In silico and in vitro insights into tyrosinase inhibitors with a 2-thioxooxazoline-4-one template

The β-phenyl-α,β-unsaturated carbonyl (PUSC) scaffold confers tyrosinase inhibitory activity, and in the present study, 16 (Z)-5-(substituted benzylidene)-3-phenyl-2-thioxooxazolidin-4-one analogues containing this scaffold were synthesized. Mushroom tyrosinase inhibitory activities were examined. C...
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Autor*in:	Inkyu Choi [verfasserIn] Yujin Park [verfasserIn] Il Young Ryu [verfasserIn] Hee Jin Jung [verfasserIn] Sultan Ullah [verfasserIn] Heejeong Choi [verfasserIn] Chaeun Park [verfasserIn] Dongwan Kang [verfasserIn] Sanggwon Lee [verfasserIn] Pusoon Chun [verfasserIn] Hae Young Chung [verfasserIn] Hyung Ryong Moon [verfasserIn]

Format:	E-Artikel
Sprache:	Englisch

Erschienen:	2021

Schlagwörter:	Tyrosinase 2-thioxooxazoline-4-one Anti-melanogenesis Kojic acid Docking simulation β-phenyl-α,β-unsaturated carbonyl scaffold

Übergeordnetes Werk:	In: Computational and Structural Biotechnology Journal - Elsevier, 2013, 19(2021), Seite 37-50
Übergeordnetes Werk:	volume:19 ; year:2021 ; pages:37-50

Links:	Link aufrufen Link aufrufen Link aufrufen Journal toc

DOI / URN:	10.1016/j.csbj.2020.12.001

Katalog-ID:	DOAJ07476912X

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allfields	10.1016/j.csbj.2020.12.001 doi (DE-627)DOAJ07476912X (DE-599)DOAJ89ae3e87421146fd846ffb9e9870e0f5 DE-627 ger DE-627 rakwb eng TP248.13-248.65 Inkyu Choi verfasserin aut In silico and in vitro insights into tyrosinase inhibitors with a 2-thioxooxazoline-4-one template 2021 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier The β-phenyl-α,β-unsaturated carbonyl (PUSC) scaffold confers tyrosinase inhibitory activity, and in the present study, 16 (Z)-5-(substituted benzylidene)-3-phenyl-2-thioxooxazolidin-4-one analogues containing this scaffold were synthesized. Mushroom tyrosinase inhibitory activities were examined. Compound 1c (IC50 = 4.70 ± 0.40 μM) and compound 1j (IC50 = 11.18 ± 0.54 μM) inhibited tyrosinase by 4.9 and 2.1-fold, respectively, and did so more potently than kojic acid (IC50 = 23.18 ± 0.11 μM). Kinetic analysis of tyrosinase inhibition revealed that 1c and 1j inhibited tyrosinase competitively. Results of docking simulation with mushroom tyrosinase using four docking programs suggested that 1c and 1j bind more strongly than kojic acid to the active site of tyrosinase and supported kinetic findings that both compounds are competitive inhibitors. The docking results of human tyrosinase homology model indicated that 1c and 1j can also strongly inhibit human tyrosinase. EZ-cytox assays revealed 1c and 1j were not cytotoxic to B16F10 melanoma cells. The effects of 1c and 1j on cellular tyrosinase activity and melanin production were also investigated in α-MSH- and IBMX-co-stimulated these cells. Both compounds significantly and dose-dependently reduced tyrosinase activity, and at 10 µM were more potent than kojic acid at 20 µM. Compounds 1c and 1j also inhibited melanogenesis, which suggested that the inhibitory effects of these compounds on melanin production were mainly attributable to their inhibitions of tyrosinase. These results indicate that compounds 1c and 1j with the PUSC scaffold have potential use as whitening agents for the treatment of hyperpigmentation-associated diseases. Tyrosinase 2-thioxooxazoline-4-one Anti-melanogenesis Kojic acid Docking simulation β-phenyl-α,β-unsaturated carbonyl scaffold Biotechnology Yujin Park verfasserin aut Il Young Ryu verfasserin aut Hee Jin Jung verfasserin aut Sultan Ullah verfasserin