Veratric acid derivatives containing benzylidene-hydrazine moieties as promising tyrosinase inhibitors and free radical scavengers |
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| Institution: | 1. Department of Medicinal Chemistry, School of Pharmacy, Shiraz University of Medical Sciences, Shiraz, Iran;2. Medicinal and Natural Products Chemistry Research Center, Shiraz University of Medical Sciences, Shiraz, Iran;3. Pharmaceutical Sciences Research Center, Shiraz University of Medical Sciences, Shiraz, Iran;1. Department of Chemistry, Susquehanna University, 514 University Avenue, Selinsgrove, PA 17870, USA;2. Bioactive Botanical Research Laboratory, Department of Biomedical and Pharmaceutical Sciences, College of Pharmacy, University of Rhode Island, Kingston, RI 02881, USA;1. Department of Biological Sciences, Kongju National University, Gongju, Chungnam 32588, Republic of Korea;2. Department of Chemistry, Kongju National University, Gongju, Chungnam 32588, Republic of Korea;3. Institute of Molecular Biology and Biotechnology, The University of Lahore, Defence Road, Lahore 54590, Pakistan;4. School of Chemical Sciences and Food Technology, Faculty of Science and Technology, Universiti Kebangsaan Malaysia (UKM), 43600 Bangi, Selangor, Malaysia;1. University of Monastir, Faculty of Science of Monastir, Laboratory of Heterocyclic Chemistry, Natural Products and Reactivity (LR11ES39), Team: Medicinal Chemistry and Natural Products, Avenue of Environment, 5019 Monastir, Tunisia;2. Laboratory of Chemistry, URCOM, EA 3221, INC3M CNRS-F3038, UFR of Sciences and Techniques, University of Havre BP: 1123, 25 rue Philipe Lebon, 76063 Le Havre Cedex, France;1. School of Chinese Materia Medica, Beijing University of Chinese Medicine, Beijing 100102, China;2. Department of Otorhinolaryngology, Peking University Third Hospital, Beijing 100191, China;1. Department of Chemistry, University of Malakand, P.O. Box 18800, Dir Lower, Khyber Pakhtunkhwa, Pakistan;2. Natural and Medical Sciences Research Center, University of Nizwa, P.O. Box 33, PC 616, Birkat Al Mauz, Nizwa, Oman;3. H.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan;1. Department of Medicinal Chemistry, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran;2. Medicinal and Natural Products Chemistry Research Center, Shiraz University of Medical Sciences, Shiraz, Iran;3. Department of Medicinal Chemistry, School of Pharmacy, Shiraz University of Medical Sciences, Shiraz, Iran;4. Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, Iran;5. Pharmaceutical Sciences Research Center, Shiraz University of Medical Sciences, Shiraz, Iran |
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| Abstract: | Tyrosinase enzyme plays a crucial role in melanin biosynthesis and enzymatic browning process of vegetables and fruits. A series of veratric acid derivatives containing benzylidene-hydrazine moieties with different substitutions were synthesized and their inhibitory effect on mushroom tyrosinase and free radical scavenging activity were evaluated. The results indicated that N′-(4-chlorobenzylidene)-3,4-dimethoxybenzohydrazide (D5) and N′-(2,3-dihydroxybenzylidene)-3,4-dimethoxybenzohydrazide (D12) showed the highest tyrosinase inhibitory activity with IC50 values of 19.72 ± 1.84 and 20.63 ± 0.79 μM, respectively, that were comparable with the IC50 value of kojic acid (19.08 ± 1.21 μM). D12 was also a potent radical scavenger with EC50 value of 0.0097 ± 0.0011 mM. The free radical scavenging activity of D12 was comparable with the standard quercetin. The inhibition kinetic analyzed by Lineweaver-Burk plots revealed that compound D5 was a competitive tyrosinase inhibitor. Molecular docking study was carried out for the derivatives demonstrating tyrosinase inhibitory activity. D5 and D12 possessed the most negative estimated free energies of binding in mushroom tyrosinase active site. Therefore, D5 and D12 could be introduced as potent tyrosinase inhibitors that might be promising leads in medicine, cosmetics and food industry. |
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| Keywords: | Tyrosinase inhibitor Benzohydrazide Kojic acid Diphenolase activity Veratric acid |
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