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Título: | Sulfonamide as amide isostere for fine-tuning the gelation properties of physical gels |
Autor: | Alegre-Requena, Juan V. CSIC ORCID; Grijalvo, Santiago CSIC ORCID; Sampedro, Diego; Mayr, Judith; Saldías, César; Marrero-Tellado, José Juan CSIC; Eritja Casadellà, Ramón CSIC ORCID ; Herrera, Raquel P. CSIC ORCID; Díaz Díaz, David CSIC ORCID | Palabras clave: | Sulfonamide Physical gels |
Fecha de publicación: | 20-mar-2020 | Editor: | Royal Society of Chemistry (UK) | Citación: | RSC Advances 19(10): 11481-11492 (2020) | 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. | Versión del editor: | https://doi.org/10.1039/D0RA00943A | URI: | http://hdl.handle.net/10261/205868 | DOI: | 10.1039/D0RA00943A |
Aparece en las colecciones: | (IQAC) Artículos (ISQCH) Artículos |
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RSCAdv2020Alegre.pdf | Artículo principal | 1,25 MB | Adobe PDF | Visualizar/Abrir |
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