Benzonitriles as tyrosinase inhibitors with hyperbolic inhibition manner
| Autor: | Isao Kubo, Ken-ichi Nihei |
|---|---|
| Rok vydání: | 2019 |
| Předmět: |
Nitrile
Stereochemistry Tyrosinase Mixed type chemistry.chemical_element 02 engineering and technology Biochemistry Catalysis Amidine 03 medical and health sciences chemistry.chemical_compound Structural Biology Nitriles Enzyme Inhibitors Molecular Biology 030304 developmental biology 0303 health sciences biology Monophenol Monooxygenase Active site General Medicine 021001 nanoscience & nanotechnology Copper chemistry biology.protein Mushroom tyrosinase 0210 nano-technology |
| Zdroj: | International Journal of Biological Macromolecules. 133:929-932 |
| ISSN: | 0141-8130 |
| Popis: | As a novel mushroom tyrosinase inhibitor, 4-methoxybenzonitrile (anisnitrile) was identified (IC50 = 111.1 μM) with hyperbolic inhibition manner. The calculated αKi (166.3 μM) was larger than Ki (66.5 μM) by Dixon plots, indicating that this nitrile acts as a competitive-noncompetitive mixed type inhibitor. Similarly, 4-isopropylbenzonitrile (cuminnitrile) partially inhibited the oxidation catalyzed by tyrosinase (IC50 = 121.5 μM, Ki = 88.8 μM, and αKi = 239.8 μM). Nine other benzonitriles also exhibited partial tyrosinase-inhibitory activity. In particular, 4-methylbenzonitrile (IC50 = 79.9 μM) is considered to be the most potent among the tested benzonitriles. Benzonitriles barely caused intermolecular amidine formation under physiologic conditions. Furthermore, they possibly coordinate copper at the active site of tyrosinase. Hence, benzonitriles exhibit different inhibition characteristics as compared with that exhibited by benzaldehydes. |
| Databáze: | OpenAIRE |
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