Inhibition kinetics of chlorobenzaldehyde thiosemicarbazones on mushroom tyrosinase. 2010

Zhi-Cong Li, and Liang-Hua Chen, and Xiao-Jie Yu, and Yong-Hua Hu, and Kang-Kang Song, and Xing-Wang Zhou, and Qing-Xi Chen
Key Laboratory of the Ministry of Education for Coastal and Wetland Ecosystems, School of Life Sciences, Xiamen University, Xiamen 361005, China.

2-Chlorobenzaldehyde thiosemicarbazone (2-Cl-BT) and 4-chlorobenzaldehyde thiosemicarbazone (4-Cl-BT) were synthesized, and their inhibitory kinetics on the activity of mushroom tyrosinase were investigated. Results showed that these compounds exhibited significant inhibitory potency on both monophenolase activity and diphenolase activity of tyrosinase. For the monophenolase activity, both compounds could decrease the steady-state activity of the enzyme sharply, without any influence on the lag period. The IC50 values of them were estimated to be 15.4 μM and 6.7 μM, respectively. For the diphenolase activity, both compounds belonged to reversible inhibitors, but their mechanisms were different: 2-Cl-BT was a noncompetitive type inhibitor, while 4-Cl-BT was a mixed-type inhibitor. Their inhibition constants were determined and compared.

UI MeSH Term Description Entries
D007700 Kinetics The rate dynamics in chemical or physical systems.
D004791 Enzyme Inhibitors Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. Enzyme Inhibitor,Inhibitor, Enzyme,Inhibitors, Enzyme
D005656 Fungal Proteins Proteins found in any species of fungus. Fungal Gene Products,Fungal Gene Proteins,Fungal Peptides,Gene Products, Fungal,Yeast Proteins,Gene Proteins, Fungal,Peptides, Fungal,Proteins, Fungal
D000363 Agaricales An extensive order of basidiomycetous fungi whose fruiting bodies are commonly called mushrooms. Agaricaceae,Mushrooms,Agaricale,Mushroom
D001547 Benzaldehydes Compounds that consist of a benzene ring with a formyl group. They occur naturally in the seeds of many fruits and are used as FLAVORING AGENTS and fragrances, as well as precursors in pharmaceutical and plastics manufacturing.
D013882 Thiosemicarbazones Thiosemicarbazone
D014442 Monophenol Monooxygenase An enzyme of the oxidoreductase class that catalyzes the reaction between L-tyrosine, L-dopa, and oxygen to yield L-dopa, dopaquinone, and water. It is a copper protein that acts also on catechols, catalyzing some of the same reactions as CATECHOL OXIDASE. EC 1.14.18.1. Dopa Oxidase,Phenoloxidase,Tyrosinase,Cresolase,Phenol Oxidase,Phenoloxidase A,Phenoloxidase B,Monooxygenase, Monophenol,Oxidase, Dopa,Oxidase, Phenol
D015394 Molecular Structure The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds. Structure, Molecular,Molecular Structures,Structures, Molecular

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