Sequence-targeted chemical modifications of nucleic acids by complementary oligonucleotides covalently linked to porphyrins
Open Access
- 1 January 1987
- journal article
- Published by Oxford University Press (OUP) in Nucleic Acids Research
- Vol. 15 (21), 8643-8659
- https://doi.org/10.1093/nar/15.21.8643
Abstract
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.Keywords
This publication has 19 references indexed in Scilit:
- 31P NMR Studies of the Binding of the Oligonucleotide (Ap)3A to an Oligodeoxythymidylate Covalently Linked to an Acridine DerivativeJournal of Biomolecular Structure and Dynamics, 1986
- Specific Cleavages of DNA by Ascorbate in the Presence of Copper Ion or Copper ChelatesThe Journal of Biochemistry, 1985
- Sequence-specific cleavage of single-stranded DNA: oligodeoxynucleotide-EDTA X Fe(II).Proceedings of the National Academy of Sciences, 1985
- Nonenzymatic sequence-specific cleavage of single-stranded DNA.Proceedings of the National Academy of Sciences, 1985
- Role of metals in oxygen radical reactionsJournal of Free Radicals in Biology & Medicine, 1985
- Functional analogs of bleomycin: sequence-specific DNA cleavage with porphyrin (Fe) intercalators.1984
- Nucleic acid-binding molecules with high affinity and base sequence specificity: intercalating agents covalently linked to oligodeoxynucleotides.Proceedings of the National Academy of Sciences, 1984
- Hydroxylation of deoxyguanosine at the C-8 position by ascorbic acid and other reducing agentsNucleic Acids Research, 1984
- Hemin-mediated DNA strand scission.Journal of Biological Chemistry, 1983
- INDUCTION OF DNA DAMAGE BY PORPHYRIN PHOTOSENSITIZERS1981