Anti-Browning Effect of 2-Mercaptobenzo[<i<d</i<]imidazole Analogs with Antioxidant Activity on Freshly-Cut Apple Slices and Their Highly Potent Tyrosinase Inhibitory Activity

Ten 2-mercaptobenzimidazole (2-MBI) analogs were synthesized as potential tyrosinase inhibitors because mercapto-containing compounds can bind to copper ions at the active site of tyrosinase to inhibit enzyme activity. Nine 2-MBI analogs showed sub-micromolar IC<sub<50</sub< values for m...
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Autor*in:	Jieun Lee [verfasserIn] Hye Soo Park [verfasserIn] Hee Jin Jung [verfasserIn] Yu Jung Park [verfasserIn] Min Kyung Kang [verfasserIn] Hye Jin Kim [verfasserIn] Dahye Yoon [verfasserIn] Sultan Ullah [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:	browning melanin tyrosinase antioxidant 2-mercaptobenzo[ docking simulation

Übergeordnetes Werk:	In: Antioxidants - MDPI AG, 2013, 12(2023), 1814, p 1814
Übergeordnetes Werk:	volume:12 ; year:2023 ; number:1814, p 1814

Links:	Link aufrufen Link aufrufen Link aufrufen Journal toc

DOI / URN:	10.3390/antiox12101814

Katalog-ID:	DOAJ093185251

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Indexfelder

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allfields	10.3390/antiox12101814 doi (DE-627)DOAJ093185251 (DE-599)DOAJ18f948aa94fc4854b9bbd821818257a9 DE-627 ger DE-627 rakwb eng RM1-950 Jieun Lee verfasserin aut Anti-Browning Effect of 2-Mercaptobenzo[<i<d</i<]imidazole Analogs with Antioxidant Activity on Freshly-Cut Apple Slices and Their Highly Potent Tyrosinase Inhibitory Activity 2023 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Ten 2-mercaptobenzimidazole (2-MBI) analogs were synthesized as potential tyrosinase inhibitors because mercapto-containing compounds can bind to copper ions at the active site of tyrosinase to inhibit enzyme activity. Nine 2-MBI analogs showed sub-micromolar IC<sub<50</sub< values for mushroom tyrosinase monophenolase activity; analog <b<4</b< was 280-fold more potent than kojic acid, and in diphenolase activity, <b<6</b< was 970-fold more potent than kojic acid. The inhibition mode of the 2-MBI analogs was investigated using kinetic studies supported by docking simulations. Benzimidazoles without the 2-mercapto substituent of the 2-MBI analogs lost their tyrosinase inhibitory activity, implying that the 2-mercapto substituent plays an important role in tyrosinase inhibition. The 2-MBI analogs exerted potent antioxidant effects against 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid (ABTS), 2,2-diphenyl-1-picrylhydrazyl (DPPH), and reactive oxygen species (ROS). The results obtained from apple slices and human embryonic kidney cells (HEK-293) suggest that most 2-MBI analogs are sufficiently safe candidates to delay the browning of apple slices effectively. Thus, these results support the potential use of 2-MBI analogs as anti-browning agents in foods such as mushrooms, vegetables, and fruits. browning melanin tyrosinase antioxidant 2-mercaptobenzo[<i<d</i<]imidazole docking simulation Therapeutics. Pharmacology Hye Soo Park verfasserin aut Hee Jin Jung verfasserin aut Yu Jung Park verfasserin aut Min Kyung Kang verfasserin aut Hye Jin Kim verfasserin aut Dahye Yoon verfasserin aut Sultan Ullah 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 Antioxidants MDPI AG, 2013 12(2023), 1814, p 1814 (DE-627)737287578 (DE-600)2704216-9 20763921 nnns volume:12 year:2023 number:1814, p 1814 https://doi.org/10.3390/antiox12101814 kostenfrei https://doaj.org/article/18f948aa94fc4854b9bbd821818257a9 kostenfrei https://www.mdpi.com/2076-3921/12/10/1814 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 12 2023 1814, p 1814
