DNA adducts in human carcinogenesis: Etiological relevance and structure-activity relationship

Mutation Research - Reviews in Genetic Toxicology

Volumn 340, Issue 2-3, 1996, Pages 67-79

  Bartsch, Helmut ^a  

^a GERMAN CANCER RESEARCH CENTER DKFZ   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BENZO[A]PYRENE; CYTOCHROME C;

ANTIBODY AFFINITY; ARTICLE; CARCINOGENIC ACTIVITY; DNA ADDUCT; DRUG CONFORMATION; DRUG DNA BINDING; DRUG POTENCY; HUMAN; LUNG CARCINOGENESIS; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE ACTIVITY RELATION;

ANIMALIA;

EID: 0029314191     PISSN: 01651110     EISSN: None     Source Type: Journal    
DOI: 10.1016/s0165-1110(96)90040-8     Document Type: Article

References (67)

1. Alexandrov K., Rojas M., Goldberg M., Camus A.M., Bartsch H. A new sensitive fluorometric assay for the metabolism of (-)-7,8-dihydroxy-7,8-dihydrobenzo[a]pyrene by human hair follicles. Carcinogenesis. 11:1990;2157-2167.
2. Alexandrov K., Rojas M., Geneste O., Castegnaro M., Camus A.M., Petruzzelli S., Giuntini C., Bartsch H. An improved fluorometric assay for dosimetry of benzo[a]pyrene diol-epoxide-DNA adducts in smokers' lung: comparisons with total bulky adducts and AHH activity. Cancer Res. 52:1992;6248-6253.
3. Anttila S., Hietanen E., Vainio H., Camus A.-M., Gelboin H.V., Park S.S., Heikkilä L., Karjalainen A., Bartsch H. Smoking and peripheral types of cancer are related to high levels of pulmonary cytochrome P450-1A1 in lung cancer patients. Int. J. Cancer. 47:1991;681-685.
4. 50) in rodents: a comparison of mono- and bifunctional alkylating agents and vinyl chloride metabolites. Mutation Res. 215:1989;95-106.
5. 4-ethenocytosine in DNA bases. Proc. Am. Assoc. Cancer Res. 34:1993;136.
6. Bartsch H., Petruzzelli S., De Flora S., Hietanen E., Camus A.M., Castegnaro M., Geneste O., Camoirano A., Saracci R., Giuntini C. Carcinogen metabolism and DNA adducts in human lung tissues affected by tobacco smoking or metabolic phenotype: a case-control study on lung cancer patients. Mutation Res. 250:1991;103-114.
7. Bartsch H., Castegnaro M., Rojas M., Camus A.M., Alexandrov K., Lang M. Expression of pulmonary CYP1A1 and carcinogen DNA adducts formation in high risk subjects tobacco-related lung cancer. Toxicol. Lett. 64/65:1992a;477-483.
8. Bartsch H., Petruzzelli S., De Flora S., Hietanen E., Camus A.M., Castegnaro M., Alexandrov K., Rojas M., Saracci R., Giuntini C. Carcinogen metabolism in human lung tissues and the effect of tobacco smoking: results from a case-control multicentre study on lung cancer patients. Environ. Health Perspect. 98:1992b;119-124.
9. Bartsch H., Barbin A., Marion M.-J., Nair J., Guichard Y. Formation, detection and role in carcinogenesis of ethenobases in DNA. Drug Metab. Rev. 26:1994;349-371.
10. Bartsch H., Rojas M., Alexandrov K., Camus A.-M., Castegnaro M., Malaveille C., Anttila S., Hirvonen K., Husgafvel-Pursiainen K., Hietanen E., Vainio H. Metabolic polymorphism affecting DNA binding and excretion of carcinogens in humans. Pharmacogenetics. 5:1995;884-890.
11. 32P-postlabelling and arylhydrocarbon hydroxylase activity in lung parenchyma of smokers and ex-smokers, Garrigues P., Lamotte M. Polycyclic Aromatic Compounds, Synthesis, Properties, Analytical Measurements, Occurrence and Biological Effects. 1992;969-976 Gordon and Breach, London, New York.
