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Nucleic Acids Research, 1987, Vol. 15, No. 21 8643-8659
© 1987

Articles

Sequence-targeted chemical modifications of nucleic acids by complementary oligonucleotides covalently linked to porphyrins

Trung Le Doan, Loïc Perrouault, Marcel Chassignol1, Nguyen T. Thuong1 and Claude Hélène

Laboratoire de Biophysique, Muséum National d'Histoire Naturelle INSERM U.201, CNRS UA.481, F-75005 Paris 1Centre de Biophysique Moléculaire CNRS, F-45071 Orléans Cédex 02, France

Received August 10, 1987. Revised September 29, 1987. Accepted September 29, 1987.

Oligo-heptathymidylates covalently linked to porphyrins bind to complementary sequences and can induce local damages on the target molecule. In dark reaction, iron porphyrin derivatives exhibited various chemical reactivities resulting in base oxidation, crosslinking and chain scission reactions. Reactions induced by reductants, such as ascorbic acid, dithiothreitol or mercapto-propionic acid, led to very localised reactions. A single base was the target for more than 50 % of the damages. Oxidising agents such a s H2O2 and its alkyl derivatives induced reactions that extended to a wider range of altered bases. The specificity of the chemical modifications observed in these systems is discussed from a mechanistic point of view.


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