Mechanism of DNA strand breakage induced by photosensitized tetracycline-Cu(II) complex

Mutation Research - Fundamental and Molecular Mechanisms of Mutagenesis

Volumn 525, Issue 1-2, 2003, Pages 109-119

  Khan, Mateen A ^a   Mustafa, Jamal ^b   Musarrat, Javed ^a  

^a ALIGARH MUSLIM UNIVERSITY   (India)

^b ALIGARH MUSLIM UNIVERSITY   (India)

Author keywords

Alkylating agents; DNA damage; Free radicals; Tetracyclines

Indexed keywords

ADENINE; BENZOIC ACID; COPPER COMPLEX; GUANINE; MANNITOL; NUCLEASE S1; REACTIVE OXYGEN METABOLITE; SINGLE STRANDED DNA; SUPEROXIDE DISMUTASE; TETRACYCLINE; THIOUREA;

ARTICLE; CATALYSIS; DNA ALKYLATION; DNA CLEAVAGE; DNA STRAND BREAKAGE; DNA STRUCTURE; DRUG DNA INTERACTION; HYDROLYSIS; MUTAGENESIS; PHOTOSENSITIZATION; PRIORITY JOURNAL;

EID: 0037427197     PISSN: 00275107     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0027-5107(03)00008-3     Document Type: Article

References (37)

