Synthesis and structure-activity relationship of tyrosinase inhibiting novel bi-heterocyclic acetamides: Mechanistic insights through enzyme inhibition,kinetics and computational studies期刊界 All Journals 搜尽天下杂志传播学术成果专业期刊搜索期刊信息化学术搜索

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Synthesis and structure-activity relationship of tyrosinase inhibiting novel bi-heterocyclic acetamides: Mechanistic insights through enzyme inhibition,kinetics and computational studies

Institution:	1. Department of Chemistry, Government College University, Lahore 54000, Pakistan;2. College of Natural Sciences, Department of Biological Sciences, Kongju National University, Gongju 32588, South Korea;3. Faculty of Pharmacy and Atta-ur-Rahman Institute for Natural Products Discovery (AuRIns), Level 9, FF3, Universiti Teknologi MARA, Puncak Alam Campus, 42300 Bandar Puncak Alam, Selangor Darul Ehsan, Malaysia;4. Department of Biochemistry, University of Agriculture, Faisalabad 38040, Pakistan;1. Department of Chemistry, Quaid-I-Azam University, Islamabad 45320, Pakistan;2. Department of Chemistry, School of Optics/Center for Research and Education in Optics and Lasers University of Central Florida, P.O. Box 162366, Orlando, FL 32816, United States;3. Institute of Biochemistry, University of Sindh, Jamshoro 76080, Pakistan;4. Department of Physiology, University of Sindh, Jamshoro 76080, Pakistan;5. Department of Biological Sciences, College of Natural Sciences, Kongju National University, 56 Gongjudehak-Ro, Gongju, Chungnam 314-701, Republic of Korea;1. Institute of Molecular Biology and Biotechnology (IMBB), The University of Lahore, Raiwind Road, 55150 Lahore, Pakistan;2. Department of Chemistry, Government College University, Lahore 54000, Pakistan;3. Institute of Molecular Science and Bioinformatics, Nisbat Road, Lahore, Pakistan;4. College of Natural Science, Department of Biological Sciences, Kongju National University, Gongju 32588, South Korea;5. Faculty of Pharmacy, Universiti Teknologi MARA, Puncak Alam Campus, 42300 Bandar Puncak Alam, Selangor Darul Ehsan, Malaysia;6. Atta-ur-Rahman Institute for Natural Products Discovery (AuRIns), Level 9, FF3, Universiti Teknologi MARA, Puncak Alam Campus, 42300 Bandar Puncak Alam, Selangor Darul Ehsan, Malaysia;7. Department of Chemistry, The Islamia University of Bahawalpur, Bahawalpur 63100, Pakistan;8. Department of Biochemistry, University of Agriculture, Faisalabad 38040, Pakistan;1. Sulaiman Bin Abdullah Aba Al-Khail-Centre for Interdisciplinary Research in Basic Sciences (SA-CIRBS), International Islamic University 44000 Islamabad, Pakistan;2. School of Chemistry and Manchester Institute of Biotechnology, The University of Manchester, 131 Princess Street, Manchester M1 7DN, United Kingdom;3. Department of Chemistry, Quaid-i-Azam University 45320 Islamabad, Pakistan;4. Department of Biological Sciences, College of Natural Science, Kongju National University, Gongju 32588, Republic of Korea;5. Department of Physiology, University of Sindh, Jamshoro, Pakistan;1. Department of Chemistry, Kongju National University, Gongju, Chungnam, 32588, Republic of Korea;2. Department of Biological Sciences, 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. Center for Chemical Analysis, Korea Research Institute of Chemical Technology, Yuseong, Daejeon, 34114, Republic of Korea;1. Department of Chemistry, Allama Iqbal Open University, Islamabad 44000, Pakistan;2. Institute of Molecular Biology and Biotechnology, The University of Lahore, Pakistan;3. Department of Physiology, University of Sindh, Jamshoro, Pakistan

Abstract:	The present research was designed for the selective synthesis of novel bi-heterocyclic acetamides, 9a-n, and their tyrosinase inhibition to overwhelm the problem of melanogenesis. The structures of newly synthesized compounds were confirmed by spectral techniques such as ¹H NMR, ¹³C NMR, and EI-MS along with elemental analysis. The inhibitory effects of these bi-heterocyclic acetamides (9a-n) were evaluated against tyrosinase and all these molecules were recognized as potent inhibitors relative to the standard used. The Kinetics mechanism was analyzed by Lineweaver-Burk plots which explored that compound, 9h, inhibited tyrosinase competitively by forming an enzyme-inhibitor complex. The inhibition constants K_i calculated from Dixon plots for this compound was 0.0027 µM. The computational study was coherent with the experimental records and these ligands exhibited good binding energy values (kcal/mol). The hemolytic analysis revealed their mild cytotoxicity towards red blood cell membranes and hence, these molecules can be pondered as nontoxic medicinal scaffolds for skin pigmentation and related disorders.

Keywords:	Thiazole Triazole Acetamides Tyrosinase Melanogenesis Hemolytic Binding energy IR"} {"#name":"keyword" "$":{"id":"k0045"} "$$":[{"#name":"text" "_":"Infra Red EI-MS"} {"#name":"keyword" "$":{"id":"k0055"} "$$":[{"#name":"text" "_":"Electron Impact Mass Spectrometry Proton Nuclear Magnetic Resonance Carbon Nuclear Magnetic Resonance Deuterated dimethyl sulfoxide s"} {"#name":"keyword" "$":{"id":"k0095"} "$$":[{"#name":"text" "_":"singlet d"} {"#name":"keyword" "$":{"id":"k0105"} "$$":[{"#name":"text" "_":"doublet dd"} {"#name":"keyword" "$":{"id":"k0115"} "$$":[{"#name":"text" "_":"doublet of doublets t"} {"#name":"keyword" "$":{"id":"k0125"} "$$":[{"#name":"text" "_":"triplet br t"} {"#name":"keyword" "$":{"id":"k0135"} "$$":[{"#name":"text" "_":"broad triplet q"} {"#name":"keyword" "$":{"id":"k0145"} "$$":[{"#name":"text" "_":"quartet quint"} {"#name":"keyword" "$":{"id":"k0155"} "$$":[{"#name":"text" "_":"quintet sex"} {"#name":"keyword" "$":{"id":"k0165"} "$$":[{"#name":"text" "_":"sextet sep"} {"#name":"keyword" "$":{"id":"k0175"} "$$":[{"#name":"text" "_":"septet m"} {"#name":"keyword" "$":{"id":"k0185"} "$$":[{"#name":"text" "_":"multiplet
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