Design, Synthesis, In Vitro, and In Silico Insights of 5-(Substituted benzylidene)-2-phenylthiazol-4(5<i<H</i<)-one Derivatives: A Novel Class of Anti-Melanogenic Compounds

(<i<Z</i<)-5-Benzylidene-2-phenylthiazol-4(5<i<H</i<)-one ((<i<Z</i<)-BPT) derivatives were designed by combining the structural characteristics of two tyrosinase inhibitors. The double-bond geometry of trisubstituted alkenes, (<i<Z</i<)-BPTs <b<...
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Autor*in:	Dahye Yoon [verfasserIn] Min Kyung Kang [verfasserIn] Hee Jin Jung [verfasserIn] Sultan Ullah [verfasserIn] Jieun Lee [verfasserIn] Yeongmu Jeong [verfasserIn] Sang Gyun Noh [verfasserIn] Dongwan Kang [verfasserIn] Yujin Park [verfasserIn] Pusoon Chun [verfasserIn] Hae Young Chung [verfasserIn] Hyung Ryong Moon [verfasserIn]

Format:	E-Artikel
Sprache:	Englisch

Erschienen:	2023

Schlagwörter:	( tyrosinase melanogenesis kojic acid antioxidant in silico

Übergeordnetes Werk:	In: Molecules - MDPI AG, 2003, 28(2023), 8, p 3293
Übergeordnetes Werk:	volume:28 ; year:2023 ; number:8, p 3293

Links:	Link aufrufen Link aufrufen Link aufrufen Journal toc

DOI / URN:	10.3390/molecules28083293

Katalog-ID:	DOAJ089803531

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245	1	0	\|a Design, Synthesis, In Vitro, and In Silico Insights of 5-(Substituted benzylidene)-2-phenylthiazol-4(5<i<H</i<)-one Derivatives: A Novel Class of Anti-Melanogenic Compounds
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520			\|a (<i<Z</i<)-5-Benzylidene-2-phenylthiazol-4(5<i<H</i<)-one ((<i<Z</i<)-BPT) derivatives were designed by combining the structural characteristics of two tyrosinase inhibitors. The double-bond geometry of trisubstituted alkenes, (<i<Z</i<)-BPTs <b<1</b<–<b<14</b<, was determined based on the <sup<3</sup<<i<J</i<<sub<C,Hβ</sub< coupling constant of <sup<1</sup<H-coupled <sup<13</sup<C NMR spectra. Three (<i<Z</i<)-BPT derivatives (<b<1</b<–<b<3</b<) showed stronger tyrosinase inhibitory activities than kojic acid; in particular, <b<2</b< was to be 189-fold more potent than kojic acid. Kinetic analysis using mushroom tyrosinase indicated that <b<1</b< and <b<2</b< were competitive inhibitors, whereas <b<3</b< was a mixed-type inhibitor. The in silico results revealed that <b<1</b<–<b<3</b< could strongly bind to the active sites of mushroom and human tyrosinases, supporting the kinetic results. Derivatives <b<1</b< and <b<2</b< decreased the intracellular melanin contents in a concentration-dependent manner in B16F10 cells, and their anti-melanogenic efficacy exceeded that of kojic acid. The anti-tyrosinase activity of <b<1</b< and <b<2</b< in B16F10 cells was similar to their anti-melanogenic effects, suggesting that their anti-melanogenic effects were primarily owing to their anti-tyrosinase activity. Western blotting of B16F10 cells revealed that the derivatives <b<1</b< and <b<2</b< inhibited tyrosinase expression, which partially contributes to their anti-melanogenic ability. Several derivatives, including <b<2</b< and <b<3</b<, exhibited potent antioxidant activities against ABTS cation radicals, DPPH radicals, ROS, and peroxynitrite. These results suggest that (<i<Z</i<)-BPT derivatives <b<1</b< and <b<2</b< have promising potential as novel anti-melanogenic agents.
