Design and Synthesis of (<i<Z</i<)-2-(Benzylamino)-5-benzylidenethiazol-4(5<i<H</i<)-one Derivatives as Tyrosinase Inhibitors and Their Anti-Melanogenic and Antioxidant Effects

In this study, (<i<Z</i<)-2-(benzylamino)-5-benzylidenethiazol-4(5<i<H</i<)-one (BABT) derivatives were designed as tyrosinase inhibitors based on the structure of MHY2081, using a simplified approach. Of the 14 BABT derivatives synthesized, two derivatives ((<i<Z</i...
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Autor*in:	Jieun Lee [verfasserIn] Yu Jung Park [verfasserIn] Hee Jin Jung [verfasserIn] Sultan Ullah [verfasserIn] Dahye Yoon [verfasserIn] Yeongmu Jeong [verfasserIn] Ga Young Kim [verfasserIn] Min Kyung Kang [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 melanin BABT antioxidant activity in silico MITF

Übergeordnetes Werk:	In: Molecules - MDPI AG, 2003, 28(2023), 2, p 848
Übergeordnetes Werk:	volume:28 ; year:2023 ; number:2, p 848

Links:	Link aufrufen Link aufrufen Link aufrufen Journal toc

DOI / URN:	10.3390/molecules28020848

Katalog-ID:	DOAJ081733119

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245	1	0	\|a Design and Synthesis of (<i<Z</i<)-2-(Benzylamino)-5-benzylidenethiazol-4(5<i<H</i<)-one Derivatives as Tyrosinase Inhibitors and Their Anti-Melanogenic and Antioxidant Effects
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520			\|a In this study, (<i<Z</i<)-2-(benzylamino)-5-benzylidenethiazol-4(5<i<H</i<)-one (BABT) derivatives were designed as tyrosinase inhibitors based on the structure of MHY2081, using a simplified approach. Of the 14 BABT derivatives synthesized, two derivatives ((<i<Z</i<)-2-(benzylamino)-5-(3-hydroxy-4-methoxybenzylidene)thiazol-4(5<i<H</i<)-one [<b<7</b<] and (<i<Z</i<)-2-(benzylamino)-5-(2,4-dihydroxybenzylidene)thiazol-4(5<i<H</i<)-one [<b<8</b<]) showed more potent mushroom tyrosinase inhibitory activities than kojic acid, regardless of the substrate used; in particular, compound <b<8</b< was 106-fold more potent than kojic acid when <span style="font-variant: small-caps;"<l</span<-tyrosine was used as the substrate. Analysis of Lineweaver–Burk plots for <b<7</b< and <b<8</b< indicated that they were competitive inhibitors, which was confirmed via in silico docking. In experiments using B16F10 cells, <b<8</b< exerted a greater ability to inhibit melanin production than kojic acid, and it inhibited cellular tyrosinase activity in a concentration-dependent manner, indicating that the anti-melanogenic effect of <b<8</b< is attributable to its ability to inhibit tyrosinase. In addition, <b<8</b< exhibited strong antioxidant activity to scavenge 2,2-diphenyl-1-picrylhydrazyl and 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) radicals and peroxynitrite and inhibited the expression of melanogenesis-associated proteins (tyrosinase and microphthalmia-associated transcription factor). These results suggest that BABT derivative <b<8</b< is a promising candidate for the treatment of hyperpigmentation-related diseases, owing to its inhibition of melanogenesis-associated protein expression, direct tyrosinase inhibition, and antioxidant activity.
