Journal
BIOORGANIC CHEMISTRY
Volume 82, Issue -, Pages 414-422Publisher
ACADEMIC PRESS INC ELSEVIER SCIENCE
DOI: 10.1016/j.bioorg.2018.10.069
Keywords
Click reaction; Hyperpigmentation; Kojic acid; 1,2,3-Triazole; Tyrosinase inhibitor
Funding
- Research Council of Mazandaran University of Medical Sciences, Sari, Iran [2781]
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series of kojic acid-derived compounds 6a-p bearing aryloxymethyl-1H-1,2,3-triazol-1-yl moiety were designed by modifying primary alcoholic group of kojic acid as tyrosinase inhibitors. The target compounds 6a-p were synthesized via click reaction. All compounds showed very potent anti-tyrosinase activity (IC(50)s = 0.06-6.80 mu M), being superior to reference drug, kojic acid. In particular, the naphthyloxy analogs 6o and 6p were found to be 31-155 times more potent than kojic acid. The metal-binding study of selected compound 6o revealed that the prototype compound possesses metal-chelating ability, particularly with Cu2+ ions. The promising compounds 6o and 6p had acceptable safety profile as demonstrated by cytotoxicity assay against melanoma (B16) cell line and Human Foreskin Fibroblast (HFF) cells.
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