In vitro studies of dna damage caused by tricyclic antidepressants: A role of peroxidase in the side effects of the drugs

Chemical Research in Toxicology

Volumn 23, Issue 9, 2010, Pages 1497-1503

  Korobkova, Ekaterina A ^a   Ng, William ^a   Venkatratnam, Abhishek ^a   Williams, Alicia K ^a   Nizamova, Madina ^a   Azar, Nikolay ^a  

^a JOHN JAY COLLEGE OF CRIMINAL JUSTICE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

10,11 DIHYDRO 5H DIBENZ[B,F]AZEPINE; AMITRIPTYLINE; BENZYL DERIVATIVE; DNA; HORSERADISH PEROXIDASE; HYDROGEN PEROXIDE; IMIPRAMINE; OPIPRAMOL; PROTRIPTYLINE; UNCLASSIFIED DRUG;

ABSORPTION; ARTICLE; CATALYSIS; CONTROLLED STUDY; DNA DAMAGE; DNA DEGRADATION; DNA EXTRACTION; DRUG OXIDATION; IN VITRO STUDY; PH; PROTEIN FUNCTION;

AMITRIPTYLINE; ANIMALS; ANTIDEPRESSIVE AGENTS, TRICYCLIC; CATTLE; DNA; DNA DAMAGE; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; HORSERADISH PEROXIDASE; HYDROGEN PEROXIDE; HYDROGEN-ION CONCENTRATION; IMIPRAMINE; OPIPRAMOL; OXIDATION-REDUCTION; PROTRIPTYLINE; SPECTROPHOTOMETRY, ULTRAVIOLET;

ARMORACIA RUSTICANA;

EID: 77956944301     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx100221b     Document Type: Article

References (37)