spelling	10.3390/antiox12101814 doi (DE-627)DOAJ093185251 (DE-599)DOAJ18f948aa94fc4854b9bbd821818257a9 DE-627 ger DE-627 rakwb eng RM1-950 Jieun Lee verfasserin aut Anti-Browning Effect of 2-Mercaptobenzo[<i<d</i<]imidazole Analogs with Antioxidant Activity on Freshly-Cut Apple Slices and Their Highly Potent Tyrosinase Inhibitory Activity 2023 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Ten 2-mercaptobenzimidazole (2-MBI) analogs were synthesized as potential tyrosinase inhibitors because mercapto-containing compounds can bind to copper ions at the active site of tyrosinase to inhibit enzyme activity. Nine 2-MBI analogs showed sub-micromolar IC<sub<50</sub< values for mushroom tyrosinase monophenolase activity; analog <b<4</b< was 280-fold more potent than kojic acid, and in diphenolase activity, <b<6</b< was 970-fold more potent than kojic acid. The inhibition mode of the 2-MBI analogs was investigated using kinetic studies supported by docking simulations. Benzimidazoles without the 2-mercapto substituent of the 2-MBI analogs lost their tyrosinase inhibitory activity, implying that the 2-mercapto substituent plays an important role in tyrosinase inhibition. The 2-MBI analogs exerted potent antioxidant effects against 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid (ABTS), 2,2-diphenyl-1-picrylhydrazyl (DPPH), and reactive oxygen species (ROS). The results obtained from apple slices and human embryonic kidney cells (HEK-293) suggest that most 2-MBI analogs are sufficiently safe candidates to delay the browning of apple slices effectively. Thus, these results support the potential use of 2-MBI analogs as anti-browning agents in foods such as mushrooms, vegetables, and fruits. browning melanin tyrosinase antioxidant 2-mercaptobenzo[<i<d</i<]imidazole docking simulation Therapeutics. Pharmacology Hye Soo Park verfasserin aut Hee Jin Jung verfasserin aut Yu Jung Park verfasserin aut Min Kyung Kang verfasserin aut Hye Jin Kim verfasserin aut Dahye Yoon verfasserin aut Sultan Ullah 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 Antioxidants MDPI AG, 2013 12(2023), 1814, p 1814 (DE-627)737287578 (DE-600)2704216-9 20763921 nnns volume:12 year:2023 number:1814, p 1814 https://doi.org/10.3390/antiox12101814 kostenfrei https://doaj.org/article/18f948aa94fc4854b9bbd821818257a9 kostenfrei https://www.mdpi.com/2076-3921/12/10/1814 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 12 2023 1814, p 1814
allfields_unstemmed	10.3390/antiox12101814 doi (DE-627)DOAJ093185251 (DE-599)DOAJ18f948aa94fc4854b9bbd821818257a9 DE-627 ger DE-627 rakwb eng RM1-950 Jieun Lee verfasserin aut Anti-Browning Effect of 2-Mercaptobenzo[<i<d</i<]imidazole Analogs with Antioxidant Activity on Freshly-Cut Apple Slices and Their Highly Potent Tyrosinase Inhibitory Activity 2023 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Ten 2-mercaptobenzimidazole (2-MBI) analogs were synthesized as potential tyrosinase inhibitors because mercapto-containing compounds can bind to copper ions at the active site of tyrosinase to inhibit enzyme activity. Nine 2-MBI analogs showed sub-micromolar IC<sub<50</sub< values for mushroom tyrosinase monophenolase activity; analog <b<4</b< was 280-fold more potent than kojic acid, and in diphenolase activity, <b<6</b< was 970-fold more potent than kojic acid. The inhibition mode of the 2-MBI analogs was investigated using kinetic studies supported by docking simulations. Benzimidazoles without the 2-mercapto substituent of the 2-MBI analogs lost their tyrosinase inhibitory activity, implying that the 2-mercapto