Molecular docking studies and biological evaluation of 1,3,4-thiadiazole derivatives bearing Schiff base moieties as tyrosinase inhibitors |
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| Institution: | 1. Department of Chemistry, Faculty of Science, Karabuk University, 78050, Karabuk, Turkey;2. Department of Medical Microbiology, Faculty of Medicine, Giresun University, Giresun, 28100, Turkey;3. Department of Chemical Engineering, Faculty of Engineering and Architecture, Ahi Evran University, 40100, K?r?ehir, Turkey;1. Department of Chemistry, Quaid-I-Azam University, Islamabad 45320, Pakistan;2. Department of Biological Sciences, College of Natural Sciences, Kongju National University, 56 Gongjudehak-Ro, Gongju, Chungnam 314-701, Republic of Korea;3. Institut für Anorganische Chemie, J.W.-Goethe-Universität, Max-von-Laue-Str.7, D-60438 Frankfurt/Main, Germany;1. Laboratoire de Valorisation des Substances Naturelles(LVSN), Université Djilali Bounaâma de Khemis Miliana, 44225, Algeria;2. Laboratoire de Physique et Chimie des Matériaux(LPCM), Université Mouloud MAMMERI de Tizi-Ouzou, 15000, Algeria;3. Laboratoire d’Electrochimie des Matériaux Moléculaires et des Complexes(LEMMC), Université Ferhat Abbas de Sétif-1, 19000, Algeria;4. Laboratoire de Génie Chimique (LGC), Université Saâd DAHLEB de Blida, 09000, Algeria;1. Division of Agricultural Chemicals, ICAR-Indian Agricultural Research Institute, New Delhi, 110 012, India;2. Division of Plant Pathology, ICAR-Indian Agricultural Research Institute, New Delhi, 110 012, India;1. State Key Laboratory of Food Science and Technology, Nanchang University, Nanchang 330047, PR China;2. Department of Chemistry, Nanchang University, Nanchang 330031, PR China;1. Department of Industrial Chemistry, Federal University Lokoja, Kogi State, Nigeria;2. Computational and Bio-Simulation Research Group, University of Calabar, Calabar, Nigeria;3. Department of Biochemistry, Cross River University, Calabar, Nigeria;4. Department of Pure and Applied Chemistry, Faculty of Physical Sciences, University of Calabar, Calabar, Nigeria;5. Department of Chemistry, Federal University Lokoja, Kogi State, Nigeria;6. Department of Chemical Sciences, Federal University Wukari, Taraba State, Nigeria;7. Department of Chemistry Education, Alex Ekwueme Federal University, Ndufu-Alike, Ebonyi State, Nigeria;8. Department of Biochemistry, Federal University Lokoja, Kogi State, Nigeria |
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| Abstract: | 1,3,4-Thiadiazole derivatives bearing Schiff base moieties were designed, synthesized, and their tyrosinase inhibitory activities were evaluated. Some compounds displayed potent tyrosinase inhibitory activities, especially, 4-(((5-mercapto-1,3,4-thiadiazol-2-yl)-imino)methyl)-2-methoxy-phenol (14) exhibited superior inhibitory effect to the other compounds with an IC50 value of 0.036 μM. The structure–activity relationships (SARs) were preliminarily discussed and docking studies showed compound 14 had strong binding affinity to mushroom tyrosinase. Hydroxy might be the active groups. The inhibition kinetics study revealed that compounds (13 and 14) inhibited tyrosinase by acting as uncompetitive inhibitors. The LD50 value of the compound 14 was 5000 mg/kg. |
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| Keywords: | 1 3 4-Thiadiazole derivatives Tyrosinase inhibitory activities Inhibition kinetics Docking studies |
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