In vitro and in silico insights into tyrosinase inhibitors with (E)-benzylidene-1-indanone derivatives

Tyrosinase is a key enzyme responsible for melanin biosynthesis and is effective in protecting skin damage caused by ultraviolet radiation. As part of ongoing efforts to discover potent tyrosinase inhibitors, we systematically designed and synthesized thirteen (E)-benzylidene-1-indanone derivatives...
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Autor*in:	Hee Jin Jung [verfasserIn] Sang Gyun Noh [verfasserIn] Yujin Park [verfasserIn] Dongwan Kang [verfasserIn] Pusoon Chun [verfasserIn] Hae Young Chung [verfasserIn] Hyung Ryong Moon [verfasserIn]

Format:	E-Artikel
Sprache:	Englisch

Erschienen:	2019

Übergeordnetes Werk:	In: Computational and Structural Biotechnology Journal - Elsevier, 2013, 17(2019), Seite 1255-1264
Übergeordnetes Werk:	volume:17 ; year:2019 ; pages:1255-1264

Links:	Link aufrufen Link aufrufen Link aufrufen Journal toc

DOI / URN:	10.1016/j.csbj.2019.07.017

Katalog-ID:	DOAJ012837601

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520			\|a Tyrosinase is a key enzyme responsible for melanin biosynthesis and is effective in protecting skin damage caused by ultraviolet radiation. As part of ongoing efforts to discover potent tyrosinase inhibitors, we systematically designed and synthesized thirteen (E)-benzylidene-1-indanone derivatives (BID1–13) and determined their inhibitory activities against tyrosinase. Among the compounds evaluated, BID3 was the most potent inhibitor of mushroom tyrosinase (IC50 = 0.034 µM, monophenolase activity; IC50 = 1.39 µM, diphenolase activity). Kinetic studies revealed that BID3 demonstrated a mixed type of tyrosinase inhibition with Ki value of 2.4 µM using l-DOPA as a substrate. In silico molecular docking simulations demonstrated that BID3 can bind to the catalytic and allosteric sites of tyrosinase to inhibit enzyme activity which confirmed in vitro experimental studies between BID3 and tyrosinase. Furthermore, melanin contents decreased and cellular tyrosinase activity was inhibited after BID3 treatment. These observations revealed that BID3 is a potent tyrosinase inhibitor and potentially could be used as a whitening agent for the treatment of pigmentation-related disorders. Keywords: 1-Indanone, 2,4-Dihydroxy benzylidene, Melanin, Tyrosinase inhibitor
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spelling	10.1016/j.csbj.2019.07.017 doi (DE-627)DOAJ012837601 (DE-599)DOAJ0cd4678c5e27499d80df3d0ea89e3f9f DE-627 ger DE-627 rakwb eng TP248.13-248.65 Hee Jin Jung verfasserin aut In vitro and in silico insights into tyrosinase inhibitors with (E)-benzylidene-1-indanone derivatives 2019 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Tyrosinase is a key enzyme responsible for melanin biosynthesis and is effective in protecting skin damage caused by ultraviolet radiation. As part of ongoing efforts to discover potent tyrosinase inhibitors, we systematically designed and synthesized thirteen (E)-benzylidene-1-indanone derivatives (BID1–13) and determined their inhibitory activities against tyrosinase. Among the compounds evaluated, BID3 was the most potent inhibitor of mushroom tyrosinase (IC50 = 0.034 µM, monophenolase activity; IC50 = 1.39 µM, diphenolase activity). Kinetic studies revealed that BID3 demonstrated a mixed type of tyrosinase inhibition with Ki value of 2.4 µM using l-DOPA as a substrate. In silico molecular docking simulations demonstrated that BID3 can bind to the catalytic and allosteric sites of tyrosinase to inhibit enzyme activity which confirmed in vitro experimental studies between BID3 and tyrosinase. Furthermore, melanin contents decreased and cellular tyrosinase activity was inhibited after BID3 treatment. These observations revealed that BID3 is a potent tyrosinase inhibitor and potentially could be used as a whitening