12. Chaudhary A.K., Nokubo M., Reddy G.R., Yeola S.N., Morrow J.D., Blair I.A., Marnett L.J. Detection of endogenous malondialdehyde-deoxyguanosine adducts in humna liver. Science. 265:1994;1580-1582.
13. Ciroussel F., Barbin A., Eberle G., Bartsch H. Investigations on the relationship between DNA ethenobase adduct levels in several organs of vinyl chloride-exposed rats and cancer susceptibility. Biochem. Pharmacol. 39:1990;1109-1113.
14. Dosanjh M.K., Chenna A., Kim E., Fraenkel-Conrat H., Samson L., Singer B. All four known cyclic adducts formed in DNA by the vinyl chloride metabolite chloroacetaldehyde are released by a human DNA glycosylase. Proc. Natl. Acad. Sci. USA. 91:1994;1024-1028.
15. 4-etheno-2′-deoxycytidine detected by monoclonal antibodies in lung and liver DNA of rats exposed to vinyl chloride. Carcinogenesis. 10:1989;209-212.
16. 4-ethenocytosine by lipid peroxidation products and nucleic acid bases. Chem. Res. Toxicol. 8:1995;278-283.
17. Friesen M.D., Garren L., Prevost V., Shuker D.E.G. Isolation of 3-methyladenine using immunoaffinity columns prior to determination by low-resolution gas chromatography-mass spectrometry. Chem. Res. Toxicol. 4:1991;102-106.
18. 32P-postlabelling and aryl hydrocarbon hydroxylase activity in lung parenchyma of smokers and ex-smokers. Carcinogenesis. 12:1991;1301-1305.
19. Greenblatt M.S., Bennett W.P., Hollstein M., Harris C.C. Mutations in the p53 tumor suppressor gene: clues to cancer etiology and molecular pathogenesis. Cancer Res. 54:1994;4855-4878.
20. 4-ethenocytosine in DNA. Phillips D.H., Castegnaro M., Bartsch H. Post-Labelling Methods for the Detection of DNA Damage. IARC Sci. Publ. No. 124. 1993;263-269 IARC, Lyon.
21. Hayashi S., Wanatabe J., Kawajiri K. High susceptibility to lung cancer analyzed in terms of combined genotypes of P450IA1 and Mu-class glutathione S-transferase genes. Jpn. J. Cancer Res. 83:1992;866-870.
22. Hirvonen A., Husgafvel-Pursiainen K., Karjalainen A., Anttila S., Vainio H. Point-mutational MspI and Ile-Val polymorphisms closely linked in the CYP1A1 gene: lack of association with susceptibility to lung cancer in Finnish study population. Cancer Epidemiol. Biomarkers Prevent. 1:1992;485-489.
23. Hirvonen A., Husgafvel-Pursiainen K., Anttila S., Vainio H. The GSTM1 null genotype as a potential risk modifier for squamous cell carcinoma of the lung. Carcinogenesis. 14:1993;1479-1481.
24. Hollstein M., Marion M.-J., Lehmann T., Welsh J., Harris C.C., Martel-Planche G., Kusters I., Montesano R. P53 mutations at A:T base pairs in angiosarcomas of vinyl chloride-exposed factory workers. Carcinogenesis. 15:1994;1-3.
25. Husgafvel-Pursiainen K., Hackmann P., Radanpää M., Anttila S., Karjalainen A., Partanen T., Taikinia-Aho O., Heikkilä L., Vainio H. K-ras mutations in human adenocarcinoma of the lung: association with smoking and occupational exposure to asbestos. Int. J. Cancer. 53:1993;250-256.
26. Izzotti A., De Flora S., Petrilli G.L., Gallagher A., Rojas M., Alexandrov K., Bartsch H., Lewtas J. Cancer biomarkers in human atherosclerotic lesions: detection of DNA adducts. Cancer Epidemiol, Biomarkers Prev. 4:1995;105-110.
27. 4-ethylthymine in human liver and peripheral blood leukocyte. Carcinogenesis. 16:1995a;1277-1280.
28. 4-ethylthymine in human lung tissues. Proc. Am. Assoc. Cancer Res. 1995b;. Abstract No. 810.