aut Heejeong Choi verfasserin aut Chaeun Park verfasserin aut Dongwan Kang verfasserin aut Sanggwon Lee verfasserin aut Pusoon Chun verfasserin aut Hae Young Chung verfasserin aut Hyung Ryong Moon verfasserin aut In Computational and Structural Biotechnology Journal Elsevier, 2013 19(2021), Seite 37-50 (DE-627)731890086 (DE-600)2694435-2 20010370 nnns volume:19 year:2021 pages:37-50 https://doi.org/10.1016/j.csbj.2020.12.001 kostenfrei https://doaj.org/article/89ae3e87421146fd846ffb9e9870e0f5 kostenfrei http://www.sciencedirect.com/science/article/pii/S2001037020305262 kostenfrei https://doaj.org/toc/2001-0370 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_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_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 19 2021 37-50
spelling	10.1016/j.csbj.2020.12.001 doi (DE-627)DOAJ07476912X (DE-599)DOAJ89ae3e87421146fd846ffb9e9870e0f5 DE-627 ger DE-627 rakwb eng TP248.13-248.65 Inkyu Choi verfasserin aut In silico and in vitro insights into tyrosinase inhibitors with a 2-thioxooxazoline-4-one template 2021 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier The β-phenyl-α,β-unsaturated carbonyl (PUSC) scaffold confers tyrosinase inhibitory activity, and in the present study, 16 (Z)-5-(substituted benzylidene)-3-phenyl-2-thioxooxazolidin-4-one analogues containing this scaffold were synthesized. Mushroom tyrosinase inhibitory activities were examined. Compound 1c (IC50 = 4.70 ± 0.40 μM) and compound 1j (IC50 = 11.18 ± 0.54 μM) inhibited tyrosinase by 4.9 and 2.1-fold, respectively, and did so more potently than kojic acid (IC50 = 23.18 ± 0.11 μM). Kinetic analysis of tyrosinase inhibition revealed that 1c and 1j inhibited tyrosinase competitively. Results of docking simulation with mushroom tyrosinase using four docking programs suggested that 1c and 1j bind more strongly than kojic acid to the active site of tyrosinase and supported kinetic findings that both compounds are competitive inhibitors. The docking results of human tyrosinase homology model indicated that 1c and 1j can also strongly inhibit human tyrosinase. EZ-cytox assays revealed 1c and 1j were not cytotoxic to B16F10 melanoma cells. The effects of 1c and 1j on cellular tyrosinase activity and melanin production were also investigated in α-MSH- and IBMX-co-stimulated these cells. Both compounds significantly and dose-dependently reduced tyrosinase activity, and at 10 µM were more potent than kojic acid at 20 µM. Compounds 1c and 1j also inhibited melanogenesis, which suggested that the inhibitory effects of these compounds on melanin production were mainly attributable to their inhibitions of tyrosinase. These results indicate that compounds 1c and 1j with the PUSC scaffold have potential use as whitening agents for the treatment of hyperpigmentation-associated diseases. Tyrosinase 2-thioxooxazoline-4-one Anti-melanogenesis Kojic acid Docking simulation β-phenyl-α,β-unsaturated carbonyl scaffold Biotechnology Yujin Park verfasserin aut Il Young Ryu verfasserin aut Hee Jin Jung verfasserin aut Sultan Ullah verfasserin aut Heejeong Choi verfasserin aut Chaeun Park verfasserin aut Dongwan Kang verfasserin aut Sanggwon Lee verfasserin aut Pusoon Chun verfasserin aut Hae Young Chung verfasserin aut Hyung Ryong Moon verfasserin aut In Computational and Structural Biotechnology Journal Elsevier, 2013 19(2021), Seite 37-50 (DE-627)731890086 (DE-600)2694435-2 20010370 nnns volume:19 year:2021 pages:37-50 https://doi.org/10.1016/j.csbj.2020.12.001 kostenfrei https://doaj.org/article/89ae3e87421146fd846ffb9e9870e0f5 kostenfrei http://www.sciencedirect.com/science/article/pii/S2001037020305262 kostenfrei https://doaj.org/toc/2001-0370 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_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_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 19 2021 37-50