agent for the treatment of pigmentation-related disorders. Keywords: 1-Indanone, 2,4-Dihydroxy benzylidene, Melanin, Tyrosinase inhibitor Biotechnology Sang Gyun Noh verfasserin aut Yujin Park verfasserin aut Dongwan Kang verfasserin aut Pusoon Chun verfasserin aut Hae Young Chung verfasserin aut Hyung Ryong Moon verfasserin aut In Computational and Structural Biotechnology Journal Elsevier, 2013 17(2019), Seite 1255-1264 (DE-627)731890086 (DE-600)2694435-2 20010370 nnns volume:17 year:2019 pages:1255-1264 https://doi.org/10.1016/j.csbj.2019.07.017 kostenfrei https://doaj.org/article/0cd4678c5e27499d80df3d0ea89e3f9f kostenfrei http://www.sciencedirect.com/science/article/pii/S2001037019301758 kostenfrei https://doaj.org/toc/2001-0370 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_39 GBV_ILN_40 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_213 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2014 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 17 2019 1255-1264
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allfieldsGer	10.1016/j.csbj.2019.07.017 doi (DE-627)DOAJ012837601 (DE-599)DOAJ0cd4678c5e27499d80df3d0ea89e3f9f DE-627 ger DE-627 rakwb eng TP248.13-248.65 Hee Jin Jung verfasserin aut In vitro and in silico insights into tyrosinase inhibitors with (E)-benzylidene-1-indanone derivatives 2019 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Tyrosinase is a key enzyme responsible for melanin biosynthesis and is effective in protecting skin damage caused by ultraviolet radiation. As part of ongoing efforts to discover potent tyrosinase inhibitors, we systematically designed and synthesized thirteen (E)-benzylidene-1-indanone derivatives (BID1–13) and determined their inhibitory activities against tyrosinase. Among the compounds evaluated, BID3 was the most potent inhibitor of mushroom tyrosinase (IC50 = 0.034 µM, monophenolase activity; IC50 = 1.39 µM, diphenolase activity). Kinetic studies revealed that BID3 demonstrated a mixed type of tyrosinase inhibition with Ki value of 2.4 µM using l-DOPA as a substrate. In silico molecular docking simulations demonstrated that BID3 can bind to the catalytic and allosteric sites of tyrosinase to inhibit enzyme activity which confirmed in vitro experimental studies between BID3 and tyrosinase. Furthermore, melanin contents decreased and cellular tyrosinase activity was inhibited after BID3 treatment. These observations revealed that BID3 is a potent tyrosinase inhibitor and potentially could be used as a whitening agent for the treatment of pigmentation-related disorders. Keywords: 1-Indanone, 2,4-Dihydroxy benzylidene, Melanin, Tyrosinase inhibitor Biotechnology Sang Gyun Noh verfasserin aut Yujin Park verfasserin aut Dongwan Kang verfasserin aut Pusoon Chun verfasserin aut Hae Young Chung verfasserin aut Hyung Ryong Moon verfasserin aut In Computational and Structural Biotechnology Journal Elsevier, 2013 17(2019), Seite 1255-1264 (DE-627)731890086 (DE-600)2694435-2 20010370 nnns volume:17 year:2019 pages:1255-1264 https://doi.org/10.1016/j.csbj.2019.07.017 kostenfrei https://doaj.org/article/0cd4678c5e27499d80df3d0ea89e3f9f kostenfrei http://www.sciencedirect.com/science/article/pii/S2001037019301758 kostenfrei https://doaj.org/toc/2001-0370 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_39 GBV_ILN_40 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_213 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2014 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 17 2019 1255-1264
