Antiaging activity, molecular docking, and prediction of percutaneous absorption parameters of quinoline?hydrazone hybrids

dc.creatorOsorio, Edison
dc.creatorBravo, Karent
dc.creatorCardona, Wilson
dc.creatorYepes, Andr?s
dc.creatorOsorio, Edison H.
dc.creatorCoa, Juan C.
dc.date2020-01-21T15:51:37Z
dc.date2020-01-21T15:51:37Z
dc.date2019-11-01
dc.date.accessioned2023-08-31T19:25:48Z
dc.date.available2023-08-31T19:25:48Z
dc.identifierOsorio, E., Bravo, K., Cardona, W. et al. Med Chem Res (2019) 28: 1959. https://doi.org/10.1007/s00044-019-02427-0
dc.identifier1054-2523
dc.identifierhttps://link.springer.com/article/10.1007%2Fs00044-019-02427-0#citeas
dc.identifier.urihttps://repositorioslatinoamericanos.uchile.cl/handle/2250/8558312
dc.descriptionThe application of antiaging agents can contribute to the prevention and control of skin photoaging. In the current research, nine quinoline?hydrazone hybrids were synthesized to obtain biologically active compounds as possible antiaging agents. The compounds were tested through a comprehensive in vitro evaluation of antielastase, anticollagenase, and antihyaluronidase activities along with the determination of their potential to quench reactive oxygen species (ROS) by the ORAC method. The selected hybrids were subsequently tested on human dermal fibroblasts (HDF) to reveal possible UVB photoprotective activity. The most potent antiaging protection of all the prepared compounds was shown by the trihydroxylated quinoline?hydrazones 5 and 9, which showed the best collagenase inhibition (IC50?=?39.4 and 45.6??M, respectively). Compound 5 also showed activity against elastase and hyaluronidase (IC50?=?164.2 and 318.8??M, respectively). The molecular docking results suggest that the difference of inhibition between 5 and 9 is principally attributed to the hydrogen bonds interactions in the residues His218 and His228, and Zn atom in collagenase, Val216 in elastase and Tyr75 in hyaluronidase. In addition, compounds 5 and 9 were able to significantly protect human skin cells from UVB radiation in vitro. These compounds significantly decreased UVB-induced MMP-1 and ROS production and inhibited the suppression of type I procollagen synthesis in cultured HDF. The in silico dermatopharmacokinetic parameters showed promising results. Therefore, our study presented promising results for antiaging drug discovery, focusing on quinoline?hydrazone hybrids as dual inhibitors of skin aging-related enzymes, antioxidants, and inhibitors of the biological effects of UVB irradiation.
dc.descriptionUniversidad de Ibagu?
dc.languageen
dc.publisherMedicinal Chemistry Research
dc.subjectQuinoline?hydrazone hybrids
dc.subjectUVB photoprotection
dc.subjectAntiaging
dc.subjectMatrix metalloproteinase
dc.subjectHuman dermal fibroblasts
dc.titleAntiaging activity, molecular docking, and prediction of percutaneous absorption parameters of quinoline?hydrazone hybrids
dc.typeArticle


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