1. Yarosh, D. B. (1985) The role of O6-methylguanine-DNA methyltransferase in cell survival, mutagenesis, and carcinogenesis Mutat. Res. 145, 1-16
2. Friedberg, E. C. (2001) How nucleotide excision repair protects against cancer Nature Rev. Cancer 1, 22-33
3. Snyder, R. D. and Arnone, M. R. (2002) Putative identification of functional interactions between DNA intercalating agents and topoisomerase II using the V79 in vitro micronucleus assay Mutat. Res. 503, 21-35
4. Snyder, R D., Ewing, D. E., and Hendry, L. B. (2004) Evaluation of DNA intercalation potential of pharmaceutical and other chemicals by cell-based and three-dimensional computational approaches Environ. Mol. Mutagen. 44, 163-173
5. Slamon, N. D., Ward, T. H., Butler, J., and Pentreath, V. W. (2001) Assessment of DNA damage in C6 glicoma cells after antidepressant treatment using an alkaline comet assay Arch. Toxicol. 75, 243-250
6. Saxena, R. and Ahuja, Y. R. (1988) Genotoxicity evaluation of the tricyclic antidepressants amitriptyline and imipramine using human lymphocyte cultures Environ. Mol. Mutagen. 12, 421-430
7. Madrigal-Bujaidar, E., Madrigal-Santillan, E. O., Alvarez-Gonzalez, I., Baez, R., and Pilar Marquez, P. (2008) Micronuclei induced by imipramine and desipramine in mice: a subchronic study Basic Clin. Pharmacol. Toxicol. 103, 569-573
8. Dungaros, R., Turkbay, T., Surer, I., Gok, F., Denli, M., and Baltaci, V. (2002) DNA damage in children treated with imipramine for primary nocturnal enuresis Pediatr. Int. 44, 617-621
9. Yamamoto, K. and Kawanishi, S. (1992) Site-specific DNA damage by phenylhydrazine and phenelzine in the presence of Cu(II) ion or Fe(III) complexes: roles of active oxygen species and carbon radicals Chem. Res. Toxicol. 5, 440-446
10. Balasubramanian, B., Pogozelski, W. K., and Tullius, T. D. (1998) DNA strand breaking by the hydroxylradical is governed by the accessible surface areas of the hydrogen atoms on the DNA back bone Proc. Natl. Acad. Sci.U.S.A. 95, 9738-9743
11. 2+-mediated Fenton reactions has possible biological implications J. Biol. Chem. 274, 962-971
12. 2-mediated DNA damage via nitrogen-centered radical formation Chem. Res. Toxicol. 14, 1421-1427
13. Eghbal, M. A., Tafazoli, S., Pennefather, P., and OBrien, P. J. (2004) Peroxidase catalyzed formation of cytotoxic prooxidant phenothiazine free radicals at physiological pH Chem.-Biol. Interact. 151, 43-51
14. 2-mediated one electron oxidation of carcinogenic N-fluorenylacetohydroxamic acids to nitroxyl free radicals Chem.-Biol. Interact. 46, 317-334
15. OBrien, P. J. (2000) Peroxidases Chem.-Biol. Interact. 129, 113-139
16. OBrien, P. J. (1988) Radical formation during the peroxydase catalyzed metabolism of carcinogens and xenobiotics: The reactivity of these radicals with GSH, DNA, and unsaturated lipid Free Radical Biol. Med. 4, 169-183
17. Miura, T., Muraoka, S., and Fujimoto, Y. (2001) Inactivation of creatine kinase during the interaction of indomethacin with horseradish peroxidase and hydrogen peroxide: Involvement of indomethacin radicals Chem.-Biol. Interact. 134, 13-25
18. OBrien, P. J. (1985) Free-radical-mediated DNA binding Environ. Health. Perspect. 64, 219-232
19. Mittmann, N. M., Lui, B. A., Bparm, M. I., Bradley, C. A., Pless, R., Shear, N. H., and Einarson, T. R. (1997) Drug-related mortality in Canada (1984-1994) Pharmacoepidemiol. Drug Saf. 6, 157-168
20. Caplan, Y. H., Ottinger, W. E., Jongsei, P., and Smith, T. D. (1985) Drug and chemical related deaths: Incidence in the state of Maryland J. Forensic Sci. 30, 1012-1021
21. Song, H.-Y., Yao, J.-H., Liu, J.-Z., Zhou, S.-J., Xiong, Y.-H., and Ji, L.-N. (2005) Effects of phthalic anhydride modification on horseradish peroxidase stability and structure Enzyme Microb. Technol. 36, 605-611
22. Suh, D. and Chaires, J. B. (1995) Criteria for the mode of binding of DNA binding agents Bioorg. Med. Chem. 3, 723-728
23. Dunford, H. B. and Stillman, J. S. (1976) On the function and mechanism of action of peroxidases Coord. Chem. Rev. 19, 187-251
24. Aitkem, S. M., Ouellet, M., Percival, M. D., and English, A. M. (2003) Mechanism of Horseradish peroxidase inactivation by benzhydrazide: a critical evaluation of arylhydrazides as peroxidase inhibitors Biochem. J. 375, 613-621
25. Ator, M. and Ortiz de Montellano, P. R. (1987) Protein control of prosthetic heme reactivity J. Biol. Chem. 262, 1542-1551
26. Ortiz de Montellano, P. R. (1986) In Cytochrome P-450: Structure, Mechanism and Biochemistry (Ortiz de Montellano, R. P. Ed.) Plenum Press, New York.
27. Borg, D. C. (1965) Free radicals from imipramine Biochem. Pharmacol. 14, 115-120
28. Saakurai, H. and Goda, T. (1983) Formation of imipramine free radical and vanadyle ion in the reaction of imipramine and pentavalent vanadium ion Inorg. Chim. Acra 78, L33-L34
29. Edwards, S. L., Raag, R., Wariishi, H., Gold, M. H., and Poulos, T. L. (1993) Crystal structure of lignin peroxidase Proc. Natl. Acad. Sci.U.S.A. 90, 750-754
30. Sivaraja, M., Goodin, D. B., Smith, M., and Hoffman, B. M. (1989) Identification by ENDOR of Trp191 as the free-radical site in cytochrome c peroxidase compound ES Science 245, 738-740
31. Griffin, B. W., Marth, C., Yasukochi, Y., and Masters, B. S. S. (1980) Radical mechanism of aminopyrine oxidation by cumene hydroperoxide catalyzed by purified liver microsomal cytochrome P-450 Arch. Biochem. Biophys. 205, 543-553
32. Perez-Gilabert, M., Sanchez-Ferrer, A., and Garcia-Carmona, F. (1997) Oxidation of aminopyrine by the hydroperoxidase activity of lipoxygenase: a new proposed mechanism of N-demethylation Free Radical Biol. Med. 23, 548-555
33. Vazquez, A., Tudela, J., Varon, R., and Garcia-Canovas, F. (1991) Determination of the molar absorptivities of phenothiazine cation radicals generated by oxidation with hydrogen peroxide/peroxidase Anal. Biochem. 202, 245-248
34. Sackett, P. H., Mayausky, J. S., Smith, T., Kalus, S., and McCreery, R. L. (1981) Side-chain effects on phenothiazine cation radical reactions J. Med. Chem. 24, 1342-1347
35. Gadelha, F. R., Hanna, P. M., Mason, R. P., and Docampo, R. (1992) Evidence for free radical formation during horseradish peroxidase-catalyzed N-demethylation of crystal violet Chem.-Biol. Interact. 85, 35-48
36. Hufford, C. D., Capiton, G. A., Clark, A. M., and Baker, J. K. (1981) Metabolism of imipramine by microorganisms J. Pharm. Sci. 70, 151-155
37. Saez, G., Thornalley, P. J., Hill, H. A. O., Hems, R., and Bannister, J. V. (1982) The production of free radicals during the authoxidation of cysteine and their effect on isolated rat hepatocytes Biochim. Biophys. Acta 719, 24-31