allfields_unstemmed	10.1016/j.csbj.2020.12.001 doi (DE-627)DOAJ07476912X (DE-599)DOAJ89ae3e87421146fd846ffb9e9870e0f5 DE-627 ger DE-627 rakwb eng TP248.13-248.65 Inkyu Choi verfasserin aut In silico and in vitro insights into tyrosinase inhibitors with a 2-thioxooxazoline-4-one template 2021 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier The β-phenyl-α,β-unsaturated carbonyl (PUSC) scaffold confers tyrosinase inhibitory activity, and in the present study, 16 (Z)-5-(substituted benzylidene)-3-phenyl-2-thioxooxazolidin-4-one analogues containing this scaffold were synthesized. Mushroom tyrosinase inhibitory activities were examined. Compound 1c (IC50 = 4.70 ± 0.40 μM) and compound 1j (IC50 = 11.18 ± 0.54 μM) inhibited tyrosinase by 4.9 and 2.1-fold, respectively, and did so more potently than kojic acid (IC50 = 23.18 ± 0.11 μM). Kinetic analysis of tyrosinase inhibition revealed that 1c and 1j inhibited tyrosinase competitively. Results of docking simulation with mushroom tyrosinase using four docking programs suggested that 1c and 1j bind more strongly than kojic acid to the active site of tyrosinase and supported kinetic findings that both compounds are competitive inhibitors. The docking results of human tyrosinase homology model indicated that 1c and 1j can also strongly inhibit human tyrosinase. EZ-cytox assays revealed 1c and 1j were not cytotoxic to B16F10 melanoma cells. The effects of 1c and 1j on cellular tyrosinase activity and melanin production were also investigated in α-MSH- and IBMX-co-stimulated these cells. Both compounds significantly and dose-dependently reduced tyrosinase activity, and at 10 µM were more potent than kojic acid at 20 µM. Compounds 1c and 1j also inhibited melanogenesis, which suggested that the inhibitory effects of these compounds on melanin production were mainly attributable to their inhibitions of tyrosinase. These results indicate that compounds 1c and 1j with the PUSC scaffold have potential use as whitening agents for the treatment of hyperpigmentation-associated diseases. Tyrosinase 2-thioxooxazoline-4-one Anti-melanogenesis Kojic acid Docking simulation β-phenyl-α,β-unsaturated carbonyl scaffold Biotechnology Yujin Park verfasserin aut Il Young Ryu verfasserin aut Hee Jin Jung verfasserin aut Sultan Ullah verfasserin aut Heejeong Choi verfasserin aut Chaeun Park verfasserin aut Dongwan Kang verfasserin aut Sanggwon Lee verfasserin aut Pusoon Chun verfasserin aut Hae Young Chung verfasserin aut Hyung Ryong Moon verfasserin aut In Computational and Structural Biotechnology Journal Elsevier, 2013 19(2021), Seite 37-50 (DE-627)731890086 (DE-600)2694435-2 20010370 nnns volume:19 year:2021 pages:37-50 https://doi.org/10.1016/j.csbj.2020.12.001 kostenfrei https://doaj.org/article/89ae3e87421146fd846ffb9e9870e0f5 kostenfrei http://www.sciencedirect.com/science/article/pii/S2001037020305262 kostenfrei https://doaj.org/toc/2001-0370 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_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_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 19 2021 37-50