29. Kat A.G., Thilly W.G. Mutational spectra of endogenous genes in mammalian cells. Hemminki K., Dipple A., Shuker D.E.G., Kadlubar F.F., Segerbäck D., Bartsch H. DNA adducts: identification and biological significance. IARC Sci. Publ. No. 125. 1994;371-384 IARC, Lyon.
30. Lawley P.D. From fluorescence spectra to mutational spectra, a historical overview of DNA-reactive compounds. Hemminki K., Dipple A., Shuker D.E.G., Kadlubar F.F., Segerbäck D., Bartsch H. DNA adducts: identification and biological significance. IARC Sci. Publ. No. 125. 1994;3-22 IARC, Lyon.
31. Marion M.J., Froment O., Trepo C. Activation of Ki-ras gene by point mutation in human liver angiosarcoma associated with vinyl chloride exposure. Mol. Carcinogen. 4:1991;450-454.
32. Marnett L.J., Burcham P.C. Endogenous DNA adducts: potential and paradox. Chem. Res. Toxicol. 6:1993;778-785.
33. McLemore T.L., Adelberg S., Liu M.C., McMahon N.A., et al. Expression of CYP1A1 gene in patients with lung cancer: evidence for cigarette smoke-induced gene expression in normal lung tissue and for altered gene regulation in primary pulmonary carcinomas. J. Natl. Cancer Inst. 82:1990;1333-1339.
34. Mustonen R., Hemminki K. 7-Methylguanine levels in DNA of smokers' and nonsmokers' total white blood cells, granulocytes, and lymphocytes. Carcinogenesis. 13:1992;1951-1955.
35. 4-ethenodeoxycytidine in liver DNA of LEC rats. J. Free Radicals Biol. Med. 1994;. Abstract T3.
36. 32P-postlabelling. Carcinogenesis. 16:1995;613-617.
37. Nakachi K., Imai K., Hayashi S.-I., Watanabe J., Kawajiri K. Genetic susceptibility to squamous cell carcinoma of the lung in relation to cigarette smoking dose. Cancer Res. 51:1991;5177-5180.
38. Nakachi K., Imai K., Hayashi S.-I., Kawajiri K. Polymorphisms of the CYP1A1 and glutathione S-transferase genes associated with susceptibility to lung cancer in relation to cigarette dose in a Japanese population. Cancer Res. 53:1993;2994-2999.
39. 2-propanodeoxyguanosine adducts as common DNA lesions in rodents and humans. Proc. Natl. Acad. Sci. USA. 91:1994;7491-7495.
40. Ohshima H., Bartsch H. Chronic infections and inflammatory processes as cancer risk factors: possible role of nitric oxide in carcinogenesis. Mutation Res. 305:1994;253-264.
41. Pelkonen O., Nebert D.W. Metabolism of polycyclic hydrocarbons: etiologic role in carcinogenesis. Pharmacol. Rev. 34:1982;189-222.
42. Petruzzelli S., Camus A.-M., Carrozzi L., Ghelarducci L., Rindi M., Menconi G., Angeletti C.A., Ahotupa M., Hietanen E., Aitio A., Saracci R., Bartsch H., Giuntini C. Long-lasting effects of tobacco smoking on pulmonary drug-metabolizing enzymes: a case-control study on lung cancer patients. Cancer Res. 48:1988;4695-4700.
43. Phillips, et al. Nature. 336:1988;790-792.
44. Phillips, et al. Int.J. Cancer. 46:1990;569-575.
45. Prevost V., Shuker D.E.G. Urinary 3-alkyladenines as markers of tobacco-smoke exposure in humans. Hum Exp. Toxicol. 11:1992;427-429.
46. Prevost V., Shuker D.E.G. Cigarette smoking and urinary 3-alkyladenine excretion in man. Chem. Res. Toxicol. 1996;. in press.
47. Prevost V., Shuker D.E.G., Bartsch H., Pastorelli R., Stillwell W.G., Trudel L.J., Tannenbaum S.R. The determination of urinary 3-methyladenine by immunoaffinity chromatography-monoclonal antibody-based ELISA: use in human biomonitoring studies. Carcinogenesis. 11:1990;1747-1751.
48. Prevost V., Shuker D.E.G., Friesen M.D., Eberle G., Rajewsky M.F., Bartsch H. Immunoaffinity purification and gas chromatography-mass spectrometric quantification of 3-alkyladenines in urine: metabolism studies and basal excretion levels in man. Carcinogenesis. 14:1993;199-204.
