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Issue 19, 2020
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Sulfonamide as amide isostere for fine-tuning the gelation properties of physical gels

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Abstract

(S)-2-Stearamidopentanedioic acid (C18-Glu) is a known LMW gelator that forms supramolecular gels in a variety of solvents. In this work, we have carried out the isosteric substitution of the amide group by a sulfonamide moiety yielding the new isosteric gelator (S)-2-(octadecylsulfonamido)pentanedioic acid (Sulfo-Glu). The gelation ability and the key properties of the corresponding gels were compared in terms of gelation concentration, gel-to-sol transition temperature, mechanical properties, morphology, and gelation kinetics in several organic solvents and water. This comparison was also extended to (S)-2-(4-hexadecyl-1H-1,2,3-triazol-4-yl)pentanedioic acid (Click-Glu), which also constitutes an isostere of C18-Glu. The stabilizing interactions were explored through computational calculations. In general, Sulfo-Glu enabled the formation of non-toxic gels at lower concentrations, faster, and with higher thermal-mechanical stabilities than those obtained with the other isosteres in most solvents. Furthermore, the amide-sulfonamide isosteric substitution also influenced the morphology of the gel networks as well as the release rate of an embedded antibiotic (vancomycin) leading to antibacterial activity in vitro against Staphylococcus aureus.

Graphical abstract: Sulfonamide as amide isostere for fine-tuning the gelation properties of physical gels

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Supplementary files

Article information


Submitted
31 Jan 2020
Accepted
06 Mar 2020
First published
20 Mar 2020

This article is Open Access

RSC Adv., 2020,10, 11481-11492
Article type
Paper

Sulfonamide as amide isostere for fine-tuning the gelation properties of physical gels

J. V. Alegre-Requena, S. Grijalvo, D. Sampedro, J. Mayr, C. Saldías, J. J. Marrero-Tellado, R. Eritja, R. P. Herrera and D. D. Díaz, RSC Adv., 2020, 10, 11481
DOI: 10.1039/D0RA00943A

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