allfieldsGer	10.1016/j.csbj.2020.12.001 doi (DE-627)DOAJ07476912X (DE-599)DOAJ89ae3e87421146fd846ffb9e9870e0f5 DE-627 ger DE-627 rakwb eng TP248.13-248.65 Inkyu Choi verfasserin aut In silico and in vitro insights into tyrosinase inhibitors with a 2-thioxooxazoline-4-one template 2021 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier The β-phenyl-α,β-unsaturated carbonyl (PUSC) scaffold confers tyrosinase inhibitory activity, and in the present study, 16 (Z)-5-(substituted benzylidene)-3-phenyl-2-thioxooxazolidin-4-one analogues containing this scaffold were synthesized. Mushroom tyrosinase inhibitory activities were examined. Compound 1c (IC50 = 4.70 ± 0.40 μM) and compound 1j (IC50 = 11.18 ± 0.54 μM) inhibited tyrosinase by 4.9 and 2.1-fold, respectively, and did so more potently than kojic acid (IC50 = 23.18 ± 0.11 μM). Kinetic analysis of tyrosinase inhibition revealed that 1c and 1j inhibited tyrosinase competitively. Results of docking simulation with mushroom tyrosinase using four docking programs suggested that 1c and 1j bind more strongly than kojic acid to the active site of tyrosinase and supported kinetic findings that both compounds are competitive inhibitors. The docking results of human tyrosinase homology model indicated that 1c and 1j can also strongly inhibit human tyrosinase. EZ-cytox assays revealed 1c and 1j were not cytotoxic to B16F10 melanoma cells. The effects of 1c and 1j on cellular tyrosinase activity and melanin production were also investigated in α-MSH- and IBMX-co-stimulated these cells. Both compounds significantly and dose-dependently reduced tyrosinase activity, and at 10 µM were more potent than kojic acid at 20 µM. Compounds 1c and 1j also inhibited melanogenesis, which suggested that the inhibitory effects of these compounds on melanin production were mainly attributable to their inhibitions of tyrosinase. These results indicate that compounds 1c and 1j with the PUSC scaffold have potential use as whitening agents for the treatment of hyperpigmentation-associated diseases. Tyrosinase 2-thioxooxazoline-4-one Anti-melanogenesis Kojic acid Docking simulation β-phenyl-α,β-unsaturated carbonyl scaffold Biotechnology Yujin Park verfasserin aut Il Young Ryu verfasserin aut Hee Jin Jung verfasserin aut Sultan Ullah verfasserin aut Heejeong Choi verfasserin aut Chaeun Park verfasserin aut Dongwan Kang verfasserin aut Sanggwon Lee verfasserin aut Pusoon Chun verfasserin aut Hae Young Chung verfasserin aut Hyung Ryong Moon verfasserin aut In Computational and Structural Biotechnology Journal Elsevier, 2013 19(2021), Seite 37-50 (DE-627)731890086 (DE-600)2694435-2 20010370 nnns volume:19 year:2021 pages:37-50 https://doi.org/10.1016/j.csbj.2020.12.001 kostenfrei https://doaj.org/article/89ae3e87421146fd846ffb9e9870e0f5 kostenfrei http://www.sciencedirect.com/science/article/pii/S2001037020305262 kostenfrei https://doaj.org/toc/2001-0370 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_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_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 19 2021 37-50
allfieldsSound	10.1016/j.csbj.2020.12.001 doi (DE-627)DOAJ07476912X (DE-599)DOAJ89ae3e87421146fd846ffb9e9870e0f5 DE-627 ger DE-627 rakwb eng TP248.13-248.65 Inkyu Choi verfasserin aut In silico and in vitro insights into tyrosinase inhibitors with a 2-thioxooxazoline-4-one template 2021 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier The β-phenyl-α,β-unsaturated carbonyl (PUSC) scaffold confers tyrosinase inhibitory activity, and in the present study, 16 (Z)-5-(substituted benzylidene)-3-phenyl-2-thioxooxazolidin-4-one analogues containing this scaffold were synthesized. Mushroom tyrosinase inhibitory activities were examined. Compound 1c (IC50 = 4.70 ± 0.40 μM) and compound 1j (IC50 = 11.18 ± 0.54 μM) inhibited tyrosinase by 4.9 and 2.1-fold, respectively, and did so more potently than kojic acid (IC50 = 23.18 ± 0.11 