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allfields	10.3390/molecules28020848 doi (DE-627)DOAJ081733119 (DE-599)DOAJ0b9d0299c49a4c6cbb8527d6178fd552 DE-627 ger DE-627 rakwb eng QD241-441 Jieun Lee verfasserin aut Design and Synthesis of (<i<Z</i<)-2-(Benzylamino)-5-benzylidenethiazol-4(5<i<H</i<)-one Derivatives as Tyrosinase Inhibitors and Their Anti-Melanogenic and Antioxidant Effects 2023 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier In this study, (<i<Z</i<)-2-(benzylamino)-5-benzylidenethiazol-4(5<i<H</i<)-one (BABT) derivatives were designed as tyrosinase inhibitors based on the structure of MHY2081, using a simplified approach. Of the 14 BABT derivatives synthesized, two derivatives ((<i<Z</i<)-2-(benzylamino)-5-(3-hydroxy-4-methoxybenzylidene)thiazol-4(5<i<H</i<)-one [<b<7</b<] and (<i<Z</i<)-2-(benzylamino)-5-(2,4-dihydroxybenzylidene)thiazol-4(5<i<H</i<)-one [<b<8</b<]) showed more potent mushroom tyrosinase inhibitory activities than kojic acid, regardless of the substrate used; in particular, compound <b<8</b< was 106-fold more potent than kojic acid when <span style="font-variant: small-caps;"<l</span<-tyrosine was used as the substrate. Analysis of Lineweaver–Burk plots for <b<7</b< and <b<8</b< indicated that they were competitive inhibitors, which was confirmed via in silico docking. In experiments using B16F10 cells, <b<8</b< exerted a greater ability to inhibit melanin production than kojic acid, and it inhibited cellular tyrosinase activity in a concentration-dependent manner, indicating that the anti-melanogenic effect of <b<8</b< is attributable to its ability to inhibit tyrosinase. In addition, <b<8</b< exhibited strong antioxidant activity to scavenge 2,2-diphenyl-1-picrylhydrazyl and 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) radicals and peroxynitrite and inhibited the expression of melanogenesis-associated proteins (tyrosinase and microphthalmia-associated transcription factor). These results suggest that BABT derivative <b<8</b< is a promising candidate for the treatment of hyperpigmentation-related diseases, owing to its inhibition of melanogenesis-associated protein expression, direct tyrosinase inhibition, and antioxidant activity. tyrosinase melanin BABT antioxidant activity in silico MITF Organic chemistry Yu Jung Park verfasserin aut Hee Jin Jung verfasserin aut Sultan Ullah verfasserin aut Dahye Yoon verfasserin aut Yeongmu Jeong verfasserin aut Ga Young Kim verfasserin aut Min Kyung Kang 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), 2, p 848 (DE-627)311313132 (DE-600)2008644-1 14203049 nnns volume:28 year:2023 number:2, p 848 https://doi.org/10.3390/molecules28020848 kostenfrei https://doaj.org/article/0b9d0299c49a4c6cbb8527d6178fd552 kostenfrei https://www.mdpi.com/1420-3049/28/2/848 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 2, p 848
spelling	10.3390/molecules28020848 doi (DE-627)DOAJ081733119 (DE-599)DOAJ0b9d0299c49a4c6cbb8527d6178fd552 DE-627 ger DE-627 rakwb eng QD241-441 Jieun Lee verfasserin aut Design and Synthesis of (<i<Z</i<)-2-(Benzylamino)-5-benzylidenethiazol-4(5<i<H</i<)-one Derivatives as Tyrosinase Inhibitors and Their Anti-Melanogenic and Antioxidant Effects 2023 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier In this study, (<i<Z</i<)-2-(benzylamino)-5-benzylidenethiazol-4(5<i<H</i<)-one (BABT) derivatives were designed as tyrosinase inhibitors based on the structure of MHY2081, using a simplified approach. Of the 14 BABT derivatives synthesized, two derivatives ((<i<Z</i<)-2-(benzylamino)-5-(3-hydroxy-4-methoxybenzylidene)thiazol-4(5<i<H</i<)-one [<b<7</b<] and (<i<Z</i<)-2-(benzylamino)-5-(2,4-dihydroxybenzylidene)thiazol-4(5<i<H</i<)-one [<b<8</b<]) showed more potent mushroom tyrosinase inhibitory activities than kojic acid, regardless of the substrate used; in particular, compound <b<8</b< was 106-fold more potent than kojic acid when <span style="font-variant: small-caps;"<l</span<-tyrosine was used as the substrate. Analysis