Structural insight into cocrystallization with zwitterionic co-formers: Cocrystals of S-naproxen
(2014) CrystEngComm — Vol. 16, n° 35, p. 8185-8196 (2014)
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- Abstract
- Screening of S-naproxen, S-oxiracetam, S-diprophylline, and levetiracetam with a series of amino acid co-formers yielded cocrystals only for S-naproxen, thus showing that amino acids are effective cocrystal formers only with compounds that contain a carboxyl group. Herein, we report the crystal structures of four S-naproxen cocrystals: S-naproxen/L-alanine, S-naproxen/D-alanine, S-naproxen/D-tyrosine, and S-naproxen/D-tryptophan monohydrate. All the described cocrystals show similar structural motifs, i.e., amino acids form head-to-tail chains with strong charge-assisted hydrogen bonding, which are similar to those found in the individual amino acids, with S-naproxen molecules grafting on them. According to the systematic search in the Cambridge Structural Database for other cocrystals that involve zwitterionic co-formers, charge-assisted hydrogen bonds between amino acid molecules play an essential role, being present in the majority of structures. The results of this work provide an insight into structural aspects of cocrystallization with zwitterionic co-formers, offer new possibilities for S-naproxen pharmaceutical formulations, and can serve as guidelines when developing new cocrystals involving zwitterionic co-formers.
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Citations
Tumanova, N., Tumanov, N., Robeyns, K., Filinchuk, Y., Wouters, J., & Leyssens, T. (2014). Structural insight into cocrystallization with zwitterionic co-formers: Cocrystals of S-naproxen. CrystEngComm, 16(35), 8185-8196. https://doi.org/10.1039/c4ce00353e (Original work published 2014)