μM). Kinetic analysis of tyrosinase inhibition revealed that 1c and 1j inhibited tyrosinase competitively. Results of docking simulation with mushroom tyrosinase using four docking programs suggested that 1c and 1j bind more strongly than kojic acid to the active site of tyrosinase and supported kinetic findings that both compounds are competitive inhibitors. The docking results of human tyrosinase homology model indicated that 1c and 1j can also strongly inhibit human tyrosinase. EZ-cytox assays revealed 1c and 1j were not cytotoxic to B16F10 melanoma cells. The effects of 1c and 1j on cellular tyrosinase activity and melanin production were also investigated in α-MSH- and IBMX-co-stimulated these cells. Both compounds significantly and dose-dependently reduced tyrosinase activity, and at 10 µM were more potent than kojic acid at 20 µM. Compounds 1c and 1j also inhibited melanogenesis, which suggested that the inhibitory effects of these compounds on melanin production were mainly attributable to their inhibitions of tyrosinase. These results indicate that compounds 1c and 1j with the PUSC scaffold have potential use as whitening agents for the treatment of hyperpigmentation-associated diseases. Tyrosinase 2-thioxooxazoline-4-one Anti-melanogenesis Kojic acid Docking simulation β-phenyl-α,β-unsaturated carbonyl scaffold Biotechnology Yujin Park verfasserin aut Il Young Ryu verfasserin aut Hee Jin Jung verfasserin aut Sultan Ullah verfasserin aut Heejeong Choi verfasserin aut Chaeun Park verfasserin aut Dongwan Kang verfasserin aut Sanggwon Lee verfasserin aut Pusoon Chun verfasserin aut Hae Young Chung verfasserin aut Hyung Ryong Moon verfasserin aut In Computational and Structural Biotechnology Journal Elsevier, 2013 19(2021), Seite 37-50 (DE-627)731890086 (DE-600)2694435-2 20010370 nnns volume:19 year:2021 pages:37-50 https://doi.org/10.1016/j.csbj.2020.12.001 kostenfrei https://doaj.org/article/89ae3e87421146fd846ffb9e9870e0f5 kostenfrei http://www.sciencedirect.com/science/article/pii/S2001037020305262 kostenfrei https://doaj.org/toc/2001-0370 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_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_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 19 2021 37-50
language	English
source	In Computational and Structural Biotechnology Journal 19(2021), Seite 37-50 volume:19 year:2021 pages:37-50
sourceStr	In Computational and Structural Biotechnology Journal 19(2021), Seite 37-50 volume:19 year:2021 pages:37-50
format_phy_str_mv	Article
institution	findex.gbv.de
topic_facet	Tyrosinase 2-thioxooxazoline-4-one Anti-melanogenesis Kojic acid Docking simulation β-phenyl-α,β-unsaturated carbonyl scaffold Biotechnology
isfreeaccess_bool	true
container_title	Computational and Structural Biotechnology Journal
authorswithroles_txt_mv	Inkyu Choi @@aut@@ Yujin Park @@aut@@ Il Young Ryu @@aut@@ Hee Jin Jung @@aut@@ Sultan Ullah @@aut@@ Heejeong Choi @@aut@@ Chaeun Park @@aut@@ Dongwan Kang @@aut@@ Sanggwon Lee @@aut@@ Pusoon Chun @@aut@@ Hae Young Chung @@aut@@ Hyung Ryong Moon @@aut@@
publishDateDaySort_date	2021-01-01T00:00:00Z
hierarchy_top_id	731890086
id	DOAJ07476912X
language_de	englisch
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callnumber-first	T - Technology
author	Inkyu Choi
spellingShingle	Inkyu Choi misc TP248.13-248.65 misc Tyrosinase misc 2-thioxooxazoline-4-one misc Anti-melanogenesis misc Kojic acid misc Docking simulation misc β-phenyl-α,β-unsaturated carbonyl scaffold misc Biotechnology In silico and in vitro insights into tyrosinase inhibitors with a 2-thioxooxazoline-4-one template
