Synthesis and tyrosinase inhibitory activity of novel N-hydroxybenzyl-N-nitrosohydroxylamines |
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Authors: | Shiino Mitsuhiro Watanabe Yumi Umezawa Kazuo |
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Affiliation: | Laboratory of Chemistry, School of Medicine, Keio University, 4-1-1 Hiyoshi, Kohoku-ku, Yokohama 223-8521, Japan. mitsuhir@hc.cc.keio.ac.jp |
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Abstract: | Several novel N-substituted N-nitrosohydroxylamines were synthesized. They all inhibited mushroom tyrosinase, but the type of inhibition was different depending on the substituent. Some N-(mono- or dihydroxybenzyl)-N-nitrosohydroxylamines exhibited uncompetitive inhibition with respect to L-dopa. Among them, compound 6 was also a competitive inhibitor with respect to oxygen. This observation suggests that another interaction by the meta- or para-hydroxyl group might stabilize the binding of the inhibitor to the enzyme through the oxygen binding site. |
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Keywords: | Nitrosohydroxylamine Tyrosinase smallcaps" >l-dopa Enzyme inhibition |
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