Alegre-Requena, Juan and Grijalvo, Santiago and Sampedro, Diego and Mayr, Judith and Saldias, Cesar and Juan Marrero-Tellado, Jose and Eritja, Ramon and Herrera, Raquel P. and Diaz Diaz, David (2020) Sulfonamide as amide isostere for fine-tuning the gelation properties of physical gels. RSC ADVANCES, 10 (19). pp. 11481-11492. ISSN , 2046-2069
Full text not available from this repository. (Request a copy)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.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | SUPRAMOLECULAR HYDROGELS; ORGANIC-SOLVENTS; ORGANOGELS; GELATORS; METAL; SUBSTITUTION; KINETICS; ENERGY; IONS; ACID; |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie > Arbeitskreis Prof. Dr. David Díaz Díaz |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 29 Mar 2021 07:19 |
| Last Modified: | 29 Mar 2021 07:19 |
| URI: | https://pred.uni-regensburg.de/id/eprint/44910 |
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