Evaluation of the Novel Synthetic Tyrosinase Inhibitor (<i<Z</i<)-3-(3-bromo-4-hydroxybenzylidene)thiochroman-4-one (MHY1498) <i<In Vitro</i< and <i<In Silico</i<

Tyrosinase is a key enzyme in melanin synthesis, catalyzing the initial rate-limiting steps of melanin synthesis. Abnormal and excessive melanin synthesis is the primary cause of serious skin disorders including melasma, senile lentigo, freckles, and age spots. In attempts to find potent and safe ty...
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Autor*in:	EunJin Bang [verfasserIn] Sang-Gyun Noh [verfasserIn] Sugyeong Ha [verfasserIn] Hee Jin Jung [verfasserIn] Dae Hyun Kim [verfasserIn] A Kyoung Lee [verfasserIn] Min Kyung Hyun [verfasserIn] Dongwan Kang [verfasserIn] Sanggwon Lee [verfasserIn] Chaeun Park [verfasserIn] Hyung Ryong Moon [verfasserIn] Hae Young Chung [verfasserIn]

Format:	E-Artikel
Sprache:	Englisch

Erschienen:	2018

Schlagwörter:	( tyrosinase B16F10 α-melanocyte-stimulating hormone

Übergeordnetes Werk:	In: Molecules - MDPI AG, 2003, 23(2018), 12, p 3307
Übergeordnetes Werk:	volume:23 ; year:2018 ; number:12, p 3307

Links:	Link aufrufen Link aufrufen Link aufrufen Journal toc

DOI / URN:	10.3390/molecules23123307

Katalog-ID:	DOAJ040036685

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520			\|a Tyrosinase is a key enzyme in melanin synthesis, catalyzing the initial rate-limiting steps of melanin synthesis. Abnormal and excessive melanin synthesis is the primary cause of serious skin disorders including melasma, senile lentigo, freckles, and age spots. In attempts to find potent and safe tyrosinase inhibitors, we designed and synthesized a novel compound, (<i<Z</i<)-3-(3-bromo-4-hydroxybenzylidene)thiochroman-4-one (MHY1498), and evaluated its tyrosinase inhibitory activity <i<in vitro</i< and <i<in silico</i<. The chemical structures of (<i<Z</i<)-3-benzylidenethiochroman-4-one analogues, including the novel compound MHY1498, were rationally designed and synthesized as hybrid structures of reported potent tyrosinase inhibitors, which were confirmed both <i<in vitro</i< and <i<in vivo</i<: (<i<Z</i<)-5-(substituted benzylidene)thiazolidine-2,4-diones (Compound A) and 2-(substituted phenyl)benzo[<i<d</i<]thiazoles (Compound B). During screening, MHY1498 showed a strong dose-dependent inhibitory effect on mushroom tyrosinase. The IC<sub<50</sub< value of MHY1498 (4.1 ± 0.6 μM) was significantly lower than that of the positive control, kojic acid (22.0 ± 4.7 μM). <i<In silico</i< molecular multi-docking simulation and inhibition mechanism studies indicated that MHY1498 interacts competitively with the tyrosinase enzyme, with greater affinity for the active site of tyrosinase than the positive control. Furthermore, in B16F10 melanoma cells treated with α-melanocyte-stimulating hormone, MHY1498 suppressed both melanin production and tyrosinase activity. In conclusion, our data demonstrate that MHY1498, a synthesized novel compound, effectively inhibits tyrosinase activity and has potential for treating hyperpigmentation and related disorders.