substituent plays an important role in tyrosinase inhibition. The 2-MBI analogs exerted potent antioxidant effects against 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid (ABTS), 2,2-diphenyl-1-picrylhydrazyl (DPPH), and reactive oxygen species (ROS). The results obtained from apple slices and human embryonic kidney cells (HEK-293) suggest that most 2-MBI analogs are sufficiently safe candidates to delay the browning of apple slices effectively. Thus, these results support the potential use of 2-MBI analogs as anti-browning agents in foods such as mushrooms, vegetables, and fruits. browning melanin tyrosinase antioxidant 2-mercaptobenzo[<i<d</i<]imidazole docking simulation Therapeutics. Pharmacology Hye Soo Park verfasserin aut Hee Jin Jung verfasserin aut Yu Jung Park verfasserin aut Min Kyung Kang verfasserin aut Hye Jin Kim verfasserin aut Dahye Yoon verfasserin aut Sultan Ullah 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 Antioxidants MDPI AG, 2013 12(2023), 1814, p 1814 (DE-627)737287578 (DE-600)2704216-9 20763921 nnns volume:12 year:2023 number:1814, p 1814 https://doi.org/10.3390/antiox12101814 kostenfrei https://doaj.org/article/18f948aa94fc4854b9bbd821818257a9 kostenfrei https://www.mdpi.com/2076-3921/12/10/1814 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 12 2023 1814, p 1814
allfieldsGer	10.3390/antiox12101814 doi (DE-627)DOAJ093185251 (DE-599)DOAJ18f948aa94fc4854b9bbd821818257a9 DE-627 ger DE-627 rakwb eng RM1-950 Jieun Lee verfasserin aut Anti-Browning Effect of 2-Mercaptobenzo[<i<d</i<]imidazole Analogs with Antioxidant Activity on Freshly-Cut Apple Slices and Their Highly Potent Tyrosinase Inhibitory Activity 2023 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Ten 2-mercaptobenzimidazole (2-MBI) analogs were synthesized as potential tyrosinase inhibitors because mercapto-containing compounds can bind to copper ions at the active site of tyrosinase to inhibit enzyme activity. Nine 2-MBI analogs showed sub-micromolar IC<sub<50</sub< values for mushroom tyrosinase monophenolase activity; analog <b<4</b< was 280-fold more potent than kojic acid, and in diphenolase activity, <b<6</b< was 970-fold more potent than kojic acid. The inhibition mode of the 2-MBI analogs was investigated using kinetic studies supported by docking simulations. Benzimidazoles without the 2-mercapto substituent of the 2-MBI analogs lost their tyrosinase inhibitory activity, implying that the 2-mercapto substituent plays an important role in tyrosinase inhibition. The 2-MBI analogs exerted potent antioxidant effects against 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid (ABTS), 2,2-diphenyl-1-picrylhydrazyl (DPPH), and reactive oxygen species (ROS). The results obtained from apple slices and human embryonic kidney cells (HEK-293) suggest that most 2-MBI analogs are sufficiently safe candidates to delay the browning of apple slices effectively. Thus, these results support the potential use of 2-MBI analogs as anti-browning agents in foods such as mushrooms, vegetables, and fruits. browning melanin tyrosinase antioxidant 2-mercaptobenzo[<i<d</i<]imidazole docking simulation Therapeutics. Pharmacology Hye Soo Park verfasserin aut Hee Jin Jung verfasserin aut Yu Jung Park verfasserin aut Min Kyung Kang verfasserin aut Hye Jin Kim verfasserin aut Dahye Yoon verfasserin aut Sultan Ullah 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 Antioxidants MDPI AG, 2013 12(2023), 1814, p 1814 (DE-627)737287578 (DE-600)2704216-9 20763921 nnns volume:12 year:2023 number:1814, p 1814 https://doi.org/10.3390/antiox12101814 kostenfrei https://doaj.org/article/18f948aa94fc4854b9bbd821818257a9 kostenfrei https://www.mdpi.com/2076-3921/12/10/1814 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 12 2023 1814, p 1814