of Lineweaver–Burk plots for <b<7</b< and <b<8</b< indicated that they were competitive inhibitors, which was confirmed via in silico docking. In experiments using B16F10 cells, <b<8</b< exerted a greater ability to inhibit melanin production than kojic acid, and it inhibited cellular tyrosinase activity in a concentration-dependent manner, indicating that the anti-melanogenic effect of <b<8</b< is attributable to its ability to inhibit tyrosinase. In addition, <b<8</b< exhibited strong antioxidant activity to scavenge 2,2-diphenyl-1-picrylhydrazyl and 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) radicals and peroxynitrite and inhibited the expression of melanogenesis-associated proteins (tyrosinase and microphthalmia-associated transcription factor). These results suggest that BABT derivative <b<8</b< is a promising candidate for the treatment of hyperpigmentation-related diseases, owing to its inhibition of melanogenesis-associated protein expression, direct tyrosinase inhibition, and antioxidant activity. tyrosinase melanin BABT antioxidant activity in silico MITF Organic chemistry Yu Jung Park verfasserin aut Hee Jin Jung verfasserin aut Sultan Ullah verfasserin aut Dahye Yoon verfasserin aut Yeongmu Jeong verfasserin aut Ga Young Kim verfasserin aut Min Kyung Kang 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), 2, p 848 (DE-627)311313132 (DE-600)2008644-1 14203049 nnns volume:28 year:2023 number:2, p 848 https://doi.org/10.3390/molecules28020848 kostenfrei https://doaj.org/article/0b9d0299c49a4c6cbb8527d6178fd552 kostenfrei https://www.mdpi.com/1420-3049/28/2/848 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 2, p 848
allfields_unstemmed	10.3390/molecules28020848 doi (DE-627)DOAJ081733119 (DE-599)DOAJ0b9d0299c49a4c6cbb8527d6178fd552 DE-627 ger DE-627 rakwb eng QD241-441 Jieun Lee verfasserin aut Design and Synthesis of (<i<Z</i<)-2-(Benzylamino)-5-benzylidenethiazol-4(5<i<H</i<)-one Derivatives as Tyrosinase Inhibitors and Their Anti-Melanogenic and Antioxidant Effects 2023 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier In this study, (<i<Z</i<)-2-(benzylamino)-5-benzylidenethiazol-4(5<i<H</i<)-one (BABT) derivatives were designed as tyrosinase inhibitors based on the structure of MHY2081, using a simplified approach. Of the 14 BABT derivatives synthesized, two derivatives ((<i<Z</i<)-2-(benzylamino)-5-(3-hydroxy-4-methoxybenzylidene)thiazol-4(5<i<H</i<)-one [<b<7</b<] and (<i<Z</i<)-2-(benzylamino)-5-(2,4-dihydroxybenzylidene)thiazol-4(5<i<H</i<)-one [<b<8</b<]) showed more potent mushroom tyrosinase inhibitory activities than kojic acid, regardless of the substrate used; in particular, compound <b<8</b< was 106-fold more potent than kojic acid when <span style="font-variant: small-caps;"<l</span<-tyrosine was used as the substrate. Analysis of Lineweaver–Burk plots for <b<7</b< and <b<8</b< indicated that they were competitive inhibitors, which was confirmed via in silico docking. In experiments using B16F10 cells, <b<8</b< exerted a greater ability to inhibit melanin production than kojic acid, and it inhibited cellular tyrosinase activity in a concentration-dependent manner, indicating that the anti-melanogenic effect of <b<8</b< is attributable to its ability to inhibit tyrosinase. In addition, <b<8</b< exhibited strong antioxidant activity to scavenge 2,2-diphenyl-1-picrylhydrazyl and 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) radicals and peroxynitrite and inhibited the expression of melanogenesis-associated proteins (tyrosinase and microphthalmia-associated transcription factor). These results suggest that BABT derivative <b<8</b< is a promising candidate for the treatment of hyperpigmentation-related diseases, owing to its inhibition of melanogenesis-associated protein expression, direct tyrosinase inhibition, and antioxidant activity. tyrosinase melanin BABT antioxidant activity in silico MITF Organic chemistry Yu Jung Park verfasserin aut Hee Jin Jung verfasserin aut Sultan Ullah verfasserin aut Dahye Yoon verfasserin aut Yeongmu Jeong verfasserin aut Ga Young Kim verfasserin aut Min Kyung Kang 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), 2, p 848 (DE-627)311313132 (DE-600)2008644-1 14203049 nnns volume:28 year:2023 number:2, p 848 https://doi.org/10.3390/molecules28020848 kostenfrei https://doaj.org/article/0b9d0299c49a4c6cbb8527d6178fd552 kostenfrei https://www.mdpi.com/1420-3049/28/2/848 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 2, p 848
