Identification and quantification of mutagenic halogenated cytosines by gas chromatography, fast atom bombardment, and electrospray ionization tandem mass spectrometry

Analytical Biochemistry - Tập 317 - Trang 201-209 - 2003
Jaeman Byun1, Jeffrey P Henderson2, Jay.W Heinecke1
1Department of Medicine, University of Washington, Seattle, WA 98195, USA
2Department of Medicine, Washington University School of Medicine, St. Louis, MO, 63110, USA

Tài liệu tham khảo

Marnett, 2000, Oxyradicals and DNA damage, Carcinogenesis, 21, 361, 10.1093/carcin/21.3.361 Ames, 1995, The causes and prevention of cancer, Proc. Natl. Acad. Sci. USA, 92, 5258, 10.1073/pnas.92.12.5258 Reynolds, 1997, An allelic association implicates myeloperoxidase in the etiology of acute promyelocytic leukemia, Blood, 90, 2730, 10.1182/blood.V90.7.2730 Schabath, 2000, Genetic variants of myeloperoxidase and lung cancer risk, Carcinogenesis, 21, 1163, 10.1093/carcin/21.6.1163 Cascorbi, 2000, Substantially reduced risk of cancer of the aerodigestive tract in subjects with variant -463A of the myeloperoxidase gene, Cancer Res., 60, 644 Le Marchand, 2000, Association of the myeloperoxidase -463G-A polymorphism with lung cancer risk, Cancer Epidemiol. Biomarkers Prev., 9, 181 London, 1997, Myeloperoxidase genetic polymorphism and lung cancer risk, Cancer Res., 57, 5001 Weitzman, 1990, Inflammation and cancer: role of phagocyte-generated oxidants in carcinogenesis, Blood, 76, 655, 10.1182/blood.V76.4.655.655 Harrison, 1976, Studies on the chlorinating activity of myeloperoxidase, J. Biol. Chem., 251, 1371, 10.1016/S0021-9258(17)33749-3 Foote, 1981, Assessment of chlorination by human neutrophils, Nature, 301, 715, 10.1038/301715a0 Weiss, 1986, Brominating oxidants generated by human eosinophils, Science, 234, 200, 10.1126/science.3018933 Mayeno, 1989, Eosinophils preferentially use bromide to generate halogenating agents, J. Biol. Chem., 264, 5660, 10.1016/S0021-9258(18)83599-2 Thomas, 1995, Oxidation of bromide by the human leukocyte enzymes myeloperoxidase and eosinophil peroxidase, J. Biol. Chem., 270, 2906, 10.1074/jbc.270.7.2906 Hazen, 1996, Human neutrophils employ chlorine gas as an oxidant during phagocytosis, J. Clin. Invest., 98, 1283, 10.1172/JCI118914 Hazen, 1997, 3-Chlorotyrosine, a specific marker of myeloperoxidase-catalyzed oxidation, is markedly elevated in low density lipoprotein isolated from human atherosclerotic intima, J. Clin. Invest., 99, 2075, 10.1172/JCI119379 Lamb, 1999, Oxidative damage to proteins of bronchoalveolar lavage fluid in patients with acute respiratory distress syndrome: evidence for neutrophil-mediated hydroxylation, nitration, and chlorination, Crit. Care Med., 27, 1738, 10.1097/00003246-199909000-00007 van der Vliet, 2000, Myeloperoxidase and protein oxidation in cystic fibrosis, Am. J. Physiol. Lung Cell. Mol. Physiol., 279, L537, 10.1152/ajplung.2000.279.3.L537 Wu, 1999, 3-Bromotyrosine and 3,5-dibromotyrosine are major products of protein oxidation by eosinophil peroxidase: potential markers for eosinophil-dependent tissue injury in vivo, Biochemistry, 38, 3538, 10.1021/bi982401l Wu, 2000, Eosinophils generate brominating oxidants in allergen-induced