650		4	\|a (<i<Z</i<)-BPT derivatives
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653		0	\|a Organic chemistry
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700	0		\|a Hyung Ryong Moon \|e verfasserin \|4 aut
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allfields	10.3390/molecules28083293 doi (DE-627)DOAJ089803531 (DE-599)DOAJ83de3ac4d88c40939741c8536066e95e DE-627 ger DE-627 rakwb eng QD241-441 Dahye Yoon verfasserin aut Design, Synthesis, In Vitro, and In Silico Insights of 5-(Substituted benzylidene)-2-phenylthiazol-4(5<i<H</i<)-one Derivatives: A Novel Class of Anti-Melanogenic Compounds 2023 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier (<i<Z</i<)-5-Benzylidene-2-phenylthiazol-4(5<i<H</i<)-one ((<i<Z</i<)-BPT) derivatives were designed by combining the structural characteristics of two tyrosinase inhibitors. The double-bond geometry of trisubstituted alkenes, (<i<Z</i<)-BPTs <b<1</b<–<b<14</b<, was determined based on the <sup<3</sup<<i<J</i<<sub<C,Hβ</sub< coupling constant of <sup<1</sup<H-coupled <sup<13</sup<C NMR spectra. Three (<i<Z</i<)-BPT derivatives (<b<1</b<–<b<3</b<) showed stronger tyrosinase inhibitory activities than kojic acid; in particular, <b<2</b< was to be 189-fold more potent than kojic acid. Kinetic analysis using mushroom tyrosinase indicated that <b<1</b< and <b<2</b< were competitive inhibitors, whereas <b<3</b< was a mixed-type inhibitor. The in silico results revealed that <b<1</b<–<b<3</b< could strongly bind to the active sites of mushroom and human tyrosinases, supporting the kinetic results. Derivatives <b<1</b< and <b<2</b< decreased the intracellular melanin contents in a concentration-dependent manner in B16F10 cells, and their anti-melanogenic efficacy exceeded that of kojic acid. The anti-tyrosinase activity of <b<1</b< and <b<2</b< in B16F10 cells was similar to their anti-melanogenic effects, suggesting that their anti-melanogenic effects were primarily owing to their anti-tyrosinase activity. Western blotting of B16F10 cells revealed that the derivatives <b<1</b< and <b<2</b< inhibited tyrosinase expression, which partially contributes to their anti-melanogenic ability. Several derivatives, including <b<2</b< and <b<3</b<, exhibited potent antioxidant activities against ABTS cation radicals, DPPH radicals, ROS, and peroxynitrite. These results suggest that (<i<Z</i<)-BPT derivatives <b<1</b< and <b<2</b< have promising potential as novel anti-melanogenic agents. (<i<Z</i<)-BPT derivatives tyrosinase melanogenesis kojic acid antioxidant in silico Organic chemistry Min Kyung Kang verfasserin aut Hee Jin Jung verfasserin aut Sultan Ullah verfasserin aut Jieun Lee verfasserin aut Yeongmu Jeong verfasserin aut Sang Gyun Noh verfasserin aut Dongwan Kang verfasserin aut Yujin Park verfasserin aut Pusoon Chun verfasserin aut Hae Young Chung verfasserin aut Hyung Ryong Moon verfasserin aut In Molecules MDPI AG, 2003 28(2023), 8, p 3293 (DE-627)311313132 (DE-600)2008644-1 14203049 nnns volume:28 year:2023 number:8, p 3293 https://doi.org/10.3390/molecules28083293 kostenfrei https://doaj.org/article/83de3ac4d88c40939741c8536066e95e kostenfrei https://www.mdpi.com/1420-3049/28/8/3293 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 28 2023 8, p 3293
spelling	10.3390/molecules28083293 doi (DE-627)DOAJ089803531 (DE-599)DOAJ83de3ac4d88c40939741c8536066e95e DE-627 ger DE-627 rakwb eng QD241-441 Dahye Yoon verfasserin aut Design, Synthesis, In Vitro, and In Silico Insights of 5-(Substituted benzylidene)-2-phenylthiazol-4(5<i<H</i<)-one Derivatives: A Novel Class of Anti-Melanogenic Compounds 2023 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier (<i<Z</i<)-5-Benzylidene-2-phenylthiazol-4(5<i<H</i<)-one ((<i<Z</i<)-BPT) derivatives were designed by combining the structural characteristics of two tyrosinase inhibitors. The