Synthesis and analysis of DNA adducts of arylamines

References

• Annan R. S., Giese R. W., Vouros P. Detection and structural characterization of amino polyaromatic hydrocarbon-deoxynucleoside adducts using fast atom bombardment and tandem mass spectrometry. Analytical Biochemistry 1990; 191: 86–95
   PubMed Web of Science ®Google Scholar
• Bakthavachalam J., Abdel-Baky S., Giese R. E. Release of 2-aminofluorene fromN-(deoxyguanosin-8-yl)-2-aminofluorene by hydrazinolysis. Journal of Chromatography 1991; 538: 447–451
   PubMed Web of Science ®Google Scholar
• Bamberger E., Rising A. Einfluŝ von Methyl auf die Reactions-geschwindigkeit der Arylhydroxylamine. Liebigs Annalen der Chemie 1901; 316: 257–292
   Google Scholar
• Beach A. C., Gupta R. C. Human biomonitoring and 32P-postlabelling assay. Carcinogenesis 1992; 13: 1053–1074
   PubMed Web of Science ®Google Scholar
• Beland F. A., Kadlubar F. F. Metabolic activation and DNA adducts of aromatic amines and nitroaromatic hydrocarbons. In Chemical Carcinogenesis and Mutagenesis 1, C. S. Cooper. Springer, Berlin 1990; Vol. 1: 267–325
   Google Scholar
• Blair I. A. Applications of mass spectrometry to toxicology. Chemical Research in Toxicology 1993; 6: 741–747
   PubMed Web of Science ®Google Scholar
• Briant M. S., Simmons H. F., Harrel R. E., Hinson J. A. 2,6-Dimethylanilinehemoglobin adducts from lidocaine in humans. Carcinogenesis 1994; 15: 2287–2290
   PubMed Web of Science ®Google Scholar
• Bryant M. S., Vineis P., Skipper P. L., Tannenbaum S. R. Hemoglobin adducts of aromatic amines: associations with smoking status and type of tobacco. Proceedings of the National Academy of Sciences of the United States of America 1988; 85: 9788–9791
   PubMed Web of Science ®Google Scholar
• Evans F. E., Miller D. W., Belando F. A. Sensitivity of the conformation of deoxyguanosine at the C-8 position byN-acetylated and unacetylated 2-aminofluorene. Carcinogenesis 1980; 1: 955–959
   PubMed Web of Science ®Google Scholar
• Famulok M., Boche G. Formation ofN-(deoxyguanosin-8-yl)aniline in thein vitro reaction ofN-acetoxyaniline with deoxyguanosine and DNA. Angewandte Chemie International Edition 1989; 28: 468–469
   Web of Science ®Google Scholar
• Famulok M., Bosold F., Boche G. Synthesis ofO-acetyl-N-(4-biphenyl)hydroxylamine ('N-acetoxy-4-aminobiphenyl'), an ultimate metabolite of carcinogenic 4-aminophenyl, and its reaction with deoxyguanosine. Angewandte. Chemie International Edition 1989; 28: 337–338
   Web of Science ®Google Scholar
• Farmer P. B., Bailey E., Naylor S., Anderson D., Brooks A., Cushnir J., Lamb J. H., Sepai O., Tang Y. Identification of endogenous electrophiles by means of mass spectrometric determination of protein an DNA adducts. Environmental Health Perspectives 1993; 99: 19–24
   PubMed Web of Science ®Google Scholar
• Friesen M. D., Kaderlik K., Lin D., Garren L., Bartsch H., Lang N. P., Kadlubar F. F. Analysis of DNA-adducts of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine in rat and human tissues by alkaline hydrolysis and gas chromatography/electron capture mass spectrometry: validation by comparison with 32P-postlabelling. Chemical Research in Toxicology 1995; 7: 733–739
   Web of Science ®Google Scholar
• Humphreys W. G., Kadlubar F. F., Guengerich F. P. Mechanism of C8 alkylation of guanine residues by activated arylamines: Evidence for initial adduct formation at the N7 position. Biochemistry 1992; 89: 8278–8282
   Google Scholar
• IARC. IARC Monographs on the evaluation of the carcinogenic risk of chemicals to man. World Health Organization, International Agency for Research on Cancer, GenevaSwitzerland 1987, Suppl. 7
