title: Synthesis and biological evaluation of helicid analogues as mushroom tyrosinase inhibitors.
abstract: A series of helicid analogues were synthesized and evaluated as tyrosinase inhibitors. The results demonstrated that some compounds had more potent inhibitory activities than arbutin (IC(50) 7.3 mM). In particular, compound 1c bearing 4,6-O-benzylidene substituent on the sugar moiety was found to be the most potent inhibitor with IC(50) value of 0.052 mM. The inhibition kinetics analyzed by Lineweaver-Burk plots revealed that helicid analogues were competitive inhibitors. The Circular dichroism spectra indicated that those compounds induced conformational changes of mushroom tyrosinase upon binding.
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: 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: Yiqian
authors.initials: Y
authors.lastname: Wan
authors.forename: Lin
authors.initials: L
authors.lastname: Ma
authors.forename: Huacan
authors.initials: H
authors.lastname: Song
mesh_terms: D000363:Agaricales / Q000201:enzymology*; D002384:Catalysis; D002626:Chemistry, Pharmaceutical / Q000379:methods; D002942:Circular Dichroism; D015195:Drug Design; D020128:Inhibitory Concentration 50; D007700:Kinetics; D008956:Models, Chemical; D014442:Monophenol Monooxygenase / Q000037:antagonists & inhibitors / Q000737:chemistry; D010455:Peptides / Q000138:chemical synthesis* / Q000494:pharmacology; D011485:Protein Binding; D011487:Protein Conformation; D017433:Protein Structure, Secondary; D013329:Structure-Activity Relationship
chemical_list: D010455:Peptides; D014442:Monophenol Monooxygenase