A Potent Tyrosinase Inhibitor, (E)-3-(2,4-Dihydroxyphenyl)-1-(thiophen-2-yl)prop-2-en-1-one, with Anti-Melanogenesis Properties in α-MSH and IBMX-Induced B16F10 Melanoma Cells

In this study, we designed and synthesized eight thiophene chalcone derivatives (1a–h) as tyrosinase inhibitors and evaluated their mushroom tyrosinase inhibitory activities. Of these eight compounds, (E)-3-(2,4-dihydroxyphenyl)-1-(thiophen-2-yl)prop-2-en-1-one (1c) showed strong competiti...
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Gespeichert in:

Autor*in:	Chang Seok Kim [verfasserIn] Sang Gyun Noh [verfasserIn] Yujin Park [verfasserIn] Dongwan Kang [verfasserIn] Pusoon Chun [verfasserIn] Hae Young Chung [verfasserIn] Hee Jin Jung [verfasserIn] Hyung Ryong Moon [verfasserIn]

Format:	E-Artikel
Sprache:	Englisch

Erschienen:	2018

Schlagwörter:	(E)-3-(2,4-dihydroxyphenyl)-1-(thiophene-2-yl)prop-2-en-1-one anti-melanogenesis thiophene chalcone tyrosinase inhibitor

Übergeordnetes Werk:	In: Molecules - MDPI AG, 2003, 23(2018), 10, p 2725
Übergeordnetes Werk:	volume:23 ; year:2018 ; number:10, p 2725

