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Molecules 2008, 13(12), 3117-3128; doi:10.3390/molecules13123117
Article

Binding of Cationic Bis-porphyrins Linked with p- or m-Xylylenediamine and Their Zinc(II) Complexes to Duplex DNA

1,* , 2
 and 3,*
1 School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka 422- 8526, Japan 2 Graduate School of Pharmaceutical Sciences, Kumamoto University, 5-1 Oe-honmachi, Kumamoto 862-0973, Japan 3 Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565- 0871, Japan
* Authors to whom correspondence should be addressed.
Received: 14 November 2008 / Revised: 8 December 2008 / Accepted: 12 December 2008 / Published: 15 December 2008
(This article belongs to the Special Issue Nucleic Acids)
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Abstract

Spectroscopic, viscometric, and molecular docking analysis of binding of cationic bis-porphyrins linked with p- or m-xylylenediamine (H2pXy and H2mXy) and their zinc(II) complexes (ZnpXy and ZnmXy) to duplex DNA are described. H2pXy and H2mXy bound to calf thymus DNA (CTDNA) stronger than unichromophoric H2TMPyP, and showed exciton-type induced circular dichroism spectra of their Soret bands. The H2TMPyP-like units of the metal-free bis-porphyrins did not intercalate into CTDNA, and thus the binding mode is outside binding with intramolecular stacking. ZnpXy showed favorable binding to A·T over G·C region, and should lie in the major groove of A·T region.
Keywords: Porphyrin; DNA; Binding mode; Zinc; Titration; Circular dichroism; Viscometry; Distamycin; Molecular docking simulation Porphyrin; DNA; Binding mode; Zinc; Titration; Circular dichroism; Viscometry; Distamycin; Molecular docking simulation
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Ishikawa, Y.; Yamakawa, N.; Uno, T. Binding of Cationic Bis-porphyrins Linked with p- or m-Xylylenediamine and Their Zinc(II) Complexes to Duplex DNA. Molecules 2008, 13, 3117-3128.

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