allfieldsGer	10.3390/molecules28020848 doi (DE-627)DOAJ081733119 (DE-599)DOAJ0b9d0299c49a4c6cbb8527d6178fd552 DE-627 ger DE-627 rakwb eng QD241-441 Jieun Lee verfasserin aut Design and Synthesis of (<i<Z</i<)-2-(Benzylamino)-5-benzylidenethiazol-4(5<i<H</i<)-one Derivatives as Tyrosinase Inhibitors and Their Anti-Melanogenic and Antioxidant Effects 2023 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier In this study, (<i<Z</i<)-2-(benzylamino)-5-benzylidenethiazol-4(5<i<H</i<)-one (BABT) derivatives were designed as tyrosinase inhibitors based on the structure of MHY2081, using a simplified approach. Of the 14 BABT derivatives synthesized, two derivatives ((<i<Z</i<)-2-(benzylamino)-5-(3-hydroxy-4-methoxybenzylidene)thiazol-4(5<i<H</i<)-one [<b<7</b<] and (<i<Z</i<)-2-(benzylamino)-5-(2,4-dihydroxybenzylidene)thiazol-4(5<i<H</i<)-one [<b<8</b<]) showed more potent mushroom tyrosinase inhibitory activities than kojic acid, regardless of the substrate used; in particular, compound <b<8</b< was 106-fold more potent than kojic acid when <span style="font-variant: small-caps;"<l</span<-tyrosine was used as the substrate. Analysis of Lineweaver–Burk plots for <b<7</b< and <b<8</b< indicated that they were competitive inhibitors, which was confirmed via in silico docking. In experiments using B16F10 cells, <b<8</b< exerted a greater ability to inhibit melanin production than kojic acid, and it inhibited cellular tyrosinase activity in a concentration-dependent manner, indicating that the anti-melanogenic effect of <b<8</b< is attributable to its ability to inhibit tyrosinase. In addition, <b<8</b< exhibited strong antioxidant activity to scavenge 2,2-diphenyl-1-picrylhydrazyl and 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) radicals and peroxynitrite and inhibited the expression of melanogenesis-associated proteins (tyrosinase and microphthalmia-associated transcription factor). These results suggest that BABT derivative <b<8</b< is a promising candidate for the treatment of hyperpigmentation-related diseases, owing to its inhibition of melanogenesis-associated protein expression, direct tyrosinase inhibition, and antioxidant activity. tyrosinase melanin BABT antioxidant activity in silico MITF Organic chemistry Yu Jung Park verfasserin aut Hee Jin Jung verfasserin aut Sultan Ullah verfasserin aut Dahye Yoon verfasserin aut Yeongmu Jeong verfasserin aut Ga Young Kim verfasserin aut Min Kyung Kang 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), 2, p 848 (DE-627)311313132 (DE-600)2008644-1 14203049 nnns volume:28 year:2023 number:2, p 848 https://doi.org/10.3390/molecules28020848 kostenfrei https://doaj.org/article/0b9d0299c49a4c6cbb8527d6178fd552 kostenfrei https://www.mdpi.com/1420-3049/28/2/848 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 2, p 848
allfieldsSound	10.3390/molecules28020848 doi (DE-627)DOAJ081733119 (DE-599)DOAJ0b9d0299c49a4c6cbb8527d6178fd552 DE-627 ger DE-627 rakwb eng QD241-441 Jieun Lee verfasserin aut Design and Synthesis of (<i<Z</i<)-2-(Benzylamino)-5-benzylidenethiazol-4(5<i<H</i<)-one Derivatives as Tyrosinase Inhibitors and Their Anti-Melanogenic and Antioxidant Effects 2023 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier In this study, (<i<Z</i<)-2-(benzylamino)-5-benzylidenethiazol-4(5<i<H</i<)-one (BABT) derivatives were designed as tyrosinase inhibitors based on the structure of MHY2081, using a simplified approach. Of the 14 BABT derivatives synthesized, two derivatives ((<i<Z</i<)-2-(benzylamino)-5-(3-hydroxy-4-methoxybenzylidene)thiazol-4(5<i<H</i<)-one [<b<7</b<] and (<i<Z</i<)-2-(benzylamino)-5-(2,4-dihydroxybenzylidene)thiazol-4(5<i<H</i<)-one [<b<8</b<]) showed more potent mushroom tyrosinase inhibitory activities than kojic acid, regardless of the substrate used; in particular, compound <b<8</b< was 106-fold more potent than kojic acid when <span style="font-variant: small-caps;"<l</span<-tyrosine was used as the substrate. Analysis of Lineweaver–Burk plots for <b<7</b< and <b<8</b< indicated that they were competitive inhibitors, which was confirmed via in silico docking. In experiments using B16F10 cells, <b<8</b< exerted a greater ability to inhibit melanin production than kojic acid, and it inhibited cellular tyrosinase activity in a concentration-dependent manner, indicating that the anti-melanogenic effect of <b<8</b< is attributable to its ability to inhibit tyrosinase. In addition, <b<8</b< exhibited strong antioxidant activity to scavenge 2,2-diphenyl-1-picrylhydrazyl and 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) radicals and peroxynitrite and inhibited the expression of melanogenesis-associated proteins (tyrosinase and microphthalmia-associated transcription factor). These results suggest that BABT derivative <b<8</b< is a promising candidate for the treatment of hyperpigmentation-related diseases, owing to its inhibition of melanogenesis-associated protein expression, direct tyrosinase inhibition, and antioxidant activity. tyrosinase melanin BABT antioxidant activity in silico MITF Organic chemistry Yu Jung Park verfasserin aut Hee Jin Jung verfasserin aut Sultan Ullah verfasserin aut Dahye Yoon verfasserin aut Yeongmu Jeong verfasserin aut Ga Young Kim verfasserin aut Min Kyung Kang 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), 2, p 848 (DE-627)311313132 (DE-600)2008644-1 14203049 nnns volume:28 year:2023 number:2, p 848 https://doi.org/10.3390/molecules28020848 kostenfrei https://doaj.org/article/0b9d0299c49a4c6cbb8527d6178fd552 kostenfrei https://www.mdpi.com/1420-3049/28/2/848 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 2, p 848
language	English
source	In Molecules 28(2023), 2, p 848 volume:28 year:2023 number:2, p 848
sourceStr	In Molecules 28(2023), 2, p 848 volume:28 year:2023 number:2, p 848
format_phy_str_mv	Article
institution	findex.gbv.de
topic_facet	tyrosinase melanin BABT antioxidant activity in silico MITF Organic chemistry
isfreeaccess_bool	true
container_title	Molecules
authorswithroles_txt_mv	Jieun Lee @@aut@@ Yu Jung Park @@aut@@ Hee Jin Jung @@aut@@ Sultan Ullah @@aut@@ Dahye Yoon @@aut@@ Yeongmu Jeong @@aut@@ Ga Young Kim @@aut@@ Min Kyung Kang @@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	DOAJ081733119
language_de	englisch
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Of the 14 BABT derivatives synthesized, two derivatives ((<i<Z</i<)-2-(benzylamino)-5-(3-hydroxy-4-methoxybenzylidene)thiazol-4(5<i<H</i<)-one [<b<7</b<] and (<i<Z</i<)-2-(benzylamino)-5-(2,4-dihydroxybenzylidene)thiazol-4(5<i<H</i<)-one [<b<8</b<]) showed more potent mushroom tyrosinase inhibitory activities than kojic acid, regardless of the substrate used; in particular, compound <b<8</b< was 106-fold more potent than kojic acid when <span style="font-variant: small-caps;"<l</span<-tyrosine was used as the substrate. Analysis of Lineweaver–Burk plots for <b<7</b< and <b<8</b< indicated that they were competitive inhibitors, which was confirmed via in silico docking. In experiments using B16F10 cells, <b<8</b< exerted a greater ability to inhibit melanin production than kojic acid, and it inhibited cellular tyrosinase activity in a concentration-dependent manner, indicating that the anti-melanogenic effect of <b<8</b< is attributable to its ability to inhibit tyrosinase. 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callnumber-first	Q - Science
author	Jieun Lee
