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Design, synthesis and biological evaluation of novel kojic acid triazole hybrids as tyrosinase inhibitors and antibrowning agents
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Design, synthesis and biological evaluation of novel kojic acid triazole hybrids as tyrosinase inhibitors and antibrowning agents
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Journal Article
Design, synthesis and biological evaluation of novel kojic acid triazole hybrids as tyrosinase inhibitors and antibrowning agents
2025
Overview
In this study, two series of kojic acid triazole hybrids, namely
6a–6p
and
13a–13t
, were designed and synthesized. Subsequently, their biological activities including anti-tyrosinase, antioxidant, and as anti-browning effects were investigated. The results showed that most of compounds demonstrated excellent inhibitory effect against mushroom tyrosinase compared with standard reference drug (kojic acid, IC
50
= 26.090 µM). Of particular note,
13t
proved to be the most potent tyrosinase inhibitor with an IC
50
value as low as 1.363 µM. Further kinetic inhibition studies suggested that
13t
presented such powerful anti-tyrosinase efficacy by functioning as a mixed-type inhibitor (
K
i
= 0.3647 µM,
K
is
= 0.8492 µM). Moreover, the results from molecular docking and fluorescence quenching studies revealed that
13t
’s inhibitory effect on tyrosinase stemmed from its ability to directly bind to the active site of mushroom tyrosinase. Besides, the antioxidant activity, anti-browning effect, and cytotoxicity of
13t
were accordingly investigated, all yielding highly satisfactory results. Collectively, these findings position
13t
as a highly promising candidate, providing a valuable molecular framework for the development of novel, efficient, and safe tyrosinase inhibitors endowed with potent antioxidant and anti-browning capabilities.
Publisher
Nature Publishing Group UK,Nature Portfolio
Subject
/ 631/45
/ Antioxidants - chemical synthesis
/ Enzyme Inhibitors - chemical synthesis
/ Enzyme Inhibitors - chemistry
/ Enzyme Inhibitors - pharmacology
/ Humanities and Social Sciences
/ Humans
/ Molecular Docking Simulation
/ Monophenol Monooxygenase - antagonists & inhibitors
/ Monophenol Monooxygenase - chemistry
/ Monophenol Monooxygenase - metabolism
/ Pyrones - chemical synthesis
/ Science
/ Structure-Activity Relationship
