Staff View: Synthesis, molecular docking and tyrosinase inhibitory activity of the decorated methoxy sulfonamide chalcones : in vitro inhibitory effects and the possible binding mode

Synthesis, molecular docking and tyrosinase inhibitory activity of the decorated methoxy sulfonamide chalcones : in vitro inhibitory effects and the possible binding mode

In this study, a series of sulfonamide chalcones derivatives was synthesized and its chemical structures were confirmed by spectral characteristics. The synthesized compounds were evaluated for their tyrosinase inhibitory activities along with molecular docking study. The tyrosinase inhibitory resul...

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Main Authors:	Thawanrat Kobkeatthawin,, Suchada Chantrapromma,, Thitipone Suwunwong,, Lydia Rhyman,, Choong, Yee Siew, Ponnadurai Ramasami,
Format:	Article
Language:	English
Published:	Penerbit Universiti Kebangsaan Malaysia 2021
Online Access:	http://journalarticle.ukm.my/18058/1/9.pdf http://journalarticle.ukm.my/18058/ https://www.ukm.my/jsm/malay_journals/jilid50bil9_2021/KandunganJilid50Bil9_2021.html
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id	my-ukm.journal.18058
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spelling	my-ukm.journal.180582022-02-18T00:43:01Z http://journalarticle.ukm.my/18058/ Synthesis, molecular docking and tyrosinase inhibitory activity of the decorated methoxy sulfonamide chalcones : in vitro inhibitory effects and the possible binding mode Thawanrat Kobkeatthawin, Suchada Chantrapromma, Thitipone Suwunwong, Lydia Rhyman, Choong, Yee Siew Ponnadurai Ramasami, In this study, a series of sulfonamide chalcones derivatives was synthesized and its chemical structures were confirmed by spectral characteristics. The synthesized compounds were evaluated for their tyrosinase inhibitory activities along with molecular docking study. The tyrosinase inhibitory results indicated that compounds 5b, 5c, 5f, 5g and 5h displayed the significant tyrosinase inhibitory activity and comparable to the standard drug (kojic acid). Compound 5c exhibits the most potent tyrosinase inhibition among the synthesized compounds with IC50 = 0.43±0.07 mM, L-DOPA as the substrate, and better than that of the standard kojic acid (IC50 = 0.60±0.20 mM). Molecular docking studies showed that the binding mode of some compounds is in the tyrosinase binding pocket surrounding the copper in the active site. The correlation between the docking results with IC50 values showed that the binding mode prediction of the test compounds would also be convincing. This comprehensive study allows for a possible mechanism for the antityrosinase activity of the sulfonamide chalcones. These sulfonamide chalcones bind to copper atoms of tyrosinase which responsible for the catalytic activity of tyrosinase. These compounds may be used as a lead for rational drug designing for the multi-functional tyrosinase inhibitor. Penerbit Universiti Kebangsaan Malaysia 2021-09 Article PeerReviewed application/pdf en http://journalarticle.ukm.my/18058/1/9.pdf Thawanrat Kobkeatthawin, and Suchada Chantrapromma, and Thitipone Suwunwong, and Lydia Rhyman, and Choong, Yee Siew and Ponnadurai Ramasami, (2021) Synthesis, molecular docking and tyrosinase inhibitory activity of the decorated methoxy sulfonamide chalcones : in vitro inhibitory effects and the possible binding mode. Sains Malaysiana, 50 (9). pp. 2603-2614. ISSN 0126-6039 https://www.ukm.my/jsm/malay_journals/jilid50bil9_2021/KandunganJilid50Bil9_2021.html
institution	Universiti Kebangsaan Malaysia
building	Tun Sri Lanang Library
collection	Institutional Repository
continent	Asia
country	Malaysia
content_provider	Universiti Kebangsaan Malaysia
content_source	UKM Journal Article Repository
url_provider	http://journalarticle.ukm.my/
language	English
description	In this study, a series of sulfonamide chalcones derivatives was synthesized and its chemical structures were confirmed by spectral characteristics. The synthesized compounds were evaluated for their tyrosinase inhibitory activities along with molecular docking study. The tyrosinase inhibitory results indicated that compounds 5b, 5c, 5f, 5g and 5h displayed the significant tyrosinase inhibitory activity and comparable to the standard drug (kojic acid). Compound 5c exhibits the most potent tyrosinase inhibition among the synthesized compounds with IC50 = 0.43±0.07 mM, L-DOPA as the substrate, and better than that of the standard kojic acid (IC50 = 0.60±0.20 mM). Molecular docking studies showed that the binding mode of some compounds is in the tyrosinase binding pocket surrounding the copper in the active site. The correlation between the docking results with IC50 values showed that the binding mode prediction of the test compounds would also be convincing. This comprehensive study allows for a possible mechanism for the antityrosinase activity of the sulfonamide chalcones. These sulfonamide chalcones bind to copper atoms of tyrosinase which responsible for the catalytic activity of tyrosinase. These compounds may be used as a lead for rational drug designing for the multi-functional tyrosinase inhibitor.
format	Article
author	Thawanrat Kobkeatthawin, Suchada Chantrapromma, Thitipone Suwunwong, Lydia Rhyman, Choong, Yee Siew Ponnadurai Ramasami,
spellingShingle	Thawanrat Kobkeatthawin, Suchada Chantrapromma, Thitipone Suwunwong, Lydia Rhyman, Choong, Yee Siew Ponnadurai Ramasami, Synthesis, molecular docking and tyrosinase inhibitory activity of the decorated methoxy sulfonamide chalcones : in vitro inhibitory effects and the possible binding mode
author_facet	Thawanrat Kobkeatthawin, Suchada Chantrapromma, Thitipone Suwunwong, Lydia Rhyman, Choong, Yee Siew Ponnadurai Ramasami,
author_sort	Thawanrat Kobkeatthawin,
title	Synthesis, molecular docking and tyrosinase inhibitory activity of the decorated methoxy sulfonamide chalcones : in vitro inhibitory effects and the possible binding mode
title_short	Synthesis, molecular docking and tyrosinase inhibitory activity of the decorated methoxy sulfonamide chalcones : in vitro inhibitory effects and the possible binding mode
title_full	Synthesis, molecular docking and tyrosinase inhibitory activity of the decorated methoxy sulfonamide chalcones : in vitro inhibitory effects and the possible binding mode
title_fullStr	Synthesis, molecular docking and tyrosinase inhibitory activity of the decorated methoxy sulfonamide chalcones : in vitro inhibitory effects and the possible binding mode
title_full_unstemmed	Synthesis, molecular docking and tyrosinase inhibitory activity of the decorated methoxy sulfonamide chalcones : in vitro inhibitory effects and the possible binding mode
title_sort	synthesis, molecular docking and tyrosinase inhibitory activity of the decorated methoxy sulfonamide chalcones : in vitro inhibitory effects and the possible binding mode
publisher	Penerbit Universiti Kebangsaan Malaysia
publishDate	2021
url	http://journalarticle.ukm.my/18058/1/9.pdf http://journalarticle.ukm.my/18058/ https://www.ukm.my/jsm/malay_journals/jilid50bil9_2021/KandunganJilid50Bil9_2021.html
_version_	1725973504875036672
score	13.211869

Synthesis, molecular docking and tyrosinase inhibitory activity of the decorated methoxy sulfonamide chalcones : in vitro inhibitory effects and the possible binding mode

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