allfieldsSound	10.3390/antiox12101814 doi (DE-627)DOAJ093185251 (DE-599)DOAJ18f948aa94fc4854b9bbd821818257a9 DE-627 ger DE-627 rakwb eng RM1-950 Jieun Lee verfasserin aut Anti-Browning Effect of 2-Mercaptobenzo[<i<d</i<]imidazole Analogs with Antioxidant Activity on Freshly-Cut Apple Slices and Their Highly Potent Tyrosinase Inhibitory Activity 2023 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Ten 2-mercaptobenzimidazole (2-MBI) analogs were synthesized as potential tyrosinase inhibitors because mercapto-containing compounds can bind to copper ions at the active site of tyrosinase to inhibit enzyme activity. Nine 2-MBI analogs showed sub-micromolar IC<sub<50</sub< values for mushroom tyrosinase monophenolase activity; analog <b<4</b< was 280-fold more potent than kojic acid, and in diphenolase activity, <b<6</b< was 970-fold more potent than kojic acid. The inhibition mode of the 2-MBI analogs was investigated using kinetic studies supported by docking simulations. Benzimidazoles without the 2-mercapto substituent of the 2-MBI analogs lost their tyrosinase inhibitory activity, implying that the 2-mercapto substituent plays an important role in tyrosinase inhibition. The 2-MBI analogs exerted potent antioxidant effects against 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid (ABTS), 2,2-diphenyl-1-picrylhydrazyl (DPPH), and reactive oxygen species (ROS). The results obtained from apple slices and human embryonic kidney cells (HEK-293) suggest that most 2-MBI analogs are sufficiently safe candidates to delay the browning of apple slices effectively. Thus, these results support the potential use of 2-MBI analogs as anti-browning agents in foods such as mushrooms, vegetables, and fruits. browning melanin tyrosinase antioxidant 2-mercaptobenzo[<i<d</i<]imidazole docking simulation Therapeutics. Pharmacology Hye Soo Park verfasserin aut Hee Jin Jung verfasserin aut Yu Jung Park verfasserin aut Min Kyung Kang verfasserin aut Hye Jin Kim verfasserin aut Dahye Yoon verfasserin aut Sultan Ullah 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 Antioxidants MDPI AG, 2013 12(2023), 1814, p 1814 (DE-627)737287578 (DE-600)2704216-9 20763921 nnns volume:12 year:2023 number:1814, p 1814 https://doi.org/10.3390/antiox12101814 kostenfrei https://doaj.org/article/18f948aa94fc4854b9bbd821818257a9 kostenfrei https://www.mdpi.com/2076-3921/12/10/1814 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 12 2023 1814, p 1814
language	English
source	In Antioxidants 12(2023), 1814, p 1814 volume:12 year:2023 number:1814, p 1814
sourceStr	In Antioxidants 12(2023), 1814, p 1814 volume:12 year:2023 number:1814, p 1814
format_phy_str_mv	Article
institution	findex.gbv.de
topic_facet	browning melanin tyrosinase antioxidant 2-mercaptobenzo[<i<d</i<]imidazole docking simulation Therapeutics. Pharmacology
isfreeaccess_bool	true
container_title	Antioxidants
authorswithroles_txt_mv	Jieun Lee @@aut@@ Hye Soo Park @@aut@@ Hee Jin Jung @@aut@@ Yu Jung Park @@aut@@ Min Kyung Kang @@aut@@ Hye Jin Kim @@aut@@ Dahye Yoon @@aut@@ Sultan Ullah @@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	737287578
id	DOAJ093185251
language_de	englisch
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callnumber-first	R - Medicine
author	Jieun Lee
spellingShingle	Jieun Lee misc RM1-950 misc browning misc melanin misc tyrosinase misc antioxidant misc 2-mercaptobenzo[<i<d</i<]imidazole misc docking simulation misc Therapeutics. Pharmacology Anti-Browning Effect of 2-Mercaptobenzo[<i<d</i<]imidazole Analogs with Antioxidant Activity on Freshly-Cut Apple Slices and Their Highly Potent Tyrosinase Inhibitory Activity
