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Evaluation and Optimization of the Anti-Melanogenic Activity of 1-(2-Cyclohexylmethoxy-6-hydroxy-phenyl)-3-(4-hydroxymethyl-phenyl)-propenone Derivatives

机译：1-（2-环己基甲氧基-6-羟基-苯基）-3-（4-羟基甲基-苯基）-丙烯酮衍生物的抗黑素活性的评价和优化

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摘要

The chemical modification and optimization of biologically active compounds are essential steps in the identification of promising lead compounds for drug development. We previously reported the anti-melanogenic activity of 1-(2-cyclohexylmethoxy-6-hydroxy-phenyl)-3-(4-hydroxymethyl-phenyl)-propenone (chalcone 21). In this study, we synthesized 21 derivatives of chalcone 21 and evaluated their anti-melanogenic activity in α-MSH-induced B16F10 cells. (E)-N-(4-(3-(2-(Cyclohexylmethoxy)phenyl)-3-oxoprop-1-en-1-yl)phenyl)acetamide (chalcone 21-21) exhibited the strongest inhibition of cellular melanin production, with an IC50 value of 0.54 μM. It was more potent than chalcone 21 and the known anti-melanogenic agents kojic acid and arbutin, whose IC50 values were 4.9, 38.5, and 148.4 μM, respectively. Chalcone 21-21 decreased the expression and activity of tyrosinase. It also decreased the expression of TRP1, TRP2 and MITF, the phosphorylation of CREB and ERK1/2, and the transcriptional activity of MITF and CRE. Our results demonstrate that chalcone-21-21 is an effective lead compound with anti-melanogenic activity.

机译：生物活性化合物的化学修饰和优化是鉴定用于药物开发的有前途的先导化合物的必要步骤。我们先前报道了1-（2-环己基甲氧基-6-羟基-苯基）-3-（4-羟基甲基-苯基）-丙烯酮（查尔酮21）的抗黑色素生成活性。在这项研究中，我们合成了查尔酮21的21种衍生物，并评估了它们在α-MSH诱导的B16F10细胞中的抗黑色素生成活性。（E）-N-（4-（3-（2-（环己基甲氧基）苯基）-3-氧代丙-1-烯-1-基）苯基）乙酰胺（查耳酮21-21）对细胞黑色素生成的抑制作用最强，IC50值为0.54μM。它比查尔酮21和已知的抗黑色素生成剂曲酸和熊果苷更有效，IC50值分别为4.9、38.5和148.4μM。查尔酮21-21降低了酪氨酸酶的表达和活性。它还降低了TRP1，TRP2和MITF的表达，CREB和ERK1 / 2的磷酸化以及MITF和CRE的转录活性。我们的结果表明查尔酮21-21是具有抗黑色素生成活性的有效铅化合物。

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期刊名称 Molecules
作者
Byung-Hak Kim; Soo-Nam Hong; Sang-Kyu Ye; Jung-Youl Park;
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作者单位

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年(卷),期 2019(24),7
年度 2019
页码 1372
总页数 15
原文格式 PDF
正文语种
中图分类分子生物学;
关键词
alpha-melanocyte stimulating hormone (α-MSH) chalcone melanin biosynthesis (E)-N-(4-(3-(2-(cyclohexylmethoxy)phenyl)-3-oxoprop-1-en-1-yl)phenyl)acetamide (chalcone 21-21) tyrosinase;

机译：α-黑素细胞刺激激素（α-MSH）;查尔酮;黑色素生物合成;（E）-N-（4-（3-（2-（环己基甲氧基）苯基）-3-氧代丙-1-烯-1-基）苯基乙酰胺（查耳酮21-21）;酪氨酸酶;

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1. Inhibition of tyrosinase activity and melanin production by the chalcone derivative 1-(2-cyclohexylmethoxy-6-hydroxy-phenyl)-3(4-hydroxymethyl-phenyl)-propenone [J] . Kim Byung-Hak, Park Kyoung Chan, Park Jeong Ho, Biochemical and Biophysical Research Communications . 2016,第4期

机译：抑制酪氨酸衍生物1-（2-环己基甲氧基-6-苯基）-3（4-羟甲基 - 苯基） - 产酮的酪氨酸酶活性和黑色素产生的抑制作用
2. Inhibition of tyrosinase activity and melanin production by the chalcone derivative 1-(2-cyclohexylmethoxy-6-hydroxy-phenyl)-3(4-hydroxymethyl-phenyl)-propenone [J] . Kim Byung-Hak, Park Kyoung Chan, Park Jeong Ho, Biochemical and Biophysical Research Communications . 2016,第4期

机译：查尔酮衍生物1-（2-环己基甲氧基-6-羟基-苯基）-3（4-羟基甲基-苯基）-丙烯酮抑制酪氨酸酶活性和黑色素生成
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4. Design, synthesis and biological activity evaluation of novel antibacterial agent (E)-1-(4-chlorobenzyl)-5-styrylindoline-2, 3-dione [C] . Han Kailin, Liu Xiao, Qin Shanshan, 2011 International Conference on Human Health and Biomedical Engineering . 2011

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8. Scoping Design Analyses for Optimized Shipping Casks Containing 1-, 2-, 3-, 5-, 7-, or 10-Year-Old PWR Spent Fuel [R] . Bucholz, J. A. 1983

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Evaluation and Optimization of the Anti-Melanogenic Activity of 1-(2-Cyclohexylmethoxy-6-hydroxy-phenyl)-3-(4-hydroxymethyl-phenyl)-propenone Derivatives

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