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allfields	10.3390/molecules23123307 doi (DE-627)DOAJ040036685 (DE-599)DOAJbe8cf39cd9dc4f9e811f15d943447dbf DE-627 ger DE-627 rakwb eng QD241-441 EunJin Bang verfasserin aut Evaluation of the Novel Synthetic Tyrosinase Inhibitor (<i<Z</i<)-3-(3-bromo-4-hydroxybenzylidene)thiochroman-4-one (MHY1498) <i<In Vitro</i< and <i<In Silico</i< 2018 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Tyrosinase is a key enzyme in melanin synthesis, catalyzing the initial rate-limiting steps of melanin synthesis. Abnormal and excessive melanin synthesis is the primary cause of serious skin disorders including melasma, senile lentigo, freckles, and age spots. In attempts to find potent and safe tyrosinase inhibitors, we designed and synthesized a novel compound, (<i<Z</i<)-3-(3-bromo-4-hydroxybenzylidene)thiochroman-4-one (MHY1498), and evaluated its tyrosinase inhibitory activity <i<in vitro</i< and <i<in silico</i<. The chemical structures of (<i<Z</i<)-3-benzylidenethiochroman-4-one analogues, including the novel compound MHY1498, were rationally designed and synthesized as hybrid structures of reported potent tyrosinase inhibitors, which were confirmed both <i<in vitro</i< and <i<in vivo</i<: (<i<Z</i<)-5-(substituted benzylidene)thiazolidine-2,4-diones (Compound A) and 2-(substituted phenyl)benzo[<i<d</i<]thiazoles (Compound B). During screening, MHY1498 showed a strong dose-dependent inhibitory effect on mushroom tyrosinase. The IC<sub<50</sub< value of MHY1498 (4.1 ± 0.6 μM) was significantly lower than that of the positive control, kojic acid (22.0 ± 4.7 μM). <i<In silico</i< molecular multi-docking simulation and inhibition mechanism studies indicated that MHY1498 interacts competitively with the tyrosinase enzyme, with greater affinity for the active site of tyrosinase than the positive control. Furthermore, in B16F10 melanoma cells treated with α-melanocyte-stimulating hormone, MHY1498 suppressed both melanin production and tyrosinase activity. In conclusion, our data demonstrate that MHY1498, a synthesized novel compound, effectively inhibits tyrosinase activity and has potential for treating hyperpigmentation and related disorders. (<i<Z</i<)-3-(3-bromo-4-hydroxybenzylidene)thiochroman-4-one tyrosinase <i<in silico</i< docking simulation B16F10 α-melanocyte-stimulating hormone Organic chemistry Sang-Gyun Noh verfasserin aut Sugyeong Ha verfasserin aut Hee Jin Jung verfasserin aut Dae Hyun Kim verfasserin aut A Kyoung Lee verfasserin aut Min Kyung Hyun verfasserin aut Dongwan Kang verfasserin aut Sanggwon Lee verfasserin aut Chaeun Park verfasserin aut Hyung Ryong Moon verfasserin aut Hae Young Chung verfasserin aut In Molecules MDPI AG, 2003 23(2018), 12, p 3307 (DE-627)311313132 (DE-600)2008644-1 14203049 nnns volume:23 year:2018 number:12, p 3307 https://doi.org/10.3390/molecules23123307 kostenfrei https://doaj.org/article/be8cf39cd9dc4f9e811f15d943447dbf kostenfrei https://www.mdpi.com/1420-3049/23/12/3307 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 12, p 3307
