Design and Synthesis of (<i<Z</i<)-5-(Substituted benzylidene)-3-cyclohexyl-2-thioxothiazolidin-4-one Analogues as Anti-Tyrosinase and Antioxidant Compounds: In Vitro and In Silico Insights

Many compounds containing the β-phenyl-α,β-unsaturated carbonyl (PUSC) scaffold, including cinnamamide derivatives, have been shown to inhibit tyrosinase potently in vitro and in vivo. Structural changes to cinnamamide derivatives were produced by adding a dithionate functional group to provide eight (<i<Z</i<)-5-(substituted benzylidene)-3-cyclohexyl-2-thioxothiazolidin-4-one analogs with high log <i<p</i< values for skin. These analogs were synthesized using a two-step reaction, and their stereochemistry was confirmed using the <sup<3</sup<<i<J</i<<sub<C4-Hβ</sub< values of C4 measured in proton-coupled <sup<13</sup<C mode. Analogs <b<2</b< (IC<sub<50</sub< = 5.21 ± 0.86 µM) and <b<3</b< (IC<sub<50</sub< = 1.03 ± 0.14 µM) more potently inhibited mushroom tyrosinase than kojic acid (IC<sub<50</sub< = 25.26 ± 1.10 µM). Docking results showed <b<2</b< binds strongly to the active site of tyrosinase, while <b<3</b< binds strongly to an allosteric site. Kinetic studies using <span style="font-variant: small-caps;"<l</span<-tyrosine as substrate indicated <b<2</b< and <b<3</b< competitively and non-competitively inhibit tyrosinase, respectively, which was supported by our docking results. In B16F10 cells, <b<3</b< significantly and concentration-dependently reduced α–MSH plus IBMX induced increases in cellular tyrosinase activity and melanin production and the similarity between these inhibitory patterns implied that the anti-melanogenic effect of <b<3</b< might be due to its tyrosinase-inhibitory ability. In addition, <b<2</b< and <b<3</b< exhibited strong antioxidant effects; for example, they reduced ROS and ONOO<sup<–</sup< levels and exhibited radical scavenging activities, suggesting that these effects might underlie their anti-melanogenic effects. Furthermore, <b<3</b< suppressed the expressions of melanogenesis-associated proteins and genes in B16F10 cells. These results suggest (<i<Z</i<)-5-(substituted benzylidene)-3-cyclohexyl-2-thioxothiazolidin-4-one analogs offer a means of producing novel anti-melanogenesis agents. Ausführliche Beschreibung

Gespeichert in:

Autor*in:	Jeongin Ko [verfasserIn] Jieun Lee [verfasserIn] Hee Jin Jung [verfasserIn] Sultan Ullah [verfasserIn] Yeongmu Jeong [verfasserIn] Sojeong Hong [verfasserIn] Min Kyung Kang [verfasserIn] Yu Jung Park [verfasserIn] YeJi Hwang [verfasserIn] Dongwan Kang [verfasserIn] Yujin Park [verfasserIn] Pusoon Chun [verfasserIn] Jin-Wook Yoo [verfasserIn] Hae Young Chung [verfasserIn] Hyung Ryong Moon [verfasserIn]

Format:	E-Artikel
Sprache:	Englisch

Erschienen:	2022

Schlagwörter:	tyrosinase PUSC scaffold antioxidant anti-melanogenesis docking rhodanine

Übergeordnetes Werk:	In: Antioxidants - MDPI AG, 2013, 11(2022), 10, p 1918
Übergeordnetes Werk:	volume:11 ; year:2022 ; number:10, p 1918

Links:	Link aufrufen Link aufrufen Link aufrufen Journal toc

DOI / URN:	10.3390/antiox11101918

Katalog-ID:	DOAJ028007697

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245	1	0	\|a Design and Synthesis of (<i<Z</i<)-5-(Substituted benzylidene)-3-cyclohexyl-2-thioxothiazolidin-4-one Analogues as Anti-Tyrosinase and Antioxidant Compounds: In Vitro and In Silico Insights
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520			\|a Many compounds containing the β-phenyl-α,β-unsaturated carbonyl (PUSC) scaffold, including cinnamamide derivatives, have been shown to inhibit tyrosinase potently in vitro and in vivo. Structural changes to cinnamamide derivatives were produced by adding a dithionate functional group to provide eight (<i<Z</i<)-5-(substituted benzylidene)-3-cyclohexyl-2-thioxothiazolidin-4-one analogs with high log <i<p</i< values for skin. These analogs were synthesized using a two-step reaction, and their stereochemistry was confirmed using the <sup<3</sup<<i<J</i<<sub<C4-Hβ</sub< values of C4 measured in proton-coupled <sup<13</sup<C mode. Analogs <b<2</b< (IC<sub<50</sub< = 5.21 ± 0.86 µM) and <b<3</b< (IC<sub<50</sub< = 1.03 ± 0.14 µM) more potently inhibited mushroom tyrosinase than kojic acid (IC<sub<50</sub< = 25.26 ± 1.10 µM). Docking results showed <b<2</b< binds strongly to the active site of tyrosinase, while <b<3</b< binds strongly to an allosteric site. Kinetic studies using <span style="font-variant: small-caps;"<l</span<-tyrosine as substrate indicated <b<2</b< and <b<3</b< competitively and non-competitively inhibit tyrosinase, respectively, which was supported by our docking results. In B16F10 cells, <b<3</b< significantly and concentration-dependently reduced α–MSH plus IBMX induced increases in cellular tyrosinase activity and melanin production and the similarity between these inhibitory patterns implied that the anti-melanogenic effect of <b<3</b< might be due to its tyrosinase-inhibitory ability. In addition, <b<2</b< and <b<3</b< exhibited strong antioxidant effects; for example, they reduced ROS and ONOO<sup<–</sup< levels and exhibited radical scavenging activities, suggesting that these effects might underlie their anti-melanogenic effects. Furthermore, <b<3</b< suppressed the expressions of melanogenesis-associated proteins and genes in B16F10 cells. These results suggest (<i<Z</i<)-5-(substituted benzylidene)-3-cyclohexyl-2-thioxothiazolidin-4-one analogs offer a means of producing novel anti-melanogenesis agents.
