A quantum chemical and chemometric study of sesquiterpene lactones with cytotoxicity against tumor cells

被引：25

作者：

Arantes, Francisco F. P. ^{[1
]}

Barbosa, Luiz C. A. ^{[1
]}

Maltha, Celia R. A. ^{[1
]}

Demuner, Antonio J. ^{[1
]}

Fidencio, Paulo H. ^{[2
]}

Carneiro, Jose Walkimar M. ^{[3
]}

机构：

[1] Univ Fed Vicosa, Dept Chem, BR-36570000 Vicosa, MG, Brazil

[2] Fed Univ Jequitinhonha & Mucuri Valleys, Dept Chem, BR-39100000 Diamantina, MG, Brazil

[3] Univ Fed Fluminense, Dept Inorgan Chem, BR-24020141 Niteroi, RJ, Brazil

来源：

JOURNAL OF CHEMOMETRICS | 2011年 / 25卷 / 08期

关键词：

sesquiterpene lactones; alpha-methylene-gamma-lactone; cytotoxicity; quantum chemical; chemometrics; SYNTHETIC NEOLIGNANS; PHYTOTOXIC ACTIVITY; ALPHA; ALLELOCHEMICALS; DERIVATIVES; MODELS; SAR;

D O I：

10.1002/cem.1385

中图分类号：

TP [自动化技术、计算机技术];

学科分类号：

080201 [机械制造及其自动化];

摘要：

The semi-empirical molecular orbital method PM6 was employed to calculate a set of molecular descriptors of 20 sesquiterpene lactones (SQLs) with cytotoxicity against HL-60 (leukemia) tumor cells. The principal component analysis (PCA) and hierarchical cluster analysis (HCA) methods were used to obtain possible relationships between the calculated descriptors and the biological activity of the lactones. Four descriptors were identified as responsible for the separation between the active and inactive compounds: E-HOMO (highest occupied molecular orbital energy); Q11 (net atomic charge on C11); Q12 (net atomic charge on C12) and Q13 (net atomic charge on C13). These results indicated that the presence of the alpha-methylene-gamma-lactone group has a significant role in the mechanism by which SQLs exert their biological activities. Copyright (C) 2011 John Wiley & Sons, Ltd.

引用

页码：401 / 407

页数：7

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