spelling	10.3390/molecules23123307 doi (DE-627)DOAJ040036685 (DE-599)DOAJbe8cf39cd9dc4f9e811f15d943447dbf DE-627 ger DE-627 rakwb eng QD241-441 EunJin Bang verfasserin aut Evaluation of the Novel Synthetic Tyrosinase Inhibitor (<i<Z</i<)-3-(3-bromo-4-hydroxybenzylidene)thiochroman-4-one (MHY1498) <i<In Vitro</i< and <i<In Silico</i< 2018 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Tyrosinase is a key enzyme in melanin synthesis, catalyzing the initial rate-limiting steps of melanin synthesis. Abnormal and excessive melanin synthesis is the primary cause of serious skin disorders including melasma, senile lentigo, freckles, and age spots. In attempts to find potent and safe tyrosinase inhibitors, we designed and synthesized a novel compound, (<i<Z</i<)-3-(3-bromo-4-hydroxybenzylidene)thiochroman-4-one (MHY1498), and evaluated its tyrosinase inhibitory activity <i<in vitro</i< and <i<in silico</i<. The chemical structures of (<i<Z</i<)-3-benzylidenethiochroman-4-one analogues, including the novel compound MHY1498, were rationally designed and synthesized as hybrid structures of reported potent tyrosinase inhibitors, which were confirmed both <i<in vitro</i< and <i<in vivo</i<: (<i<Z</i<)-5-(substituted benzylidene)thiazolidine-2,4-diones (Compound A) and 2-(substituted phenyl)benzo[<i<d</i<]thiazoles (Compound B). During screening, MHY1498 showed a strong dose-dependent inhibitory effect on mushroom tyrosinase. The IC<sub<50</sub< value of MHY1498 (4.1 ± 0.6 μM) was significantly lower than that of the positive control, kojic acid (22.0 ± 4.7 μM). <i<In silico</i< molecular multi-docking simulation and inhibition mechanism studies indicated that MHY1498 interacts competitively with the tyrosinase enzyme, with greater affinity for the active site of tyrosinase than the positive control. Furthermore, in B16F10 melanoma cells treated with α-melanocyte-stimulating hormone, MHY1498 suppressed both melanin production and tyrosinase activity. In conclusion, our data demonstrate that MHY1498, a synthesized novel compound, effectively inhibits tyrosinase activity and has potential for treating hyperpigmentation and related disorders. (<i<Z</i<)-3-(3-bromo-4-hydroxybenzylidene)thiochroman-4-one tyrosinase <i<in silico</i< docking simulation B16F10 α-melanocyte-stimulating hormone Organic chemistry Sang-Gyun Noh verfasserin aut Sugyeong Ha verfasserin aut Hee Jin Jung verfasserin aut Dae Hyun Kim verfasserin aut A Kyoung Lee verfasserin aut Min Kyung Hyun verfasserin aut Dongwan Kang verfasserin aut Sanggwon Lee verfasserin aut Chaeun Park verfasserin aut Hyung Ryong Moon verfasserin aut Hae Young Chung verfasserin aut In Molecules MDPI AG, 2003 23(2018), 12, p 3307 (DE-627)311313132 (DE-600)2008644-1 14203049 nnns volume:23 year:2018 number:12, p 3307 https://doi.org/10.3390/molecules23123307 kostenfrei https://doaj.org/article/be8cf39cd9dc4f9e811f15d943447dbf kostenfrei https://www.mdpi.com/1420-3049/23/12/3307 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 12, p 3307
allfields_unstemmed	10.3390/molecules23123307 doi (DE-627)DOAJ040036685 (DE-599)DOAJbe8cf39cd9dc4f9e811f15d943447dbf DE-627 ger DE-627 rakwb eng QD241-441 EunJin Bang verfasserin aut Evaluation of the Novel Synthetic Tyrosinase Inhibitor (<i<Z</i<)-3-(3-bromo-4-hydroxybenzylidene)thiochroman-4-one (MHY1498) <i<In Vitro</i< and <i<In Silico</i< 2018 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Tyrosinase is a key enzyme in melanin synthesis, catalyzing the initial rate-limiting steps of melanin synthesis. Abnormal and excessive melanin synthesis is the primary cause of serious skin disorders including melasma, senile lentigo, freckles, and age spots. In attempts to find potent and safe tyrosinase inhibitors, we designed and synthesized a novel compound, (<i<Z</i<)-3-(3-bromo-4-hydroxybenzylidene)thiochroman-4-one (MHY1498), and evaluated its tyrosinase inhibitory activity <i<in vitro</i< and <i<in silico</i<. The chemical structures of (<i<Z</i<)-3-benzylidenethiochroman-4-one analogues, including the novel compound MHY1498, were rationally designed and synthesized as