Synthesis and biological evaluation of novel 4-hydroxybenzaldehyde derivatives as tyrosinase inhibitors.
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.
Yi
Wei
W
School of Chemistry and Chemical Engineering, Sun Yat-Sen University, 135 Xin Gang West Road, Guangzhou 510275, PR China.
Cao
Rihui
R
Peng
Wenlie
W
Wen
Huan
H
Yan
Qin
Q
Zhou
Binhua
B
Ma
Lin
L
Song
Huacan
H
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*
D001547:Benzaldehydes; D004791:Enzyme Inhibitors; D014442:Monophenol Monooxygenase; C011483:4-hydroxybenzaldehyde