CONTENTS ARTICLES and COLUMNS Letter from the Editor…..…..……..............13
NEWS SHORTS Device 'smells' seawater to discover, detect novel molecules………………………..…….5 A step to prevent opioid overdose deaths with light-activated naloxone treatment…..6 Plastic-eating bacteria turn waste into useful starting materials for other products….......7 Sunflower extract fights fungi to keep blueberries fresh………………………………....8 Cocoa pods — a source of chocolate, and potentially, flame retardants.…........................9 AI identifies antimalarial drug as possible osteoporosis treatment..……..…………….10 AROUND THE AREA UT Dallas INDEX OF ADVERTISERS Huffman Laboratories……………..….........3 TMJ Data Entry and Editing.……….......…3 ANA-LAB…………………………...…..…..4
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SERVICES and ANNOUNCEMENTS
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From the ACS Press Room Device 'smells' seawater to discover, detect novel molecules “In Situ Capture and Real-Time Enrichment of Marine Chemical Diversity”
tists need to capture and concentrate these molecules. Yet, many underwater environments are threatened, especially those with ACS Central Science unique — and potentially bioactive — compounds. So, Thierry Pérez, Charlotte SimmUnder the ocean’s surface, marine organisms ler and colleagues wanted to develop an unare constantly releasing invisible molecules. derwater instrument that captures and enrichSome of the chemical clues reveal which es dissolved compounds produced by spongcreatures are nearby, while others could be es or other marine organisms without harmused someday as medications. Now, re- ing their source and their ecosystem. searchers in ACS Central Science report a The researchers created a waterproof device proof-of-concept device that “sniffs” sea- that could be easily handled by an underwawater, trapping dissolved compounds for ter diver and that could pump seawater analyses. The team showed that the system through disks, which have a similar feel and thickness as make-up remover pads. These disks adsorbed dissolved molecules for subsequent analysis. They tested the instrument, called the In Situ Marine moleculE Logger or “I-SMEL,” in 65-foot-deep Mediterranean Sea caves that contained a variety of massive sponges. After sampling the water, the researchers assessed the captured compounds with mass spectrometry. The compounds had diverse elemental compositions, and many had molecular structures that are unknown, which the team says makes it promising for the discovery of new natural products. This proof-of-concept device “smells” seawater by trapping Several metabolites, including brominated dissolved compounds that sponges release. alkaloids and furanoterpenoids, captured Adapted from ACS Central Science 2023, DOI: 10.1021/ from seawater were present in three sponge acscentsci.3c00661 species that the researchers had examined in could easily concentrate molecules that are detail. And in some cases, the system conpresent in underwater caves and holds prom- centrated compounds released by sponges. ise for drug discovery in fragile ecosystems, For example, aeroplysinin-1 was approxiincluding coral reefs. mately 20 times more abundant in the exA drop of seawater is like a spoonful of di- tracts from seawater than within a yellow lute soup: It’s a complex broth of dissolved molecules from ocean-dwelling organisms. Continued on page 11 And to identify what’s in the mixture, scienNovember 2023
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From the ACS Press Room A step to prevent opioid overdose deaths with lightactivated naloxone treatment “On-demand Opioid Reversal with An Injectable Light-Triggered Polymer-Naloxone Conjugate” Nano Letters By rapidly reversing the effects of an opioid overdose, naloxone saves lives ― if it’s available at the right time. To eliminate this element of chance, researchers are exploring ways to have the medication available in the body before it’s needed. In a proof-ofconcept in ACS’ Nano Letters, a team has designed injectable nanoparticles that released naloxone when triggered by blue light. In experiments with mice, this system was activated a month after injection. Since it began more than two decades ago, the opioid epidemic has taken an enormous toll on people’s lives. In 2022 alone, the U.S. Centers for Disease Control estimates that approximately 80,000 people died of overdoses involving opioids. This class of drugs, which includes both naturally derived and synthetic compounds, binds to specific receptors in the brain, suppressing breathing when taken in large quantities. Naloxone blocks the effects of opioids by binding to the same receptors. Currently, the medication is delivered as an injection or a nasal spray that needs to be taken as soon as possible after an overdose. Building on research into ways to control the timing of medication delivery, Daniel Kohane and colleagues sought to develop a nanoparticle-based system that healthcare providers could inject under the skin of someone with opioid use disorder to deliver naloxone, should that person require the medication. November 2023
Kohane’s team created the nanoparticles by attaching molecules of naloxone to a polymer considered safe for humans, rendering the medication temporarily inert. The connection between naloxone and the polymer was made with a light-sensitive molecule known as coumarin. Light with a wavelength
Researchers are working on an injectable system that would treat overdoses by releasing naloxone on demand, when triggered by light. Liam Hill-Allan/ Shutterstock.com
