Caged single and double strand breaks

Bioconjugate Chemistry

Volumn 11, Issue 1, 2000, Pages 94-103

  Ordoukhanian, Phillip ^a   Taylor, John Stephen ^a  

^a WASHINGTON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL REACTIONS; CHROMOPHORES; DNA; IRRADIATION; RADIATION SHIELDING;

BLEOMYCINS; DOUBLE STRAND BREAK REPAIR; DOUBLE STRAND BREAKS; NEOCARZINOSTATIN CHROMOPHORES; SINGLE-STRAND BREAK REPAIRS; SINGLE-STRAND BREAKS; STRAND BREAKS; STRUCTURE-ACTIVITY RELATIONSHIPS; SYNTHETIC AGENTS; Β-ELIMINATION REACTION;

IONIZING RADIATION;

EID: 0033980441     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc9900993     Document Type: Article

References (26)

1. Sonntag, C. v. (1987) The Chemical Basis of Radiation Biology, Taylor & Francis, New York.
2. Obe, G., Johannes, C., and Schulte-Frohlinde, D. (1992) DNA double-strand breaks induced by sparsely ionizing radiation and endonucleases as critical lesions for cell death, chromosomal aberrations, mutations and oncogenic transformation. Mutagenesis 7, 3-12.
3. Ward, J. F. (1995) Radiation mutagenesis: the initial DNA lesions responsible [published erratum appears in Radiat. Res. (1995) 143 (3), 355]. Radiat. Res. 142, 362-368.
4. Povirk, L. F. (1996) DNA damage and mutagenesis by radiomimetic DNA-cleaving agents: bleomycin, neocarzinostatin and other enediynes. Mutat. Res. 355, 71-89.
5. Dedon, P. C., and Goldberg, I. H. (1992) Free-radical mechanisms involved in the formation of sequence-dependent bistranded DNA lesions by the antitumor antibiotics bleomycin, neocarzinostatin, and calicheamicin. Chem. Res. Toxicol. 5, 311-332.
6. Thacker, J. (1994) The study of responses to "model" DNA breaks induced by restriction endonucleases in cells and cell-free systems: achievements and difficulties. Int. J. Radiat. Biol. 66, 591-596.
7. Giese, B., Dussy, A., Elie, C., Erdmann, P., and Schwitter, U. (1994) Synthesis and selective radical cleavage of C-4′-modified oligonucleotides. Angew. Chem., Int. Ed. Engl. 33, 1861-1863.
8. Friedberg, E. C., Walker, G. C., and Siede, W. (1995) DNA Repair and Mutagenesis, ASM Press, Washington DC.
9. Marriott, G. (1998) Caged compounds. Methods in Enzymology, Academic Press, New York.
10. Engels, J., and Schlaeger, E. J. (1977) Synthesis, structure, and reactivity of adenosine cyclic 3′,5′-phosphate benzyl triesters. J. Med. Chem. 20, 907-911.
11. Hoffman, J. F., Forbush, B., III, and Kaplan, J. H. (1978) Rapid photolytic release of adenosine 5′-triphosphate from a protected analogue: utilization by the Na:K pump of human red blood ghosts. Biochemistry 17, 1929-1935.
12. Horn, T., Downing, K., Gee, Y., and Urdea, M. S. (1991) Controlled chemical cleavage of synthetic DNA at specific sites. Nucleosides Nucleotides 10, 299-302.
13. Kotera, M., Bourdat, A.-G., Defrancq, E., and Lhomme, J. (1998) A highly efficient synthesis of oligodeoxyribonucleotides containing the 2′-deoxyribonolactone lesion. J. Am. Chem. Soc. 120, 11810-11811.
14. Chaulk, S. G., and MacMillan, A. M. (1998) Caged RNA: photocontrol of a ribozyme reaction. Nucleic Acids Res. 26, 3173-3178.
15. Nadji, S., Wang, C.-I., and Taylor, J.-S. (1992) Photochemically and photoenzymatically cleavable DNA. J. Am. Chem. Soc. 114, 9266-9269.
16. Giese, B., Beyrich-Graf, X., Erdmann, P., Giraud, L., Imwinkelried, P., Muller, S. N., and Schwitter, U. (1995) Cleavage of single-stranded 4′-oligonucleotide radicals in the presence of oxygen. J. Am. Chem. Soc. 117, 6146-6147.
17. Ordoukhanian, P., and Taylor, J.-S. (1995) Design and synthesis of a versatile photocleavable DNA building block. Application to phototriggered hybridization. J. Am. Chem. Soc. 117, 9570-9571.
18. Fasman, G. D. (1975) Nucleic Acids. Handbook of Biochemistry and Molecular Biology, Vol. I CRC Press, Cleveland.
19. Sambrook, J., Fritsch, E. F., and Maniatis, T. (1989) Molecular Cloning: A Laboratory Manual, 2nd ed., Vol. 1, Cold Spring Harbor Laboratory Press, Plainview, NY.
20. Maxam, A. M., and Gilbert, W. (1980) Sequencing end-labeled DNA with base-specific chemical cleavages. Methods Enzymol. 65, 499-560.
21. Trentham, D. R., Corrie, J. E. T., Barth, A., Gradwell, M. J., Maeda, Y., Mantele, W., and Meir, T. (1997) Time-resolved infrared spectroscopy of intermediates and products from photolysis of 1-(2-nitrophenyl)ethyl phosphates: reaction of the 2-nitrosoacetophenone byproduct with thiols. J. Am. Chem. Soc. 119, 4149-4159.
22. Stubbe, J., Absalon, M. J., and Kozarich, J. W. (1995) Sequence-specific double-strand cleavage of DNA by Febleomycin. The detection of sequence-specific double-strand breaks using hairpin oligonucleotides. Biochemistry 34, 2065-2075.
23. Churchill, M. E., Peak, J. G., and Peak, M. (1991) Correlation between cell survival and DNA single-strand break repair proficiency in the Chinese hamster ovary cell line AA8 and EM9 irraidated with 365-nm ultraviolet-A radiation. Photochem. Photobiol. 53, 229-236.
24. Basu, A. K., and Essigmann, J. M. (1988) Site-specifically modified oligodeoxynucleotides as probes for the structural and biological effects of DNA-damaging agents. Chem. Res. Toxicol. 1, 1-18.
25. Banerjee, S. K., Christensen, R. B., Lawrence, C. W., and LeClerc, J. E. (1988) Frequency and spectrum of mutations produced by a single cis-syn thymine-thymine cyclobutane dimer in a single-stranded vector. Proc. Natl. Acad. Sci. U.S.A. 85, 8141-8145.
26. Huang, J. C., Hsu, D. S., Kazantsev, A., and Sancar, A. (1994) Substrate spectrum of human excinuciease: repair of abasic sites, methylated bases, mismatches, and bulky adducts. Proc. Natl. Acad. Sci. U.S.A. 91, 12213-12217.