Ethylation and methylation of hemoglobin in smokers and non-smokers

Carcinogenesis

Volumn 23, Issue 11, 2002, Pages 1903-1910

  Carmella, Steven g ^a   Chen, Menglan ^a   Villalta, Peter W ^a   Gurney, James G ^a   Hatsukami, Dorothy K ^a   Hecht, Stephen S ^a  

^a UNIVERSITY OF MINNESOTA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADENINE DERIVATIVE; CIGARETTE SMOKE; HEMOGLOBIN; HYDANTOIN DERIVATIVE; ISOTHIOCYANIC ACID DERIVATIVE; PEPTIDE DERIVATIVE; THIOHYDANTOIN DERIVATIVE; VALINE;

AGE; ALKYLATION; AMINO TERMINAL SEQUENCE; ARTICLE; CARCINOGENESIS; CONTROLLED STUDY; DNA ADDUCT; DNA DAMAGE; GAS CHROMATOGRAPHY; GENDER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; IONIZATION; METHYLATION; PRIORITY JOURNAL; PURIFICATION; QUANTITATIVE ANALYSIS; SENSITIVITY ANALYSIS; SMOKING; STANDARD; STATISTICAL SIGNIFICANCE; TANDEM MASS SPECTROMETRY; TUMOR PROMOTION;

EID: 0036848495     PISSN: 01433334     EISSN: None     Source Type: Journal    
DOI: 10.1093/carcin/23.11.1903     Document Type: Article

References (49)

