Phenolic acid derivatives with potential anticancer properties - a structure-activity relationship study. Part 1: Methyl, propyl and octyl esters of caffeic and gallic acids

被引：279

作者：

Fiuza, SM

Gomes, C

Teixeira, LJ

da Cruz, MTG

Cordeiro, MNDS

Milhazes, N

Borges, F

Marques, MPM ^{[1
]}

机构：

[1] Univ Coimbra, Res Unit Mol Phys Chem, Coimbra, Portugal

[2] Univ Coimbra, Dept Biochem, Coimbra, Portugal

[3] Univ Coimbra, Ctr Neurosci & Cellular Biol, Coimbra, Portugal

[4] Univ Porto, Fac Sci, Dept Chem, REQUIMTE, P-4100 Oporto, Portugal

[5] Univ Porto, Fac Pharm, Dept Organ Chem, P-4100 Oporto, Portugal

[6] Inst Hlth Sci N, Gandra Paredes, Portugal

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2004年 / 12卷 / 13期

关键词：

caffeates; gallates; anticancer activity; ab initio calculations;

D O I：

10.1016/j.bmc.2004.04.026

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The antiproliferative and cytotoxic properties of polyphenolic acid derivatives, structurally related with the natural models caffeic and gallic acids. have been tested in human cervix adenocarcinoma cells (HeLa). Simultaneous structural information was obtained for these Compounds through theoretical ab initio methods. This study was conducted for the following esters: methyl caffeate (MC, 1), propyl caffeate (PC, 2), octyl caffeate (OC, 3), methyl gallate (MG, 4), propyl gallate (PG, 5) and octyl gallate (OG, 6). A significant growth-inhibition effect was assessed for some of these compounds, clearly dependent on their structural characteristics. Marked structure-activity relationships (SARs)-namely the number of hydroxyl ring substituents-were found to rule the biological effect of such systems. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：3581 / 3589

页数：9

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[41] EFFECTIVE CORE POTENTIALS FOR DFT CALCULATIONS [J].