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

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Tilborg, Anaëlle [FUNDP] Springuel, Géraldine [UCL] Norberg, Bernadette [FUNDP] Wouters, Johan [FUNDP] Leyssens, Tom [UCL]

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.

Document type Article de périodique (Journal article) – Article de recherche
Access type Accès restreint
Publication date 2013
Language Anglais
Journal information "CrystEngComm" - Vol. 15, no. 17, p. 3341-3350 (2013)
Peer reviewed yes
Publisher RSC Publishing
issn 1466-8033
Publication status Publié
Affiliations FUNDP - SCHI_GCPTS (groupe de chimie physique, théorique et structurale)
UCL - SST/IMCN/MOST - Molecules, Solids and Reactivity
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Bibliographic reference Tilborg, Anaëlle ; Springuel, Géraldine ; Norberg, Bernadette ; Wouters, Johan ; Leyssens, Tom. On the influence of using a zwitterionic coformer for cocrystallization: Structural focus on naproxen - proline cocrystals. In: CrystEngComm, Vol. 15, no. 17, p. 3341-3350 (2013)
Permanent URL http://hdl.handle.net/2078.1/127200