   Google Scholar
• IARC. IARC Monographs on the evaluation of carcinogenic risks to humans, vol. 57, Occupational exposures of hairdressers and barbers and personal use of hair colourants; some hair dyes, cosmetic colourants, industrial dyestuffs and aromatic amines. International Agency for Research on Cancer, LyonFrance 1993
   Google Scholar
• Jacobsen M. D., Shapiro R., Underwood G. R., Broyde S., Vera L., Hingerty B. E. Synthesis and conformation of a dinucleoside monophosphate modified by aniline. Chemical Research in Toxicology 1988; 1: 152–159
   PubMed Web of Science ®Google Scholar
• Kederlik K., Talaska G., De Bord D. G., Osorio A. M., Kadlubar F. F. 4,4′Methylenbis(2-chloroaniline)-DNA adduct analysis in human exfoliated cells by 32P-postlabeling. Cancer Epidemiology, Biomarkers & Prevention 1993; 2: 63–69
   PubMed Web of Science ®Google Scholar
• Kadlubar F. F. DNA adducts of carcinogenic aromatic amines. In DNA Adducts: ldentification and Biological Significance, K. Hemminki, A. Dipple, D. E. G. Shuker, F. F. Kadlubar, D. Segerbäck, H. Bartsch. International Agency for Research on Cancer, LyonFrance 1994; 196–216, IARC Monographs
   Google Scholar
• Kadlubar F. F., Bw F. A. Chemical properties of ultimate carcinogenic metabolites of arylamines and arylamides. Polycyclic Hydrocarbons and Carcinogenesis, R. G. Harvey. American Chemical Society, Washington, DC 1985; 341–370, ACS Symposium Series No. 283
   Google Scholar
• Kadlubar F. F., Belano F. A., Beranek D. T., Dooley K. L., Heflich R. H., Evans F. E. Arylamine-DNA adduct formation in relation to urinary bladder carcinogenesis and salmonella typhimurium mutagenesis. Environmental Mutagens and Carcinogens, T. Sugimara, S. Kondo, H. Takebe. University of Tokyo Press, Tokyo 1982; 385–396
   Google Scholar
• Kriek E. Persistent binding of a new reaction product of the carcinogenN-hydroxy-N-2-acetylaminofluorene with guanine in rat liver DNA in vivo. Cancer Research 1972; 32: 2042–2048
   PubMed Web of Science ®Google Scholar
• Lasko D. D., Basu A. K., Kadlubar F. F., Evans F. E., Lay J. O., Jr, Essigmann J. M. A probe for the mutagenic activity of the carcinogen 4-aminobiphenyl: synthesis and characterization of an M13mp10 genome containing the major carcinogen-DNA adduct at a unique site. Biochemistry 1987; 26: 3072–3081
   PubMed Web of Science ®Google Scholar
• Lin D., Lay J. O., Bryant M. S., Malaveille C, Friesen M., Bartsch H., Lang N. P., Kadlubar F. F. Analysis of 4-aminobiophenyl-DNA adducts in human urinary bladder and lung by alkaline hydrolysis and negative ion gas chromatography-mass spectrometry. Environmental Health. Perspectives 1994; 102(6)11–16, Supplement
   Google Scholar
• Lunares J., Elguero J., Faure R., Vincet E.-J. Carbon-13 NMR studies of nitrogen compounds. Journal of Organic Magnetic Resonance 1980; 14: 20–24
   Google Scholar
• Lobo A. M., Marques M. M., Prabhakar S., Rzepa H. S. Tetrahedral intermediates formed during acyl transfer reactions of acetyl cyanide. Journal of the Chemical Society, Chemical Communications 1985; 1113–1115
   Google Scholar
• Luceri F., Pieraccini G., Moneti G., Dolara P. Primary aromatic amines from side-stream cigarette smoke are common contaminants of indoor air. Toxicology and Industrial Health 1993; 9: 405–413
   PubMed Web of Science ®Google Scholar
• Marques M. M., Beland F. A. DNA adducts of aromatic amines present in tobacco smoke. DNA Adducts: Identification and Biological Significance, K. Hemminki, A. Dipple, D. E. G. Shuker, F. F. Kadlubar, D. Segerbäck, H. Bartsch. International Agency for Research on Cancer, LyonFrance 1994; 45–56, IARC Monographs
