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Nucleic Acids Research, 1990, Vol. 18, No. 13 3887-3891
© 1990

CHEMISTRY

Formation of a DNA monofunctional cis-platinum adduct cross-linking the intercalating drug N-methyl-2, 7-diazapyrenium

Jean-Marc Malinge, Miroslav Sip, A.John Blacker1, Jean-Marie Lehn1 and Marc Leng

Center de Biophysique Moléculaire, CNRS, 1A avenue de la Recherche Scientifique 45071 Orléans Cedex 2 1Institute Le Bel, Université Louis Pasteur 4 rue Blaise Pascel, 6700 Strasbourg, France

Received March 20, 1990. Revised May 8, 1990. Accepted May 8, 1990.

Our purpose was to better understand the mutual influence of cis-diamminedichloroplatinum (II) (cis-DDP) and intercalating drugs in their interactions with DNA. The present study deals with the intercalating drug N-methyl-2,7-diazapyrenium (MDAP). Two sets of experiments have been performed. In one set, the reaction between cis-DDP and nucleic acid was carried out in the presence of MDAP. The main adduct is a guanine residue chelated by platinum to a MDAP residue. It has the same spectroscopic properties as the synthesized compound cis-[Pt (NH3)2 (N7-d-guanosine) (N7-MDAP)] +++, the structure of which has been determined by 1H NMR. This adduct was only formed with double-stranded nucleic acids which reveals the importance of DNA matrix in orienting favorably the reactants. In the second set of experiments, the triamine complex cis-[Pt(NH3)2 (MDAP)CI]++ was reacted with the nucleic acids. At molar ratios drug over nucleotide residue equal or less than 0.10, all the added triamine complexes bind by covalent coordination to double-stranded nucleic acids. With natural DNA, the major adduct is cis-[Pt(NH3)2(d-guanosine) (MDAP)] +++. Thus the same adduct is formed on one hand in the reaction between DNA, MDAP and cis-DDP and on the other hand in the reaction between the triamine complex and DNA. The triamine complex offers the possibility to study the biological role of the new adduct.


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