double-bond geometry of trisubstituted alkenes, (<i<Z</i<)-BPTs <b<1</b<–<b<14</b<, was determined based on the <sup<3</sup<<i<J</i<<sub<C,Hβ</sub< coupling constant of <sup<1</sup<H-coupled <sup<13</sup<C NMR spectra. Three (<i<Z</i<)-BPT derivatives (<b<1</b<–<b<3</b<) showed stronger tyrosinase inhibitory activities than kojic acid; in particular, <b<2</b< was to be 189-fold more potent than kojic acid. Kinetic analysis using mushroom tyrosinase indicated that <b<1</b< and <b<2</b< were competitive inhibitors, whereas <b<3</b< was a mixed-type inhibitor. The in silico results revealed that <b<1</b<–<b<3</b< could strongly bind to the active sites of mushroom and human tyrosinases, supporting the kinetic results. Derivatives <b<1</b< and <b<2</b< decreased the intracellular melanin contents in a concentration-dependent manner in B16F10 cells, and their anti-melanogenic efficacy exceeded that of kojic acid. The anti-tyrosinase activity of <b<1</b< and <b<2</b< in B16F10 cells was similar to their anti-melanogenic effects, suggesting that their anti-melanogenic effects were primarily owing to their anti-tyrosinase activity. Western blotting of B16F10 cells revealed that the derivatives <b<1</b< and <b<2</b< inhibited tyrosinase expression, which partially contributes to their anti-melanogenic ability. Several derivatives, including <b<2</b< and <b<3</b<, exhibited potent antioxidant activities against ABTS cation radicals, DPPH radicals, ROS, and peroxynitrite. These results suggest that (<i<Z</i<)-BPT derivatives <b<1</b< and <b<2</b< have promising potential as novel anti-melanogenic agents. (<i<Z</i<)-BPT derivatives tyrosinase melanogenesis kojic acid antioxidant in silico Organic chemistry Min Kyung Kang verfasserin aut Hee Jin Jung verfasserin aut Sultan Ullah verfasserin aut Jieun Lee verfasserin aut Yeongmu Jeong verfasserin aut Sang Gyun Noh verfasserin aut Dongwan Kang verfasserin aut Yujin Park verfasserin aut Pusoon Chun verfasserin aut Hae Young Chung verfasserin aut Hyung Ryong Moon verfasserin aut In Molecules MDPI AG, 2003 28(2023), 8, p 3293 (DE-627)311313132 (DE-600)2008644-1 14203049 nnns volume:28 year:2023 number:8, p 3293 https://doi.org/10.3390/molecules28083293 kostenfrei https://doaj.org/article/83de3ac4d88c40939741c8536066e95e kostenfrei https://www.mdpi.com/1420-3049/28/8/3293 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 28 2023 8, p 3293
allfields_unstemmed	10.3390/molecules28083293 doi (DE-627)DOAJ089803531 (DE-599)DOAJ83de3ac4d88c40939741c8536066e95e DE-627 ger DE-627 rakwb eng QD241-441 Dahye Yoon verfasserin aut Design, Synthesis, In Vitro, and In Silico Insights of 5-(Substituted benzylidene)-2-phenylthiazol-4(5<i<H</i<)-one Derivatives: A Novel Class of Anti-Melanogenic Compounds 2023 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier (<i<Z</i<)-5-Benzylidene-2-phenylthiazol-4(5<i<H</i<)-one ((<i<Z</i<)-BPT) derivatives were designed by combining the structural characteristics of two tyrosinase inhibitors. The double-bond geometry of trisubstituted alkenes, (<i<Z</i<)-BPTs <b<1</b<–<b<14</b<, was determined based on the <sup<3</sup<<i<J</i<<sub<C,Hβ</sub< coupling constant of <sup<1</sup<H-coupled <sup<13</sup<C NMR spectra. Three (<i<Z</i<)-BPT derivatives (<b<1</b<–<b<3</b<) showed stronger tyrosinase inhibitory activities than kojic acid; in particular, <b<2</b< was to be 189-fold more potent than kojic acid. Kinetic analysis using mushroom tyrosinase indicated that <b<1</b< and <b<2</b< were competitive inhibitors, whereas <b<3</b< was a mixed-type inhibitor. The in silico results revealed that <b<1</b<–<b<3</b< could strongly bind to the active sites of mushroom and human tyrosinases, supporting the kinetic results. Derivatives <b<1</b< and <b<2</b< decreased the intracellular melanin contents in a concentration-dependent manner in B16F10 