RT info:eu-repo/semantics/article
T1 Sulfonamide as amide isostere for fine-tuning the gelation properties of physical gels
A1 Alegre-Requena, Juan V.
A1 Grijalvo, Santiago
A1 Sampedro, Diego
A1 Mayr, Judith
A1 Sald´ıas, César
A1 Marrero Tellado, José Juan
A1 Eritja, Ram´on
A1 Herrera, Raquel P.
A1 Díaz Díaz, David
K1 Sulfo-Glu
K1 Click-Glu
K1 gels
K1 geles
AB (S)-2-Stearamidopentanedioic acid (C18-Glu) is a known LMW gelator that forms supramolecular gels ina variety of solvents. In this work, we have carried out the isosteric substitution of the amide group bya 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 interms 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 ofC18-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 higherthermal-mechanical stabilities than those obtained with the other isosteres in most solvents.Furthermore, the amide-sulfonamide isosteric substitution also influenced the morphology of the gelnetworks as well as the release rate of an embedded antibiotic (vancomycin) leading to antibacterialactivity in vitro against Staphylococcus aureus.
PB Royal Society of Chemistry
YR 2020
FD 2020
LK http://riull.ull.es/xmlui/handle/915/21484
UL http://riull.ull.es/xmlui/handle/915/21484
LA en
NO University of Regensburg
DS Repositorio institucional de la Universidad de La Laguna
RD 28-nov-2024