Links:	Link aufrufen Link aufrufen Link aufrufen Journal toc

DOI / URN:	10.3390/molecules23102725

Katalog-ID:	DOAJ008404798

Internformat


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245	1	2	\|a A Potent Tyrosinase Inhibitor, (E)-3-(2,4-Dihydroxyphenyl)-1-(thiophen-2-yl)prop-2-en-1-one, with Anti-Melanogenesis Properties in α-MSH and IBMX-Induced B16F10 Melanoma Cells
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520			\|a In this study, we designed and synthesized eight thiophene chalcone derivatives (1a–h) as tyrosinase inhibitors and evaluated their mushroom tyrosinase inhibitory activities. Of these eight compounds, (E)-3-(2,4-dihydroxyphenyl)-1-(thiophen-2-yl)prop-2-en-1-one (1c) showed strong competitive inhibition activity against mushroom tyrosinase with IC50 values of 0.013 μM for tyrosine hydroxylase and 0.93 μM for dopa oxidase. In addition, we used enzyme kinetics study and docking program to further evaluate the inhibitory mechanism of 1c toward tyrosinase. As an underlying mechanism of 1c mediated anti-melanogenic effect, we investigated the inhibitory activity against melanin contents and cellular tyrosinase in B16F10 melanoma cells. As the results, the enzyme kinetics and docking results supports that 1c highly interacts with tyrosinase residues in the tyrosinase active site and it can directly inhibit tyrosinase as competitive inhibitor. In addition, 1c exhibited dose-dependent inhibitory effects in melanin contents and intracellular tyrosinase on a-MSH and IBMX-induced B16F10 cells. Overall, our results suggested that 1c might be considered potent tyrosinase inhibitor for use in the development of therapeutic agents for diseases associated with hyperpigment disorders.
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matchkey_str	article:14203049:2018----::ptntrsnsihbtr34iyrxpey1hohnypo2noeihnieaoeeipoeteim
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allfields	10.3390/molecules23102725 doi (DE-627)DOAJ008404798 (DE-599)DOAJf656a47f20474f16a21c3d76a3cea61e DE-627 ger DE-627 rakwb eng QD241-441 Chang Seok Kim verfasserin aut A Potent Tyrosinase Inhibitor, (E)-3-(2,4-Dihydroxyphenyl)-1-(thiophen-2-yl)prop-2-en-1-one, with Anti-Melanogenesis Properties in α-MSH and IBMX-Induced B16F10 Melanoma Cells 2018 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier In this study, we designed and synthesized eight thiophene chalcone derivatives (1a–h) as tyrosinase inhibitors and evaluated their mushroom tyrosinase inhibitory activities. Of these eight compounds, (E)-3-(2,4-dihydroxyphenyl)-1-(thiophen-2-yl)prop-2-en-1-one (1c) showed strong competitive inhibition activity against mushroom tyrosinase with IC50 values of 0.013 μM for tyrosine hydroxylase and 0.93 μM for dopa oxidase. In addition, we used enzyme kinetics study and docking program to further evaluate the inhibitory mechanism of 1c toward tyrosinase. As an underlying mechanism of 1c mediated anti-melanogenic effect, we investigated the inhibitory activity against melanin contents and cellular tyrosinase in B16F10 melanoma cells. As the results, the enzyme kinetics and docking results supports that 1c highly interacts with tyrosinase residues in the tyrosinase active site and it can directly inhibit tyrosinase as competitive inhibitor. In addition, 1c exhibited dose-dependent inhibitory effects in melanin contents and intracellular tyrosinase on a-MSH and IBMX-induced B16F10 cells. Overall, our results suggested that 1c might be considered potent tyrosinase inhibitor for use in the development of therapeutic agents for diseases associated with hyperpigment disorders. (E)-3-(2,4-dihydroxyphenyl)-1-(thiophene-2-yl)prop-2-en-1-one anti-melanogenesis thiophene chalcone tyrosinase inhibitor Organic chemistry Sang Gyun Noh verfasserin aut Yujin Park verfasserin aut Dongwan Kang verfasserin aut Pusoon Chun verfasserin aut Hae Young Chung verfasserin aut Hee Jin Jung verfasserin aut Hyung Ryong Moon verfasserin aut In Molecules MDPI AG, 2003 23(2018), 10, p 2725 (DE-627)311313132 (DE-600)2008644-1 14203049 nnns volume:23 year:2018 number:10, p 2725 https://doi.org/10.3390/molecules23102725 kostenfrei https://doaj.org/article/f656a47f20474f16a21c3d76a3cea61e kostenfrei http://www.mdpi.com/1420-3049/23/10/2725 kostenfrei https://doaj.org/toc/1420-3049 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_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2005 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2055 GBV_ILN_2111 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 23 2018 10, p 2725