cells, and their anti-melanogenic efficacy exceeded that of kojic acid. The anti-tyrosinase activity of <b<1</b< and <b<2</b< in B16F10 cells was similar to their anti-melanogenic effects, suggesting that their anti-melanogenic effects were primarily owing to their anti-tyrosinase activity. Western blotting of B16F10 cells revealed that the derivatives <b<1</b< and <b<2</b< inhibited tyrosinase expression, which partially contributes to their anti-melanogenic ability. Several derivatives, including <b<2</b< and <b<3</b<, exhibited potent antioxidant activities against ABTS cation radicals, DPPH radicals, ROS, and peroxynitrite. These results suggest that (<i<Z</i<)-BPT derivatives <b<1</b< and <b<2</b< have promising potential as novel anti-melanogenic agents. (<i<Z</i<)-BPT derivatives tyrosinase melanogenesis kojic acid antioxidant in silico Organic chemistry Min Kyung Kang verfasserin aut Hee Jin Jung verfasserin aut Sultan Ullah verfasserin aut Jieun Lee verfasserin aut Yeongmu Jeong verfasserin aut Sang Gyun Noh verfasserin aut Dongwan Kang verfasserin aut Yujin Park verfasserin aut Pusoon Chun verfasserin aut Hae Young Chung verfasserin aut Hyung Ryong Moon verfasserin aut In Molecules MDPI AG, 2003 28(2023), 8, p 3293 (DE-627)311313132 (DE-600)2008644-1 14203049 nnns volume:28 year:2023 number:8, p 3293 https://doi.org/10.3390/molecules28083293 kostenfrei https://doaj.org/article/83de3ac4d88c40939741c8536066e95e kostenfrei https://www.mdpi.com/1420-3049/28/8/3293 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 28 2023 8, p 3293
allfieldsGer	10.3390/molecules28083293 doi (DE-627)DOAJ089803531 (DE-599)DOAJ83de3ac4d88c40939741c8536066e95e DE-627 ger DE-627 rakwb eng QD241-441 Dahye Yoon verfasserin aut Design, Synthesis, In Vitro, and In Silico Insights of 5-(Substituted benzylidene)-2-phenylthiazol-4(5<i<H</i<)-one Derivatives: A Novel Class of Anti-Melanogenic Compounds 2023 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier (<i<Z</i<)-5-Benzylidene-2-phenylthiazol-4(5<i<H</i<)-one ((<i<Z</i<)-BPT) derivatives were designed by combining the structural characteristics of two tyrosinase inhibitors. The double-bond geometry of trisubstituted alkenes, (<i<Z</i<)-BPTs <b<1</b<–<b<14</b<, was determined based on the <sup<3</sup<<i<J</i<<sub<C,Hβ</sub< coupling constant of <sup<1</sup<H-coupled <sup<13</sup<C NMR spectra. Three (<i<Z</i<)-BPT derivatives (<b<1</b<–<b<3</b<) showed stronger tyrosinase inhibitory activities than kojic acid; in particular, <b<2</b< was to be 189-fold more potent than kojic acid. Kinetic analysis using mushroom tyrosinase indicated that <b<1</b< and <b<2</b< were competitive inhibitors, whereas <b<3</b< was a mixed-type inhibitor. The in silico results revealed that <b<1</b<–<b<3</b< could strongly bind to the active sites of mushroom and human tyrosinases, supporting the kinetic results. Derivatives <b<1</b< and <b<2</b< decreased the intracellular melanin contents in a concentration-dependent manner in B16F10 cells, and their anti-melanogenic efficacy exceeded that of kojic acid. The anti-tyrosinase activity of <b<1</b< and <b<2</b< in B16F10 cells was similar to their anti-melanogenic effects, suggesting that their anti-melanogenic effects were primarily owing to their anti-tyrosinase activity. Western blotting of B16F10 cells revealed that the derivatives <b<1</b< and <b<2</b< inhibited tyrosinase expression, which partially contributes to their anti-melanogenic ability. Several derivatives, including <b<2</b< and <b<3</b<, exhibited potent antioxidant activities against ABTS cation radicals, DPPH radicals, ROS, and peroxynitrite. These results suggest that (<i<Z</i<)-BPT derivatives <b<1</b< and <b<2</b< have promising potential as novel anti-melanogenic agents. (<i<Z</i<)-BPT derivatives tyrosinase melanogenesis kojic acid antioxidant in silico Organic