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Indexfelder

author_variant	j k jk j l jl h j j hjj s u su y j yj s h sh m k k mkk y j p yjp y h yh d k dk y p yp p c pc j w y jwy h y c hyc h r m hrm
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allfields	10.3390/antiox11101918 doi (DE-627)DOAJ028007697 (DE-599)DOAJ5137a8168c4242748a642c8b1280a248 DE-627 ger DE-627 rakwb eng RM1-950 Jeongin Ko verfasserin aut Design and Synthesis of (<i<Z</i<)-5-(Substituted benzylidene)-3-cyclohexyl-2-thioxothiazolidin-4-one Analogues as Anti-Tyrosinase and Antioxidant Compounds: In Vitro and In Silico Insights 2022 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Many compounds containing the β-phenyl-α,β-unsaturated carbonyl (PUSC) scaffold, including cinnamamide derivatives, have been shown to inhibit tyrosinase potently in vitro and in vivo. Structural changes to cinnamamide derivatives were produced by adding a dithionate functional group to provide eight (<i<Z</i<)-5-(substituted benzylidene)-3-cyclohexyl-2-thioxothiazolidin-4-one analogs with high log <i<p</i< values for skin. These analogs were synthesized using a two-step reaction, and their stereochemistry was confirmed using the <sup<3</sup<<i<J</i<<sub<C4-Hβ</sub< values of C4 measured in proton-coupled <sup<13</sup<C mode. Analogs <b<2</b< (IC<sub<50</sub< = 5.21 ± 0.86 µM) and <b<3</b< (IC<sub<50</sub< = 1.03 ± 0.14 µM) more potently inhibited mushroom tyrosinase than kojic acid (IC<sub<50</sub< = 25.26 ± 1.10 µM). Docking results showed <b<2</b< binds strongly to the active site of tyrosinase, while <b<3</b< binds strongly to an allosteric site. Kinetic studies using <span style="font-variant: small-caps;"<l</span<-tyrosine as substrate indicated <b<2</b< and <b<3</b< competitively and non-competitively inhibit tyrosinase, respectively, which was supported by our docking results. In B16F10 cells, <b<3</b< significantly and concentration-dependently reduced α–MSH plus IBMX induced increases in cellular tyrosinase activity and melanin production and the similarity between these inhibitory patterns implied that the anti-melanogenic effect of <b<3</b< might be due to its tyrosinase-inhibitory ability. In addition, <b<2</b< and <b<3</b< exhibited strong antioxidant effects; for example, they reduced ROS and ONOO<sup<–</sup< levels and exhibited radical scavenging activities, suggesting that these effects might underlie their anti-melanogenic effects. Furthermore, <b<3</b< suppressed the expressions of melanogenesis-associated proteins and genes in B16F10 cells. These results suggest (<i<Z</i<)-5-(substituted benzylidene)-3-cyclohexyl-2-thioxothiazolidin-4-one analogs offer a means of producing novel anti-melanogenesis agents. tyrosinase PUSC scaffold antioxidant anti-melanogenesis docking rhodanine Therapeutics. Pharmacology Jieun Lee verfasserin aut Hee Jin Jung verfasserin aut Sultan Ullah verfasserin aut Yeongmu Jeong verfasserin aut Sojeong Hong verfasserin aut Min Kyung Kang verfasserin aut Yu Jung Park verfasserin aut YeJi Hwang verfasserin aut Dongwan Kang verfasserin aut Yujin Park verfasserin aut Pusoon Chun verfasserin aut Jin-Wook Yoo verfasserin aut Hae Young Chung verfasserin aut Hyung Ryong Moon verfasserin aut In Antioxidants MDPI AG, 2013 11(2022), 10, p 1918 (DE-627)737287578 (DE-600)2704216-9 20763921 nnns volume:11 year:2022 number:10, p 1918 https://doi.org/10.3390/antiox11101918 kostenfrei https://doaj.org/article/5137a8168c4242748a642c8b1280a248 kostenfrei https://www.mdpi.com/2076-3921/11/10/1918 kostenfrei https://doaj.org/toc/2076-3921 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_74 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_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2014 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 11 2022 10, p 1918
spelling	10.3390/antiox11101918 doi (DE-627)DOAJ028007697 (DE-599)DOAJ5137a8168c4242748a642c8b1280a248 DE-627 ger DE-627 rakwb eng RM1-950 Jeongin Ko verfasserin aut Design and Synthesis of (<i<Z</i<)-5-(Substituted benzylidene)-3-cyclohexyl-2-thioxothiazolidin-4-one Analogues as Anti-Tyrosinase and Antioxidant Compounds: In Vitro and In Silico Insights 2022 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Many compounds containing the β-phenyl-α,β-unsaturated carbonyl (PUSC) scaffold, including cinnamamide derivatives, have been shown to inhibit tyrosinase potently in vitro and in vivo. Structural changes to cinnamamide derivatives were produced by adding a dithionate functional group to provide eight (<i<Z</i<)-5-(substituted