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3D-QSAR studies of cytotoxic heterocyclic quinones using calculated reduction potential

Title
3D-QSAR studies of cytotoxic heterocyclic quinones using calculated reduction potential
Authors
Lee Y.Kim S.Rhee H.-K.Doh K.-E.Park J.Lee C.-O.Choi S.Choo H.-Y.P.
Ewha Authors
박혜영최선
SCOPUS Author ID
박혜영scopus; 최선scopus
Issue Date
2009
Journal Title
Drug Development Research
ISSN
0272-4391JCR Link
Citation
vol. 70, no. 6, pp. 438 - 444
Indexed
SCI; SCIE; SCOPUS WOS scopus
Abstract
Most quinones with 2-4 fused aromatic rings exhibit cytostatic activity via DNA intercalation that causes enzyme blockade and reading errors during the replication process. The redox activity of quinones plays a role in the DNA cleavage mediated by oxygen or sulfur radicals. To develop novel anticancer agents based on nitrogen-containing heterocyclic quinones, pharmacophore models of representative molecules with high activity were generated using Genetic Algorithm with Linear Assignment of Hypermolecular Alignment of Database (GALAHAD). A series of compounds were aligned to the selected pharmacophore model and the 3D-quantitative structure activity relationships (QSAR) were analyzed using comparative molecular field analysis (CoMFA) and comparative molecular similarity indices analysis (CoMSIA), resulting in q 2 values of 0.734 and r 2 of 0.951, and q 2 of 0.803 and r 2 of 0.917, respectively, in each study. In addition, the potentials for the one-electron reduction of quinones were calculated from LUMO energies using the semi-empirical Austin Model 1 (AM1) method. These also showed a good correlation (r 2 of 0.816) with the cytotoxic activities of the quinones. © 2009 Wiley-Liss, Inc.
DOI
10.1002/ddr.20320
Appears in Collections:
약학대학 > 약학과 > Journal papers
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