hybrid structures of reported potent tyrosinase inhibitors, which were confirmed both <i<in vitro</i< and <i<in vivo</i<: (<i<Z</i<)-5-(substituted benzylidene)thiazolidine-2,4-diones (Compound A) and 2-(substituted phenyl)benzo[<i<d</i<]thiazoles (Compound B). During screening, MHY1498 showed a strong dose-dependent inhibitory effect on mushroom tyrosinase. The IC<sub<50</sub< value of MHY1498 (4.1 ± 0.6 μM) was significantly lower than that of the positive control, kojic acid (22.0 ± 4.7 μM). <i<In silico</i< molecular multi-docking simulation and inhibition mechanism studies indicated that MHY1498 interacts competitively with the tyrosinase enzyme, with greater affinity for the active site of tyrosinase than the positive control. Furthermore, in B16F10 melanoma cells treated with α-melanocyte-stimulating hormone, MHY1498 suppressed both melanin production and tyrosinase activity. In conclusion, our data demonstrate that MHY1498, a synthesized novel compound, effectively inhibits tyrosinase activity and has potential for treating hyperpigmentation and related disorders. (<i<Z</i<)-3-(3-bromo-4-hydroxybenzylidene)thiochroman-4-one tyrosinase <i<in silico</i< docking simulation B16F10 α-melanocyte-stimulating hormone Organic chemistry Sang-Gyun Noh verfasserin aut Sugyeong Ha verfasserin aut Hee Jin Jung verfasserin aut Dae Hyun Kim verfasserin aut A Kyoung Lee verfasserin aut Min Kyung Hyun verfasserin aut Dongwan Kang verfasserin aut Sanggwon Lee verfasserin aut Chaeun Park verfasserin aut Hyung Ryong Moon verfasserin aut Hae Young Chung verfasserin aut In Molecules MDPI AG, 2003 23(2018), 12, p 3307 (DE-627)311313132 (DE-600)2008644-1 14203049 nnns volume:23 year:2018 number:12, p 3307 https://doi.org/10.3390/molecules23123307 kostenfrei https://doaj.org/article/be8cf39cd9dc4f9e811f15d943447dbf kostenfrei https://www.mdpi.com/1420-3049/23/12/3307 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 12, p 3307
allfieldsGer	10.3390/molecules23123307 doi (DE-627)DOAJ040036685 (DE-599)DOAJbe8cf39cd9dc4f9e811f15d943447dbf DE-627 ger DE-627 rakwb eng QD241-441 EunJin Bang verfasserin aut Evaluation of the Novel Synthetic Tyrosinase Inhibitor (<i<Z</i<)-3-(3-bromo-4-hydroxybenzylidene)thiochroman-4-one (MHY1498) <i<In Vitro</i< and <i<In Silico</i< 2018 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Tyrosinase is a key enzyme in melanin synthesis, catalyzing the initial rate-limiting steps of melanin synthesis. Abnormal and excessive melanin synthesis is the primary cause of serious skin disorders including melasma, senile lentigo, freckles, and age spots. In attempts to find potent and safe tyrosinase inhibitors, we designed and synthesized a novel compound, (<i<Z</i<)-3-(3-bromo-4-hydroxybenzylidene)thiochroman-4-one (MHY1498), and evaluated its tyrosinase inhibitory activity <i<in vitro</i< and <i<in silico</i<. The chemical structures of (<i<Z</i<)-3-benzylidenethiochroman-4-one analogues, including the novel compound MHY1498, were rationally designed and synthesized as hybrid structures of reported potent tyrosinase inhibitors, which were confirmed both <i<in vitro</i< and <i<in vivo</i<: (<i<Z</i<)-5-(substituted benzylidene)thiazolidine-2,4-diones (Compound A) and 2-(substituted phenyl)benzo[<i<d</i<]thiazoles (Compound B). During screening, MHY1498 showed a strong dose-dependent inhibitory effect on mushroom tyrosinase. The IC<sub<50</sub< value of MHY1498 (4.1 ± 0.6 μM) was significantly lower than that of the positive control, kojic acid (22.0 ± 4.7 μM). <i<In silico</i< molecular multi-docking simulation and inhibition mechanism