of 400 nanometers, which the human eye perceives as blue, detached coumarin from the naloxone, which allowed it to freely move to receptors and block the effect of opioids. The intensity of blue light required to split the chemical bond makes it unlikely for sunlight or ambient indoor light to accidentally trigger the system, the researchers say. After injecting mice with the nanoparticles and the opioid morphine, the researchers found they could reverse the morphine’s effects by exposing the skin at the injection Continued on page 11
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From the ACS Press Room
Plastic-eating bacteria turn waste into useful starting materials for other products “Microbial Upcycling of Waste PET to Adipic Acid” ACS Central Science Mountains of used plastic bottles get thrown away every day, but microbes could potentially tackle this problem. Now, researchers in ACS Central Science report that they’ve developed a plastic-eating E. coli that can efficiently turn polyethylene terephthalate (PET) waste into adipic acid, which is used to make nylon materials, drugs and fragrances. Previously, a team of researchers including Stephen Wallace engineered a strain of E. coli to transform the main These beads contain engineered E. coli that compoin efficiently transform PET waste into a high- nent old PET value compound. Adapted from ACS Central Science 2023, bottles, DOI: 10.1021/acscentsci.3c00414 terephthalic acid, into something tastier and more valuable: the vanilla flavor compound vanillin. At the same time, other researchers engineered microbes to metabolize terephthalic acid into a variety of small molecules, including short November 2023
acids. So, Wallace and a new team from the University of Edinburgh wanted to expand E. coli’s biosynthetic pathways to include the metabolism of terephthalic acid into adipic acid, a feedstock for many everyday products that’s typically generated from fossil fuels using energy-intensive processes. The team developed a new E. coli strain that produced enzymes that could transform terephthalic acid into compounds such as muconic acid and adipic acid. Then, to transform the muconic acid into adipic acid, they used a second type of E. coli, which produced hydrogen gas, and a palladium catalyst. In experiments, the team found that attaching the engineered microbial cells to alginate hydrogel beads improved their efficiency, and up to 79% of the terephthalic acid was converted into adipic acid. Using realworld samples of terephthalic acid from a discarded bottle and a coating taken from waste packaging labels, the engineered E. coli system efficiently produced adipic acid. In the future, the researchers say they will look for pathways to biosynthesize additional higher-value products.
The authors acknowledge funding from the Carnegie Trust for the Universities of Scotland; the Industrial Biotechnology Innovation Centre; a Future Leaders Fellowship from UK Research and Innovation; and an Engineering and Physical Sciences Research Council Sustainable Manufacturing grant.
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From the ACS Press Room
Sunflower extract fights fungi to keep blueberries fresh “New and Antifungal Diterpenoids of Sunflower against Gray Mold”
pounds. Most of the diterpenoids showed activity against gray mold. Four of the compounds — including two of the newly identiJournal of Agricultural and Food Chemisfied ones — were effective at destroying the try plasma membrane of this fungus, causing its cells to leak and preventing it from forming Opening a clamshell of berries and seeing biofilms. In another test, the researchers them coated in fuzzy mold is a downer. And briefly wet blueberries with the receptacle it’s no small problem. Gray mold and other extracts, fungi, which cause fruit to rot, lead to signifi- then cant economic losses and food waste. Now, dried the researchers report in ACS’ Journal of Agri- fruits cultural and Food Chemistry that com- and inpounds from sunflower crop waste prevented jected rotting in blueberries. They suggest the food them industry could use these natural compounds with to protect against postharvest diseases. mold spores. Sunflowers are cultivated around the world Over a for their seeds and oil, but the flower stems period — known as receptacles — are generally of six considered to be a waste product. Noting that days, the this crop is particularly resistant to many receptaplant diseases, Xiao-Dong Luo, Yun Zhao cle ex- “New and Antifungal Diterpenoids of Sunand colleagues decided to investigate wheth- tracts pro- flower against Gray Mold” er its receptacles might contain chemical tected alconstituents responsible for this protective most half Journal of Agricultural and Food Chemistry effect. They also wanted to find out if these the berries compounds could be used to fend off fungal from mold growth. The scientists conclude plant pathogens in fruit, as a way to avoid the that sunflower stem extracts could be used as toxicity and resistance associated with chem- a natural biocontrol agent to prevent postharical fungicides. vest disease in fruit. The researchers used methanol and ethyl acetate to prepare extracts from sunflower stems. They then isolated and identified the components in these extracts, focusing on diterpenoids, which are known to have biological activity. They found 17 diterpenoids, including four previously unknown comNovember 2023
The authors acknowledge support from the High-level Talent Promotion and Training Project of Kunming, the Project of Yunnan Characteristic Plant Screening and R&D Service CXO Platform, and the Scientific and Technological Innovation Team of Yunnan Province.