benzylidene)-3-cyclohexyl-2-thioxothiazolidin-4-one analogs with high log <i<p</i< values for skin. These analogs were synthesized using a two-step reaction, and their stereochemistry was confirmed using the <sup<3</sup<<i<J</i<<sub<C4-Hβ</sub< values of C4 measured in proton-coupled <sup<13</sup<C mode. Analogs <b<2</b< (IC<sub<50</sub< = 5.21 ± 0.86 µM) and <b<3</b< (IC<sub<50</sub< = 1.03 ± 0.14 µM) more potently inhibited mushroom tyrosinase than kojic acid (IC<sub<50</sub< = 25.26 ± 1.10 µM). Docking results showed <b<2</b< binds strongly to the active site of tyrosinase, while <b<3</b< binds strongly to an allosteric site. Kinetic studies using <span style="font-variant: small-caps;"<l</span<-tyrosine as substrate indicated <b<2</b< and <b<3</b< competitively and non-competitively inhibit tyrosinase, respectively, which was supported by our docking results. In B16F10 cells, <b<3</b< significantly and concentration-dependently reduced α–MSH plus IBMX induced increases in cellular tyrosinase activity and melanin production and the similarity between these inhibitory patterns implied that the anti-melanogenic effect of <b<3</b< might be due to its tyrosinase-inhibitory ability. In addition, <b<2</b< and <b<3</b< exhibited strong antioxidant effects; for example, they reduced ROS and ONOO<sup<–</sup< levels and exhibited radical scavenging activities, suggesting that these effects might underlie their anti-melanogenic effects. Furthermore, <b<3</b< suppressed the expressions of melanogenesis-associated proteins and genes in B16F10 cells. These results suggest (<i<Z</i<)-5-(substituted benzylidene)-3-cyclohexyl-2-thioxothiazolidin-4-one analogs offer a means of producing novel anti-melanogenesis agents. tyrosinase PUSC scaffold antioxidant anti-melanogenesis docking rhodanine Therapeutics. Pharmacology Jieun Lee verfasserin aut Hee Jin Jung verfasserin aut Sultan Ullah verfasserin aut Yeongmu Jeong verfasserin aut Sojeong Hong verfasserin aut Min Kyung Kang verfasserin aut Yu Jung Park verfasserin aut YeJi Hwang verfasserin aut Dongwan Kang verfasserin aut Yujin Park verfasserin aut Pusoon Chun verfasserin aut Jin-Wook Yoo verfasserin aut Hae Young Chung verfasserin aut Hyung Ryong Moon verfasserin aut In Antioxidants MDPI AG, 2013 11(2022), 10, p 1918 (DE-627)737287578 (DE-600)2704216-9 20763921 nnns volume:11 year:2022 number:10, p 1918 https://doi.org/10.3390/antiox11101918 kostenfrei https://doaj.org/article/5137a8168c4242748a642c8b1280a248 kostenfrei https://www.mdpi.com/2076-3921/11/10/1918 kostenfrei https://doaj.org/toc/2076-3921 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_74 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_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2014 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 11 2022 10, p 1918
allfields_unstemmed	10.3390/antiox11101918 doi (DE-627)DOAJ028007697 (DE-599)DOAJ5137a8168c4242748a642c8b1280a248 DE-627 ger DE-627 rakwb eng RM1-950 Jeongin Ko verfasserin aut Design and Synthesis of (<i<Z</i<)-5-(Substituted benzylidene)-3-cyclohexyl-2-thioxothiazolidin-4-one Analogues as Anti-Tyrosinase and Antioxidant Compounds: In Vitro and In Silico Insights 2022 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Many compounds containing the β-phenyl-α,β-unsaturated carbonyl (PUSC) scaffold, including cinnamamide derivatives, have been shown to inhibit tyrosinase potently in vitro and in vivo. Structural changes to cinnamamide derivatives were produced by adding a dithionate functional group to provide eight (<i<Z</i<)-5-(substituted benzylidene)-3-cyclohexyl-2-thioxothiazolidin-4-one analogs with high log <i<p</i< values for skin. These analogs were synthesized using a two-step reaction, and their stereochemistry was confirmed using the <sup<3</sup<<i<J</i<<sub<C4-Hβ</sub< values of C4 measured in proton-coupled <sup<13</sup<C mode. Analogs <b<2</b< (IC<sub<50</sub< = 5.21 ± 0.86 µM) and <b<3</b< (IC<sub<50</sub< = 1.03 ± 0.14 µM) more potently inhibited mushroom tyrosinase than kojic acid (IC<sub<50</sub< = 25.26 ± 1.10 µM). Docking results showed <b<2</b< binds strongly to the active site of tyrosinase, while <b<3</b< binds strongly to an allosteric site. Kinetic studies using <span style="font-variant: small-caps;"<l</span<-tyrosine as substrate indicated <b<2</b< and <b<3</b< competitively and non-competitively inhibit tyrosinase, respectively, which was supported by our docking results. In B16F10 cells, <b<3</b< significantly and concentration-dependently reduced α–MSH plus IBMX induced increases in cellular tyrosinase activity and