   Google Scholar
• Meier C., Boche G. N-Aryl-O(α-aminoacyl)hydroxylarylamine: Modellreaktionen mit Desoxyguanosin, Guanosin und 5′-guanosinmonophosphat zur Aktivierung monocyclischer aromatischer Amine (Z.B. Phenacetinzu ukimalen Carcinogen. Chemische Berichte 1990; 123: 1699–1705
   Google Scholar
• Meier C., Boche G. The modification of guanine nucleosides and nucleotides by the borderline arylamine carcinogens 4methyl- and 4-methoxyaniline: chemistry and structural characterization. Carcinogenesis 1991; 12: 1633–1640
   PubMed Web of Science ®Google Scholar
• O'Handey S. F., Sanford D. G., Xu R., Lester C. C., Hingerty B. E., Broyde S., Krugh T. R. Structural characterization of anN-acetyl-2-aminofluorene (AAFmodified DNA oligomer by NMR, energy minimization, and molecular dynamics. Biochemistry 1993; 32: 2481–2497
   PubMed Web of Science ®Google Scholar
• Patra A., Mukhopadhyay A. K. Carbon13 NMR signals of some benzodiazepine drugs. Journal of Organic Magnetic Resonance 1981; 15: 99–101
   Web of Science ®Google Scholar
• Poirier M. C., Weston A., Gupta-Burt S., Reed E. Measurement of DNA adducts by immunoassays. Basic Life Science 1990; 53: 1–11
   PubMedGoogle Scholar
• Prabhakar S., Lobo A. M., Marques M. M. Reactions between hydroxylamines and aroyl cyanides. Tetrahedron Letters 1982; 23: 1391–1394
   Web of Science ®Google Scholar
• Sanbioni G., Beyerbach A. Determination of hemoglobin adducts of arylamines in humans. Journal of Chromatography B 1995; 667: 75–83
   PubMedGoogle Scholar
• Swenson D. H., El-Bayoumy K., Shuie G.-H., Hecht S. S., Fiala E., Kadlubar F. F., Freeman J. P. Synthesis of N-(purin-8-yl)arytamines. Chemical Research in Toxicology 1993; 6: 480–485
   PubMed Web of Science ®Google Scholar
• Talaska G., Roth J. H., Getek T. 32P-Postlabeling and mass spectrometric methods for analysis of bulky, polyaromatic carcinogen-DNA adducts in humans. Journal of Chromatography 1992; 580: 293–323
   PubMed Web of Science ®Google Scholar
• Talaska G., Schamer M., Casetta G., Tizzani A., Vineis P. Carcinoge-DNA adducts in bladder biopsies and urothelial cells: a risk exercise. Cancer letters 1994; 84: 93–97
   PubMed Web of Science ®Google Scholar
• Talaska G., Schamer M., Skipper P., Tannenbaum S., Caporaso N., Unruh L., Kadlubar F. F., Bartsch H., Malaveille C., Vineis P. Detection of carcinoge-DNA adducts in exfoliated urothelial cells of cigarette smokers: association with smoking, hemoglobin adducts, and urinary mutagenicity. Cancer Epidemiology, Biomarkers & Prevention 1991; 1: 61–66
   PubMed Web of Science ®Google Scholar
• Ward E., Carpenter A., Markowitz S., Roberts D., Haplerin W. Excess number of bladder cancers in workers exposed to ortho-toluidine and aniline. Journal of the National Cancer Institute 1991; 83: 501–506
   PubMed Web of Science ®Google Scholar
• Westra J. G. A rapid and simple synthesis of reactive metabolites of carcinogenic amines in high yield. Carcinogenesis 1981; 2: 355–357
   PubMed Web of Science ®Google Scholar
• Wolf S. M., Vouros P. Application of capillary chromatography coupled with tandem mass spectrometric methods to the rapid screening of adducts formed by the reaction ofN-acetoxy-N-acetyl-2-aminofluorene wth calf thymus DNA. Chemical Research in Toxicology 1994; 7: 82–88
   PubMed Web of Science ®Google Scholar
• Wolf S. M., Vouros P. Incorporation of sample stacking techniques into the capillary electrophoresis CF-FAB mass spectrometric analysis of DNA adducts. Analytical Chemistry 1995; 67: 891–900
   PubMed Web of Science ®Google Scholar