Hydroxyl-specific fluorescence labeling of ABP-deoxyguanosine, PhIP-deoxyguanosine, and AFB1-formamidopyrimidine with BODIPY-FL

Analytical Biochemistry

Volumn 359, Issue 2, 2006, Pages 151-160

  Jang, Hyun Gyung ^a   Park, Misun ^a   Wishnok, John S ^a   Tannenbaum, Steven R ^a   Wogan, Gerald N ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

Aflatoxin; Aminobiphenyl; BODIPY; DNA adducts; Laser induced fluorescence; PhIP

Indexed keywords

AFLATOXINS; DICHLOROMETHANE; DNA; FLUORESCENCE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LASER OPTICS; LASER PRODUCED PLASMAS; MASS SPECTROMETRY; MOLAR RATIO; PROPIONIC ACID; RISK ASSESSMENT;

AMINOBIPHENYL; BODIPY; DNA ADDUCTS; LASER INDUCED FLUORESCENCE; PHIP;

BIOMOLECULES;

1,3 DICYCLOHEXYLCARBODIIMIDE; 4 DIMETHYLAMINOPYRIDINE; 4,4 DIFLUORO 5,7 DIMETHYL 4 BORA 3A,4A DIAZA S INDACENE 3 PROPIONIC ACID; AFLATOXIN B1; DEOXYGUANOSINE DERIVATIVE; DEOXYRIBOSE; DICHLOROMETHANE; DICYCLOHEXYLCARBODIIMIDE; FLUORESCENT DYE; HYDROXYL GROUP; N (2' DEOXYGUANOSIN 8 YL) 2 AMINO 1 METHYL 6 PHENYLIMIDAZO[4,5 B]PYRIDINE; N (2' DEOXYGUANOSIN 8 YL) 4 AMINOBIPHENYL; PYRIMIDINE DERIVATIVE;

ACYLATION; ARTICLE; COLLISIONALLY ACTIVATED DISSOCIATION; CONCENTRATION (PARAMETERS); DNA ADDUCT; DRUG LABELING; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LASER; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; QUANTITATIVE ANALYSIS; SENSITIVITY AND SPECIFICITY; TEMPERATURE;

EID: 33751407016     PISSN: 00032697     EISSN: 10960309     Source Type: Journal    
DOI: 10.1016/j.ab.2006.08.030     Document Type: Article

References (27)