chemistry Min Kyung Kang verfasserin aut Hee Jin Jung verfasserin aut Sultan Ullah verfasserin aut Jieun Lee verfasserin aut Yeongmu Jeong verfasserin aut Sang Gyun Noh verfasserin aut Dongwan Kang verfasserin aut Yujin Park verfasserin aut Pusoon Chun verfasserin aut Hae Young Chung verfasserin aut Hyung Ryong Moon verfasserin aut In Molecules MDPI AG, 2003 28(2023), 8, p 3293 (DE-627)311313132 (DE-600)2008644-1 14203049 nnns volume:28 year:2023 number:8, p 3293 https://doi.org/10.3390/molecules28083293 kostenfrei https://doaj.org/article/83de3ac4d88c40939741c8536066e95e kostenfrei https://www.mdpi.com/1420-3049/28/8/3293 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 28 2023 8, p 3293
allfieldsSound	10.3390/molecules28083293 doi (DE-627)DOAJ089803531 (DE-599)DOAJ83de3ac4d88c40939741c8536066e95e DE-627 ger DE-627 rakwb eng QD241-441 Dahye Yoon verfasserin aut Design, Synthesis, In Vitro, and In Silico Insights of 5-(Substituted benzylidene)-2-phenylthiazol-4(5<i<H</i<)-one Derivatives: A Novel Class of Anti-Melanogenic Compounds 2023 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier (<i<Z</i<)-5-Benzylidene-2-phenylthiazol-4(5<i<H</i<)-one ((<i<Z</i<)-BPT) derivatives were designed by combining the structural characteristics of two tyrosinase inhibitors. The double-bond geometry of trisubstituted alkenes, (<i<Z</i<)-BPTs <b<1</b<–<b<14</b<, was determined based on the <sup<3</sup<<i<J</i<<sub<C,Hβ</sub< coupling constant of <sup<1</sup<H-coupled <sup<13</sup<C NMR spectra. Three (<i<Z</i<)-BPT derivatives (<b<1</b<–<b<3</b<) showed stronger tyrosinase inhibitory activities than kojic acid; in particular, <b<2</b< was to be 189-fold more potent than kojic acid. Kinetic analysis using mushroom tyrosinase indicated that <b<1</b< and <b<2</b< were competitive inhibitors, whereas <b<3</b< was a mixed-type inhibitor. The in silico results revealed that <b<1</b<–<b<3</b< could strongly bind to the active sites of mushroom and human tyrosinases, supporting the kinetic results. Derivatives <b<1</b< and <b<2</b< decreased the intracellular melanin contents in a concentration-dependent manner in B16F10 cells, and their anti-melanogenic efficacy exceeded that of kojic acid. The anti-tyrosinase activity of <b<1</b< and <b<2</b< in B16F10 cells was similar to their anti-melanogenic effects, suggesting that their anti-melanogenic effects were primarily owing to their anti-tyrosinase activity. Western blotting of B16F10 cells revealed that the derivatives <b<1</b< and <b<2</b< inhibited tyrosinase expression, which partially contributes to their anti-melanogenic ability. Several derivatives, including <b<2</b< and <b<3</b<, exhibited potent antioxidant activities against ABTS cation radicals, DPPH radicals, ROS, and peroxynitrite. These results suggest that (<i<Z</i<)-BPT derivatives <b<1</b< and <b<2</b< have promising potential as novel anti-melanogenic agents. (<i<Z</i<)-BPT derivatives tyrosinase melanogenesis kojic acid antioxidant in silico Organic chemistry Min Kyung Kang verfasserin aut Hee Jin Jung verfasserin aut Sultan Ullah verfasserin aut Jieun Lee verfasserin aut Yeongmu Jeong verfasserin aut Sang Gyun Noh verfasserin aut Dongwan Kang verfasserin aut Yujin Park verfasserin aut Pusoon Chun verfasserin aut Hae Young Chung verfasserin aut Hyung Ryong Moon verfasserin aut In Molecules MDPI AG, 2003 28(2023), 8, p 3293 (DE-627)311313132 (DE-600)2008644-1 14203049 nnns volume:28 year:2023 number:8, p 3293 https://doi.org/10.3390/molecules28083293 kostenfrei https://doaj.org/article/83de3ac4d88c40939741c8536066e95e kostenfrei https://www.mdpi.com/1420-3049/28/8/3293 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 28 2023 8, p 3293
language	English
source	In Molecules 28(2023), 8, p 3293 volume:28 year:2023 number:8, p 3293
sourceStr	In Molecules 28(2023), 8, p 3293 volume:28 year:2023 number:8, p 3293