1. International Agency for Research on Cancer (1986) Tobacco smoking. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. IARC Scientific Publications, IARC, Lyon, pp. 127-135.
2. Baron,J.A. and Roham,T.E. (1996) Tobacco. Cancer Epidemiology and Prevention. Oxford University Press, New York, pp. 269-289.
3. Doll,R. (1996) Cancers weakly related to smoking. Br. Med. J., 52, 35-49.
4. Chao,A., Thun,M.J., Jacobs,E.J., Henley,S.J., Rodriguez,C. and Calle,E.E. (2000) Cigarette smoking and colorectal cancer mortality in the cancer prevention study II. J. Natl Cancer Inst., 92, 1888-1896.
5. Schiffman,M.H., Brinton,L.A., Devesa,S.S. and Fraumeni,J.F. Jr (1996) Cervical cancer. Cancer Epidemiology and Prevention. Oxford University Press, New York, pp. 1090-1116.
6. Hecht,S.S. (1999) Tobacco smoke carcinogens and lung cancer. J. Natl Cancer Inst., 91, 1194-1210.
7. Rodenhuis,S., Slebos,R.J.C., Boot,A.J.M., Evers,S.G., Mooi,W.J., Wagenaar,S.S., van Bodegom,P.C. and Bos,J.L. (1988) Incidence and possible clinical signifinance of K-ras oncogene activation in adenocarcinoma of the human lung. Cancer Res., 48, 5738-5741.
8. Hussain,S.P. and Harris,C.C. (1998) Molecular epidemiology of human cancer: contribution of mutation spectra studies of tumor suppressor genes. Cancer Res., 85, 4023-4037.
9. Golkar,S.O., Ehrenberg,L., Segerback,D. and Hallstrom,I. (1976) Evaluation of genetic risks of alkyating agents II. Haemoglobin as a dose monitor. Mutat. Res., 34, 1-10.
10. Skipper,P.L. and Tannenbaum,S.R. (1990) Protein adducts in the molecular dosimetry of chemical carcinogens. Carcinogenesis, 11, 507-518.
11. Carmella,S.G., Kagan,S.S., Kagan,M., Foiles,P.G., Palladino,G., Quart, A.M., Quart,E. and Hecht,S.S. (1990) Mass spectrometric analysis of tobacco-specific nitrosamine hemoglobin adducts in snuff dippers, smokers, and non-smokers. Cancer Res., 50, 5438-5445.
12. Branner,B., Kutzer,C., Zwickenpflug,W., Scherer,G., Heller,W. and Richter,E. (1998) Haemoglobin adducts from aromatic amines and tobacco-specific nitrosamines in pregnant smoking and non-smoking women. Biomarkers, 3, 35-47.
13. Bergmark,E. (1997) Hemoglobin adducts of acrylamide and acrylonitrile in laboratory workers, smokers and nonsmokers. Chem. Res. Toxicol., 10, 78-84.
14. Fennell,T.R., MacNeela,J.P., Morris,R.W., Watson,M., Thompson,C.L. and Bell,D.A. (2000) Hemoglobin adducts from acrylonitrile and ethylene oxide in cigarette smokers: effects of glutathione S-transferase T1-null and M1-null genotypes. Cancer Epidemiol. Biomarkers Prev., 9, 705-712.
15. Castelao,J.E., Yuan,J.M., Skipper,P.L., Tannenbaum,S.R., Gago-Dominguez,M., Crowder,J.S., Ross,R.K. and Yu,M.C. (2001) Gender- and smoking-related bladder cancer risk. J. Natl Cancer Inst., 93, 538-545.
16. Törnqvist,M. (1994) Epoxide adducts to N-terminal valine of hemoglobin. In Everse,J., Vandegriff,K.D. and Winslow,R.M. (eds) Hemoglobins. Part B. Biochemical and Analytical Methods, Vol. 231. Academic Press, San Diego, pp. 650-657.
17. van Sittert,N.J. (1997) N-2-cyanoethylvaline, N-2-hydroxyethylvaline, N-methylvaline (as evidence of exposure to acrylonitrile, ethylene oxide as well as methylating agents). Anal. Hazard. Sub. Biol. Mat., 5, 181-210.
18. Kopplin,A., Eberle-Adamkiewicz,G., Glusenkmo,K.H., Nehls,P. and Kirstein,U. (1995) Urinary excretion of 3-methyladenine and 3-ethyladenine after controlled exposure to tobacco smoke. Carcinogenesis, 16, 2637-2641.
19. Prevost,V. and Shuker,D.E.G. (1996) Cigarette smoking and urinary 3-alkyladenine excretion in man. Chem. Res. Toxicol., 9, 439-444.
20. 6-methylguanine, in transcribed genes prevents mutation of H-ras in rat mammary tumorigenesis induced by ethylnitrosourea in place of methylnitrosourea. Proc. Natl Acad. Sci. USA, 95, 1635-1640.
21. 6-ethyldeoxyguanosine, accumulates in hepatocyte DNA of rats exposed continuously to diethylnitrosamine. Proc. Natl Acad. Sci. USA, 81, 1692-1695.
22. 6-ethylguanine in DNA protects rat 208F cells from tumorigenic conversion by N-ethyl-N-nitrosourea. Proc. Natl Acad. Sci. USA, 87, 9883-9887.
23. Tornqvist,M., Mowrer,J., Jensen,S. and Ehrenberg,L. (1986) Monitoring of environmental cancer initiators through hemoglobin adducts by a modified Edman degradation method. Anal. Biochem., 154, 255-266.
24. Kautiainen,A., Tornqvist,M., Svensson,K. and Osterman-Golkar,S. (1989) Adducts of malonaldehyde and a few other aldehydes to hemoglobin. Carcinogenesis, 10, 2123-2130.
25. Gurney,J.G., Chen,M., Skluzacek,M.C., Kasum,C.M., Carmella,S.G., Villalta,P.W. and Hecht,S.S. (2002) Null association between frequency of cured meat consumption and methylvaline and ethylvaline hemoglobin adduct levels: the N-nitroso brain cancer hypothesis. Cancer Epidemiol. Biomarkers Prev., 11, 421-422.
