Structure-based modification of 3-/4-aminoacetophenones giving a profound change of activity on tyrosinase: From potent activators to highly efficient inhibitors
文献类型：期刊论文
| 作者 | You, Ao2; Zhou, Jie1,2; Song, Senchuan2; Zhu, Guoxun2; Song, Huacan2; Yi, Wei1,2 |
| 刊名 | EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
 |
| 出版日期 | 2015-03-26 |
| 卷号 | 93页码:255-262 |
| 关键词 | Aminophenylethylidenethiosemicarbazide compounds Tyrosinase activator Tyrosinase inhibitor SARs Inhibition mechanism Inhibitory kinetics |
| ISSN号 | 0223-5234 |
| DOI | 10.1016/j.ejmech.2015.02.013 |
| 文献子类 | Article |
| 英文摘要 | In this study, we developed 3-/4-aminoacetophenones and their structure-based 3-/4-aminophenylethylidenethiosemicarbazide derivatives, respectively, as novel tyrosinase activators and inhibitors. Notably, all the obtained thiosemicarbazones displayed more potent tyrosinase inhibitory activities than kojic acid. Especially, compound 7k was found to be the most active tyrosinase inhibitor with IC50 value of 0.291 mu M. The structure-activity relationships (SARs) analysis showed that: (1) the amine group was absolutely necessarily for determining the tyrosinase activation activity; (2) the introduction of thiosemicarbazide group played a very vital role in transforming tyrosinase activators into tyrosinase inhibitors; (3) the phenylethylenethiosemicarbazide moiety was crucial for determining the tyrosinase inhibitory activity; (4) the type of acyl group had no obvious effect on the inhibitory activity; (5) the position of amide substituent on the phenyl ring influenced the tyrosinase inhibitory potency. Moreover, the inhibition mechanism and inhibition kinetics study revealed that compound 7k was reversible and non-competitive inhibitor, and compound 8h was reversible and competitive-uncompetitive mixed-II type inhibitor. (C) 2015 Elsevier Masson SAS. All rights reserved. |
| WOS关键词 | RADIX POLYGONI-MULTIFLORI ; MUSHROOM TYROSINASE ; BIOLOGICAL EVALUATION ; ANTIBACTERIAL ACTIVITIES ; CRYSTAL-STRUCTURE ; DICOPPER CENTER ; DERIVATIVES ; MECHANISM ; DESIGN ; KINETICS |
| 资助项目 | Science and Technology Project of Guangdong Province, China[2009B060700048] ; Shanghai Municipal Natural Science Foundation[15ZR1447800] ; Fundamental Research Funds for the Central Universities[00000000] |
| WOS研究方向 | Pharmacology & Pharmacy |
| 语种 | 英语 |
| WOS记录号 | WOS:000351646100026 |
| 出版者 | ELSEVIER FRANCE-EDITIONS SCIENTIFIQUES MEDICALES ELSEVIER |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/276599]  |
| 专题 | 药物靶标结构与功能中心 |
| 通讯作者 | Song, Huacan |
| 作者单位 | 1.Chinese Acad Sci, Shanghai Inst Mat Med, VARI SIMM Ctr,Ctr Struct & Funct Drug Targets, CAS Key Lab Receptor Res, Shanghai 201203, Peoples R China 2.Sun Yat Sen Univ, Sch Chem & Chem Engn, Guangzhou 510275, Guangdong, Peoples R China; |
| 推荐引用方式 GB/T 7714 | You, Ao,Zhou, Jie,Song, Senchuan,et al. Structure-based modification of 3-/4-aminoacetophenones giving a profound change of activity on tyrosinase: From potent activators to highly efficient inhibitors[J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY,2015,93:255-262. |
| APA | You, Ao,Zhou, Jie,Song, Senchuan,Zhu, Guoxun,Song, Huacan,&Yi, Wei.(2015).Structure-based modification of 3-/4-aminoacetophenones giving a profound change of activity on tyrosinase: From potent activators to highly efficient inhibitors.EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY,93,255-262. |
| MLA | You, Ao,et al."Structure-based modification of 3-/4-aminoacetophenones giving a profound change of activity on tyrosinase: From potent activators to highly efficient inhibitors".EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY 93(2015):255-262. |
入库方式： OAI收割
来源：上海药物研究所
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