authorStr	Jieun Lee
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topic_title	RM1-950 Anti-Browning Effect of 2-Mercaptobenzo[<i<d</i<]imidazole Analogs with Antioxidant Activity on Freshly-Cut Apple Slices and Their Highly Potent Tyrosinase Inhibitory Activity browning melanin tyrosinase antioxidant 2-mercaptobenzo[<i<d</i<]imidazole docking simulation
topic	misc RM1-950 misc browning misc melanin misc tyrosinase misc antioxidant misc 2-mercaptobenzo[<i<d</i<]imidazole misc docking simulation misc Therapeutics. Pharmacology
topic_unstemmed	misc RM1-950 misc browning misc melanin misc tyrosinase misc antioxidant misc 2-mercaptobenzo[<i<d</i<]imidazole misc docking simulation misc Therapeutics. Pharmacology
topic_browse	misc RM1-950 misc browning misc melanin misc tyrosinase misc antioxidant misc 2-mercaptobenzo[<i<d</i<]imidazole misc docking simulation misc Therapeutics. Pharmacology
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title	Anti-Browning Effect of 2-Mercaptobenzo[<i<d</i<]imidazole Analogs with Antioxidant Activity on Freshly-Cut Apple Slices and Their Highly Potent Tyrosinase Inhibitory Activity
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title_full	Anti-Browning Effect of 2-Mercaptobenzo[<i<d</i<]imidazole Analogs with Antioxidant Activity on Freshly-Cut Apple Slices and Their Highly Potent Tyrosinase Inhibitory Activity
author_sort	Jieun Lee
journal	Antioxidants
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author_browse	Jieun Lee Hye Soo Park Hee Jin Jung Yu Jung Park Min Kyung Kang Hye Jin Kim Dahye Yoon Sultan Ullah Dongwan Kang Yujin Park Pusoon Chun Hae Young Chung Hyung Ryong Moon
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doi_str_mv	10.3390/antiox12101814
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title_sort	anti-browning effect of 2-mercaptobenzo[<i<d</i<]imidazole analogs with antioxidant activity on freshly-cut apple slices and their highly potent tyrosinase inhibitory activity
callnumber	RM1-950
title_auth	Anti-Browning Effect of 2-Mercaptobenzo[<i<d</i<]imidazole Analogs with Antioxidant Activity on Freshly-Cut Apple Slices and Their Highly Potent Tyrosinase Inhibitory Activity
abstract	Ten 2-mercaptobenzimidazole (2-MBI) analogs were synthesized as potential tyrosinase inhibitors because mercapto-containing compounds can bind to copper ions at the active site of tyrosinase to inhibit enzyme activity. Nine 2-MBI analogs showed sub-micromolar IC<sub<50</sub< values for mushroom tyrosinase monophenolase activity; analog <b<4</b< was 280-fold more potent than kojic acid, and in diphenolase activity, <b<6</b< was 970-fold more potent than kojic acid. The inhibition mode of the 2-MBI analogs was investigated using kinetic studies supported by docking simulations. Benzimidazoles without the 2-mercapto substituent of the 2-MBI analogs lost their tyrosinase inhibitory activity, implying that the 2-mercapto substituent plays an important role in tyrosinase inhibition. The 2-MBI analogs exerted potent antioxidant effects against 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid (ABTS), 2,2-diphenyl-1-picrylhydrazyl (DPPH), and reactive oxygen species (ROS). The results obtained from apple slices and human embryonic kidney cells (HEK-293) suggest that most 2-MBI analogs are sufficiently safe candidates to delay the browning of apple slices effectively. Thus, these results support the potential use of 2-MBI analogs as anti-browning agents in foods such as mushrooms, vegetables, and fruits.
