On the influence of using a zwitterionic coformer for cocrystallization: Structural focus on naproxen-proline cocrystals

A. Tilborg, B. Norberg, J. Wouters, G. Springuel, T. Leyssens

Research output: Contribution to journalArticle

Abstract

Four original cocrystal structures incorporating a zwitterionic amino acid, prolinium, and a therapeutical agent from profen pharmaceutical family, naproxen, are highlighted and characterized in this study. Powder X-ray diffraction and differential scanning calorimetry permits the observation of the formation of the new structures, obtained by liquid-assisted grinding with methanol. Single-crystal X-ray diffraction gives us a precise outlook of the crystalline network, and allows us to accurately determine the main structural supramolecular synthon: column-like motifs, formed by prolinium entities, around whom the pharmaceutical coformer is organized. From comparison with the CSD, a similar structural pattern emerged in several other structures incorporating prolinium moieties, but not in the case of cocrystals incorporating naproxen and other non-zwitterionic coformers. This result leads us to the conclusion that zwitterionic compounds, such as amino acids, can force a pharmaceutical coformer to structure itself following a known common motif guided only by the zwitterionic entity; a very challenging aspect to take into account when developing new solid forms of therapeutical agents.
Original languageEnglish
Pages (from-to)3341-3350
Number of pages10
JournalCrystEngComm
Volume15
Issue number17
DOIs
Publication statusPublished - 7 May 2013

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  • Datasets

    CCDC 914593: Experimental Crystal Structure Determination

    Leyssens, T. (Contributor), NORBERG, B. (Contributor), Springuel, G. (Contributor), Tilborg, A. (Contributor) & WOUTERS, J. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2013

    Dataset

    CCDC 915284: Experimental Crystal Structure Determination

    Leyssens, T. (Contributor), NORBERG, B. (Contributor), Springuel, G. (Contributor), Tilborg, A. (Contributor) & WOUTERS, J. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2013

    Dataset

    CCDC 902844: Experimental Crystal Structure Determination

    Leyssens, T. (Contributor), NORBERG, B. (Contributor), Springuel, G. (Contributor), Tilborg, A. (Contributor) & WOUTERS, J. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2013

    Dataset

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