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

Anna Patterson, Lamisse El-Qarra, David Kelham Smith

Research output: Contribution to journalArticlepeer-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 languageEnglish
Pages (from-to)3941-3944
JournalChemical communications
Volume58
Early online date4 Mar 2022
Publication statusPublished - Mar 2022

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