PMID: 3756304Jul 1, 1986Paper

The effect of intercalator structure on binding strength and base-pair specificity in DNA interactions

Biophysical Chemistry
W D WilsonD W Boykin

Abstract

The interaction of naphthothiophene, phenanthrene and anthracene ring systems, which have amide and ester side chains with cationic groups (synthesized from the aromatic acid chlorides and appropriate amines and alcohols), with calf thymus DNA has been investigated by using viscometric titrations, spectrophotometric binding experiments and 1H-, 31P- and 17O-NMR methods. The viscosity and NMR experiments suggest that all of these compounds bind to DNA by intercalation. These experiments and spectrophotometric binding studies, however, indicate that there is considerable variation in the interaction of these compounds with DNA. These variations can all be explained by the geometry of the ring systems, the position of protons adjacent to the side chains, and the relative sizes of the amide and ester side chains. With the naphthothiophene ester and amide, for example, the planar amide cannot rotate into the plane of the naphthothiophene ring whereas the smaller planar ester can. With this ring system the ester has a significantly higher binding constant than the amide derivative. Additional binding studies with poly[d(A-T)2] and poly[d(G-C)2] have shown that all of these compounds bind more strongly to the A-T- than the G-C-contain...Continue Reading

Citations

Oct 1, 1991·Pharmacology & Therapeutics·D W Fry
Oct 1, 1987·Journal of Biomolecular Structure & Dynamics·W D WilsonS Neidle
Dec 1, 1996·Journal of Biomolecular Structure & Dynamics·Z R LiuR L Rill
Dec 1, 1988·European Journal of Biochemistry·F J Van de Ven, C W Hilbers
Dec 29, 2004·Nucleosides, Nucleotides & Nucleic Acids·K H ChandramouliCletus J M D'Souza
Jul 6, 2014·Journal of Labelled Compounds & Radiopharmaceuticals·Vassiliki TheodorouIoannis P Gerothanassis
Oct 1, 2005·Photochemistry and Photobiology·Willy B TanChalla V Kumar
Oct 19, 2016·Anti-cancer Drugs·Mei HongZhonglin Hao
Dec 5, 2012·The Journal of Physical Chemistry. B·Héctor J LozanoJosé M Leal

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