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Nucleic Acids Research, 1990, Vol. 18, No. 21 6283-6291
© 1990

CHEMISTRY

Sequence-selective binding of an ellipticine derivative to DNA

Christian Bailly, Colm OhUigin, Christian Rivalle1, Emile Bisagni1, Jean-Pierre Hénichart2 and Michael J. Waring

Department of Pharmacology, University of Cambridge Tennis Court Road, Cambridge CB2 1QJ, UK 1UA 533 CNRS, laboratoire de Synthése Organique, Institut Curie-Biologie Bât. 110–112, 15 rue G. Clemenceau, 91405 Orsay 2INSERM U16 Place de Verdun, 59045 Lille Cedex, France

Received July 24, 1990. Revised October 9, 1990. Accepted October 9, 1990.

The DNA sequence specificity of an ellipticine derivative bearing an aminoalkyl side chain has been determined by a variety of footprinting methods. The drug exhibits sequence selective binding and discriminates against runs of adenines or thymines. Binding is shown to occur at various sequences with a preference for GC rich regions of DNA. A large enhancement of DNAase I and of hydroxyl radical cleavage in regions rich in A's or T's is observed together with hyperreactlvlty of adenines towards dlethylpyrocarbonate in the presence of drug. This indicates the occurrence of drug-induced changes in critical conformational features of DNA. The total absence of hyperreactivity of guanine residues towards diethylpyrocarbonate appears to be related to the sequence selectivity of drug binding. No alteration of the dimethyl sulphate and methylene blue-induced cleavage of DNA Is observed. Irradiation of ellipticine derivative-DNA complexes with UV light followed by alkali treatment leads to selective photocleavage at guanine residues, consistent with the deduced degree of selectivity of the binding reaction


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