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From the ACS Press Room
Cocoa pods — a source of chocolate, and potentially, flame retardants “Organosolv Pretreatment of Cocoa Pod Husks: Isolation, Analysis, and Use of Lignin from an Abundant Waste Product” ACS Sustainable Chemistry & Engineering As Halloween approaches, so too does the anticipation of a trick-or-treating stash filled with fun-sized chocolate candy bars. But to satisfy our collective craving for this indulgence, millions of cocoa pods are harvested annually. While the beans and pulp go to make chocolate, their husks are thrown away. Now, researchers reporting in ACS Sustainable Chemistry & Engineering show that cocoa pod husks could be a useful starting material for flame retardants.
Cocoa pods, like this one with parts of the husk removed for analyses, could be a useful starting material for flame retardants. Dimitris Charalampopoulos
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It’s estimated that about 24 million tons of leftover cocoa pod husks are produced yearly. Waste husks have been explored as a source of carbohydrates and sugars, but they also contain lignin, a tough lipid polymer found in many woody plants. And lignin could be a renewable re-
placement for some substances typically derived from petroleum, such as flame retardants. While most methods to produce lignin have centered on hardwood trees, some scientists have processed other plant materials that would otherwise go to waste, such as rice husks and pomegranate peels. So, Nicholas J. Westwood and coworkers wanted to see if high-quality lignin could be extracted from cocoa pod husks and determine whether it has the potential to make valuable, practical materials. The researchers obtained cocoa husks and milled them into a powder. After rinsing to remove fatty residues, they boiled the powdered husks in a mixture of butanol and acid, a standard lignin extraction method called the butanosolv process. They next confirmed the isolated lignin’s quality and high purity, finding no evidence of carbohydrates or other contaminants. Then, over the course of three chemical steps, the team modified the pure lignin biopolymer to have flame-retardant properties. They attached 9,10-dihydro-9-oxa-10phosphaphenanthrene-10-oxide, which is a fire suppressant molecule called DOPO, into the backbone of the lignin polymer. In experiments, when the modified lignin was heated, it charred — but did not burn up — a sign that it could act as a flame retardant. The researchers recognize that human safety tests are important and plan to conduct them after the next phase of testing. In the future, the
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From the ACS Press Room
AI identifies antimalarial drug as possible osteoporosis treatment “Deep Learning-Predicted Dihydroartemisinin Rescues Osteoporosis by Maintaining Mesenchymal Stem Cell Stemness through Activating Histone 3 Lys 9 Acetylation” ACS Central Science
small-molecule drugs reversed changes to gene expression associated with the disease. This time, joined by Yan Liu and Weiran Li, they wanted to use the algorithm to find a new treatment strategy for osteoporosis that focused on BMMSCs.
