STEREOELECTRONIC FACTORS IN THE INTERACTION WITH DNA OF SMALL AROMATIC-MOLECULES SUBSTITUTED WITH A SHORT CATIONIC CHAIN - IMPORTANCE OF THE POLARITY OF THE AROMATIC SYSTEM OF THE MOLECULE

被引:29
作者
STREKOWSKI, L [1 ]
MOKROSZ, JL [1 ]
WILSON, WD [1 ]
MOKROSZ, MJ [1 ]
STREKOWSKI, A [1 ]
机构
[1] INST PHARMACOL,PL-31343 KRAKOW,POLAND
关键词
D O I
10.1021/bi00159a022
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
We have performed a quantitative analysis of the interaction with DNA of several unfused aromatic compounds synthesized in our laboratory and substituted with one or two short cationic chains. These and similar literature compounds, for which DNA binding data are available, bind with DNA by partial intercalation of the aromatic system, groove interaction of the linker chain, and groove electrostatic interactions of the terminal cationic group. Several independent quantitative and qualitative approaches show consistently that the strength of the interaction of the aromatic unit of the molecule with DNA binding sites depends on the direction and magnitude of polarity of the aromatic system. The phenomenon is explained in terms of the greatest negative potential in the DNA grooves, a concept extensively elaborated by Pullman and Pullman [cf. Lavery, R. and Pullman, B. [(1985) J. Biomol. Struct. Dyn. 2,1021-1032] and references therein]. Classical, fused-ring planar intercalators do not follow the polarity-DNA affinity correlation, presumably because the intercalative forces depend more strongly on polarizability than on polarity of the aromatic system.
引用
收藏
页码:10802 / 10808
页数:7
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