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topic_title	TP248.13-248.65 In silico and in vitro insights into tyrosinase inhibitors with a 2-thioxooxazoline-4-one template Tyrosinase 2-thioxooxazoline-4-one Anti-melanogenesis Kojic acid Docking simulation β-phenyl-α,β-unsaturated carbonyl scaffold
topic	misc TP248.13-248.65 misc Tyrosinase misc 2-thioxooxazoline-4-one misc Anti-melanogenesis misc Kojic acid misc Docking simulation misc β-phenyl-α,β-unsaturated carbonyl scaffold misc Biotechnology
topic_unstemmed	misc TP248.13-248.65 misc Tyrosinase misc 2-thioxooxazoline-4-one misc Anti-melanogenesis misc Kojic acid misc Docking simulation misc β-phenyl-α,β-unsaturated carbonyl scaffold misc Biotechnology
topic_browse	misc TP248.13-248.65 misc Tyrosinase misc 2-thioxooxazoline-4-one misc Anti-melanogenesis misc Kojic acid misc Docking simulation misc β-phenyl-α,β-unsaturated carbonyl scaffold misc Biotechnology
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title	In silico and in vitro insights into tyrosinase inhibitors with a 2-thioxooxazoline-4-one template
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title_full	In silico and in vitro insights into tyrosinase inhibitors with a 2-thioxooxazoline-4-one template
author_sort	Inkyu Choi
journal	Computational and Structural Biotechnology Journal
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author_browse	Inkyu Choi Yujin Park Il Young Ryu Hee Jin Jung Sultan Ullah Heejeong Choi Chaeun Park Dongwan Kang Sanggwon Lee Pusoon Chun Hae Young Chung Hyung Ryong Moon
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author-letter	Inkyu Choi
doi_str_mv	10.1016/j.csbj.2020.12.001
author2-role	verfasserin
title_sort	in silico and in vitro insights into tyrosinase inhibitors with a 2-thioxooxazoline-4-one template
callnumber	TP248.13-248.65
title_auth	In silico and in vitro insights into tyrosinase inhibitors with a 2-thioxooxazoline-4-one template
abstract	The β-phenyl-α,β-unsaturated carbonyl (PUSC) scaffold confers tyrosinase inhibitory activity, and in the present study, 16 (Z)-5-(substituted benzylidene)-3-phenyl-2-thioxooxazolidin-4-one analogues containing this scaffold were synthesized. Mushroom tyrosinase inhibitory activities were examined. Compound 1c (IC50 = 4.70 ± 0.40 μM) and compound 1j (IC50 = 11.18 ± 0.54 μM) inhibited tyrosinase by 4.9 and 2.1-fold, respectively, and did so more potently than kojic acid (IC50 = 23.18 ± 0.11 μM). Kinetic analysis of tyrosinase inhibition revealed that 1c and 1j inhibited tyrosinase competitively. Results of docking simulation with mushroom tyrosinase using four docking programs suggested that 1c and 1j bind more strongly than kojic acid to the active site of tyrosinase and supported kinetic findings that both compounds are competitive inhibitors. The docking results of human tyrosinase homology model indicated that 1c and 1j can also strongly inhibit human tyrosinase. EZ-cytox assays revealed 1c and 1j were not cytotoxic to B16F10 melanoma cells. The effects of 1c and 1j on cellular tyrosinase activity and melanin production were also investigated in α-MSH- and IBMX-co-stimulated these cells. Both compounds significantly and dose-dependently reduced tyrosinase activity, and at 10 µM were more potent than kojic acid at 20 µM. Compounds 1c and 1j also inhibited melanogenesis, which suggested that the inhibitory effects of these compounds on melanin production were mainly attributable to their inhibitions of tyrosinase. These results indicate that compounds 1c and 1j with the PUSC scaffold have potential use as whitening agents for the treatment of hyperpigmentation-associated diseases.