abstractGer	Ten 2-mercaptobenzimidazole (2-MBI) analogs were synthesized as potential tyrosinase inhibitors because mercapto-containing compounds can bind to copper ions at the active site of tyrosinase to inhibit enzyme activity. Nine 2-MBI analogs showed sub-micromolar IC<sub<50</sub< values for mushroom tyrosinase monophenolase activity; analog <b<4</b< was 280-fold more potent than kojic acid, and in diphenolase activity, <b<6</b< was 970-fold more potent than kojic acid. The inhibition mode of the 2-MBI analogs was investigated using kinetic studies supported by docking simulations. Benzimidazoles without the 2-mercapto substituent of the 2-MBI analogs lost their tyrosinase inhibitory activity, implying that the 2-mercapto substituent plays an important role in tyrosinase inhibition. The 2-MBI analogs exerted potent antioxidant effects against 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid (ABTS), 2,2-diphenyl-1-picrylhydrazyl (DPPH), and reactive oxygen species (ROS). The results obtained from apple slices and human embryonic kidney cells (HEK-293) suggest that most 2-MBI analogs are sufficiently safe candidates to delay the browning of apple slices effectively. Thus, these results support the potential use of 2-MBI analogs as anti-browning agents in foods such as mushrooms, vegetables, and fruits.
abstract_unstemmed	Ten 2-mercaptobenzimidazole (2-MBI) analogs were synthesized as potential tyrosinase inhibitors because mercapto-containing compounds can bind to copper ions at the active site of tyrosinase to inhibit enzyme activity. Nine 2-MBI analogs showed sub-micromolar IC<sub<50</sub< values for mushroom tyrosinase monophenolase activity; analog <b<4</b< was 280-fold more potent than kojic acid, and in diphenolase activity, <b<6</b< was 970-fold more potent than kojic acid. The inhibition mode of the 2-MBI analogs was investigated using kinetic studies supported by docking simulations. Benzimidazoles without the 2-mercapto substituent of the 2-MBI analogs lost their tyrosinase inhibitory activity, implying that the 2-mercapto substituent plays an important role in tyrosinase inhibition. The 2-MBI analogs exerted potent antioxidant effects against 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid (ABTS), 2,2-diphenyl-1-picrylhydrazyl (DPPH), and reactive oxygen species (ROS). The results obtained from apple slices and human embryonic kidney cells (HEK-293) suggest that most 2-MBI analogs are sufficiently safe candidates to delay the browning of apple slices effectively. Thus, these results support the potential use of 2-MBI analogs as anti-browning agents in foods such as mushrooms, vegetables, and fruits.
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container_issue	1814, p 1814
title_short	Anti-Browning Effect of 2-Mercaptobenzo[<i<d</i<]imidazole Analogs with Antioxidant Activity on Freshly-Cut Apple Slices and Their Highly Potent Tyrosinase Inhibitory Activity
url	https://doi.org/10.3390/antiox12101814 https://doaj.org/article/18f948aa94fc4854b9bbd821818257a9 https://www.mdpi.com/2076-3921/12/10/1814 https://doaj.org/toc/2076-3921
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author2	Hye Soo Park Hee Jin Jung Yu Jung Park Min Kyung Kang Hye Jin Kim Dahye Yoon Sultan Ullah Dongwan Kang Yujin Park Pusoon Chun Hae Young Chung Hyung Ryong Moon
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doi_str	10.3390/antiox12101814
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up_date	2024-07-03T15:47:23.773Z
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Anti-Browning Effect of 2-Mercaptobenzo[<i<d</i<]imidazole Analogs with Antioxidant Activity on Freshly-Cut Apple Slices and Their Highly Potent Tyrosinase Inhibitory Activity

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