Bioscience, Biotechnology, and Biochemistry 2012-01-01

Effects of isorhamnetin on tyrosinase: inhibition kinetics and computational simulation.

Yue-Xiu Si, Zhi-Jiang Wang, Daeui Park, Hyoung Oh Jeong, Sen Ye, Hae Young Chung, Jun-Mo Yang, Shang-Jun Yin, Guo-Ying Qian

Index: Biosci. Biotechnol. Biochem. 76(6) , 1091-7, (2012)

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Abstract

We studied the inhibitory effects of isorhamnetin on mushroom tyrosinase by inhibition kinetics and computational simulation. Isorhamnetin reversibly inhibited tyrosinase in a mixed-type manner at Ki=0.235±0.013 mM. Measurements of intrinsic and 1-anilinonaphthalene-8-sulfonate(ANS)-binding fluorescence showed that isorhamnetin did not induce significant changes in the tertiary structure of tyrosinase. To gain insight into the inactivation process, the kinetics were computed via time-interval measurements and continuous substrate reactions. The results indicated that inactivation induced by isorhamnetin was a first-order reaction with biphasic processes. To gain further insight, we simulated docking between tyrosinase and isorhamnetin. Simulation was successful (binding energies for Dock6.3: -32.58 kcal/mol, for AutoDock4.2: -5.66 kcal/mol, and for Fred2.2: -48.86 kcal/mol), suggesting that isorhamnetin interacts with several residues, such as HIS244 and MET280. This strategy of predicting tyrosinase interaction in combination with kinetics based on a flavanone compound might prove useful in screening for potential natural tyrosinase inhibitors.


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