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

Alegre-Requena, Juan V. ; Grijalvo, Santiago ; Sampedro, Diego ; Mayr, Judith ; Saldías, César ; Marrero-Tellado, José Juan ; Eritja, Ramón ; Pérez Herrera, Raquel (Universidad de Zaragoza) ; Díaz Díaz, David

Resumen: (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.

Idioma: Inglés

DOI: 10.1039/d0ra00943a

Año: 2020

Publicado en: RSC Advances 10, 19 (2020), 11481-11492
ISSN: 2046-2069

Factor impacto JCR: 3.361 (2020)

Categ. JCR: CHEMISTRY, MULTIDISCIPLINARY rank: 81 / 178 = 0.455 (2020) - Q2 - T2

Factor impacto SCIMAGO: 0.746 - Chemistry (miscellaneous) (Q1) - Chemical Engineering (miscellaneous) (Q1)

Financiación: info:eu-repo/grantAgreement/ES/DGA/E07-17R
Financiación: info:eu-repo/grantAgreement/ES/MINECO/CTQ2017-88091-P

Tipo y forma: Article (Published version)

Área (Departamento): Área Química Orgánica (Dpto. Química Orgánica)