Alexander A. Chernonosov, Vladimir V. Koval, Dmitrii G. Knorre, Alexander A. Chernenko, Valentina M. Derkacheva, Eugenii A. Lukyanets, Olga S. Fedorova, "Conjugates of Phthalocyanines with Oligonucleotides as Reagents for Sensitized or Catalytic DNA Modification", Bioinorganic Chemistry and Applications, vol. 2006, Article ID 063703, 8 pages, 2006. https://doi.org/10.1155/BCA/2006/63703
Conjugates of Phthalocyanines with Oligonucleotides as Reagents for Sensitized or Catalytic DNA Modification
Several conjugates of metallophthalocyanines with deoxyribooligonucleotides were synthesized to investigate sequence-specific modification of DNA by them. Oligonucleotide parts of these conjugates were responsible for the recognition of selected complementary sequences on the DNA target. Metallophthalocyanines were able to induce the DNA modification: phthalocyanines of Zn(II) and Al(III) were active as photosensitizers in the generation of singlet oxygen , while phthalocyanine of Co(II) promoted DNA oxidation by molecular oxygen through the catalysis of formation of reactive oxygen species (, , OH). Irradiation of the reaction mixture containing either Zn(II)- or Al(III)-tetracarboxyphthalocyanine conjugates of oligonucleotide pd(TCTTCCCA) with light of > 340 nm wavelength (Hg lamp or He/Ne laser) resulted in the modification of the 22-nucleotide target d(TGAATGGGAAGAGGGTCAGGTT). A conjugate of Co(II)-tetracarboxyphthalocyanine with the oligonucleotide was found to modify the DNA target in the presence of and 2-mercaptoethanol or in the presence of . Under both sensitized and catalyzed conditions, the nucleotides – were mainly modified, providing evidence that the reaction proceeded in the double-stranded oligonucleotide. These results suggest the possible use of phthalocyanine-oligonucleotide conjugates as novel artificial regulators of gene expression and therapeutic agents for treatment of cancer.
- D G Knorre, V V Vlassov, V F Zarytova, A V Lebedev, and O S Fedorova, Design and Targeted Reactions of Oligonucleotide Derivatives, CRC Press, Boca Raton, Fla, 1994.
- A M Belikova, V F Zarytova, and N I Grineva, “Synthesis of ribonucleosides and diribonucleoside phosphates containing 2-chloro-ethylamine and nitrogen mustard residues,” Tetrahedron Letters, vol. 8, no. 37, pp. 3557–3562, 1967.
- E Uhlmann and A Peyman, “Antisense oligonucleotides: a new therapeutic principle,” Chemical Reviews, vol. 90, no. 4, pp. 543–584, 1990.
- H E Moser and P B Dervan, “Sequence-specific cleavage of double helical DNA by triple helix formation,” Science, vol. 238, no. 4827, pp. 645–650, 1987.
- T Le Doan, L Perrouault, D Praseuth et al., “Sequence-specific recognition, photocrosslinking and cleavage of the DNA double helix by an oligo-[alpha]-thymidylate covalently linked to an azidoproflavine derivative,” Nucleic Acids Research, vol. 15, no. 19, pp. 7749–7760, 1987.
- O S Fedorova, D G Knorre, L M Podust, and V F Zarytova, “Complementary addressed modification of double-stranded DNA within a ternary complex,” FEBS Letters, vol. 228, no. 2, pp. 273–276, 1988.
- G Jori, “Far-red-absorbing photosensitizers: their use in the photodynamic therapy of tumours,” Journal of Photochemistry and Photobiology A: Chemistry, vol. 62, no. 3, pp. 371–378, 1992.
- J D Spikes, “Phthalocyanines as photosensitizers in biological systems and for the photodynamic therapy of tumors,” Photochemistry and Photobiology, vol. 43, no. 6, pp. 691–699, 1986.
- I E Kochevar, “Singlet oxygen signaling: from intimate to global,” Science's STKE: Signal Transduction Knowledge Environment, vol. 2004, no. 221, p. pe7, 2004.
- B Halliwell and J MC Gutteridge, Free Radicals in Biology and Medicine, Oxford University Press, Oxford, UK, 3rd edition, 1999.
- M E Vol'pin, N Yu Krainova, I V Moskaleva et al., “Transition-metal complexes as catalysts of active oxygen species formation in autooxidation reactions. 1. Cobalt and iron phthalocyanine complexes,” Russian Chemical Bulletin, vol. 45, no. 8, pp. 2000–2007, 1996.
- P N Borer, “Optical properties of nucleic acids, absorption and circular dichroism spectra,” in Handbook of Biochemistry and Molecular Biology: Nucleic Acids, G D Fasman, Ed., vol. 1, pp. 589–595, CRC Press, Cleveland, Ohio, 3rd edition, 1975.
- V V Koval, A A Chernonosov, T V Abramova et al., “Photosensitized and catalytic oxidation of DNA by metallophthalocyanine-oligonucleotide conjugates,” Nucleosides, Nucleotides & Nucleic Acids, vol. 20, no. 4–7, pp. 1259–1262, 2001.
- C G Hatchard and C A Parker, “A new sensitive chemical actinometer. II. Potassium ferrioxalate as a standard chemical actinometer,” Proceedings of the Royal Society of London. Series A, Mathematical and Physical Sciences, vol. 235, no. 1203, pp. 518–536, 1956.
- A M Maxam and W Gilbert, “Sequencing end-labeled DNA with base-specific chemical cleavages,” Methods in Enzymology, vol. 65, no. 1, pp. 499–560, 1980.
- V V Koval, A A Chernonosov, T V Abramova, T M Ivanova, O S Fedorova, and D G Knorre, “The synthesis of a cobalt(II) tetracarboxyphthalocyanine-deoxyribooligonucleotide conjugate as a reagent for the directed DNA modification,” Russian Journal of Bioorganic Chemistry, vol. 26, no. 2, pp. 104–110, 2000.
- J Stubbe and J W Kozarich, “Mechanisms of bleomycin-induced DNA degradation,” Chemical Reviews, vol. 87, no. 5, pp. 1107–1136, 1987.
- P T Henderson, D Jones, G Hampikian, Y Kan, and G B Schuster, “Long-distance charge transport in duplex DNA: the phonon-assisted polaron-like hopping mechanism,” Proceedings of the National Academy of Sciences of the United States of America, vol. 96, no. 15, pp. 8353–8358, 1999.
- A L Lehninger, D L Nelson, and M M Cox, Principles of Biochemistry, Worth, New York, NY, 2nd edition, 1993.
- O S Fedorova, A P Savitskii, K G Shoikhet, and G V Ponomarev, “Palladium(II)-coproporphyrin I as a photoactivable group in sequence-specific modification of nucleic acids by oligonucleotide derivatives,” FEBS Letters, vol. 259, no. 2, pp. 335–337, 1990.
- A S Boutorine, D Brault, M Takasugi, O Delgado, and C Hélène, “Chlorin-oligonucleotide conjugates: synthesis, properties, and red light-induced photochemical sequence-specific DNA cleavage in duplexes and triplexes,” Journal of the American Chemical Society, vol. 118, no. 40, pp. 9469–9476, 1996.
- D Magda, M Wright, R A Miller, J L Sessler, and P I Sansom, “Sequence-specific photocleavage of DNA by an expanded porphyrin with irradiation above 700 nm,” Journal of the American Chemical Society, vol. 117, no. 12, pp. 3629–3630, 1995.
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