format_phy_str_mv	Article
institution	findex.gbv.de
topic_facet	(<i<Z</i<)-BPT derivatives tyrosinase melanogenesis kojic acid antioxidant in silico Organic chemistry
isfreeaccess_bool	true
container_title	Molecules
authorswithroles_txt_mv	Dahye Yoon @@aut@@ Min Kyung Kang @@aut@@ Hee Jin Jung @@aut@@ Sultan Ullah @@aut@@ Jieun Lee @@aut@@ Yeongmu Jeong @@aut@@ Sang Gyun Noh @@aut@@ Dongwan Kang @@aut@@ Yujin Park @@aut@@ Pusoon Chun @@aut@@ Hae Young Chung @@aut@@ Hyung Ryong Moon @@aut@@
publishDateDaySort_date	2023-01-01T00:00:00Z
hierarchy_top_id	311313132
id	DOAJ089803531
language_de	englisch
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The double-bond geometry of trisubstituted alkenes, (<i<Z</i<)-BPTs <b<1</b<–<b<14</b<, was determined based on the <sup<3</sup<<i<J</i<<sub<C,Hβ</sub< coupling constant of <sup<1</sup<H-coupled <sup<13</sup<C NMR spectra. Three (<i<Z</i<)-BPT derivatives (<b<1</b<–<b<3</b<) showed stronger tyrosinase inhibitory activities than kojic acid; in particular, <b<2</b< was to be 189-fold more potent than kojic acid. Kinetic analysis using mushroom tyrosinase indicated that <b<1</b< and <b<2</b< were competitive inhibitors, whereas <b<3</b< was a mixed-type inhibitor. The in silico results revealed that <b<1</b<–<b<3</b< could strongly bind to the active sites of mushroom and human tyrosinases, supporting the kinetic results. Derivatives <b<1</b< and <b<2</b< decreased the intracellular melanin contents in a concentration-dependent manner in B16F10 cells, and their anti-melanogenic efficacy exceeded that of kojic acid. 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callnumber-first	Q - Science
author	Dahye Yoon
spellingShingle	Dahye Yoon misc QD241-441 misc (<i<Z</i<)-BPT derivatives misc tyrosinase misc melanogenesis misc kojic acid misc antioxidant misc in silico misc Organic chemistry Design, Synthesis, In Vitro, and In Silico Insights of 5-(Substituted benzylidene)-2-phenylthiazol-4(5<i<H</i<)-one Derivatives: A Novel Class of Anti-Melanogenic Compounds
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topic_title	QD241-441 Design, Synthesis, In Vitro, and In Silico Insights of 5-(Substituted benzylidene)-2-phenylthiazol-4(5<i<H</i<)-one Derivatives: A Novel Class of Anti-Melanogenic Compounds (<i<Z</i<)-BPT derivatives tyrosinase melanogenesis kojic acid antioxidant in silico
topic	misc QD241-441 misc (<i<Z</i<)-BPT derivatives misc tyrosinase misc melanogenesis misc kojic acid misc antioxidant misc in silico misc Organic chemistry
topic_unstemmed	misc QD241-441 misc (<i<Z</i<)-BPT derivatives misc tyrosinase misc melanogenesis misc kojic acid misc antioxidant misc in silico misc Organic chemistry
topic_browse	misc QD241-441 misc (<i<Z</i<)-BPT derivatives misc tyrosinase misc melanogenesis misc kojic acid misc antioxidant misc in silico misc Organic chemistry
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title	Design, Synthesis, In Vitro, and In Silico Insights of 5-(Substituted benzylidene)-2-phenylthiazol-4(5<i<H</i<)-one Derivatives: A Novel Class of Anti-Melanogenic Compounds
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title_full	Design, Synthesis, In Vitro, and In Silico Insights of 5-(Substituted benzylidene)-2-phenylthiazol-4(5<i<H</i<)-one Derivatives: A Novel Class of Anti-Melanogenic Compounds
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author_browse	Dahye Yoon Min Kyung Kang Hee Jin Jung Sultan Ullah Jieun Lee Yeongmu Jeong Sang Gyun Noh Dongwan Kang Yujin Park Pusoon Chun Hae Young Chung Hyung Ryong Moon
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doi_str_mv	10.3390/molecules28083293
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title_sort	design, synthesis, in vitro, and in silico insights of 5-(substituted benzylidene)-2-phenylthiazol-4(5<i<h</i<)-one derivatives: a novel class of anti-melanogenic compounds
