Chirality-directed hydrogel assembly and interactions with enantiomers of an active pharmaceutical ingredient

Anna Patterson; Lamisse El-Qarra; David Kelham Smith

doi:10.1039/d1cc06942j

Chirality-directed hydrogel assembly and interactions with enantiomers of an active pharmaceutical ingredient

Anna Patterson, Lamisse El-Qarra, David Kelham Smith

Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

Enantiomers of the low-molecular-weight gelator (LMWG) DBS CONHNH2, based on D- or L- 1,3:2,4-dibenzylidenesorbitol (DBS), were synthesised. Enantiomeric gels are equivalent, but when mixtures of enantiomers are used, although gels still form, they are weaker than homochiral gels. Nanoscale chirality is lost on adding even a small proportion of the opposite enantiomer – homochiral assembly underpins effective gelation. Enantiomeric gels encapsulate the two enantiomers of anti-inflammatory drug naproxen, with thermal & mechanical differences between diastereomeric systems. We hence demonstrate the importance of chirality in DBS assembly and its interactions with chiral additives.

Original language	English
Pages (from-to)	3941-3944
Number of pages	4
Journal	Chemical communications
Volume	58
Issue number	24
Early online date	4 Mar 2022
DOIs	https://doi.org/10.1039/d1cc06942j
Publication status	Published - 25 Mar 2022

Bibliographical note

© Royal Society of Chemistry 2022. This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy. Further copying may not be permitted; contact the publisher for details.

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10.1039/d1cc06942jLicence: CC BY

Chirality-directed hydrogel assembly and interactions with enantiomers of an active pharmaceutical ingredient
© The Royal Society of Chemistry 2022
Final published version, 1.89 MBLicence: CC BY

Cite this

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abstract = "Enantiomers of the low-molecular-weight gelator (LMWG) DBS CONHNH2, based on D- or L- 1,3:2,4-dibenzylidenesorbitol (DBS), were synthesised. Enantiomeric gels are equivalent, but when mixtures of enantiomers are used, although gels still form, they are weaker than homochiral gels. Nanoscale chirality is lost on adding even a small proportion of the opposite enantiomer – homochiral assembly underpins effective gelation. Enantiomeric gels encapsulate the two enantiomers of anti-inflammatory drug naproxen, with thermal & mechanical differences between diastereomeric systems. We hence demonstrate the importance of chirality in DBS assembly and its interactions with chiral additives.",

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