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Lists of Chemical Warfare Agents and Precursors from International Nonproliferation Frameworks: Structural Annotation and Chemical Fingerprint Analysis
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    Chemical Information

    Lists of Chemical Warfare Agents and Precursors from International Nonproliferation Frameworks: Structural Annotation and Chemical Fingerprint Analysis
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    • Stefano Costanzi*
      Stefano Costanzi
      Department of Chemistry, American University, 4400 Massachusetts Avenue, NW, Washington, District of Columbia 20016, United States
      *Email: [email protected]. Phone: +1-202-885-1722.
    • Charlotte K. Slavick
      Charlotte K. Slavick
      Department of Chemistry, American University, 4400 Massachusetts Avenue, NW, Washington, District of Columbia 20016, United States
    • Brent O. Hutcheson
      Brent O. Hutcheson
      Department of Chemistry, American University, 4400 Massachusetts Avenue, NW, Washington, District of Columbia 20016, United States
    • Gregory D. Koblentz
      Gregory D. Koblentz
      Schar School of Policy and Government, George Mason University, 3351 Fairfax Drive, Arlington, Virginia 22201, United States
    • Richard T. Cupitt
      Richard T. Cupitt
      Stimson Center, 1211 Connecticut Avenue, NW, Washington, District of Columbia 20036, United States
    Other Access OptionsSupporting Information (2)

    Journal of Chemical Information and Modeling

    Cite this: J. Chem. Inf. Model. 2020, 60, 10, 4804–4816
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    https://doi.org/10.1021/acs.jcim.0c00896
    Published September 11, 2020
    Copyright © 2020 American Chemical Society

    Abstract

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    To support efforts to stem the proliferation of chemical weapons (CWs), we have curated and structurally annotated CW-control lists from three key international nonproliferation frameworks: the Chemical Weapons Convention (CWC), the Australia Group (AG), and the Wassenaar Arrangement. The curated lists are available as web tables at the Costanzi Research website (https://costanziresearch.com/cw-control-lists/). The annotations include manually curated 2D structural images, which provide a means to appreciate at a glance the similarities and differences between different entries, as well as downloadable 2D structures, in two different formats and three different structural identifiers, namely, simplified molecular-input line-entry system, standard InChI, and standard InChIKey, which are intended to provide a platform for cheminformatics analyses. The tables also include links to National Center for Biotechnology Information’s PubChem and National Institute of Standards and Technology’s Chemistry WebBook cards, hence providing prompt access to a wealth of physicochemical, analytical chemistry, and toxicological information. To showcase the importance of structural annotations, we discuss a discrepancy in a CW-control list covering the defoliant Agent Orange, which we identified through our curation process, and propose a solution to address it. Moreover, we present the results of chemical fingerprinting analyses, through which we clustered the entries of the three CW-control lists under study into structurally related groups and studied the overlaps between the three lists. As an application of this study, we examine the recent updates of CWC Schedule 1 and the AG precursors list, highlighting the relationships between the two amendments and proposing the possible addition of further chemicals. Our research is intended to facilitate the communication between scientific advisors and policymakers as well as the work of chemists and cheminformaticians involved in the CW nonproliferation field. Ultimately, we seek to provide tools to bolster the control of CWs and support the global efforts to rid the world of this category of weapons.

    Copyright © 2020 American Chemical Society

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    Supporting Information

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.jcim.0c00896.

    • Fan plot showing the clustering of CW-control lists based on chemical structures; annotated CWC schedules; annotated AG CWs precursors list; annotated WA ML7; and synoptic table (PDF)

    • Downloadable versions of the tables, in SDF, CSV, and Microsoft Excel formats (CIF)

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    Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system: http://pubs.acs.org/page/copyright/permissions.html.

    Cited By

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    This article is cited by 13 publications.

    1. Jin Young Seo, Min Hyuk Choi, Bo Woo Lee, Jung-Hyun Lee, Seunghan Shin, Sangho Cho, Kie Yong Cho, Kyung-Youl Baek. Feasible Detoxification Coating Material for Chemical Warfare Agents Using Poly(methyl methacrylate)–Branched Poly(ethyleneimine) Copolymer and Metal–Organic Framework Composites. ACS Applied Materials & Interfaces 2022, 14 (44) , 50246-50255. https://doi.org/10.1021/acsami.2c15961
    2. Hye-Min Lee, Ju-Hwan Kim, Byung-Joo Kim. Effects of electron beam irradiation on dimethyl methlyphosphonate adsorption behavior of activated carbon fibers. Energy Conversion and Management 2024, 314 , 118641. https://doi.org/10.1016/j.enconman.2024.118641
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    7. Stefano Costanzi, Gregory D. Koblentz, Richard T. Cupitt. Expanding the Australia Group’s chemical weapons precursors control list with a family-based approach. Pure and Applied Chemistry 2023, 95 (3) , 261-271. https://doi.org/10.1515/pac-2022-1113
    8. Raychelle Burks, Agnes Winokur. Presumptive Chemical Tests. 2023, 263-277. https://doi.org/10.1016/B978-0-12-823677-2.00112-4
    9. Stefano Costanzi, Charlotte K. Slavick, Joyce M. Abides, Gregory D. Koblentz, Mary Vecellio, Richard T. Cupitt. Supporting the fight against the proliferation of chemical weapons through cheminformatics. Pure and Applied Chemistry 2022, 94 (7) , 783-798. https://doi.org/10.1515/pac-2021-1107
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    11. Georgia Melagraki. Reducing health & environmental impacts of chemical warfare agents: Computational chemistry contributions. Chemosphere 2022, 288 , 132564. https://doi.org/10.1016/j.chemosphere.2021.132564
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    Journal of Chemical Information and Modeling

    Cite this: J. Chem. Inf. Model. 2020, 60, 10, 4804–4816
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.jcim.0c00896
    Published September 11, 2020
    Copyright © 2020 American Chemical Society

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