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Biomacromolecules ; 16(11): 3603-12, 2015 Nov 09.
Artículo en Inglés | MEDLINE | ID: mdl-26444385

RESUMEN

Conjugates of antioxidants p-anisic (p-AA) and vanillic (VA) acids with nontoxic, biocompatible, and biodegradedable oligo-(R,S)-(3-hydoxybutyrate) carrier were synthesized, and their structural and biological characterization was performed. The molecular structure of the bioconjugates, in which antioxidants are covalently bonded with oligo(3-hydroxybutyrate) (OHB) chains, has been proven by mass spectrometry supported by NMR. The bioconjugate hydrolytic degradation studies allowed gaining thorough insight into the hydrolysis process and confirmed the release of p-AA and VA. In vitro studies demonstrated that all of the conjugates studied were well tolerated by KB and HaCaT cell lines, as they had no marked cytotoxicity, while conjugates with a relatively short OHB carrier are optimal to support keratinocyte function. The preliminary study of the biological activity confirmed the protective effect of VA-OHB conjugates against H2O2-induced lipid peroxidation in human keratinocytes (HaCaT). It was also demonstrated that the selected bioconjugates can penetrate all layers of the skin, which shows their functionality and opens up their potential application in cosmetology.


Asunto(s)
Antioxidantes/farmacología , Cosméticos/química , Sistemas de Liberación de Medicamentos , Ácido 3-Hidroxibutírico/química , Antioxidantes/química , Materiales Biocompatibles , Línea Celular , Proliferación Celular/efectos de los fármacos , Supervivencia Celular , Humanos , Peróxido de Hidrógeno/metabolismo , Hidrólisis , Éteres de Hidroxibenzoatos/química , Éteres de Hidroxibenzoatos/farmacología , Queratinocitos/citología , Queratinocitos/efectos de los fármacos , Peroxidación de Lípido/efectos de los fármacos , Estructura Molecular , Piel/citología , Piel/metabolismo , Ácido Vanílico/química , Ácido Vanílico/farmacología
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