1. Wogan G.N. Markers of exposure to carcinogens. Environ. Health Perspect. 81 (1989) 9-17
2. Poirier M.C. DNA adducts as exposure biomarkers and indicators of cancer risk. Environ. Health Perspect. 105 Suppl 4 (1997) 907-912
3. Santella R.M. DNA damage as an intermediate biomarker in intervention studies. Proc. Soc. Exp. Biol. Med. 216 (1997) 166-171
4. Warren A.J., and Shields P.G. Molecular epidemiology: carcinogen-DNA adducts and genetic susceptibility. Proc. Soc. Exp. Biol. Med. 216 (1997) 172-180
5. Lippman S.M., Lee J.S., Lotan R., Hittelman W., Wargovich M.J., and Hong W.K. Biomarkers as intermediate end points in chemoprevention trials. J. Natl. Cancer Inst. 82 (1990) 555-560
6. Kensler T.W., Groopman J.D., Sutter T.R., Curphey T.J., and Roebuck B.D. Development of cancer chemopreventive agents: oltipraz as a paradigm. Chem. Res. Toxicol. 12 (1999) 113-126
7. 32P-postlabeling assay. Carcinogenesis 13 (1992) 1053-1074
8. Wohlin P., Zeisig M., Gustafsson J.A., and Moller L. 32-P-HPLC analysis of DNA adducts formed in vitro and in vivo by 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine and 2-amino-3,4,8-trimethyl-3H-imidazo[4,5-f]quinoxaline, utilizing an improved adduct enrichment procedure. Chem. Res. Toxicol. 9 (1996) 1050-1056
9. Poirier M.C. Antisera specific for carcinogen-DNA adducts and carcinogen-modified DNA: applications for detection of xenobiotics in biological samples. Mutat. Res. 288 (1993) 31-38
10. Godschalk R.W., Vermeer I.T., Kriek E., Floot B., Schilderman P.A., Moonen E.J., Kleinjans J.C., and Van Schooten F.J. Comparison of 32P-postlabeling and HPLC-FD analysis of DNA adducts in rats acutely exposed to benzo(a)pyrene. Chem. Biol. Interact. 104 (1997) 41-54
11. Turner P.C., Dingley K.H., Coxhead J., Russell S., and Garner C.R. Detectable levels of serum aflatoxin B1-albumin adducts in the United Kingdom population: implications for aflatoxin-B1 exposure in the United Kingdom. Cancer Epidemiol. Biomarkers Prev. 7 (1998) 441-447
12. Farinati F., Cardin R., Degan P., Rugge M., Mario F.D., Bonvicini P., and Naccarato R. Oxidative DNA damage accumulation in gastric carcinogenesis. Gut 42 (1998) 351-356
13. Shinozaki R., Inoue S., and Choi K.S. Flow cytometric measurement of benzo[a]pyrene-diol-epoxide-DNA adducts in normal human peripheral lymphocytes and cultured human lung cancer cells. Cytometry 31 (1998) 300-306
14. Leclercq L.L.C., and De Pauw E. High-Performance Liquid Chromatography/Electrospray Mass Spectrometry for the Analysis of Modified Bases in DNA: 7-(2-Hydroxyethyl)Guanine, the Major Ethylene Oxide-DNA Adduct. Anal. Chem. 69 (1997) 1952-1955
15. Rouzer C.A., Chaudhary A.K., Nokubo M., Ferguson D.M., Reddy G.R., Blair I.A., and Marnett L.J. Analysis of the malondialdehyde-2′-deoxyguanosine adduct pyrimidopurinone in human leukocyte DNA by gas chromatography/electron capture/negative chemical ionization/mass spectrometry. Chem. Res. Toxicol. 10 (1997) 181-188
16. Ding J., and Vouros P. Capillary electrochromatography and capillary electrochromatography-mass spectrometry for the analysis of DNA adduct mixtures. Anal. Chem 69 (1997) 379-384
17. Sharma M., Jain R., Ionescu E., and Slocum H.K. Capillary electrophoretic separation and laser-induced fluorescence detection of the major DNA adducts of cisplatin and carboplatin. Anal. Biochem. 228 (1995) 307-311
18. 35S]methionine: analysis of DNA adducts of 4-aminobiphenyl. Proc. Natl. Acad. Sci. USA 91 (1994) 1696-1700
19. Sheabar F.Z., Morningstar M.L., and Wogan G.N. Peracylation of nucleosides with methionine: foundation for a method to detect carcinogen adducts. Chem. Res. Toxicol. 7 (1994) 650-658
20. Weston A. Physical methods for the detection of carcinogen-DNA adducts in humans. Mutat. Res. 288 (2006) 19-29
21. Thompson P.A., Seyedi F., Lang N.P., MacLeod S.L., Wogan G.N., Anderson K.E., Tang Y.M., Coles B., and Kadlubar F.F. Comparison of DNA adduct levels associated with exogenous and endogenous exposures in human pancreas in relation to metabolic genotype. Mutat. Res. 424 (1999) 263-274
22. Famulk M., Bosold F., and Boche G. Synthesis of O-Acetyl-N (4-biphenylyl)hydroxylamine (NAcetoxy-4-aminobiphenyl), an Ultimate Metabolite of Carcinogenic 4-Aminobiphenyl, and Its Reaction with Deoxyguanosine. Angew. Chem. Int. Ed. Engl 28 (1989) 337-338
23. Kartha V.B., Dasari R.R., Ozbal C.C., Skipper P.L., and Tannenbaum S.R. In: Roy A.P. (Ed). Spectroscopy: Perspectives and Frontiers (1997), Narosa Publishing House, New Dehli 271-283
24. Ozbal C.C., Skipper P.L., Yu M.C., London S.J., Dasari R.R., and Tannenbaum S.R. Quantification of (7S,8R)-dihydroxy-(9R,10S)-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene adducts in human serum albumin by laser-induced fluorescence: implications for the in vivo metabolism of benzo[a]pyrene. Cancer Epidemiol. Biomarkers Prev. 9 (2000) 733-739
25. Wilson M.S., and McCloskey J.A. Chemical ionization mass spectrometry of nucleosides. Mechanisms of ion formation and estimations of proton affinity. J. Am. Chem. Soc. 97 (1975) 3436-3444
26. Crow F.W., Tomer K.B., Gross M.L., McCloskey J.A., and Bergstrom D.E. Fast atom bombardment combined with tandem mass spectrometry for the determination of nucleosides. Anal. Biochem. 139 (1984) 243-262
27. Hua Y., Wainhaus S.B., Yang Y., Shen L., Xiong Y., Xu X., Zhang F., Bolton J.L., and van Breemen R.B. Comparison of negative and positive ion electrospray tandem mass spectrometry for the liquid chromatography tandem mass spectrometry analysis of oxidized deoxynucleosides. J. Am. Soc. Mass Spectrom. 12 (2001) 80-87