callnumber	QD241-441
title_auth	Design, Synthesis, In Vitro, and In Silico Insights of 5-(Substituted benzylidene)-2-phenylthiazol-4(5<i<H</i<)-one Derivatives: A Novel Class of Anti-Melanogenic Compounds
abstract	(<i<Z</i<)-5-Benzylidene-2-phenylthiazol-4(5<i<H</i<)-one ((<i<Z</i<)-BPT) derivatives were designed by combining the structural characteristics of two tyrosinase inhibitors. The double-bond geometry of trisubstituted alkenes, (<i<Z</i<)-BPTs <b<1</b<–<b<14</b<, was determined based on the <sup<3</sup<<i<J</i<<sub<C,Hβ</sub< coupling constant of <sup<1</sup<H-coupled <sup<13</sup<C NMR spectra. Three (<i<Z</i<)-BPT derivatives (<b<1</b<–<b<3</b<) showed stronger tyrosinase inhibitory activities than kojic acid; in particular, <b<2</b< was to be 189-fold more potent than kojic acid. Kinetic analysis using mushroom tyrosinase indicated that <b<1</b< and <b<2</b< were competitive inhibitors, whereas <b<3</b< was a mixed-type inhibitor. The in silico results revealed that <b<1</b<–<b<3</b< could strongly bind to the active sites of mushroom and human tyrosinases, supporting the kinetic results. Derivatives <b<1</b< and <b<2</b< decreased the intracellular melanin contents in a concentration-dependent manner in B16F10 cells, and their anti-melanogenic efficacy exceeded that of kojic acid. The anti-tyrosinase activity of <b<1</b< and <b<2</b< in B16F10 cells was similar to their anti-melanogenic effects, suggesting that their anti-melanogenic effects were primarily owing to their anti-tyrosinase activity. Western blotting of B16F10 cells revealed that the derivatives <b<1</b< and <b<2</b< inhibited tyrosinase expression, which partially contributes to their anti-melanogenic ability. Several derivatives, including <b<2</b< and <b<3</b<, exhibited potent antioxidant activities against ABTS cation radicals, DPPH radicals, ROS, and peroxynitrite. These results suggest that (<i<Z</i<)-BPT derivatives <b<1</b< and <b<2</b< have promising potential as novel anti-melanogenic agents.
abstractGer	(<i<Z</i<)-5-Benzylidene-2-phenylthiazol-4(5<i<H</i<)-one ((<i<Z</i<)-BPT) derivatives were designed by combining the structural characteristics of two tyrosinase inhibitors. The double-bond geometry of trisubstituted alkenes, (<i<Z</i<)-BPTs <b<1</b<–<b<14</b<, was determined based on the <sup<3</sup<<i<J</i<<sub<C,Hβ</sub< coupling constant of <sup<1</sup<H-coupled <sup<13</sup<C NMR spectra. Three (<i<Z</i<)-BPT derivatives (<b<1</b<–<b<3</b<) showed stronger tyrosinase inhibitory activities than kojic acid; in particular, <b<2</b< was to be 189-fold more potent than kojic acid. Kinetic analysis using mushroom tyrosinase indicated that <b<1</b< and <b<2</b< were competitive inhibitors, whereas <b<3</b< was a mixed-type inhibitor. The in silico results revealed that <b<1</b<–<b<3</b< could strongly bind to the active sites of mushroom and human tyrosinases, supporting the kinetic results. Derivatives <b<1</b< and <b<2</b< decreased the intracellular melanin contents in a concentration-dependent manner in B16F10 cells, and their anti-melanogenic efficacy exceeded that of kojic acid. The anti-tyrosinase activity of <b<1</b< and <b<2</b< in B16F10 cells was similar to their anti-melanogenic effects, suggesting that their anti-melanogenic effects were primarily owing to their anti-tyrosinase activity. Western blotting of B16F10 cells revealed that the derivatives <b<1</b< and <b<2</b< inhibited tyrosinase expression, which partially contributes to their anti-melanogenic ability. Several derivatives, including <b<2</b< and <b<3</b<, exhibited potent antioxidant activities against ABTS cation radicals, DPPH radicals, ROS, and peroxynitrite. These results suggest that (<i<Z</i<)-BPT derivatives <b<1</b< and <b<2</b< have promising potential as novel anti-melanogenic agents.