studies indicated that MHY1498 interacts competitively with the tyrosinase enzyme, with greater affinity for the active site of tyrosinase than the positive control. Furthermore, in B16F10 melanoma cells treated with α-melanocyte-stimulating hormone, MHY1498 suppressed both melanin production and tyrosinase activity. In conclusion, our data demonstrate that MHY1498, a synthesized novel compound, effectively inhibits tyrosinase activity and has potential for treating hyperpigmentation and related disorders. (<i<Z</i<)-3-(3-bromo-4-hydroxybenzylidene)thiochroman-4-one tyrosinase <i<in silico</i< docking simulation B16F10 α-melanocyte-stimulating hormone Organic chemistry Sang-Gyun Noh verfasserin aut Sugyeong Ha verfasserin aut Hee Jin Jung verfasserin aut Dae Hyun Kim verfasserin aut A Kyoung Lee verfasserin aut Min Kyung Hyun verfasserin aut Dongwan Kang verfasserin aut Sanggwon Lee verfasserin aut Chaeun Park verfasserin aut Hyung Ryong Moon verfasserin aut Hae Young Chung verfasserin aut In Molecules MDPI AG, 2003 23(2018), 12, p 3307 (DE-627)311313132 (DE-600)2008644-1 14203049 nnns volume:23 year:2018 number:12, p 3307 https://doi.org/10.3390/molecules23123307 kostenfrei https://doaj.org/article/be8cf39cd9dc4f9e811f15d943447dbf kostenfrei https://www.mdpi.com/1420-3049/23/12/3307 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 12, p 3307
allfieldsSound	10.3390/molecules23123307 doi (DE-627)DOAJ040036685 (DE-599)DOAJbe8cf39cd9dc4f9e811f15d943447dbf DE-627 ger DE-627 rakwb eng QD241-441 EunJin Bang verfasserin aut Evaluation of the Novel Synthetic Tyrosinase Inhibitor (<i<Z</i<)-3-(3-bromo-4-hydroxybenzylidene)thiochroman-4-one (MHY1498) <i<In Vitro</i< and <i<In Silico</i< 2018 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Tyrosinase is a key enzyme in melanin synthesis, catalyzing the initial rate-limiting steps of melanin synthesis. Abnormal and excessive melanin synthesis is the primary cause of serious skin disorders including melasma, senile lentigo, freckles, and age spots. In attempts to find potent and safe tyrosinase inhibitors, we designed and synthesized a novel compound, (<i<Z</i<)-3-(3-bromo-4-hydroxybenzylidene)thiochroman-4-one (MHY1498), and evaluated its tyrosinase inhibitory activity <i<in vitro</i< and <i<in silico</i<. The chemical structures of (<i<Z</i<)-3-benzylidenethiochroman-4-one analogues, including the novel compound MHY1498, were rationally designed and synthesized as hybrid structures of reported potent tyrosinase inhibitors, which were confirmed both <i<in vitro</i< and <i<in vivo</i<: (<i<Z</i<)-5-(substituted benzylidene)thiazolidine-2,4-diones (Compound A) and 2-(substituted phenyl)benzo[<i<d</i<]thiazoles (Compound B). During screening, MHY1498 showed a strong dose-dependent inhibitory effect on mushroom tyrosinase. The IC<sub<50</sub< value of MHY1498 (4.1 ± 0.6 μM) was significantly lower than that of the positive control, kojic acid (22.0 ± 4.7 μM). <i<In silico</i< molecular multi-docking simulation and inhibition mechanism studies indicated that MHY1498 interacts competitively with the tyrosinase enzyme, with greater affinity for the active site of tyrosinase than the positive control. Furthermore, in B16F10 melanoma cells treated with α-melanocyte-stimulating hormone, MHY1498 suppressed both melanin production and tyrosinase activity. In conclusion, our data demonstrate that MHY1498, a synthesized novel compound, effectively inhibits tyrosinase activity and has potential for treating hyperpigmentation and related disorders. (<i<Z</i<)-3-(3-bromo-4-hydroxybenzylidene)thiochroman-4-one