Artificial intelligence has exploded in popularity and is being harnessed by some scientists to predict which molecules could treat illnesses, or to quickly screen existing medicines for new applications. Researchers reporting in ACS Central Science have used one such deep learning algorithm, and found that dihydroartemisinin (DHA), an antimalarial drug and derivative of a traditional Chinese medicine, could treat osteoporosis as well. The team showed that in mice, DHA effectively reversed osteoporosis-related bone loss. In healthy people, there is a balance between the osteoblasts that build new bone and osteoclasts that break it down. But when the “demolition crew” becomes overactive, it can result in bone loss and a disease called osteoporosis, which typically affects older adults. Current treatments for osteoporosis primarily focus on slowing the activity of osteoclasts. But osteoblasts — or more specifically, their precursors known as bone marrow mesenchymal stem cells (BMMSCs) — could be the basis for a different approach. During osteoporosis, these multipotent cells tend to turn into fat-creating cells instead, but they could be reprogrammed to help treat the disease. Previously, Zhengwei Xie and colleagues developed a deep learning algorithm that could predict how effectively certain November 2023
Osteoporotic mice treated with dihydroartemisinin (DHA) had significantly improved bone density (bottom) compared to controls (top). Adapted from ACS Central Science, 2023, DOI: 10.1021/ acscentsci.3c00794
The team ran the program on a profile of differently expressed genes in newborn and adult mice. One of the top-ranked compounds identified was DHA, a derivative of artemisinin and a key component of malaria treatments. Administering DHA extract for six weeks to mice with induced osteoporosis significantly reduced bone loss in their fe-
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From ACS Press Room Continued murs and nearly completely preserved bone structure. To improve delivery, the team designed a more robust system using injected, DHA-loaded nanoparticles. Bones of mice with osteoporosis that received the treatment were similar to those of the control group, and the treatment showed no evidence of toxicity. In further tests, the team determined that DHA interacted with BMMSCs to maintain their stemness and ultimately produce more osteoblasts. The researchers say that this work demonstrates that DHA is a promising therapeutic agent for osteoporosis. The authors acknowledge funding from the National Natural Science Foundations of China, the Beijing International Science and Technology Cooperation, the Beijing Natural Science Foundation, Peking University Clinical Medicine Plus X - Young Scholars Project, the Ten-Thousand Talents Program, the Key R & D Plan of Ningxia Hui Autonomous Region, the Innovative Research Team of High-Level Local Universities in Shanghai, the Beijing Nova Program, the China National Postdoctoral Program for Innovative Talents, the China Postdoctoral Science Foundation, and the Peking University Medicine Sailing Program for Young Scholars’ Scientific & Technological Innovation.
vide insights into an ecosystem’s health or detect novel molecules for future drug discovery efforts. The next step, they add, is to adapt the device for autonomous long-term seawater filtration and remote operation in deeper water. The authors acknowledge funding from the French National Research Agency; Total Foundation; the Institute of Ecology and Environment from the National Center for Scientific Research for their First Support for Exploratory Projects; the Mission for Transversal and Interdisciplinary Initiatives of the National Center for Scientific Research; and the National Association for Technical Research.
A step to prevent opioid overdose Continued from page 6
site to a blue LED light for two minutes. The team also succeeded in releasing naloxone from the same place on mice three times over 10 days. Although its effectiveness declined somewhat, the system continued to counteract morphine up to a month after injection. With further development, that timeline could be extended, according to the researchers. They also note that the blue LED needed to release the naloxone could be incorporated into a bracelet and possibly even worn over the injection site to make treatment as efficient as
Device “Smells” Seawater possible. The authors acknowledge funding from the Continued from page 5
National Institutes of Health (National Insticave-sponge extract. The researchers say tute of General Medical Sciences) and the that “I-SMEL” represents a non-invasive CHMC Anesthesia Foundation, Inc. way to capture molecules of interest to proNovember 2023
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From ACS Press Room
Around the Area
Continued
UT Dallas: Ph.D. Candiates Syed Fahad Bin Haqe (Ferraris Lab), Thomas Howlett (Gassensmith Lab), and Muhammad Abbas (Balkus Lab) were awarded 1st, 2nd, and 3rd place, respectively, at the Graduate Student Poster Symposium at the 2023 Welch Foundation Conference.
Cocoa pods Continued from page 9 researchers say they will optimize the properties of their cocoa pod husk-based flameretardant materials. The authors acknowledge funding from the UK Biotechnology and Biological Sciences Research Council through the Global Challenges Research Fund and for in-kind contributions from Mars Wrigley Confectionery.
The DFW local section is working towards building and strengthening the section after the pandemic. The executive committee has unanimously voted to postpone the present election for the year 2024. The next election will be held in the coming year 2024.
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From the Editor As you probably know by now, my favorite ACS journal is Journal of Agricultural and Food Chemistry; I almost always find a press release from that journal. (I think I mentioned before that my dissertation research was all published in JAgFoodChem!) This month the article deals with antifungals from sunflower waste. Sunflowers, which are particularly resistant to diseases, are grown for their seeds and oil. However, the stems (usually discarded) contain various diterpenoids active against mold growth; on blueberries (which are NOT resistant to mold growth!), these compounds prevented the fruit molding. It just goes to show that you never know where you’re going to find it…
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