spellingShingle	Jieun Lee misc QD241-441 misc tyrosinase misc melanin misc BABT misc antioxidant activity misc in silico misc MITF misc Organic chemistry Design and Synthesis of (<i<Z</i<)-2-(Benzylamino)-5-benzylidenethiazol-4(5<i<H</i<)-one Derivatives as Tyrosinase Inhibitors and Their Anti-Melanogenic and Antioxidant Effects
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topic_title	QD241-441 Design and Synthesis of (<i<Z</i<)-2-(Benzylamino)-5-benzylidenethiazol-4(5<i<H</i<)-one Derivatives as Tyrosinase Inhibitors and Their Anti-Melanogenic and Antioxidant Effects tyrosinase melanin BABT antioxidant activity in silico MITF
topic	misc QD241-441 misc tyrosinase misc melanin misc BABT misc antioxidant activity misc in silico misc MITF misc Organic chemistry
topic_unstemmed	misc QD241-441 misc tyrosinase misc melanin misc BABT misc antioxidant activity misc in silico misc MITF misc Organic chemistry
topic_browse	misc QD241-441 misc tyrosinase misc melanin misc BABT misc antioxidant activity misc in silico misc MITF misc Organic chemistry
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title	Design and Synthesis of (<i<Z</i<)-2-(Benzylamino)-5-benzylidenethiazol-4(5<i<H</i<)-one Derivatives as Tyrosinase Inhibitors and Their Anti-Melanogenic and Antioxidant Effects
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title_full	Design and Synthesis of (<i<Z</i<)-2-(Benzylamino)-5-benzylidenethiazol-4(5<i<H</i<)-one Derivatives as Tyrosinase Inhibitors and Their Anti-Melanogenic and Antioxidant Effects
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author_browse	Jieun Lee Yu Jung Park Hee Jin Jung Sultan Ullah Dahye Yoon Yeongmu Jeong Ga Young Kim Min Kyung Kang Dongwan Kang Yujin Park Pusoon Chun Hae Young Chung Hyung Ryong Moon
container_volume	28
class	QD241-441
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author-letter	Jieun Lee
doi_str_mv	10.3390/molecules28020848
author2-role	verfasserin
title_sort	design and synthesis of (<i<z</i<)-2-(benzylamino)-5-benzylidenethiazol-4(5<i<h</i<)-one derivatives as tyrosinase inhibitors and their anti-melanogenic and antioxidant effects
callnumber	QD241-441
title_auth	Design and Synthesis of (<i<Z</i<)-2-(Benzylamino)-5-benzylidenethiazol-4(5<i<H</i<)-one Derivatives as Tyrosinase Inhibitors and Their Anti-Melanogenic and Antioxidant Effects
abstract	In this study, (<i<Z</i<)-2-(benzylamino)-5-benzylidenethiazol-4(5<i<H</i<)-one (BABT) derivatives were designed as tyrosinase inhibitors based on the structure of MHY2081, using a simplified approach. Of the 14 BABT derivatives synthesized, two derivatives ((<i<Z</i<)-2-(benzylamino)-5-(3-hydroxy-4-methoxybenzylidene)thiazol-4(5<i<H</i<)-one [<b<7</b<] and (<i<Z</i<)-2-(benzylamino)-5-(2,4-dihydroxybenzylidene)thiazol-4(5<i<H</i<)-one [<b<8</b<]) showed more potent mushroom tyrosinase inhibitory activities than kojic acid, regardless of the substrate used; in particular, compound <b<8</b< was 106-fold more potent than kojic acid when <span style="font-variant: small-caps;"<l</span<-tyrosine was used as the substrate. Analysis of Lineweaver–Burk plots for <b<7</b< and <b<8</b< indicated that they were competitive inhibitors, which was confirmed via in silico docking. In experiments using B16F10 cells, <b<8</b< exerted a greater ability to inhibit melanin production than kojic acid, and it inhibited cellular tyrosinase activity in a concentration-dependent manner, indicating that the anti-melanogenic effect of <b<8</b< is attributable to its ability to inhibit tyrosinase. In addition, <b<8</b< exhibited strong antioxidant activity to scavenge 2,2-diphenyl-1-picrylhydrazyl and 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) radicals and peroxynitrite and inhibited the expression of melanogenesis-associated proteins (tyrosinase and microphthalmia-associated transcription factor). These results suggest that BABT derivative <b<8</b< is a promising candidate for the treatment of hyperpigmentation-related diseases, owing to its inhibition of melanogenesis-associated protein expression, direct tyrosinase inhibition, and antioxidant activity.