abstractGer	The β-phenyl-α,β-unsaturated carbonyl (PUSC) scaffold confers tyrosinase inhibitory activity, and in the present study, 16 (Z)-5-(substituted benzylidene)-3-phenyl-2-thioxooxazolidin-4-one analogues containing this scaffold were synthesized. Mushroom tyrosinase inhibitory activities were examined. Compound 1c (IC50 = 4.70 ± 0.40 μM) and compound 1j (IC50 = 11.18 ± 0.54 μM) inhibited tyrosinase by 4.9 and 2.1-fold, respectively, and did so more potently than kojic acid (IC50 = 23.18 ± 0.11 μM). Kinetic analysis of tyrosinase inhibition revealed that 1c and 1j inhibited tyrosinase competitively. Results of docking simulation with mushroom tyrosinase using four docking programs suggested that 1c and 1j bind more strongly than kojic acid to the active site of tyrosinase and supported kinetic findings that both compounds are competitive inhibitors. The docking results of human tyrosinase homology model indicated that 1c and 1j can also strongly inhibit human tyrosinase. EZ-cytox assays revealed 1c and 1j were not cytotoxic to B16F10 melanoma cells. The effects of 1c and 1j on cellular tyrosinase activity and melanin production were also investigated in α-MSH- and IBMX-co-stimulated these cells. Both compounds significantly and dose-dependently reduced tyrosinase activity, and at 10 µM were more potent than kojic acid at 20 µM. Compounds 1c and 1j also inhibited melanogenesis, which suggested that the inhibitory effects of these compounds on melanin production were mainly attributable to their inhibitions of tyrosinase. These results indicate that compounds 1c and 1j with the PUSC scaffold have potential use as whitening agents for the treatment of hyperpigmentation-associated diseases.
abstract_unstemmed	The β-phenyl-α,β-unsaturated carbonyl (PUSC) scaffold confers tyrosinase inhibitory activity, and in the present study, 16 (Z)-5-(substituted benzylidene)-3-phenyl-2-thioxooxazolidin-4-one analogues containing this scaffold were synthesized. Mushroom tyrosinase inhibitory activities were examined. Compound 1c (IC50 = 4.70 ± 0.40 μM) and compound 1j (IC50 = 11.18 ± 0.54 μM) inhibited tyrosinase by 4.9 and 2.1-fold, respectively, and did so more potently than kojic acid (IC50 = 23.18 ± 0.11 μM). Kinetic analysis of tyrosinase inhibition revealed that 1c and 1j inhibited tyrosinase competitively. Results of docking simulation with mushroom tyrosinase using four docking programs suggested that 1c and 1j bind more strongly than kojic acid to the active site of tyrosinase and supported kinetic findings that both compounds are competitive inhibitors. The docking results of human tyrosinase homology model indicated that 1c and 1j can also strongly inhibit human tyrosinase. EZ-cytox assays revealed 1c and 1j were not cytotoxic to B16F10 melanoma cells. The effects of 1c and 1j on cellular tyrosinase activity and melanin production were also investigated in α-MSH- and IBMX-co-stimulated these cells. Both compounds significantly and dose-dependently reduced tyrosinase activity, and at 10 µM were more potent than kojic acid at 20 µM. Compounds 1c and 1j also inhibited melanogenesis, which suggested that the inhibitory effects of these compounds on melanin production were mainly attributable to their inhibitions of tyrosinase. These results indicate that compounds 1c and 1j with the PUSC scaffold have potential use as whitening agents for the treatment of hyperpigmentation-associated diseases.
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title_short	In silico and in vitro insights into tyrosinase inhibitors with a 2-thioxooxazoline-4-one template
url	https://doi.org/10.1016/j.csbj.2020.12.001 https://doaj.org/article/89ae3e87421146fd846ffb9e9870e0f5 http://www.sciencedirect.com/science/article/pii/S2001037020305262 https://doaj.org/toc/2001-0370
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author2	Yujin Park Il Young Ryu Hee Jin Jung Sultan Ullah Heejeong Choi Chaeun Park Dongwan Kang Sanggwon Lee Pusoon Chun Hae Young Chung Hyung Ryong Moon
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