melanin production and the similarity between these inhibitory patterns implied that the anti-melanogenic effect of <b<3</b< might be due to its tyrosinase-inhibitory ability. In addition, <b<2</b< and <b<3</b< exhibited strong antioxidant effects; for example, they reduced ROS and ONOO<sup<–</sup< levels and exhibited radical scavenging activities, suggesting that these effects might underlie their anti-melanogenic effects. Furthermore, <b<3</b< suppressed the expressions of melanogenesis-associated proteins and genes in B16F10 cells. These results suggest (<i<Z</i<)-5-(substituted benzylidene)-3-cyclohexyl-2-thioxothiazolidin-4-one analogs offer a means of producing novel anti-melanogenesis agents. tyrosinase PUSC scaffold antioxidant anti-melanogenesis docking rhodanine Therapeutics. Pharmacology Jieun Lee verfasserin aut Hee Jin Jung verfasserin aut Sultan Ullah verfasserin aut Yeongmu Jeong verfasserin aut Sojeong Hong verfasserin aut Min Kyung Kang verfasserin aut Yu Jung Park verfasserin aut YeJi Hwang verfasserin aut Dongwan Kang verfasserin aut Yujin Park verfasserin aut Pusoon Chun verfasserin aut Jin-Wook Yoo verfasserin aut Hae Young Chung verfasserin aut Hyung Ryong Moon verfasserin aut In Antioxidants MDPI AG, 2013 11(2022), 10, p 1918 (DE-627)737287578 (DE-600)2704216-9 20763921 nnns volume:11 year:2022 number:10, p 1918 https://doi.org/10.3390/antiox11101918 kostenfrei https://doaj.org/article/5137a8168c4242748a642c8b1280a248 kostenfrei https://www.mdpi.com/2076-3921/11/10/1918 kostenfrei https://doaj.org/toc/2076-3921 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_74 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_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2014 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 11 2022 10, p 1918
allfieldsGer	10.3390/antiox11101918 doi (DE-627)DOAJ028007697 (DE-599)DOAJ5137a8168c4242748a642c8b1280a248 DE-627 ger DE-627 rakwb eng RM1-950 Jeongin Ko verfasserin aut Design and Synthesis of (<i<Z</i<)-5-(Substituted benzylidene)-3-cyclohexyl-2-thioxothiazolidin-4-one Analogues as Anti-Tyrosinase and Antioxidant Compounds: In Vitro and In Silico Insights 2022 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Many compounds containing the β-phenyl-α,β-unsaturated carbonyl (PUSC) scaffold, including cinnamamide derivatives, have been shown to inhibit tyrosinase potently in vitro and in vivo. Structural changes to cinnamamide derivatives were produced by adding a dithionate functional group to provide eight (<i<Z</i<)-5-(substituted benzylidene)-3-cyclohexyl-2-thioxothiazolidin-4-one analogs with high log <i<p</i< values for skin. These analogs were synthesized using a two-step reaction, and their stereochemistry was confirmed using the <sup<3</sup<<i<J</i<<sub<C4-Hβ</sub< values of C4 measured in proton-coupled <sup<13</sup<C mode. Analogs <b<2</b< (IC<sub<50</sub< = 5.21 ± 0.86 µM) and <b<3</b< (IC<sub<50</sub< = 1.03 ± 0.14 µM) more potently inhibited mushroom tyrosinase than kojic acid (IC<sub<50</sub< = 25.26 ± 1.10 µM). Docking results showed <b<2</b< binds strongly to the active site of tyrosinase, while <b<3</b< binds strongly to an allosteric site. Kinetic studies using <span style="font-variant: small-caps;"<l</span<-tyrosine as substrate indicated <b<2</b< and <b<3</b< competitively and non-competitively inhibit tyrosinase, respectively, which was supported by our docking results. In B16F10 cells, <b<3</b< significantly and concentration-dependently reduced α–MSH plus IBMX induced increases in cellular tyrosinase activity and melanin production and the similarity between these inhibitory patterns implied that the anti-melanogenic effect of <b<3</b< might be due to its tyrosinase-inhibitory ability. In addition, <b<2</b< and <b<3</b< exhibited strong antioxidant effects; for example, they reduced ROS and ONOO<sup<–</sup< levels and exhibited radical scavenging activities, suggesting that these effects might underlie their anti-melanogenic effects. Furthermore, <b<3</b< suppressed the expressions of melanogenesis-associated proteins and genes in B16F10 cells. These results suggest (<i<Z</i<)-5-(substituted benzylidene)-3-cyclohexyl-2-thioxothiazolidin-4-one analogs offer a means of producing novel anti-melanogenesis agents. tyrosinase PUSC scaffold antioxidant anti-melanogenesis docking rhodanine Therapeutics. Pharmacology Jieun Lee verfasserin aut Hee Jin Jung verfasserin aut Sultan Ullah verfasserin aut Yeongmu Jeong verfasserin aut Sojeong Hong verfasserin aut Min Kyung Kang verfasserin aut Yu Jung Park verfasserin aut