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Expanding the Pool of Multicomponent Crystal Forms of the Antibiotic 4-Aminosalicylic Acid: The Influence of Crystallization Conditions

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    Expanding the Pool of Multicomponent Crystal Forms of the Antibiotic 4-Aminosalicylic Acid: The Influence of Crystallization Conditions
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    † Centro de Química Estrutural, Instituto Superior Técnico, Universidade de Lisboa, Av. Rovisco Pais 1, 1049-001 Lisbon, Portugal
    ‡ Dipartimento di Chimica “Giacomo Ciamician”, Università di Bologna, Via Selmi 2, 40126 Bologna, Italy
    *E-mail: [email protected]
    *E-mail: [email protected]
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    Crystal Growth & Design

    Cite this: Cryst. Growth Des. 2017, 17, 12, 6417–6425
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    https://doi.org/10.1021/acs.cgd.7b01075
    Published October 25, 2017
    Copyright © 2017 American Chemical Society
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    Abstract

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    Finding new multicomponent crystal forms of commercially available pharmaceuticals is important, as they represent a straightforward way to drastically influence the solid-state properties of a drug. The antibiotic 4-aminosalicylic acid (ASA) is known to exist in several multicomponent crystal forms, and in this work we expand the world of ASA cocrystals and salts by reporting new crystalline forms comprising diazabicyclo[2.2.2]octane (DABCO), and caffeine. All species were characterized by X-ray single crystal, powder diffraction, and thermal behavior. This study contributes to the rationalization of preferred functional groups for the synthesis of 4-aminosalicylic acid new multicomponent crystal forms and highlights the relevance of the reaction conditions in the achievement of those forms.

    Copyright © 2017 American Chemical Society

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    Supporting Information

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.cgd.7b01075.

    • Powder X-ray diffraction, TGA, and DSC data (PDF)

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    CCDC 1561330–1561333 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif, or by emailing [email protected], or by contacting The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336033.

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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.

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    This article is cited by 6 publications.

    1. Oleksii Shemchuk, Simone d’Agostino, Cecilia Fiore, Vittorio Sambri, Silvia Zannoli, Fabrizia Grepioni, Dario Braga. Natural Antimicrobials Meet a Synthetic Antibiotic: Carvacrol/Thymol and Ciprofloxacin Cocrystals as a Promising Solid-State Route to Activity Enhancement. Crystal Growth & Design 2020, 20 (10) , 6796-6803. https://doi.org/10.1021/acs.cgd.0c00900
    2. Mark G. Smith, Andreas Lemmerer. Covalent Assisted Supramolecular Synthesis: The Influence of Crystallization Conditions on Co-Crystals of “Masked” Isoniazid Derivatives. Crystal Growth & Design 2018, 18 (8) , 4777-4789. https://doi.org/10.1021/acs.cgd.8b00871
    3. Ala' Salem, Esam Khanfar, Sándor Nagy, Aleksandar Széchenyi. Cocrystals of tuberculosis antibiotics: Challenges and missed opportunities. International Journal of Pharmaceutics 2022, 623 , 121924. https://doi.org/10.1016/j.ijpharm.2022.121924
    4. Vânia André, M. Teresa Duarte, Clara S. B. Gomes, Mafalda C. Sarraguça. Mechanochemistry in Portugal—A Step towards Sustainable Chemical Synthesis. Molecules 2022, 27 (1) , 241. https://doi.org/10.3390/molecules27010241
    5. Jean Lombard, Vincent J. Smith, Tanya le Roex, Delia A. Haynes. Crystallisation of organic salts by sublimation: salt formation from the gas phase. CrystEngComm 2020, 22 (45) , 7826-7831. https://doi.org/10.1039/D0CE01470B
    6. Renke Chang, Xiang Chen, Huijuan Yu, Guizhen Tan, Hongli Wen, Jianxin Huang, Zhifeng Hao. Modified EDTA selectively recognized Cu2+ and its application in the disaggregation of β-amyloid-Cu (II)/Zn (II) aggregates. Journal of Inorganic Biochemistry 2020, 203 , 110929. https://doi.org/10.1016/j.jinorgbio.2019.110929
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    Crystal Growth & Design

    Cite this: Cryst. Growth Des. 2017, 17, 12, 6417–6425
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.cgd.7b01075
    Published October 25, 2017
    Copyright © 2017 American Chemical Society
    Request reuse permissions

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