abstractGer	In this study, (<i<Z</i<)-2-(benzylamino)-5-benzylidenethiazol-4(5<i<H</i<)-one (BABT) derivatives were designed as tyrosinase inhibitors based on the structure of MHY2081, using a simplified approach. Of the 14 BABT derivatives synthesized, two derivatives ((<i<Z</i<)-2-(benzylamino)-5-(3-hydroxy-4-methoxybenzylidene)thiazol-4(5<i<H</i<)-one [<b<7</b<] and (<i<Z</i<)-2-(benzylamino)-5-(2,4-dihydroxybenzylidene)thiazol-4(5<i<H</i<)-one [<b<8</b<]) showed more potent mushroom tyrosinase inhibitory activities than kojic acid, regardless of the substrate used; in particular, compound <b<8</b< was 106-fold more potent than kojic acid when <span style="font-variant: small-caps;"<l</span<-tyrosine was used as the substrate. Analysis of Lineweaver–Burk plots for <b<7</b< and <b<8</b< indicated that they were competitive inhibitors, which was confirmed via in silico docking. In experiments using B16F10 cells, <b<8</b< exerted a greater ability to inhibit melanin production than kojic acid, and it inhibited cellular tyrosinase activity in a concentration-dependent manner, indicating that the anti-melanogenic effect of <b<8</b< is attributable to its ability to inhibit tyrosinase. In addition, <b<8</b< exhibited strong antioxidant activity to scavenge 2,2-diphenyl-1-picrylhydrazyl and 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) radicals and peroxynitrite and inhibited the expression of melanogenesis-associated proteins (tyrosinase and microphthalmia-associated transcription factor). These results suggest that BABT derivative <b<8</b< is a promising candidate for the treatment of hyperpigmentation-related diseases, owing to its inhibition of melanogenesis-associated protein expression, direct tyrosinase inhibition, and antioxidant activity.
abstract_unstemmed	In this study, (<i<Z</i<)-2-(benzylamino)-5-benzylidenethiazol-4(5<i<H</i<)-one (BABT) derivatives were designed as tyrosinase inhibitors based on the structure of MHY2081, using a simplified approach. Of the 14 BABT derivatives synthesized, two derivatives ((<i<Z</i<)-2-(benzylamino)-5-(3-hydroxy-4-methoxybenzylidene)thiazol-4(5<i<H</i<)-one [<b<7</b<] and (<i<Z</i<)-2-(benzylamino)-5-(2,4-dihydroxybenzylidene)thiazol-4(5<i<H</i<)-one [<b<8</b<]) showed more potent mushroom tyrosinase inhibitory activities than kojic acid, regardless of the substrate used; in particular, compound <b<8</b< was 106-fold more potent than kojic acid when <span style="font-variant: small-caps;"<l</span<-tyrosine was used as the substrate. Analysis of Lineweaver–Burk plots for <b<7</b< and <b<8</b< indicated that they were competitive inhibitors, which was confirmed via in silico docking. In experiments using B16F10 cells, <b<8</b< exerted a greater ability to inhibit melanin production than kojic acid, and it inhibited cellular tyrosinase activity in a concentration-dependent manner, indicating that the anti-melanogenic effect of <b<8</b< is attributable to its ability to inhibit tyrosinase. In addition, <b<8</b< exhibited strong antioxidant activity to scavenge 2,2-diphenyl-1-picrylhydrazyl and 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) radicals and peroxynitrite and inhibited the expression of melanogenesis-associated proteins (tyrosinase and microphthalmia-associated transcription factor). These results suggest that BABT derivative <b<8</b< is a promising candidate for the treatment of hyperpigmentation-related diseases, owing to its inhibition of melanogenesis-associated protein expression, direct tyrosinase inhibition, and antioxidant activity.
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title_short	Design and Synthesis of (<i<Z</i<)-2-(Benzylamino)-5-benzylidenethiazol-4(5<i<H</i<)-one Derivatives as Tyrosinase Inhibitors and Their Anti-Melanogenic and Antioxidant Effects
url	https://doi.org/10.3390/molecules28020848 https://doaj.org/article/0b9d0299c49a4c6cbb8527d6178fd552 https://www.mdpi.com/1420-3049/28/2/848 https://doaj.org/toc/1420-3049
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up_date	2024-07-03T21:37:16.291Z
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Design and Synthesis of (<i<Z</i<)-2-(Benzylamino)-5-benzylidenethiazol-4(5<i<H</i<)-one Derivatives as Tyrosinase Inhibitors and Their Anti-Melanogenic and Antioxidant Effects

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