YeJi Hwang verfasserin aut Dongwan Kang verfasserin aut Yujin Park verfasserin aut Pusoon Chun verfasserin aut Jin-Wook Yoo verfasserin aut Hae Young Chung verfasserin aut Hyung Ryong Moon verfasserin aut In Antioxidants MDPI AG, 2013 11(2022), 10, p 1918 (DE-627)737287578 (DE-600)2704216-9 20763921 nnns volume:11 year:2022 number:10, p 1918 https://doi.org/10.3390/antiox11101918 kostenfrei https://doaj.org/article/5137a8168c4242748a642c8b1280a248 kostenfrei https://www.mdpi.com/2076-3921/11/10/1918 kostenfrei https://doaj.org/toc/2076-3921 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_74 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_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2014 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 11 2022 10, p 1918
allfieldsSound	10.3390/antiox11101918 doi (DE-627)DOAJ028007697 (DE-599)DOAJ5137a8168c4242748a642c8b1280a248 DE-627 ger DE-627 rakwb eng RM1-950 Jeongin Ko verfasserin aut Design and Synthesis of (<i<Z</i<)-5-(Substituted benzylidene)-3-cyclohexyl-2-thioxothiazolidin-4-one Analogues as Anti-Tyrosinase and Antioxidant Compounds: In Vitro and In Silico Insights 2022 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Many compounds containing the β-phenyl-α,β-unsaturated carbonyl (PUSC) scaffold, including cinnamamide derivatives, have been shown to inhibit tyrosinase potently in vitro and in vivo. Structural changes to cinnamamide derivatives were produced by adding a dithionate functional group to provide eight (<i<Z</i<)-5-(substituted benzylidene)-3-cyclohexyl-2-thioxothiazolidin-4-one analogs with high log <i<p</i< values for skin. These analogs were synthesized using a two-step reaction, and their stereochemistry was confirmed using the <sup<3</sup<<i<J</i<<sub<C4-Hβ</sub< values of C4 measured in proton-coupled <sup<13</sup<C mode. Analogs <b<2</b< (IC<sub<50</sub< = 5.21 ± 0.86 µM) and <b<3</b< (IC<sub<50</sub< = 1.03 ± 0.14 µM) more potently inhibited mushroom tyrosinase than kojic acid (IC<sub<50</sub< = 25.26 ± 1.10 µM). Docking results showed <b<2</b< binds strongly to the active site of tyrosinase, while <b<3</b< binds strongly to an allosteric site. Kinetic studies using <span style="font-variant: small-caps;"<l</span<-tyrosine as substrate indicated <b<2</b< and <b<3</b< competitively and non-competitively inhibit tyrosinase, respectively, which was supported by our docking results. In B16F10 cells, <b<3</b< significantly and concentration-dependently reduced α–MSH plus IBMX induced increases in cellular tyrosinase activity and melanin production and the similarity between these inhibitory patterns implied that the anti-melanogenic effect of <b<3</b< might be due to its tyrosinase-inhibitory ability. In addition, <b<2</b< and <b<3</b< exhibited strong antioxidant effects; for example, they reduced ROS and ONOO<sup<–</sup< levels and exhibited radical scavenging activities, suggesting that these effects might underlie their anti-melanogenic effects. Furthermore, <b<3</b< suppressed the expressions of melanogenesis-associated proteins and genes in B16F10 cells. These results suggest (<i<Z</i<)-5-(substituted benzylidene)-3-cyclohexyl-2-thioxothiazolidin-4-one analogs offer a means of producing novel anti-melanogenesis agents. tyrosinase PUSC scaffold antioxidant anti-melanogenesis docking rhodanine Therapeutics. Pharmacology Jieun Lee verfasserin aut Hee Jin Jung verfasserin aut Sultan Ullah verfasserin aut Yeongmu Jeong verfasserin aut Sojeong Hong verfasserin aut Min Kyung Kang verfasserin aut Yu Jung Park verfasserin aut YeJi Hwang verfasserin aut Dongwan Kang verfasserin aut Yujin Park verfasserin aut Pusoon Chun verfasserin aut Jin-Wook Yoo verfasserin aut Hae Young Chung verfasserin aut Hyung Ryong Moon verfasserin aut In Antioxidants MDPI AG, 2013 11(2022), 10, p 1918 (DE-627)737287578 (DE-600)2704216-9 20763921 nnns volume:11 year:2022 number:10, p 1918 https://doi.org/10.3390/antiox11101918 kostenfrei https://doaj.org/article/5137a8168c4242748a642c8b1280a248 kostenfrei https://www.mdpi.com/2076-3921/11/10/1918 kostenfrei https://doaj.org/toc/2076-3921 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_74 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_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2014 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 11 2022 10, p 1918
language	English
source	In Antioxidants 11(2022), 10, p 1918 volume:11 year:2022 number:10, p 1918
sourceStr	In Antioxidants 11(2022), 10, p 1918 volume:11 year:2022 number:10, p 1918
format_phy_str_mv	Article