allfieldsSound	10.1016/j.csbj.2019.07.017 doi (DE-627)DOAJ012837601 (DE-599)DOAJ0cd4678c5e27499d80df3d0ea89e3f9f DE-627 ger DE-627 rakwb eng TP248.13-248.65 Hee Jin Jung verfasserin aut In vitro and in silico insights into tyrosinase inhibitors with (E)-benzylidene-1-indanone derivatives 2019 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Tyrosinase is a key enzyme responsible for melanin biosynthesis and is effective in protecting skin damage caused by ultraviolet radiation. As part of ongoing efforts to discover potent tyrosinase inhibitors, we systematically designed and synthesized thirteen (E)-benzylidene-1-indanone derivatives (BID1–13) and determined their inhibitory activities against tyrosinase. Among the compounds evaluated, BID3 was the most potent inhibitor of mushroom tyrosinase (IC50 = 0.034 µM, monophenolase activity; IC50 = 1.39 µM, diphenolase activity). Kinetic studies revealed that BID3 demonstrated a mixed type of tyrosinase inhibition with Ki value of 2.4 µM using l-DOPA as a substrate. In silico molecular docking simulations demonstrated that BID3 can bind to the catalytic and allosteric sites of tyrosinase to inhibit enzyme activity which confirmed in vitro experimental studies between BID3 and tyrosinase. Furthermore, melanin contents decreased and cellular tyrosinase activity was inhibited after BID3 treatment. These observations revealed that BID3 is a potent tyrosinase inhibitor and potentially could be used as a whitening agent for the treatment of pigmentation-related disorders. Keywords: 1-Indanone, 2,4-Dihydroxy benzylidene, Melanin, Tyrosinase inhibitor Biotechnology Sang Gyun Noh verfasserin aut Yujin Park verfasserin aut Dongwan Kang verfasserin aut Pusoon Chun verfasserin aut Hae Young Chung verfasserin aut Hyung Ryong Moon verfasserin aut In Computational and Structural Biotechnology Journal Elsevier, 2013 17(2019), Seite 1255-1264 (DE-627)731890086 (DE-600)2694435-2 20010370 nnns volume:17 year:2019 pages:1255-1264 https://doi.org/10.1016/j.csbj.2019.07.017 kostenfrei https://doaj.org/article/0cd4678c5e27499d80df3d0ea89e3f9f kostenfrei http://www.sciencedirect.com/science/article/pii/S2001037019301758 kostenfrei https://doaj.org/toc/2001-0370 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_39 GBV_ILN_40 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_213 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2014 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 17 2019 1255-1264
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callnumber-first	T - Technology
author	Hee Jin Jung
spellingShingle	Hee Jin Jung misc TP248.13-248.65 misc Biotechnology In vitro and in silico insights into tyrosinase inhibitors with (E)-benzylidene-1-indanone derivatives
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topic_title	TP248.13-248.65 In vitro and in silico insights into tyrosinase inhibitors with (E)-benzylidene-1-indanone derivatives
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title	In vitro and in silico insights into tyrosinase inhibitors with (E)-benzylidene-1-indanone derivatives
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title_full	In vitro and in silico insights into tyrosinase inhibitors with (E)-benzylidene-1-indanone derivatives
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author_browse	Hee Jin Jung Sang Gyun Noh Yujin Park Dongwan Kang Pusoon Chun Hae Young Chung Hyung Ryong Moon
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author-letter	Hee Jin Jung
doi_str_mv	10.1016/j.csbj.2019.07.017
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title_sort	in vitro and in silico insights into tyrosinase inhibitors with (e)-benzylidene-1-indanone derivatives
callnumber	TP248.13-248.65
title_auth	In vitro and in silico insights into tyrosinase inhibitors with (E)-benzylidene-1-indanone derivatives