spelling	10.3390/molecules23102725 doi (DE-627)DOAJ008404798 (DE-599)DOAJf656a47f20474f16a21c3d76a3cea61e DE-627 ger DE-627 rakwb eng QD241-441 Chang Seok Kim verfasserin aut A Potent Tyrosinase Inhibitor, (E)-3-(2,4-Dihydroxyphenyl)-1-(thiophen-2-yl)prop-2-en-1-one, with Anti-Melanogenesis Properties in α-MSH and IBMX-Induced B16F10 Melanoma Cells 2018 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier In this study, we designed and synthesized eight thiophene chalcone derivatives (1a–h) as tyrosinase inhibitors and evaluated their mushroom tyrosinase inhibitory activities. Of these eight compounds, (E)-3-(2,4-dihydroxyphenyl)-1-(thiophen-2-yl)prop-2-en-1-one (1c) showed strong competitive inhibition activity against mushroom tyrosinase with IC50 values of 0.013 μM for tyrosine hydroxylase and 0.93 μM for dopa oxidase. In addition, we used enzyme kinetics study and docking program to further evaluate the inhibitory mechanism of 1c toward tyrosinase. As an underlying mechanism of 1c mediated anti-melanogenic effect, we investigated the inhibitory activity against melanin contents and cellular tyrosinase in B16F10 melanoma cells. As the results, the enzyme kinetics and docking results supports that 1c highly interacts with tyrosinase residues in the tyrosinase active site and it can directly inhibit tyrosinase as competitive inhibitor. In addition, 1c exhibited dose-dependent inhibitory effects in melanin contents and intracellular tyrosinase on a-MSH and IBMX-induced B16F10 cells. Overall, our results suggested that 1c might be considered potent tyrosinase inhibitor for use in the development of therapeutic agents for diseases associated with hyperpigment disorders. (E)-3-(2,4-dihydroxyphenyl)-1-(thiophene-2-yl)prop-2-en-1-one anti-melanogenesis thiophene chalcone tyrosinase inhibitor Organic chemistry Sang Gyun Noh verfasserin aut Yujin Park verfasserin aut Dongwan Kang verfasserin aut Pusoon Chun verfasserin aut Hae Young Chung verfasserin aut Hee Jin Jung verfasserin aut Hyung Ryong Moon verfasserin aut In Molecules MDPI AG, 2003 23(2018), 10, p 2725 (DE-627)311313132 (DE-600)2008644-1 14203049 nnns volume:23 year:2018 number:10, p 2725 https://doi.org/10.3390/molecules23102725 kostenfrei https://doaj.org/article/f656a47f20474f16a21c3d76a3cea61e kostenfrei http://www.mdpi.com/1420-3049/23/10/2725 kostenfrei https://doaj.org/toc/1420-3049 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_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2005 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2055 GBV_ILN_2111 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 23 2018 10, p 2725
allfields_unstemmed	10.3390/molecules23102725 doi (DE-627)DOAJ008404798 (DE-599)DOAJf656a47f20474f16a21c3d76a3cea61e DE-627 ger DE-627 rakwb eng QD241-441 Chang Seok Kim verfasserin aut A Potent Tyrosinase Inhibitor, (E)-3-(2,4-Dihydroxyphenyl)-1-(thiophen-2-yl)prop-2-en-1-one, with Anti-Melanogenesis Properties in α-MSH and IBMX-Induced B16F10 Melanoma Cells 2018 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier In this study, we designed and synthesized eight thiophene chalcone derivatives (1a–h) as tyrosinase inhibitors and evaluated their mushroom tyrosinase inhibitory activities. Of these eight compounds, (E)-3-(2,4-dihydroxyphenyl)-1-(thiophen-2-yl)prop-2-en-1-one (1c) showed strong competitive inhibition activity against mushroom tyrosinase with IC50 values of 0.013 μM for tyrosine hydroxylase and 0.93 μM for dopa oxidase. In addition, we used enzyme kinetics study and docking program to further evaluate the inhibitory mechanism of 1c toward tyrosinase. As an underlying mechanism of 1c mediated anti-melanogenic effect, we investigated the inhibitory activity against melanin contents and cellular tyrosinase in B16F10 melanoma cells. As the results, the enzyme kinetics and docking results supports that 1c highly interacts with tyrosinase residues in the tyrosinase active site and it can directly inhibit tyrosinase as competitive inhibitor. In addition, 1c exhibited dose-dependent inhibitory effects in melanin contents and intracellular tyrosinase on a-MSH and IBMX-induced B16F10 cells. Overall, our results suggested that 1c might be considered potent tyrosinase inhibitor for use in the development of therapeutic agents for diseases associated with hyperpigment disorders. (E)-3-(2,4-dihydroxyphenyl)-1-(thiophene-2-yl)prop-2-en-1-one anti-melanogenesis thiophene chalcone tyrosinase inhibitor Organic chemistry Sang Gyun Noh verfasserin aut Yujin Park verfasserin aut Dongwan Kang verfasserin aut Pusoon Chun verfasserin aut Hae Young Chung verfasserin aut Hee Jin Jung verfasserin aut Hyung Ryong Moon verfasserin aut In Molecules MDPI AG, 2003 23(2018), 10, p 2725 (DE-627)311313132 (DE-600)2008644-1 14203049 nnns volume:23 year:2018 number:10, p 2725 https://doi.org/10.3390/molecules23102725 kostenfrei https://doaj.org/article/f656a47f20474f16a21c3d76a3cea61e kostenfrei http://www.mdpi.com/1420-3049/23/10/2725 kostenfrei https://doaj.org/toc/1420-3049 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_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2005 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2055 GBV_ILN_2111 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 23 2018 10, p 2725