tyrosinase <i<in silico</i< docking simulation B16F10 α-melanocyte-stimulating hormone Organic chemistry Sang-Gyun Noh verfasserin aut Sugyeong Ha verfasserin aut Hee Jin Jung verfasserin aut Dae Hyun Kim verfasserin aut A Kyoung Lee verfasserin aut Min Kyung Hyun verfasserin aut Dongwan Kang verfasserin aut Sanggwon Lee verfasserin aut Chaeun Park verfasserin aut Hyung Ryong Moon verfasserin aut Hae Young Chung verfasserin aut In Molecules MDPI AG, 2003 23(2018), 12, p 3307 (DE-627)311313132 (DE-600)2008644-1 14203049 nnns volume:23 year:2018 number:12, p 3307 https://doi.org/10.3390/molecules23123307 kostenfrei https://doaj.org/article/be8cf39cd9dc4f9e811f15d943447dbf kostenfrei https://www.mdpi.com/1420-3049/23/12/3307 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 12, p 3307
language	English
source	In Molecules 23(2018), 12, p 3307 volume:23 year:2018 number:12, p 3307
sourceStr	In Molecules 23(2018), 12, p 3307 volume:23 year:2018 number:12, p 3307
format_phy_str_mv	Article
institution	findex.gbv.de
topic_facet	(<i<Z</i<)-3-(3-bromo-4-hydroxybenzylidene)thiochroman-4-one tyrosinase <i<in silico</i< docking simulation B16F10 α-melanocyte-stimulating hormone Organic chemistry
isfreeaccess_bool	true
container_title	Molecules
authorswithroles_txt_mv	EunJin Bang @@aut@@ Sang-Gyun Noh @@aut@@ Sugyeong Ha @@aut@@ Hee Jin Jung @@aut@@ Dae Hyun Kim @@aut@@ A Kyoung Lee @@aut@@ Min Kyung Hyun @@aut@@ Dongwan Kang @@aut@@ Sanggwon Lee @@aut@@ Chaeun Park @@aut@@ Hyung Ryong Moon @@aut@@ Hae Young Chung @@aut@@
publishDateDaySort_date	2018-01-01T00:00:00Z
hierarchy_top_id	311313132
id	DOAJ040036685
language_de	englisch
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Abnormal and excessive melanin synthesis is the primary cause of serious skin disorders including melasma, senile lentigo, freckles, and age spots. In attempts to find potent and safe tyrosinase inhibitors, we designed and synthesized a novel compound, (<i<Z</i<)-3-(3-bromo-4-hydroxybenzylidene)thiochroman-4-one (MHY1498), and evaluated its tyrosinase inhibitory activity <i<in vitro</i< and <i<in silico</i<. The chemical structures of (<i<Z</i<)-3-benzylidenethiochroman-4-one analogues, including the novel compound MHY1498, were rationally designed and synthesized as hybrid structures of reported potent tyrosinase inhibitors, which were confirmed both <i<in vitro</i< and <i<in vivo</i<: (<i<Z</i<)-5-(substituted benzylidene)thiazolidine-2,4-diones (Compound A) and 2-(substituted phenyl)benzo[<i<d</i<]thiazoles (Compound B). During screening, MHY1498 showed a strong dose-dependent inhibitory effect on mushroom tyrosinase. 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callnumber-first	Q - Science
author	EunJin Bang
spellingShingle	EunJin Bang misc QD241-441 misc (<i<Z</i<)-3-(3-bromo-4-hydroxybenzylidene)thiochroman-4-one misc tyrosinase misc <i<in silico</i< docking simulation misc B16F10 misc α-melanocyte-stimulating hormone misc Organic chemistry Evaluation of the Novel Synthetic Tyrosinase Inhibitor (<i<Z</i<)-3-(3-bromo-4-hydroxybenzylidene)thiochroman-4-one (MHY1498) <i<In Vitro</i< and <i<In Silico</i<
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topic_title	QD241-441 Evaluation of the Novel Synthetic Tyrosinase Inhibitor (<i<Z</i<)-3-(3-bromo-4-hydroxybenzylidene)thiochroman-4-one (MHY1498) <i<In Vitro</i< and <i<In Silico</i< (<i<Z</i<)-3-(3-bromo-4-hydroxybenzylidene)thiochroman-4-one tyrosinase <i<in silico</i< docking simulation B16F10 α-melanocyte-stimulating hormone