institution	findex.gbv.de
topic_facet	tyrosinase PUSC scaffold antioxidant anti-melanogenesis docking rhodanine Therapeutics. Pharmacology
isfreeaccess_bool	true
container_title	Antioxidants
authorswithroles_txt_mv	Jeongin Ko @@aut@@ Jieun Lee @@aut@@ Hee Jin Jung @@aut@@ Sultan Ullah @@aut@@ Yeongmu Jeong @@aut@@ Sojeong Hong @@aut@@ Min Kyung Kang @@aut@@ Yu Jung Park @@aut@@ YeJi Hwang @@aut@@ Dongwan Kang @@aut@@ Yujin Park @@aut@@ Pusoon Chun @@aut@@ Jin-Wook Yoo @@aut@@ Hae Young Chung @@aut@@ Hyung Ryong Moon @@aut@@
publishDateDaySort_date	2022-01-01T00:00:00Z
hierarchy_top_id	737287578
id	DOAJ028007697
language_de	englisch
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Structural changes to cinnamamide derivatives were produced by adding a dithionate functional group to provide eight (<i<Z</i<)-5-(substituted benzylidene)-3-cyclohexyl-2-thioxothiazolidin-4-one analogs with high log <i<p</i< values for skin. These analogs were synthesized using a two-step reaction, and their stereochemistry was confirmed using the <sup<3</sup<<i<J</i<<sub<C4-Hβ</sub< values of C4 measured in proton-coupled <sup<13</sup<C mode. Analogs <b<2</b< (IC<sub<50</sub< = 5.21 ± 0.86 µM) and <b<3</b< (IC<sub<50</sub< = 1.03 ± 0.14 µM) more potently inhibited mushroom tyrosinase than kojic acid (IC<sub<50</sub< = 25.26 ± 1.10 µM). Docking results showed <b<2</b< binds strongly to the active site of tyrosinase, while <b<3</b< binds strongly to an allosteric site. Kinetic studies using <span style="font-variant: small-caps;"<l</span<-tyrosine as substrate indicated <b<2</b< and <b<3</b< competitively and non-competitively inhibit tyrosinase, respectively, which was supported by our docking results. In B16F10 cells, <b<3</b< significantly and concentration-dependently reduced α–MSH plus IBMX induced increases in cellular tyrosinase activity and melanin production and the similarity between these inhibitory patterns implied that the anti-melanogenic effect of <b<3</b< might be due to its tyrosinase-inhibitory ability. In addition, <b<2</b< and <b<3</b< exhibited strong antioxidant effects; for example, they reduced ROS and ONOO<sup<–</sup< levels and exhibited radical scavenging activities, suggesting that these effects might underlie their anti-melanogenic effects. Furthermore, <b<3</b< suppressed the expressions of melanogenesis-associated proteins and genes in B16F10 cells. 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callnumber-first	R - Medicine
author	Jeongin Ko
spellingShingle	Jeongin Ko misc RM1-950 misc tyrosinase misc PUSC scaffold misc antioxidant misc anti-melanogenesis misc docking misc rhodanine misc Therapeutics. Pharmacology Design and Synthesis of (<i<Z</i<)-5-(Substituted benzylidene)-3-cyclohexyl-2-thioxothiazolidin-4-one Analogues as Anti-Tyrosinase and Antioxidant Compounds: In Vitro and In Silico Insights
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topic_title	RM1-950 Design and Synthesis of (<i<Z</i<)-5-(Substituted benzylidene)-3-cyclohexyl-2-thioxothiazolidin-4-one Analogues as Anti-Tyrosinase and Antioxidant Compounds: In Vitro and In Silico Insights tyrosinase PUSC scaffold antioxidant anti-melanogenesis docking rhodanine
topic	misc RM1-950 misc tyrosinase misc PUSC scaffold misc antioxidant misc anti-melanogenesis misc docking misc rhodanine misc Therapeutics. Pharmacology
topic_unstemmed	misc RM1-950 misc tyrosinase misc PUSC scaffold misc antioxidant misc anti-melanogenesis misc docking misc rhodanine misc Therapeutics. Pharmacology
topic_browse	misc RM1-950 misc tyrosinase misc PUSC scaffold misc antioxidant misc anti-melanogenesis misc docking misc rhodanine misc Therapeutics. Pharmacology
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title	Design and Synthesis of (<i<Z</i<)-5-(Substituted benzylidene)-3-cyclohexyl-2-thioxothiazolidin-4-one Analogues as Anti-Tyrosinase and Antioxidant Compounds: In Vitro and In Silico Insights
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title_full	Design and Synthesis of (<i<Z</i<)-5-(Substituted benzylidene)-3-cyclohexyl-2-thioxothiazolidin-4-one Analogues as Anti-Tyrosinase and Antioxidant Compounds: In Vitro and In Silico Insights
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author_browse	Jeongin Ko Jieun Lee Hee Jin Jung Sultan Ullah Yeongmu Jeong Sojeong Hong Min Kyung Kang Yu Jung Park YeJi Hwang Dongwan Kang Yujin Park Pusoon Chun Jin-Wook Yoo Hae Young Chung Hyung Ryong Moon
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author-letter	Jeongin Ko
doi_str_mv	10.3390/antiox11101918