allfieldsGer	10.3390/molecules23102725 doi (DE-627)DOAJ008404798 (DE-599)DOAJf656a47f20474f16a21c3d76a3cea61e DE-627 ger DE-627 rakwb eng QD241-441 Chang Seok Kim verfasserin aut A Potent Tyrosinase Inhibitor, (E)-3-(2,4-Dihydroxyphenyl)-1-(thiophen-2-yl)prop-2-en-1-one, with Anti-Melanogenesis Properties in α-MSH and IBMX-Induced B16F10 Melanoma Cells 2018 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier In this study, we designed and synthesized eight thiophene chalcone derivatives (1a–h) as tyrosinase inhibitors and evaluated their mushroom tyrosinase inhibitory activities. Of these eight compounds, (E)-3-(2,4-dihydroxyphenyl)-1-(thiophen-2-yl)prop-2-en-1-one (1c) showed strong competitive inhibition activity against mushroom tyrosinase with IC50 values of 0.013 μM for tyrosine hydroxylase and 0.93 μM for dopa oxidase. In addition, we used enzyme kinetics study and docking program to further evaluate the inhibitory mechanism of 1c toward tyrosinase. As an underlying mechanism of 1c mediated anti-melanogenic effect, we investigated the inhibitory activity against melanin contents and cellular tyrosinase in B16F10 melanoma cells. As the results, the enzyme kinetics and docking results supports that 1c highly interacts with tyrosinase residues in the tyrosinase active site and it can directly inhibit tyrosinase as competitive inhibitor. In addition, 1c exhibited dose-dependent inhibitory effects in melanin contents and intracellular tyrosinase on a-MSH and IBMX-induced B16F10 cells. Overall, our results suggested that 1c might be considered potent tyrosinase inhibitor for use in the development of therapeutic agents for diseases associated with hyperpigment disorders. (E)-3-(2,4-dihydroxyphenyl)-1-(thiophene-2-yl)prop-2-en-1-one anti-melanogenesis thiophene chalcone tyrosinase inhibitor Organic chemistry Sang Gyun Noh verfasserin aut Yujin Park verfasserin aut Dongwan Kang verfasserin aut Pusoon Chun verfasserin aut Hae Young Chung verfasserin aut Hee Jin Jung verfasserin aut Hyung Ryong Moon verfasserin aut In Molecules MDPI AG, 2003 23(2018), 10, p 2725 (DE-627)311313132 (DE-600)2008644-1 14203049 nnns volume:23 year:2018 number:10, p 2725 https://doi.org/10.3390/molecules23102725 kostenfrei https://doaj.org/article/f656a47f20474f16a21c3d76a3cea61e kostenfrei http://www.mdpi.com/1420-3049/23/10/2725 kostenfrei https://doaj.org/toc/1420-3049 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_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2005 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2055 GBV_ILN_2111 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 23 2018 10, p 2725
allfieldsSound	10.3390/molecules23102725 doi (DE-627)DOAJ008404798 (DE-599)DOAJf656a47f20474f16a21c3d76a3cea61e DE-627 ger DE-627 rakwb eng QD241-441 Chang Seok Kim verfasserin aut A Potent Tyrosinase Inhibitor, (E)-3-(2,4-Dihydroxyphenyl)-1-(thiophen-2-yl)prop-2-en-1-one, with Anti-Melanogenesis Properties in α-MSH and IBMX-Induced B16F10 Melanoma Cells 2018 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier In this study, we designed and synthesized eight thiophene chalcone derivatives (1a–h) as tyrosinase inhibitors and evaluated their mushroom tyrosinase inhibitory activities. Of these eight compounds, (E)-3-(2,4-dihydroxyphenyl)-1-(thiophen-2-yl)prop-2-en-1-one (1c) showed strong competitive inhibition activity against mushroom tyrosinase with IC50 values of 0.013 μM for tyrosine hydroxylase and 0.93 μM for dopa oxidase. In addition, we used enzyme kinetics study and docking program to further evaluate the inhibitory mechanism of 1c toward tyrosinase. As an underlying mechanism of 1c mediated anti-melanogenic effect, we investigated the inhibitory activity against melanin contents and cellular tyrosinase in B16F10 melanoma cells. As the results, the enzyme kinetics and docking results supports that 1c highly interacts with tyrosinase residues in the tyrosinase active site and it can directly inhibit tyrosinase as competitive inhibitor. In addition, 1c exhibited dose-dependent inhibitory effects in melanin contents and intracellular tyrosinase on a-MSH