topic	misc QD241-441 misc (<i<Z</i<)-3-(3-bromo-4-hydroxybenzylidene)thiochroman-4-one misc tyrosinase misc <i<in silico</i< docking simulation misc B16F10 misc α-melanocyte-stimulating hormone misc Organic chemistry
topic_unstemmed	misc QD241-441 misc (<i<Z</i<)-3-(3-bromo-4-hydroxybenzylidene)thiochroman-4-one misc tyrosinase misc <i<in silico</i< docking simulation misc B16F10 misc α-melanocyte-stimulating hormone misc Organic chemistry
topic_browse	misc QD241-441 misc (<i<Z</i<)-3-(3-bromo-4-hydroxybenzylidene)thiochroman-4-one misc tyrosinase misc <i<in silico</i< docking simulation misc B16F10 misc α-melanocyte-stimulating hormone misc Organic chemistry
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title	Evaluation of the Novel Synthetic Tyrosinase Inhibitor (<i<Z</i<)-3-(3-bromo-4-hydroxybenzylidene)thiochroman-4-one (MHY1498) <i<In Vitro</i< and <i<In Silico</i<
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title_full	Evaluation of the Novel Synthetic Tyrosinase Inhibitor (<i<Z</i<)-3-(3-bromo-4-hydroxybenzylidene)thiochroman-4-one (MHY1498) <i<In Vitro</i< and <i<In Silico</i<
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author_browse	EunJin Bang Sang-Gyun Noh Sugyeong Ha Hee Jin Jung Dae Hyun Kim A Kyoung Lee Min Kyung Hyun Dongwan Kang Sanggwon Lee Chaeun Park Hyung Ryong Moon Hae Young Chung
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author-letter	EunJin Bang
doi_str_mv	10.3390/molecules23123307
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title_sort	evaluation of the novel synthetic tyrosinase inhibitor (<i<z</i<)-3-(3-bromo-4-hydroxybenzylidene)thiochroman-4-one (mhy1498) <i<in vitro</i< and <i<in silico</i<
callnumber	QD241-441
title_auth	Evaluation of the Novel Synthetic Tyrosinase Inhibitor (<i<Z</i<)-3-(3-bromo-4-hydroxybenzylidene)thiochroman-4-one (MHY1498) <i<In Vitro</i< and <i<In Silico</i<
abstract	Tyrosinase is a key enzyme in melanin synthesis, catalyzing the initial rate-limiting steps of melanin synthesis. Abnormal and excessive melanin synthesis is the primary cause of serious skin disorders including melasma, senile lentigo, freckles, and age spots. In attempts to find potent and safe tyrosinase inhibitors, we designed and synthesized a novel compound, (<i<Z</i<)-3-(3-bromo-4-hydroxybenzylidene)thiochroman-4-one (MHY1498), and evaluated its tyrosinase inhibitory activity <i<in vitro</i< and <i<in silico</i<. The chemical structures of (<i<Z</i<)-3-benzylidenethiochroman-4-one analogues, including the novel compound MHY1498, were rationally designed and synthesized as hybrid structures of reported potent tyrosinase inhibitors, which were confirmed both <i<in vitro</i< and <i<in vivo</i<: (<i<Z</i<)-5-(substituted benzylidene)thiazolidine-2,4-diones (Compound A) and 2-(substituted phenyl)benzo[<i<d</i<]thiazoles (Compound B). During screening, MHY1498 showed a strong dose-dependent inhibitory effect on mushroom tyrosinase. The IC<sub<50</sub< value of MHY1498 (4.1 ± 0.6 μM) was significantly lower than that of the positive control, kojic acid (22.0 ± 4.7 μM). <i<In silico</i< molecular multi-docking simulation and inhibition mechanism studies indicated that MHY1498 interacts competitively with the tyrosinase enzyme, with greater affinity for the active site of tyrosinase than the positive control. Furthermore, in B16F10 melanoma cells treated with α-melanocyte-stimulating hormone, MHY1498 suppressed both melanin production and tyrosinase activity. In conclusion, our data demonstrate that MHY1498, a synthesized novel compound, effectively inhibits tyrosinase activity and has potential for treating hyperpigmentation and related disorders.
