title: Synthesis and biological evaluation of novel 4-hydroxybenzaldehyde derivatives as tyrosinase inhibitors.
abstract: A series of novel 4-hydroxybenzaldehyde derivatives were synthesized and their inhibitory effects on the diphenolase activity of mushroom tyrosinase were investigated. Most of target compounds had more potent inhibitory activities than the parent compound 4-hydroxybenzaldehyde (IC(50)=1.22 mM). Interestingly, compound 3c bearing a dimethoxyl phosphate was found to be the most potent inhibitor with IC(50) value of 0.059 mM. The inhibition kinetics analyzed by Lineweaver-Burk plots revealed that compound 3c was a non-competitive inhibitor (K(I)=0.0368 mM). In particular, compound 3c showed no side effects at dose of 1600 mg/kg in mice. These results suggested that such compounds might be served as lead compounds for further designing new potential tyrosinase inhibitors.
authors.affiliation: School of Chemistry and Chemical Engineering, Sun Yat-Sen University, 135 Xin Gang West Road, Guangzhou 510275, PR China.
authors.forename: Wei
authors.initials: W
authors.lastname: Yi
authors.forename: Rihui
authors.initials: R
authors.lastname: Cao
authors.forename: Wenlie
authors.initials: W
authors.lastname: Peng
authors.forename: Huan
authors.initials: H
authors.lastname: Wen
authors.forename: Qin
authors.initials: Q
authors.lastname: Yan
authors.forename: Binhua
authors.initials: B
authors.lastname: Zhou
authors.forename: Lin
authors.initials: L
authors.lastname: Ma
authors.forename: Huacan
authors.initials: H
authors.lastname: Song
mesh_terms: D000363:Agaricales / Q000201:enzymology; D000818:Animals; D001547:Benzaldehydes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology* / Q000633:toxicity; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology* / Q000633:toxicity; D020128:Inhibitory Concentration 50; D051379:Mice; D014442:Monophenol Monooxygenase / Q000037:antagonists & inhibitors*
chemical_list: D001547:Benzaldehydes; D004791:Enzyme Inhibitors; D014442:Monophenol Monooxygenase; C011483:4-hydroxybenzaldehyde