and IBMX-induced B16F10 cells. Overall, our results suggested that 1c might be considered potent tyrosinase inhibitor for use in the development of therapeutic agents for diseases associated with hyperpigment disorders. (E)-3-(2,4-dihydroxyphenyl)-1-(thiophene-2-yl)prop-2-en-1-one anti-melanogenesis thiophene chalcone tyrosinase inhibitor Organic chemistry Sang Gyun Noh verfasserin aut Yujin Park verfasserin aut Dongwan Kang verfasserin aut Pusoon Chun verfasserin aut Hae Young Chung verfasserin aut Hee Jin Jung verfasserin aut Hyung Ryong Moon verfasserin aut In Molecules MDPI AG, 2003 23(2018), 10, p 2725 (DE-627)311313132 (DE-600)2008644-1 14203049 nnns volume:23 year:2018 number:10, p 2725 https://doi.org/10.3390/molecules23102725 kostenfrei https://doaj.org/article/f656a47f20474f16a21c3d76a3cea61e kostenfrei http://www.mdpi.com/1420-3049/23/10/2725 kostenfrei https://doaj.org/toc/1420-3049 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_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2005 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2055 GBV_ILN_2111 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 23 2018 10, p 2725
language	English
source	In Molecules 23(2018), 10, p 2725 volume:23 year:2018 number:10, p 2725
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topic_facet	(E)-3-(2,4-dihydroxyphenyl)-1-(thiophene-2-yl)prop-2-en-1-one anti-melanogenesis thiophene chalcone tyrosinase inhibitor Organic chemistry
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authorswithroles_txt_mv	Chang Seok Kim @@aut@@ Sang Gyun Noh @@aut@@ Yujin Park @@aut@@ Dongwan Kang @@aut@@ Pusoon Chun @@aut@@ Hae Young Chung @@aut@@ Hee Jin Jung @@aut@@ Hyung Ryong Moon @@aut@@
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callnumber-first	Q - Science
author	Chang Seok Kim
spellingShingle	Chang Seok Kim misc QD241-441 misc (E)-3-(2,4-dihydroxyphenyl)-1-(thiophene-2-yl)prop-2-en-1-one misc anti-melanogenesis misc thiophene chalcone misc tyrosinase inhibitor misc Organic chemistry A Potent Tyrosinase Inhibitor, (E)-3-(2,4-Dihydroxyphenyl)-1-(thiophen-2-yl)prop-2-en-1-one, with Anti-Melanogenesis Properties in α-MSH and IBMX-Induced B16F10 Melanoma Cells
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topic_title	QD241-441 A Potent Tyrosinase Inhibitor, (E)-3-(2,4-Dihydroxyphenyl)-1-(thiophen-2-yl)prop-2-en-1-one, with Anti-Melanogenesis Properties in α-MSH and IBMX-Induced B16F10 Melanoma Cells (E)-3-(2,4-dihydroxyphenyl)-1-(thiophene-2-yl)prop-2-en-1-one anti-melanogenesis thiophene chalcone tyrosinase inhibitor
topic	misc QD241-441 misc (E)-3-(2,4-dihydroxyphenyl)-1-(thiophene-2-yl)prop-2-en-1-one misc anti-melanogenesis misc thiophene chalcone misc tyrosinase inhibitor misc Organic chemistry
topic_unstemmed	misc QD241-441 misc (E)-3-(2,4-dihydroxyphenyl)-1-(thiophene-2-yl)prop-2-en-1-one misc anti-melanogenesis misc thiophene chalcone misc tyrosinase inhibitor misc Organic chemistry
topic_browse	misc QD241-441 misc (E)-3-(2,4-dihydroxyphenyl)-1-(thiophene-2-yl)prop-2-en-1-one misc anti-melanogenesis misc thiophene chalcone misc tyrosinase inhibitor misc Organic chemistry
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title	A Potent Tyrosinase Inhibitor, (E)-3-(2,4-Dihydroxyphenyl)-1-(thiophen-2-yl)prop-2-en-1-one, with Anti-Melanogenesis Properties in α-MSH and IBMX-Induced B16F10 Melanoma Cells
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title_full	A Potent Tyrosinase Inhibitor, (E)-3-(2,4-Dihydroxyphenyl)-1-(thiophen-2-yl)prop-2-en-1-one, with Anti-Melanogenesis Properties in α-MSH and IBMX-Induced B16F10 Melanoma Cells
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author_browse	Chang Seok Kim Sang Gyun Noh Yujin Park Dongwan Kang Pusoon Chun Hae Young Chung Hee Jin Jung Hyung Ryong Moon
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title_sort	potent tyrosinase inhibitor, (e)-3-(2,4-dihydroxyphenyl)-1-(thiophen-2-yl)prop-2-en-1-one, with anti-melanogenesis properties in α-msh and ibmx-induced b16f10 melanoma cells
callnumber	QD241-441
title_auth	A Potent Tyrosinase Inhibitor, (E)-3-(2,4-Dihydroxyphenyl)-1-(thiophen-2-yl)prop-2-en-1-one, with Anti-Melanogenesis Properties in α-MSH and IBMX-Induced B16F10 Melanoma Cells