abstract	Tyrosinase is a key enzyme responsible for melanin biosynthesis and is effective in protecting skin damage caused by ultraviolet radiation. As part of ongoing efforts to discover potent tyrosinase inhibitors, we systematically designed and synthesized thirteen (E)-benzylidene-1-indanone derivatives (BID1–13) and determined their inhibitory activities against tyrosinase. Among the compounds evaluated, BID3 was the most potent inhibitor of mushroom tyrosinase (IC50 = 0.034 µM, monophenolase activity; IC50 = 1.39 µM, diphenolase activity). Kinetic studies revealed that BID3 demonstrated a mixed type of tyrosinase inhibition with Ki value of 2.4 µM using l-DOPA as a substrate. In silico molecular docking simulations demonstrated that BID3 can bind to the catalytic and allosteric sites of tyrosinase to inhibit enzyme activity which confirmed in vitro experimental studies between BID3 and tyrosinase. Furthermore, melanin contents decreased and cellular tyrosinase activity was inhibited after BID3 treatment. These observations revealed that BID3 is a potent tyrosinase inhibitor and potentially could be used as a whitening agent for the treatment of pigmentation-related disorders. Keywords: 1-Indanone, 2,4-Dihydroxy benzylidene, Melanin, Tyrosinase inhibitor
abstractGer	Tyrosinase is a key enzyme responsible for melanin biosynthesis and is effective in protecting skin damage caused by ultraviolet radiation. As part of ongoing efforts to discover potent tyrosinase inhibitors, we systematically designed and synthesized thirteen (E)-benzylidene-1-indanone derivatives (BID1–13) and determined their inhibitory activities against tyrosinase. Among the compounds evaluated, BID3 was the most potent inhibitor of mushroom tyrosinase (IC50 = 0.034 µM, monophenolase activity; IC50 = 1.39 µM, diphenolase activity). Kinetic studies revealed that BID3 demonstrated a mixed type of tyrosinase inhibition with Ki value of 2.4 µM using l-DOPA as a substrate. In silico molecular docking simulations demonstrated that BID3 can bind to the catalytic and allosteric sites of tyrosinase to inhibit enzyme activity which confirmed in vitro experimental studies between BID3 and tyrosinase. Furthermore, melanin contents decreased and cellular tyrosinase activity was inhibited after BID3 treatment. These observations revealed that BID3 is a potent tyrosinase inhibitor and potentially could be used as a whitening agent for the treatment of pigmentation-related disorders. Keywords: 1-Indanone, 2,4-Dihydroxy benzylidene, Melanin, Tyrosinase inhibitor
abstract_unstemmed	Tyrosinase is a key enzyme responsible for melanin biosynthesis and is effective in protecting skin damage caused by ultraviolet radiation. As part of ongoing efforts to discover potent tyrosinase inhibitors, we systematically designed and synthesized thirteen (E)-benzylidene-1-indanone derivatives (BID1–13) and determined their inhibitory activities against tyrosinase. Among the compounds evaluated, BID3 was the most potent inhibitor of mushroom tyrosinase (IC50 = 0.034 µM, monophenolase activity; IC50 = 1.39 µM, diphenolase activity). Kinetic studies revealed that BID3 demonstrated a mixed type of tyrosinase inhibition with Ki value of 2.4 µM using l-DOPA as a substrate. In silico molecular docking simulations demonstrated that BID3 can bind to the catalytic and allosteric sites of tyrosinase to inhibit enzyme activity which confirmed in vitro experimental studies between BID3 and tyrosinase. Furthermore, melanin contents decreased and cellular tyrosinase activity was inhibited after BID3 treatment. These observations revealed that BID3 is a potent tyrosinase inhibitor and potentially could be used as a whitening agent for the treatment of pigmentation-related disorders. Keywords: 1-Indanone, 2,4-Dihydroxy benzylidene, Melanin, Tyrosinase inhibitor
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title_short	In vitro and in silico insights into tyrosinase inhibitors with (E)-benzylidene-1-indanone derivatives
url	https://doi.org/10.1016/j.csbj.2019.07.017 https://doaj.org/article/0cd4678c5e27499d80df3d0ea89e3f9f http://www.sciencedirect.com/science/article/pii/S2001037019301758 https://doaj.org/toc/2001-0370
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