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

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dc.contributor.authorAlegre-Requena, Juan, V
dc.contributor.authorGrijalvo, Santiago
dc.contributor.authorSampedro, Diego
dc.contributor.authorMayr, Judith
dc.contributor.authorSaldias, Cesar
dc.contributor.authorJuan Marrero-Tellado, Jose
dc.contributor.authorEritja, Ramon
dc.contributor.authorHerrera, Raquel P.
dc.contributor.authorDiaz Diaz, David
dc.date.accessioned2025-01-23T19:52:37Z
dc.date.available2025-01-23T19:52:37Z
dc.date.issued2020
dc.description.abstract(S)-2-Stearamidopentanedioic acid (C-18-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 C-18-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.
dc.fuente.origenWOS
dc.identifier.doi10.1039/d0ra00943a
dc.identifier.eissn2046-2069
dc.identifier.urihttps://doi.org/10.1039/d0ra00943a
dc.identifier.urihttps://repositorio.uc.cl/handle/11534/100637
dc.identifier.wosidWOS:000523640500059
dc.issue.numero19
dc.language.isoen
dc.pagina.final11492
dc.pagina.inicio11481
dc.revistaRsc advances
dc.rightsacceso restringido
dc.subject.ods03 Good Health and Well-being
dc.subject.odspa03 Salud y bienestar
dc.titleSulfonamide as amide isostere for fine-tuning the gelation properties of physical gels
dc.typeartículo
dc.volumen10
sipa.indexWOS
sipa.trazabilidadWOS;2025-01-12
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