asthma, J. Clin. Invest., 105, 1455, 10.1172/JCI9702 Gaut, 2001, Neutrophils employ the myeloperoxidase system to generate antimicrobial brominating and chlorinating oxidants during sepsis, Proc. Natl. Acad. Sci. USA, 98, 11961, 10.1073/pnas.211190298 Henderson, 1999, Molecular chlorine generated by the myeloperoxidase-hydrogen peroxide-chloride system of phagocytes produces 5-chlorocytosine in bacterial RNA, J. Biol. Chem., 274, 33440, 10.1074/jbc.274.47.33440 Henderson, 2001, Production of brominating intermediates by myeloperoxidase: a transhalogenation pathway for generating mutagenic nucleobases during inflammation, J. Biol. Chem., 276, 7867, 10.1074/jbc.M005379200 Henderson, 2001, Bromination of deoxycytidine by eosinophil peroxidase: a mechanism for mutagenesis by oxidative damage of nucleotide precursors, Proc. Natl. Acad. Sci. USA, 98, 1631, 10.1073/pnas.98.4.1631 Henderson, 2001, The eosinophil peroxidase–hydrogen peroxide–bromide system of human eosinophils generates 5-bromouracil, a mutagenic thymine analogue, Biochemistry, 40, 2052, 10.1021/bi002015f Morris, 1991, The genetic toxicology of 5-bromodeoxyuridine in mammalian cells, Mutat. Res., 258, 161, 10.1016/0165-1110(91)90007-I Morris, 1993, The genetic toxicology of 5-fluoropyrimidines and 5-chlorouracil, Mutat. Res., 297, 39, 10.1016/0165-1110(93)90006-9 O’Neill, 1983, Sister-chromatid exchanges and gene mutations are induced by the replication of 5-bromo- and 5-chloro-deoxyuridine substituted DNA, Mutat. Res., 109, 259, 10.1016/0027-5107(83)90051-9 Whiteman, 1997, Hypochlorous acid-induced base modifications in isolated calf thymus DNA, Chem. Res. Tox., 10, 1240, 10.1021/tx970086i Chen, 2002, Detection and quantification of 5-chlorocytosine in DNA by stable isotope dilution and gas chromatography/negative ion chemical ionization/mass spectrometry, Chem. Res. Toxicol., 15, 262, 10.1021/tx015578g Crain, 1990, Preparation and enzymatic hydrolysis of DNA and RNA for mass spectrometry, Methods Enzymol., 193, 782, 10.1016/0076-6879(90)93450-Y Chaudhary, 1994, Detection of endogenous malondialdehyde–deoxyguanosine adducts in human liver, Science, 265, 1580, 10.1126/science.8079172 RamaKrishna, 1992, Synthesis and structure determination of the adducts of the potent carcinogen 7,12-dimethylbenz[a]anthracene and deoxyribonucleosides formed by electrochemical oxidation: models for metabolic activation by one-electron oxidation, J. Am. Chem. Soc., 114, 1863, 10.1021/ja00031a047 Wellemens, 1994, Tandem mass spectrometry for the determination of deoxyribonucleic acid damage by polycyclic aromatic hydrocarbons, Analyst, 114, 497, 10.1039/an9941900497 Kok, 1985, Highly sensitive determination of 5-fluorouracil in human plasma by capillary gas chromatography and negative ion chemical ionization mass spectrometry, J. Chromatogr., 343, 59, 10.1016/S0378-4347(00)84568-5 Stetson, 1986, Simultaneous determination of thymine and 5-bromouracil in DNA hydrolysates using gas chromatography–mass spectrometry with selected-ion monitoring, J. Chromatogr., 375, 1, 10.1016/S0378-4347(00)83686-5 Gross, 1990, Tandem mass spectrometry: multisector magnetic instruments, Methods Enzymol., 193, 131, 10.1016/0076-6879(90)93414-G