Inhibitory effects of 5-benzylidene barbiturate derivatives on mushroom tyrosinase and their antibacterial activities.
A series of novel 5-benzylidene barbiturate and thiobarbiturate derivatives were synthesized and evaluated as tyrosinase inhibitors and antibacterial agents. The results demonstrated that some compounds had more potent inhibitory activities than the parent compound 4-hydroxybenzaldehyde (IC(50)=1.22 mM). Particularly, compounds 1a and 2a were found to be the most potent inhibitors with IC(50) value of 13.98 microM and 14.49 microM, respectively. The inhibition mechanism study revealed that these compounds were irreversible inhibitors. The circular dichroism spectra indicated that these compounds induced conformational changes of mushroom tyrosinase upon binding. In addition, these compounds exhibited selectively antibacterial activity against Staphylococcus aureus. All these results suggested that further development of such compounds may be of interest.
Yan
Qin
Q
School of Chemistry and Chemical Engineering, Sun Yat-sen University, Guangzhou 510275, PR China.
Cao
Rihui
R
Yi
Wei
W
Chen
Zhiyong
Z
Wen
Huan
H
Ma
Lin
L
Song
Huacan
H
D000363:Agaricales / Q000201:enzymology*; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D001419:Bacteria / Q000187:drug effects; D001463:Barbiturates / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D001597:Benzylidene Compounds / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D008826:Microbial Sensitivity Tests; D014442:Monophenol Monooxygenase / Q000037:antagonists & inhibitors* / Q000737:chemistry / Q000378:metabolism; D017433:Protein Structure, Secondary; D013329:Structure-Activity Relationship; D013858:Thiobarbiturates / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*
D000900:Anti-Bacterial Agents; D001463:Barbiturates; D001597:Benzylidene Compounds; D013858:Thiobarbiturates; D014442:Monophenol Monooxygenase; C029684:thiobarbituric acid