1. Cullen S.T., Catalano P.M., Helfman R.J. Tetracycline sun sensitivity. Arch. Dermatol. 93:1966;77.
2. Orientrich N., Harber L.C., Tromovitch T.A. Photosensitivity and photo-onycholysis due to demethylchlortetracycline. Arch. Dermatol. 83:1961;730-737.
3. Frost P., Weinstein G.D., Gomez E.C. Methacycline and demeclocycline in relation to sunlight. JAMA. 216:1971;326-329.
4. Moore D.E., Fallon N.P., Burt C.D. Photo-oxidation of tetracycline - a differential pulse polarographic study. Int. J. Pharmacol. 14:1983;133-142.
5. Davies A.K., McKeller J.F., Phillips G.O., Reid A.G. Photochemical oxidation of tetracycline in aqueous solution. J. Chem. Soc. Perkin II. 12:1979;369-375.
6. Green M.J., Hill H.A.O. Chemistry of dioxygen. Methods Enzymol. 105:1984;3-22.
7. Sanderberg S., Glette J., Hopen G., Solberg C.O. Doxycycline induced photo damage to human neutrophils and tryptophan. Photochem. Photobiol. 39:1984;43-48.
8. Li A.S.W., Chignell C.F., Hall R.D. Cutaneous phototoxicity of tetracycline antibiotics: generation of free radicals and singlet oxygen during photolysis as measured by spin-trapping and phosphorescence of singlet molecular oxygen. Photochem. Photobiol. 46:1987;379-382.
9. Nilsson R., Swanbeck G., Wennersten G. Primary mechanism of erythrocyte photolysis induced by biological sensitizers and phototoxic drugs. Photochem. Photobiol. 22:1975;183-186.
10. Rebout A.M., Dubost S., Reboud J.P. Photoincorporation of tetracycline into rat liver ribosomes and subunit. Eur. J. Biochem. 124:1982;389-396.
11. Goldman R.A., Hasan T., Hall C.C., Strycharg W.A., Cooperman B.S. Photoincorporation of tetracycline into Escherichia coli ribosomes. Identification of the major protein photolabeled by native tetracycline and tetracycline products and implications for the inhibitory action of tetracycline on protein synthesis. Biochemistry. 22:1983;359-368.
12. Khan M.A., Musarrat J. Tetracycline-Cu(II) photo-induced fragmentation of serum albumin. Comp. Biochem. Physiol. Part C. 131:2002;439-446.
13. Epe B., Hegler J., Wild D. Singlet oxygen as an ultimately reactive species in Salmonella typhimurium DNA damage induced by methylene blue/visible light. Carcinogenesis. 10:1989;2019-2024.
14. Halliwell B., Aruoma O.I. DNA damage by oxygen-derived species. Its mechanism and measurement in mammalian system. FEBS Lett. 291:1991;9-19.
15. Buschfort C., Witte I. Induction and mechanism of DNA single and double strand breaks by tetracycline/Cu(II) in the absence of light. Carcinogenesis. 15:1994;2927-2930.
16. Piette J., Decuyper B.S., van de Vorst A. DNA alterations photosensitized by tetracycline and some of its derivatives. J. Invest. Dermatol. 86:1986;653-658.
17. B. Singer, D. Grunberger, Molecular Biology of Mutagens and Carcinogens, Plenum Press, New York, 1983.
18. Lawley P.D., Brooks P. Further studies on the alkylation of nucleic acids and their constituent nucleotides. Biochem. J. 89:1963;127-138.
19. Singer B. In vivo formation and persistence of modified nucleosides resulting from alkylation agents. Environ. Health Perspect. 62:1985;41-48.
20. Schneider W.C. Determination of nucleic acid in tissues by pentose analysis. Methods Enzymol. 3:1957;680-684.
21. Kanter P.M., Schwartz A. A hydroxyapatite batch assay for quantitation of cellular DNA damage. Anal. Biochem. 97:1979;77-84.
22. Rydberg B. The rate of strand separation in alkali and DNA of irradiated mammalian cells. Radiat. Res. 61:1975;274-287.
23. Daniel F.B., Hass D.L., Pyle S.M. Quantitation of chemically induced DNA strand breaks in human cells via an alkaline unwinding assay. Anal. Biochem. 144:1985;390-402.
24. Wani A.A., Hadi S.M., Ahmad N.S. Effect of dimethyl sulfate on the secondary structure of DNA. Specialia. 25:1978;392-394.
25. R.B. Martin, Tetracyclines and daunorubicin, in: H. Sigel (Ed.), Metal Ions in Biological systems: Antibiotics and their Complexes, vol. 19, Marcel Dekker, New York, 1986, pp. 19-52.
26. Lawley P.D., Warren W. Removal of minor methylation products 7-methyladenine and 3-methylguanine from DNA to Escherichia coli treated with dimethylsulfate. Chem. Biol. Interact. 12:1976;211-220.
27. Crathron A.R., Shooter K.V. The alkaline hydrolysis of phosphotriesters in alkylated mammalian DNA. Biochim. Biophys. Acta. 697:1982;259-261.
28. Quinlan G.J., Gutteridge J.M.C. DNA base damage by beta-lactam, tetracycline, bacitracin and rifamycin antibacterial antibiotics. Biochem. Pharmacol. 42:1991;1595-1599.
29. Wong A., Huang C.H., Crooke S.T. Mechanism of deoxyribonucleic acid breakage induced by 4′-(9-acridinylamino) methanesulfon-m-anisidide and copper: role of cuprous ion and oxygen free radicals. Biochemistry. 23:1984;2946-2952.
30. Eliot H., Gianni L., Myers C. Oxidative destruction of DNA by the adriamycin iron complex. Biochemistry. 23:1984;928-936.
31. Chu B.C.F., Orgel L.E. Non-enzymatic sequence specific cleavage of single stranded DNA. Proc. Natl. Acad. Sci. U.S.A. 82:1985;963-967.
32. Dreyer G.B., Dervan P.B. Sequence specific cleavage of single stranded DNA. Proc. Natl. Acad. Sci. U.S.A. 82:1985;968-972.
33. Graham D.R., Marshall L.E., Reich L.E., Sigman D.S. Cleavage of DNA by coordination complexes. Superoxide formation in the oxidation of 1,10-phenanthroline cuprous complexes by oxygen: relevance to DNA cleavage reaction. J. Am. Chem. Soc. 102:1981;5419-5421.
34. 2 and molecular oxygen. J. Am. Chem. Soc. 108:1986;2244-2250.
35. Hagenfeldt K. Intrauterine contraception with copper-T device. I. Effect on trace elements in the endometrium. Contraception. 6:1972;37-54.
36. Doluisio J.T., Dittert L.W. Influence of repetitive dosing of tetracycline on biological half-life in serum. Clin. Pharmacol. Ther. 10:1969;690-701.
37. Hartmann A., Wess D., Witte I. Enhanced cyto- and genotoxicity of tetracycline in Wilson disease fibroblast. Mutat. Res. 348:1995;7-12.