Effect of p-aminophenols on tyrosinase activity |
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| Institution: | 1. Laboratory of Physiological Chemistry, Institute of Medicinal Chemistry, Hoshi University, 2-4-41 Ebara, Shinagawa, Tokyo 142-8501, Japan;2. Synthetic Organic Chemistry Research Laboratory, Institute of Medicinal Chemistry, Hoshi University, 2-4-41 Ebara, Shinagawa, Tokyo 142-8501, Japan;1. Key Laboratory of Plant Resources Conservation and Sustainable Utilization, South China Botanical Garden, Chinese Academy of Sciences, 723 Xingke Road, Tianhe District, Guangzhou 510650, China;2. Guangdong Institute of Eco-environment and Soil Sciences, 808 Tianyuan Road, Tianhe District, Guangzhou 510650, China;3. University of Chinese Academy of Sciences, 19A Yuquan Road, Beijing 100049, China;1. DipNeT, Sassari University (Italy), via Piandanna 4, 07100 Sassari, Italy;2. Dipartimento dj Scienze Chimiche e Geologiche, Cagliari University (Italy), via Trentino 51, 09127, Italy;1. Department of Dermatology, Course of Integrated Medicine, Graduate School of Medicine, Osaka University, Osaka, Japan;2. Department of Dermatology, Graduate School of Medicine, Osaka City University, Osaka, Japan |
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| Abstract: | Tyrosinase is involved in the synthesis of melanin in the skin and hair as well as neuromelanin in the brain. This rate limiting enzyme catalyzes two critical steps (reactions) in melanogenesis; the hydroxylation of tyrosine to form DOPA and the subsequent oxidation of DOPA into dopaquinone. Several new aminophenol derivatives have been synthesized based on structure–activity relationship studies of N-(4-hydroxyphenyl)retinamide (1), a derivative of retinoic acid. In order to find new tyrosinase inhibitors, we investigated the effects of these p-aminophenols, including p-decylaminophenol (3), on the activity of mushroom tyrosinase. Compound 3 was the most potent agent, showing significant inhibition as compared with control. The inhibitory effects of 3 on tyrosinase activities were greater than seen with kojic acid, a well-known potent inhibitor of tyrosinase activity, which also causes adverse effects, including rash and dermatitis. A Lineweaver–Burk kinetic analysis of inhibition showed that 3 suppresses tyrosinase activity in a non-competitive fashion for both substrates, tyrosine and DOPA. These results suggest that 3 might be a useful alternative to kojic acid as a tyrosinase inhibitor. |
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| Keywords: | Tyrosinase activity Kojic acid Melanin |
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