abstractGer	Tyrosinase is a key enzyme in melanin synthesis, catalyzing the initial rate-limiting steps of melanin synthesis. Abnormal and excessive melanin synthesis is the primary cause of serious skin disorders including melasma, senile lentigo, freckles, and age spots. In attempts to find potent and safe tyrosinase inhibitors, we designed and synthesized a novel compound, (<i<Z</i<)-3-(3-bromo-4-hydroxybenzylidene)thiochroman-4-one (MHY1498), and evaluated its tyrosinase inhibitory activity <i<in vitro</i< and <i<in silico</i<. The chemical structures of (<i<Z</i<)-3-benzylidenethiochroman-4-one analogues, including the novel compound MHY1498, were rationally designed and synthesized as hybrid structures of reported potent tyrosinase inhibitors, which were confirmed both <i<in vitro</i< and <i<in vivo</i<: (<i<Z</i<)-5-(substituted benzylidene)thiazolidine-2,4-diones (Compound A) and 2-(substituted phenyl)benzo[<i<d</i<]thiazoles (Compound B). During screening, MHY1498 showed a strong dose-dependent inhibitory effect on mushroom tyrosinase. The IC<sub<50</sub< value of MHY1498 (4.1 ± 0.6 μM) was significantly lower than that of the positive control, kojic acid (22.0 ± 4.7 μM). <i<In silico</i< molecular multi-docking simulation and inhibition mechanism studies indicated that MHY1498 interacts competitively with the tyrosinase enzyme, with greater affinity for the active site of tyrosinase than the positive control. Furthermore, in B16F10 melanoma cells treated with α-melanocyte-stimulating hormone, MHY1498 suppressed both melanin production and tyrosinase activity. In conclusion, our data demonstrate that MHY1498, a synthesized novel compound, effectively inhibits tyrosinase activity and has potential for treating hyperpigmentation and related disorders.
abstract_unstemmed	Tyrosinase is a key enzyme in melanin synthesis, catalyzing the initial rate-limiting steps of melanin synthesis. Abnormal and excessive melanin synthesis is the primary cause of serious skin disorders including melasma, senile lentigo, freckles, and age spots. In attempts to find potent and safe tyrosinase inhibitors, we designed and synthesized a novel compound, (<i<Z</i<)-3-(3-bromo-4-hydroxybenzylidene)thiochroman-4-one (MHY1498), and evaluated its tyrosinase inhibitory activity <i<in vitro</i< and <i<in silico</i<. The chemical structures of (<i<Z</i<)-3-benzylidenethiochroman-4-one analogues, including the novel compound MHY1498, were rationally designed and synthesized as hybrid structures of reported potent tyrosinase inhibitors, which were confirmed both <i<in vitro</i< and <i<in vivo</i<: (<i<Z</i<)-5-(substituted benzylidene)thiazolidine-2,4-diones (Compound A) and 2-(substituted phenyl)benzo[<i<d</i<]thiazoles (Compound B). During screening, MHY1498 showed a strong dose-dependent inhibitory effect on mushroom tyrosinase. The IC<sub<50</sub< value of MHY1498 (4.1 ± 0.6 μM) was significantly lower than that of the positive control, kojic acid (22.0 ± 4.7 μM). <i<In silico</i< molecular multi-docking simulation and inhibition mechanism studies indicated that MHY1498 interacts competitively with the tyrosinase enzyme, with greater affinity for the active site of tyrosinase than the positive control. Furthermore, in B16F10 melanoma cells treated with α-melanocyte-stimulating hormone, MHY1498 suppressed both melanin production and tyrosinase activity. In conclusion, our data demonstrate that MHY1498, a synthesized novel compound, effectively inhibits tyrosinase activity and has potential for treating hyperpigmentation and related disorders.
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title_short	Evaluation of the Novel Synthetic Tyrosinase Inhibitor (<i<Z</i<)-3-(3-bromo-4-hydroxybenzylidene)thiochroman-4-one (MHY1498) <i<In Vitro</i< and <i<In Silico</i<
url	https://doi.org/10.3390/molecules23123307 https://doaj.org/article/be8cf39cd9dc4f9e811f15d943447dbf https://www.mdpi.com/1420-3049/23/12/3307 https://doaj.org/toc/1420-3049
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Evaluation of the Novel Synthetic Tyrosinase Inhibitor (<i<Z</i<)-3-(3-bromo-4-hydroxybenzylidene)thiochroman-4-one (MHY1498) <i<In Vitro</i< and <i<In Silico</i<

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