The Effect of the Side Chain on Gelation Properties of Bile Acid Alkyl Amides

Overview

Journal ChemistryOpen

Specialty Chemistry

Date 2021 Nov 22

PMID 34806846

Citations 2

Authors

Riikka T Kuosmanen

Khai-Nghi Truong

Kari T Rissanen

Elina I Sievanen

Affiliations

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Abstract

Six bile acid alkyl amide derivatives were studied with respect to their gelation properties. The derivatives were composed of three different bile acids with hexyl or cyclohexyl side chains. The gelation behaviour of all six compounds were studied for 36 solvents with varying polarities. Gelation was observed mainly in aromatic solvents, which is characteristic for bile-acid-based low molecular weight gelators. Out of 108 bile acid-solvent combinations, a total of 44 gel systems were formed, 28 of which from lithocholic acid derivatives, only two from deoxycholic acid derivatives, and 14 from cholic acid derivatives. The majority of the gel systems were formed from bile acids with hexyl side chains, contrary to the cyclohexyl group, which seems to be a poor gelation moiety. These results indicate that the spatial demand of the side chain is the key feature for the gelation properties of the bile acid amides.

Citing Articles

The Effect of Branched Alkyl Chain Length on the Properties of Supramolecular Organogels from Mono--Alkylated Primary Oxalamides.

Azyat K, Makeiff D, Smith B, Wiebe M, Launspach S, Wagner A Gels. 2023; 9(1).

PMID: 36661773 PMC: 9858617. DOI: 10.3390/gels9010005.

The Effect of the Side Chain on Gelation Properties of Bile Acid Alkyl Amides.

Kuosmanen R, Truong K, Rissanen K, Sievanen E ChemistryOpen. 2021; 10(11):1150-1157.

PMID: 34806846 PMC: 8607806. DOI: 10.1002/open.202100245.

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