Design, synthesis, and biological evaluation of symmetrical azine derivatives as novel tyrosinase inhibitors
A series of symmetrical azine derivatives containing different substituted benzyl moieties were designed, synthesized, and evaluated for their inhibitory activity against tyrosinase. The results showed that compounds 3e , 3f , 3h , 3i , 3j, and 3k possess effective tyrosinase inhibition with IC 50 v...
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Veröffentlicht in: | BMC chemistry 2021-09, Vol.15 (1), p.54-54, Article 54 |
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Hauptverfasser: | , , , , , , , , , |
Format: | Artikel |
Sprache: | eng |
Schlagworte: | |
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Zusammenfassung: | A series of symmetrical azine derivatives containing different substituted benzyl moieties were designed, synthesized, and evaluated for their inhibitory activity against tyrosinase. The results showed that compounds
3e
,
3f
,
3h
,
3i
,
3j,
and
3k
possess effective tyrosinase inhibition with IC
50
values ranging from 7.30 μM to 62.60 μM. Particularly, compounds
3f
displayed around three-fold improvement in the potency (IC
50
= 7.30 ± 1.15 μM) compared to that of kojic acid (IC
50
= 20.24 ± 2.28 μM) as the positive control. Kinetic study of compound
3f
confirmed uncompetitive inhibitory activity towards tyrosinase indicating that it can bind to enzyme–substrate complex. Next, molecular docking analysis was performed to study the interactions and binding mode of the most potent compound
3f
in the tyrosinase active site. Besides, the cytotoxicity of
3f
, as well as its potency to reduce the melanin content were also measured on invasive melanoma B16F10 cell line. Also,
3f
exhibited above 82% cell viability in the A375 cell line at 10 µM. Consequently, compounds
3f
could be introduced as a potent tyrosinase inhibitor that might be a promising candidate in the cosmetics, medicine, and food industry. |
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ISSN: | 2661-801X 2661-801X |
DOI: | 10.1186/s13065-021-00780-z |