49. Reynolds S.H., Anderson M.W. Activation of protooncogenes in human and mouse lung tumors. Environ. Health Perspect. 93:1991;145-148.
50. Rojas M., Camus A.M., Alexandrov K., Husgafvel-Pursiainen K., Antilla S., Vainio H., Bartsch H. Stereoselective metabolism of (-)-benzo[a]pyrene-7,8-diol by human lung microsomes and peripheral blood lymphocytes: effect of smoking. Carcinogenesis. 13:1992;929-933.
51. Rojas, et al. Carcinogenesis. 15:1994;557-560.
52. Rojas M., Alexandrov K., Auburtin G., Wastiaux-Denamur A., Mayer L., Mahieu B., Sebastien P., Bartsch H. Anti-benzo[a]pyrene diolepoxide-DNA adduct levels in peripheral mononuclear cells from coke oven workers and the enhancing effect of smoking. Carcinogenesis. 16:1995;1373-1376.
53. Ryberg, et al. Cancer Res. 54:1994;5801-5804.
54. Shapiro R. Reactions with purines and pyrimidines. Ann. NY Acad. Sci. 163:1969;624-630.
55. Shapiro R., Hachmann J. The reactions of guanine derivatives with 1,2-dicarbonyl compounds. Biochemistry. 5:1966;2799-2807.
56. Shuker D.E.G., Bartsch H. Detection of human exposure to carcinogens by measurement of alkyl-DNA adducts using immunoaffinity clean-up in combination with gas chromatography-mass spectrometry and other methods of quantitation. Mutation Res. 313:1994;263-268.
57. Shuker D.E.G., Farmer P.B. Relevance of urinary DNA adducts as markers of carcinogen exposure. Chem. Res. Toxicol. 5:1992;450-460.
58. Shuker D.E.G., Prevost V., Friesen M.D., Bartsch H. Noninvasive methods for measuring DNA alkylation in experimental animals and humans. Environ. Health Perspect. 101:(Suppl. 3):1993;151-153.
59. Singer B., Bartsch H. The role of cyclic nucleic acid adducts in carcinogenesis and mutagenesis. IARC Sci. Publ. No. 70. 1986;IARC, Lyon.
60. Sodum R.S., Chung F.-L. Cancer Res. 51:1991;137-143.
61. Swenberg J.A., Fedtke N., Ciroussel F., Barbin A., Bartsch H. Etheno adducts formed in DNA of vinyl chloride exposed rats are highly persistent in liver. Carcinogenesis. 13:1992;727-729.
62. 1450) gene: lack of association between the MspI restriction fragment length polymorphism and incidence of lung cancer in a Norwegian population. Pharmacogenetics. 1:1991;20-25.
63. van Schooten F.J., Jongeneelen F.J., Hillebrand M.J.X., van Leeuwen F.E., de Loof A.J.A., Dijkmans A.P.G., van Rooij J.G.M., den Engelse L., Kriek E. Polycyclic aromatic hydrocarbon-DNA adducts in white blood cell DNA and 1-hydroxypyrene in the urine of aluminum workers: relation with job category and synergistic effect of smoking. Cancer Epidemiol. Biomarkers Prev. 4:1995;69-77.
64. Vogel E.W., Nivard M.J.M. The subtlety of alkylating agents in reactions with biological macromolecules. Mutation Res. 395:1994;13-32.
65. Vogel E.W., Barbin A., Nivard M.J., Bartsch H. Nucleophilic selectivity of alkylating agents and their hyper-mutability in Drosophila as predictors of carcinogenic potency in rodents. Carcinogenesis. 11:1990;2211-2217.
66. Wagner J.R., Hu C.-C., Ames B.N. Endogenous oxidative damage of deoxycytidine in DNA. Proc. Natl. Acad. Sci. USA. 89:1992;3380-3384.
67. Yamamoto F., Kasai H., Togashi Y., Takeichi N., Hori T., Nishimura S. Elevated level of 8-hydroxydeoxyguanosine in DNA of liver, kidneys, and brain of Long-Evans Cinnamon rats. Jpn. J. Cancer Res. 84:1993;508-511.