26. Rydberg,P., Lüning,B., Wachtmeister,C.A. and Törnqvist,M. (1993) Synthesis and characterization of N-substituted valines and their phenyl-and pentafluorophenyl-thiohydantions. Acta. Chem. Scand, 47, 813-817.
27. Murthy,M.S.S., Calleman,C.J., Osterman-Golkar,S., Segerback,D. and Svensson,K. (1984) Relationships between ethylation of hemoglobin, ethylation of DNA and administered amount of ethyl methanesulfonate in the mouse. Mutat. Res., 127, 1-8.
28. 4-Ethylthymidine and etheno-DNA adducts in human lung tissue and sputum cells: Effect of cigarette smoking. Proc. Am. Assoc. Cancer Res., 43, 347.
29. Hoffmann,D., Hoffmann,I. and El Bayoumy,K. (2001) The less: harmful cigarette: a controversial issue. A tribute to Ernst L. Wynder. Chem. Res. Toxicol., 14, 767-790.
30. Bartsch,H., Ohshima,H., Pignatelli,B. and Calmels,S. (1989) Human exposure to endogenous N-nitroso compounds: quantitative estimates in subjects at high risk for cancer of the oral cavity, oesophagus, stomach and urinary bladder. Cancer Surv., 8, 335-362.
31. Tsuda,M. and Kurashima,Y. (1991) Tobacco smoking, chewing and snuff dipping: factors contributing to the endogenous formation of N-nitroso compounds. Crit. Rev. Toxicol., 21, 243-253.
32. Tricker,A.R. (1997) N-nitroso compounds and man: sources of exposure, endogenous formation and occurrence in body fluids. Eur. J. Cancer Prev., 6, 226-268.
33. Schmeltz,I. and Hoffmann,D. (1977) Nitrogen containing compounds in tobacco and tobacco smoke. Chem. Rev., 77, 295-311.
34. Preussmann,R. and Stewart,B.W. (1984) N-Nitroso Carcinogens. In Searle,C.E. (ed.) Chemical Carcinogens, Second Edition, ACS Monograph 182, Vol. 2. American Chemical Society, Washington, DC, pp. 643-828.
35. Chepiga,T.A., Morton,M.J., Murphy,P.A., Avalos,J.T., Bombick,B.R., Doolittle,D.J., Borgerding,M.F. and Swauger,J.E. (2000) A comparison of the mainstream smoke chemistry and mutagenicity of a representative sample of the U.S. cigarette market with two Kentucky reference cigarettes (K1R4F and K1R5F). Food Chem. Toxicol., 38, 949-962.
36. Tornqvist,M., Golkar,S.O., Kautiainen,A., Naslund,M., Callemen,C.J. and Ehrenberg,L. (1988) Methylations in human hemoglobin. Mutat. Res., 204, 521-529.
37. Fang,J.L. and Vaca,C.E. (1997) Detection of DNA adducts of acetaldehyde in peripheral white blood cells of alcohol abusers. Carcinogenesis, 18, 627-632.
38. Törnqvist,M., Svartengren,M. and Ericsson,C.H. (1992) Methylations in hemoglobin from monozygotic twins discordant for cigarette smoking: hereditary and tobacco-related factors. Chem.-Biol. Interact., 82, 91-98.
39. Bader,M., Lewalter,J. and Angerer,J. (1995) Analysis of N-alkylated amino acids in human hemoglobin: evidence for elevated N-methylvaline levels in smokers. Int. Arch. Occup. Environ. Health, 67, 237-242.
40. Clarke,S. (1993) Protein methylation. Curr. Opin. Cell Biol., 5, 977-983.
41. Paik,W.K. and Kim,S. (eds) (1990) Protein Methylation. CRC Press, Boca Raton, FL.
42. Hecht,S.S. (1998) Biochemistry, biology and carcinogenicity of tobacco-specific N-nitrosamines. Chem. Res. Toxicol., 11, 559-603.
43. Hecht,S.S. and Tricker,A.R. (1999) Nitrosamines derived from nicotine and other tobacco alkaloids. In Gorrod,J.W. and Jacob,P. III (eds) Analytical Determination of Nicotine and Related Compounds and Their Metabolites. Elsevier Science, Amsterdam, pp. 421-488.
44. Hoffmann,D. and Hecht,S.S. (1990) Advances in tobacco carcinogenesis. In Cooper,C.S. and Grover,P.L. (eds) Handbook of Experimental Pharmacology. Springer-Verlag, Heidelberg, pp. 63-102.
45. Scherer,G., Frank,S., Riedel,K., Merger-Kossien,I. and Renner,T. (2000) Biomonitoring of exposure to polycyclic aromatic hydrocarbons of nonoccupationally exposed persons. Cancer Epidemiol. Biomarkers Prev., 9, 373-380.
46. Melikian,A.A., Sun,P., Pierpont,C., Coleman,S. and Hecht,S.S. (1997) Gas chromatography-mass spectrometric determination of benzo[a]pyrene and chrysene diol epoxide globin adducts in humans. Cancer Epidemiol. Biomarkers Prev., 6, 833-839.
47. Bailey,E., Brooks,A.G.F., Dollery,C.T., Farmer,P.B., Passingham,B.J., Sleightholm,M.A. and Yates,D.W. (1988) Hydroxyethylvaline adduct formation in haemoglobin as a biological monitor of cigarette smoke intake. Arch. Toxicol., 62, 247-253.
48. Tornqvist,M., Osterman-Golkar,S., Kautiainen,A., Hensen,S., Farmer,P.B. and Ehrenberg,L. (1986) Tissue doses of ethylene oxide in cigarette smokers determined from adduct levels in hemoglobin. Carcinogenesis, 7, 1519-1521.
49. Scherer,G., Frank,S., Riedel,K., Meger-Kossien,I. and Renner,T. (2000) Biomonitoring of exposure to polycyclic aromatic hydrocarbons of nonoccupationally exposed persons. Cancer Epidemiol. Biomarkers Prev., 9, 373-380.