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Synthesis, molecular docking and kinetic studies of novel quinolinyl based acyl thioureas as mushroom tyrosinase inhibitors and free radical scavengers.
Bioorg Chem. 2019 09; 90:103063.BC

Abstract

The enzyme tyrosinase plays a vital role in melanin biosynthesis and enzymatic browning of vegetables and fruits. A series of novel quinolinyl thiourea analogues (11a-j) were synthesized by reaction of 3-aminoquinoline and corresponding isothiocyanates, in moderate to excellent yields with different substitutions and their inhibitory effect on mushroom tyrosinase and free radical scavenging activity were evaluated. The compound N-(quinolin-3-ylcarbamothioyl)hexanamide (11c) exhibited the maximum tyrosinase inhibitory effect (IC50 = 0.0070 ± 0.0098 µM) compared to other derivatives and the reference Kojic acid (IC50 = 16.8320 ± 0.0621 µM). The docking studies were carried out and the compound (11c) showed most negative estimated free energy of -7.2 kcal/mol in mushroom tyrosinase active site. The kinetic analysis revealed that the compound (11c) inhibits the enzyme tyrosinase non-competitively to form the complex of enzyme and inhibitor. The results revealed that 11c could be identified as putative lead compound for the design of efficient tyrosinase inhibitors.

Authors+Show Affiliations

Department of Chemistry, Quaid-I-Azam University, Islamabad 45320, Pakistan.Department of Chemistry, Quaid-I-Azam University, Islamabad 45320, Pakistan. Electronic address: asaeed@qau.edu.pk.Department of Chemistry, Quaid-I-Azam University, Islamabad 45320, Pakistan.Department of Chemistry, Quaid-I-Azam University, Islamabad 45320, Pakistan.Department of Chemistry, Quaid-I-Azam University, Islamabad 45320, Pakistan.Department of Chemistry, Quaid-I-Azam University, Islamabad 45320, Pakistan.Department of Physiology, University of Sindh, Jamshoro 76080, Pakistan.Department of Biological Sciences, College of Natural Sciences, Kongju National University, 56 Gongjudehak-Ro, Gongju, Chungnam 314-701, Republic of Korea.Department of Biological Sciences, College of Natural Sciences, Kongju National University, 56 Gongjudehak-Ro, Gongju, Chungnam 314-701, Republic of Korea.Department of Biological Sciences, College of Natural Sciences, Kongju National University, 56 Gongjudehak-Ro, Gongju, Chungnam 314-701, Republic of Korea.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

31220666

Citation

Mustafa, Muhammad Naeem, et al. "Synthesis, Molecular Docking and Kinetic Studies of Novel Quinolinyl Based Acyl Thioureas as Mushroom Tyrosinase Inhibitors and Free Radical Scavengers." Bioorganic Chemistry, vol. 90, 2019, p. 103063.
Mustafa MN, Saeed A, Channar PA, et al. Synthesis, molecular docking and kinetic studies of novel quinolinyl based acyl thioureas as mushroom tyrosinase inhibitors and free radical scavengers. Bioorg Chem. 2019;90:103063.
Mustafa, M. N., Saeed, A., Channar, P. A., Larik, F. A., Zain-Ul Abideen, M., Shabir, G., Abbas, Q., Hassan, M., Raza, H., & Seo, S. Y. (2019). Synthesis, molecular docking and kinetic studies of novel quinolinyl based acyl thioureas as mushroom tyrosinase inhibitors and free radical scavengers. Bioorganic Chemistry, 90, 103063. https://doi.org/10.1016/j.bioorg.2019.103063
Mustafa MN, et al. Synthesis, Molecular Docking and Kinetic Studies of Novel Quinolinyl Based Acyl Thioureas as Mushroom Tyrosinase Inhibitors and Free Radical Scavengers. Bioorg Chem. 2019;90:103063. PubMed PMID: 31220666.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis, molecular docking and kinetic studies of novel quinolinyl based acyl thioureas as mushroom tyrosinase inhibitors and free radical scavengers. AU - Mustafa,Muhammad Naeem, AU - Saeed,Aamer, AU - Channar,Pervaiz Ali, AU - Larik,Fayaz Ali, AU - Zain-Ul Abideen,Muhammad, AU - Shabir,Ghulam, AU - Abbas,Qamar, AU - Hassan,Mubashir, AU - Raza,Hussain, AU - Seo,Sung-Yum, Y1 - 2019/06/12/ PY - 2019/01/27/received PY - 2019/06/08/revised PY - 2019/06/09/accepted PY - 2019/6/21/pubmed PY - 2020/10/21/medline PY - 2019/6/21/entrez KW - Free radical scavengers KW - Kinetics KW - Molecular docking KW - Mushroom tyrosinase inhibitors KW - Quinolinyl acyl thioureas SP - 103063 EP - 103063 JF - Bioorganic chemistry JO - Bioorg Chem VL - 90 N2 - The enzyme tyrosinase plays a vital role in melanin biosynthesis and enzymatic browning of vegetables and fruits. A series of novel quinolinyl thiourea analogues (11a-j) were synthesized by reaction of 3-aminoquinoline and corresponding isothiocyanates, in moderate to excellent yields with different substitutions and their inhibitory effect on mushroom tyrosinase and free radical scavenging activity were evaluated. The compound N-(quinolin-3-ylcarbamothioyl)hexanamide (11c) exhibited the maximum tyrosinase inhibitory effect (IC50 = 0.0070 ± 0.0098 µM) compared to other derivatives and the reference Kojic acid (IC50 = 16.8320 ± 0.0621 µM). The docking studies were carried out and the compound (11c) showed most negative estimated free energy of -7.2 kcal/mol in mushroom tyrosinase active site. The kinetic analysis revealed that the compound (11c) inhibits the enzyme tyrosinase non-competitively to form the complex of enzyme and inhibitor. The results revealed that 11c could be identified as putative lead compound for the design of efficient tyrosinase inhibitors. SN - 1090-2120 UR - https://www.unboundmedicine.com/medline/citation/31220666/Synthesis_molecular_docking_and_kinetic_studies_of_novel_quinolinyl_based_acyl_thioureas_as_mushroom_tyrosinase_inhibitors_and_free_radical_scavengers_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0045-2068(19)30132-4 DB - PRIME DP - Unbound Medicine ER -