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title_sort	design and synthesis of (<i<z</i<)-5-(substituted benzylidene)-3-cyclohexyl-2-thioxothiazolidin-4-one analogues as anti-tyrosinase and antioxidant compounds: in vitro and in silico insights
callnumber	RM1-950
title_auth	Design and Synthesis of (<i<Z</i<)-5-(Substituted benzylidene)-3-cyclohexyl-2-thioxothiazolidin-4-one Analogues as Anti-Tyrosinase and Antioxidant Compounds: In Vitro and In Silico Insights
abstract	Many compounds containing the β-phenyl-α,β-unsaturated carbonyl (PUSC) scaffold, including cinnamamide derivatives, have been shown to inhibit tyrosinase potently in vitro and in vivo. Structural changes to cinnamamide derivatives were produced by adding a dithionate functional group to provide eight (<i<Z</i<)-5-(substituted benzylidene)-3-cyclohexyl-2-thioxothiazolidin-4-one analogs with high log <i<p</i< values for skin. These analogs were synthesized using a two-step reaction, and their stereochemistry was confirmed using the <sup<3</sup<<i<J</i<<sub<C4-Hβ</sub< values of C4 measured in proton-coupled <sup<13</sup<C mode. Analogs <b<2</b< (IC<sub<50</sub< = 5.21 ± 0.86 µM) and <b<3</b< (IC<sub<50</sub< = 1.03 ± 0.14 µM) more potently inhibited mushroom tyrosinase than kojic acid (IC<sub<50</sub< = 25.26 ± 1.10 µM). Docking results showed <b<2</b< binds strongly to the active site of tyrosinase, while <b<3</b< binds strongly to an allosteric site. Kinetic studies using <span style="font-variant: small-caps;"<l</span<-tyrosine as substrate indicated <b<2</b< and <b<3</b< competitively and non-competitively inhibit tyrosinase, respectively, which was supported by our docking results. In B16F10 cells, <b<3</b< significantly and concentration-dependently reduced α–MSH plus IBMX induced increases in cellular tyrosinase activity and melanin production and the similarity between these inhibitory patterns implied that the anti-melanogenic effect of <b<3</b< might be due to its tyrosinase-inhibitory ability. In addition, <b<2</b< and <b<3</b< exhibited strong antioxidant effects; for example, they reduced ROS and ONOO<sup<–</sup< levels and exhibited radical scavenging activities, suggesting that these effects might underlie their anti-melanogenic effects. Furthermore, <b<3</b< suppressed the expressions of melanogenesis-associated proteins and genes in B16F10 cells. These results suggest (<i<Z</i<)-5-(substituted benzylidene)-3-cyclohexyl-2-thioxothiazolidin-4-one analogs offer a means of producing novel anti-melanogenesis agents.
abstractGer	Many compounds containing the β-phenyl-α,β-unsaturated carbonyl (PUSC) scaffold, including cinnamamide derivatives, have been shown to inhibit tyrosinase potently in vitro and in vivo. Structural changes to cinnamamide derivatives were produced by adding a dithionate functional group to provide eight (<i<Z</i<)-5-(substituted benzylidene)-3-cyclohexyl-2-thioxothiazolidin-4-one analogs with high log <i<p</i< values for skin. These analogs were synthesized using a two-step reaction, and their stereochemistry was confirmed using the <sup<3</sup<<i<J</i<<sub<C4-Hβ</sub< values of C4 measured in proton-coupled <sup<13</sup<C mode. Analogs <b<2</b< (IC<sub<50</sub< = 5.21 ± 0.86 µM) and <b<3</b< (IC<sub<50</sub< = 1.03 ± 0.14 µM) more potently inhibited mushroom tyrosinase than kojic acid (IC<sub<50</sub< = 25.26 ± 1.10 µM). Docking results showed <b<2</b< binds strongly to the active site of tyrosinase, while <b<3</b< binds strongly to an allosteric site. Kinetic studies using <span style="font-variant: small-caps;"<l</span<-tyrosine as substrate indicated <b<2</b< and <b<3</b< competitively and non-competitively inhibit tyrosinase, respectively, which was supported by our docking results. In B16F10 cells, <b<3</b< significantly and concentration-dependently reduced α–MSH plus IBMX induced increases in cellular tyrosinase activity and melanin production and the similarity between these inhibitory patterns implied that the anti-melanogenic effect of <b<3</b< might be due to its tyrosinase-inhibitory ability. In addition, <b<2</b< and <b<3</b< exhibited strong antioxidant effects; for example, they reduced ROS and ONOO<sup<–</sup< levels and exhibited radical scavenging activities, suggesting that these effects might underlie their anti-melanogenic effects. Furthermore, <b<3</b< suppressed the expressions of melanogenesis-associated proteins and genes in B16F10 cells. These results suggest (<i<Z</i<)-5-(substituted benzylidene)-3-cyclohexyl-2-thioxothiazolidin-4-one analogs offer a means of producing novel anti-melanogenesis agents.
