Synthesis and characterization of a hydrophobic association hydrogel for drug delivery

•A hydrophobic association hydrogel in an aqueous surfactant solution was prepared.•Water absorption of hydrogel increased with addition of a hydrophobic molecule.•Hydrophobic molecule gives a pH-dependent and retardant effect for caffeine release.•Caffeine release is controlled by swelling, macromo...

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Veröffentlicht in:Journal of molecular liquids 2023-02, Vol.372, p.120709, Article 120709
Hauptverfasser: Henrique Carline de Lima, Hugo, Mansano Santos, Gabrielly, Thiago Pereira da Silva, Cleiser, Calvi Mori, Julia, de Carvalho Rinaldi, Jaqueline, Seki Kioshima Cotica, Érika, Tambourgi, Elias Basile, Rogério Guilherme, Marcos, Wellington Rinaldi, Andrelson
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Sprache:eng
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Zusammenfassung:•A hydrophobic association hydrogel in an aqueous surfactant solution was prepared.•Water absorption of hydrogel increased with addition of a hydrophobic molecule.•Hydrophobic molecule gives a pH-dependent and retardant effect for caffeine release.•Caffeine release is controlled by swelling, macromolecular relaxation, and erosion.•Hydrogel is biocompatible with uses in delivery of poorly water-soluble drug. This work reports the synthesis, characterization, and evaluation of a hydrophobic association hydrogel containing vinyl alginate (SA), acrylamide, and the hydrophobic molecule N,N'-(disulfanediylbis(4,1-phenylene))diacrylamide (SPDAAm) for release of drug very slightly water-soluble in water. The SPDAAm molecule was synthetized with acrylic acid and 4-Aminophenyl disulfide and further characterized by H1 NMR spectroscopy. The hydrogel was prepared with a crosslinking chemistry using vinyl SA and acrylamide in an aqueous surfactant solution at a concentration less than the (critical micellar concentration) CMC. The introduction of SPDAAm in the hydrogel increases the swelling degree owing to hydrophobic association. Furthermore, SPDAAm gives a pH-dependent and retardant effect for caffeine (CFN) release. At a pH of 7.4, the CFN release mechanism is controlled by swelling, macromolecular relaxation of the polymer, and erosion of the hydrogel. The hydrogel with SPDAAm shows acceptable biocompatibility and has potential applications as a biomaterial in controlled release of poorly water-soluble molecules, like CFN.
ISSN:0167-7322
1873-3166
DOI:10.1016/j.molliq.2022.120709