abstract_unstemmed	(<i<Z</i<)-5-Benzylidene-2-phenylthiazol-4(5<i<H</i<)-one ((<i<Z</i<)-BPT) derivatives were designed by combining the structural characteristics of two tyrosinase inhibitors. The double-bond geometry of trisubstituted alkenes, (<i<Z</i<)-BPTs <b<1</b<–<b<14</b<, was determined based on the <sup<3</sup<<i<J</i<<sub<C,Hβ</sub< coupling constant of <sup<1</sup<H-coupled <sup<13</sup<C NMR spectra. Three (<i<Z</i<)-BPT derivatives (<b<1</b<–<b<3</b<) showed stronger tyrosinase inhibitory activities than kojic acid; in particular, <b<2</b< was to be 189-fold more potent than kojic acid. Kinetic analysis using mushroom tyrosinase indicated that <b<1</b< and <b<2</b< were competitive inhibitors, whereas <b<3</b< was a mixed-type inhibitor. The in silico results revealed that <b<1</b<–<b<3</b< could strongly bind to the active sites of mushroom and human tyrosinases, supporting the kinetic results. Derivatives <b<1</b< and <b<2</b< decreased the intracellular melanin contents in a concentration-dependent manner in B16F10 cells, and their anti-melanogenic efficacy exceeded that of kojic acid. The anti-tyrosinase activity of <b<1</b< and <b<2</b< in B16F10 cells was similar to their anti-melanogenic effects, suggesting that their anti-melanogenic effects were primarily owing to their anti-tyrosinase activity. Western blotting of B16F10 cells revealed that the derivatives <b<1</b< and <b<2</b< inhibited tyrosinase expression, which partially contributes to their anti-melanogenic ability. Several derivatives, including <b<2</b< and <b<3</b<, exhibited potent antioxidant activities against ABTS cation radicals, DPPH radicals, ROS, and peroxynitrite. These results suggest that (<i<Z</i<)-BPT derivatives <b<1</b< and <b<2</b< have promising potential as novel anti-melanogenic agents.
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title_short	Design, Synthesis, In Vitro, and In Silico Insights of 5-(Substituted benzylidene)-2-phenylthiazol-4(5<i<H</i<)-one Derivatives: A Novel Class of Anti-Melanogenic Compounds
url	https://doi.org/10.3390/molecules28083293 https://doaj.org/article/83de3ac4d88c40939741c8536066e95e https://www.mdpi.com/1420-3049/28/8/3293 https://doaj.org/toc/1420-3049
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The anti-tyrosinase activity of <b<1</b< and <b<2</b< in B16F10 cells was similar to their anti-melanogenic effects, suggesting that their anti-melanogenic effects were primarily owing to their anti-tyrosinase activity. Western blotting of B16F10 cells revealed that the derivatives <b<1</b< and <b<2</b< inhibited tyrosinase expression, which partially contributes to their anti-melanogenic ability. Several derivatives, including <b<2</b< and <b<3</b<, exhibited potent antioxidant activities against ABTS cation radicals, DPPH radicals, ROS, and peroxynitrite. 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Design, Synthesis, In Vitro, and In Silico Insights of 5-(Substituted benzylidene)-2-phenylthiazol-4(5<i<H</i<)-one Derivatives: A Novel Class of Anti-Melanogenic Compounds

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