abstract_unstemmed	Many compounds containing the β-phenyl-α,β-unsaturated carbonyl (PUSC) scaffold, including cinnamamide derivatives, have been shown to inhibit tyrosinase potently in vitro and in vivo. Structural changes to cinnamamide derivatives were produced by adding a dithionate functional group to provide eight (<i<Z</i<)-5-(substituted benzylidene)-3-cyclohexyl-2-thioxothiazolidin-4-one analogs with high log <i<p</i< values for skin. These analogs were synthesized using a two-step reaction, and their stereochemistry was confirmed using the <sup<3</sup<<i<J</i<<sub<C4-Hβ</sub< values of C4 measured in proton-coupled <sup<13</sup<C mode. Analogs <b<2</b< (IC<sub<50</sub< = 5.21 ± 0.86 µM) and <b<3</b< (IC<sub<50</sub< = 1.03 ± 0.14 µM) more potently inhibited mushroom tyrosinase than kojic acid (IC<sub<50</sub< = 25.26 ± 1.10 µM). Docking results showed <b<2</b< binds strongly to the active site of tyrosinase, while <b<3</b< binds strongly to an allosteric site. Kinetic studies using <span style="font-variant: small-caps;"<l</span<-tyrosine as substrate indicated <b<2</b< and <b<3</b< competitively and non-competitively inhibit tyrosinase, respectively, which was supported by our docking results. In B16F10 cells, <b<3</b< significantly and concentration-dependently reduced α–MSH plus IBMX induced increases in cellular tyrosinase activity and melanin production and the similarity between these inhibitory patterns implied that the anti-melanogenic effect of <b<3</b< might be due to its tyrosinase-inhibitory ability. In addition, <b<2</b< and <b<3</b< exhibited strong antioxidant effects; for example, they reduced ROS and ONOO<sup<–</sup< levels and exhibited radical scavenging activities, suggesting that these effects might underlie their anti-melanogenic effects. Furthermore, <b<3</b< suppressed the expressions of melanogenesis-associated proteins and genes in B16F10 cells. These results suggest (<i<Z</i<)-5-(substituted benzylidene)-3-cyclohexyl-2-thioxothiazolidin-4-one analogs offer a means of producing novel anti-melanogenesis agents.
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container_issue	10, p 1918
title_short	Design and Synthesis of (<i<Z</i<)-5-(Substituted benzylidene)-3-cyclohexyl-2-thioxothiazolidin-4-one Analogues as Anti-Tyrosinase and Antioxidant Compounds: In Vitro and In Silico Insights
url	https://doi.org/10.3390/antiox11101918 https://doaj.org/article/5137a8168c4242748a642c8b1280a248 https://www.mdpi.com/2076-3921/11/10/1918 https://doaj.org/toc/2076-3921
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Structural changes to cinnamamide derivatives were produced by adding a dithionate functional group to provide eight (<i<Z</i<)-5-(substituted benzylidene)-3-cyclohexyl-2-thioxothiazolidin-4-one analogs with high log <i<p</i< values for skin. These analogs were synthesized using a two-step reaction, and their stereochemistry was confirmed using the <sup<3</sup<<i<J</i<<sub<C4-Hβ</sub< values of C4 measured in proton-coupled <sup<13</sup<C mode. Analogs <b<2</b< (IC<sub<50</sub< = 5.21 ± 0.86 µM) and <b<3</b< (IC<sub<50</sub< = 1.03 ± 0.14 µM) more potently inhibited mushroom tyrosinase than kojic acid (IC<sub<50</sub< = 25.26 ± 1.10 µM). Docking results showed <b<2</b< binds strongly to the active site of tyrosinase, while <b<3</b< binds strongly to an allosteric site. Kinetic studies using <span style="font-variant: small-caps;"<l</span<-tyrosine as substrate indicated <b<2</b< and <b<3</b< competitively and non-competitively inhibit tyrosinase, respectively, which was supported by our docking results. In B16F10 cells, <b<3</b< significantly and concentration-dependently reduced α–MSH plus IBMX induced increases in cellular tyrosinase activity and melanin production and the similarity between these inhibitory patterns implied that the anti-melanogenic effect of <b<3</b< might be due to its tyrosinase-inhibitory ability. In addition, <b<2</b< and <b<3</b< exhibited strong antioxidant effects; for example, they reduced ROS and ONOO<sup<–</sup< levels and exhibited radical scavenging activities, suggesting that these effects might underlie their anti-melanogenic effects. Furthermore, <b<3</b< suppressed the expressions of melanogenesis-associated proteins and genes in B16F10 cells. 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Design and Synthesis of (<i<Z</i<)-5-(Substituted benzylidene)-3-cyclohexyl-2-thioxothiazolidin-4-one Analogues as Anti-Tyrosinase and Antioxidant Compounds: In Vitro and In Silico Insights

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