abstract	In this study, we designed and synthesized eight thiophene chalcone derivatives (1a–h) as tyrosinase inhibitors and evaluated their mushroom tyrosinase inhibitory activities. Of these eight compounds, (E)-3-(2,4-dihydroxyphenyl)-1-(thiophen-2-yl)prop-2-en-1-one (1c) showed strong competitive inhibition activity against mushroom tyrosinase with IC50 values of 0.013 μM for tyrosine hydroxylase and 0.93 μM for dopa oxidase. In addition, we used enzyme kinetics study and docking program to further evaluate the inhibitory mechanism of 1c toward tyrosinase. As an underlying mechanism of 1c mediated anti-melanogenic effect, we investigated the inhibitory activity against melanin contents and cellular tyrosinase in B16F10 melanoma cells. As the results, the enzyme kinetics and docking results supports that 1c highly interacts with tyrosinase residues in the tyrosinase active site and it can directly inhibit tyrosinase as competitive inhibitor. In addition, 1c exhibited dose-dependent inhibitory effects in melanin contents and intracellular tyrosinase on a-MSH and IBMX-induced B16F10 cells. Overall, our results suggested that 1c might be considered potent tyrosinase inhibitor for use in the development of therapeutic agents for diseases associated with hyperpigment disorders.
abstractGer	In this study, we designed and synthesized eight thiophene chalcone derivatives (1a–h) as tyrosinase inhibitors and evaluated their mushroom tyrosinase inhibitory activities. Of these eight compounds, (E)-3-(2,4-dihydroxyphenyl)-1-(thiophen-2-yl)prop-2-en-1-one (1c) showed strong competitive inhibition activity against mushroom tyrosinase with IC50 values of 0.013 μM for tyrosine hydroxylase and 0.93 μM for dopa oxidase. In addition, we used enzyme kinetics study and docking program to further evaluate the inhibitory mechanism of 1c toward tyrosinase. As an underlying mechanism of 1c mediated anti-melanogenic effect, we investigated the inhibitory activity against melanin contents and cellular tyrosinase in B16F10 melanoma cells. As the results, the enzyme kinetics and docking results supports that 1c highly interacts with tyrosinase residues in the tyrosinase active site and it can directly inhibit tyrosinase as competitive inhibitor. In addition, 1c exhibited dose-dependent inhibitory effects in melanin contents and intracellular tyrosinase on a-MSH and IBMX-induced B16F10 cells. Overall, our results suggested that 1c might be considered potent tyrosinase inhibitor for use in the development of therapeutic agents for diseases associated with hyperpigment disorders.
abstract_unstemmed	In this study, we designed and synthesized eight thiophene chalcone derivatives (1a–h) as tyrosinase inhibitors and evaluated their mushroom tyrosinase inhibitory activities. Of these eight compounds, (E)-3-(2,4-dihydroxyphenyl)-1-(thiophen-2-yl)prop-2-en-1-one (1c) showed strong competitive inhibition activity against mushroom tyrosinase with IC50 values of 0.013 μM for tyrosine hydroxylase and 0.93 μM for dopa oxidase. In addition, we used enzyme kinetics study and docking program to further evaluate the inhibitory mechanism of 1c toward tyrosinase. As an underlying mechanism of 1c mediated anti-melanogenic effect, we investigated the inhibitory activity against melanin contents and cellular tyrosinase in B16F10 melanoma cells. As the results, the enzyme kinetics and docking results supports that 1c highly interacts with tyrosinase residues in the tyrosinase active site and it can directly inhibit tyrosinase as competitive inhibitor. In addition, 1c exhibited dose-dependent inhibitory effects in melanin contents and intracellular tyrosinase on a-MSH and IBMX-induced B16F10 cells. Overall, our results suggested that 1c might be considered potent tyrosinase inhibitor for use in the development of therapeutic agents for diseases associated with hyperpigment disorders.
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container_issue	10, p 2725
title_short	A Potent Tyrosinase Inhibitor, (E)-3-(2,4-Dihydroxyphenyl)-1-(thiophen-2-yl)prop-2-en-1-one, with Anti-Melanogenesis Properties in α-MSH and IBMX-Induced B16F10 Melanoma Cells
url	https://doi.org/10.3390/molecules23102725 https://doaj.org/article/f656a47f20474f16a21c3d76a3cea61e http://www.mdpi.com/1420-3049/23/10/2725 https://doaj.org/toc/1420-3049
remote_bool	true
author2	Sang Gyun Noh Yujin Park Dongwan Kang Pusoon Chun Hae Young Chung Hee Jin Jung Hyung Ryong Moon
author2Str	Sang Gyun Noh Yujin Park Dongwan Kang Pusoon Chun Hae Young Chung Hee Jin Jung Hyung Ryong Moon
ppnlink	311313132
callnumber-subject	QD - Chemistry
mediatype_str_mv	c
isOA_txt	true
hochschulschrift_bool	false
doi_str	10.3390/molecules23102725
callnumber-a	QD241-441
up_date	2024-07-03T17:46:54.152Z
_version_	1803580933830344704
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A Potent Tyrosinase Inhibitor, (E)-3-(2,4-Dihydroxyphenyl)-1-(thiophen-2-yl)prop-2-en-1-one, with Anti-Melanogenesis Properties in α-MSH and IBMX-Induced B16F10 Melanoma Cells

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