APPENDIX 3 DNA-ADDUCTION AND PROTEIN-ADDUCT

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APPENDIX 3 DNA-ADDUCTION AND PROTEIN-ADDUCT IMMUNOASSAYS

Vanderlaan et al.; Immunoassays or Trace Chemical Analysis ACS Symposium Series; American Chemical Society: Washington, DC, 1990.

354

IMMUNOASSAYS FOR TRACE CHEMICAL ANALYSIS

One volume stands out above others because it contains so many papers on this subject. Rather than list each paper individually, readers are refered to the entire volume for a comprehensive overview. It is: Bartsch, H.; Hemminki, K.; O'Neill, I. K., Editors. Methods for detecting DNA damaging agents in humans: Applications in cancer epidemiology and prevention. IARC Scientific Publications vol 89, International Agency for Research on Cancer, Lyon, France. 1988. Primary Publications.


Baan, R. Α.; Lansbergen, M. J.; De Bruin, P. A. F.; Willems, M. I.; Lohman, P. H. M. The organ-specific induction of DNA adducts in 2-acetylaminofluorene -treated rats studied by means of a sensitive immunochemical method. Mutat. Res., 150:23-32. 1985. Ball, S. S.; Quaranta, V.; Shadravan, F.; Walford, R. L. An ELISA for Detection of DNA-bound carcinogen using a monoclonal antibody to N-acetoxy-2acetylaminofluorene-modified DNA. J. Immunol. Meth., 98: 195-200. 1987. Bartolone, J. B.; Birge, R. B.; Sparks, K.; Cohen, S. D.; Khairallah, E. A. Immunochemical analysis of acetaminophen Covalent binding to proteins partial characterization of the major acetaminophen-binding liver proteins. Biochem. Pharmacol., 37: 4763-74. 1988. Brylawski, B. P.; Cordeiro-Stone, M.; Kaufman, D. G. Ferritin-labeled rabbit Fab fragments for the single-step detection of benzo-a-pyrene-diol-epoxide adducts in DNA by electron microscopy. Carcinogenesis (Lond), 10: 199-202. 1989. Chung, F.; Young, R.; Hecht, S. S. Detection of cyclic 1 N-2propanodeoxyguanosine adducts in DNA of rats treated with n-nitrosopyrrolidine and mice treated with crotonaldehyde. Carcinogenesis (Lond), 10: 1291-8. 1989. Degan, P.; Montesano, R.; Wild, C. P. Antibodies against 7methyldeoxyguanosine: Its detection in rat peripheral blood lymphocyte DNA and potential applications to molecular epidemiology. Cancer Res., 48: 5065-70. 1988. Fichtinger-Schepman, A. M. J.; Baan, R. Α.; Luiten-Schuite, Α.; Van Dijk, M.; Lohman, P. Η. M. Immunochemical quantitation of adducts induced in DNA by cis diamminedichloroplatinum-II and analysis of adduct-related DNA-unwinding. Chem-Biol. Interact., 55: 275-88. 1985. Fichtinger-Schepman, A. M. J.; Baan, R. Α.; Berends, F. Influence of the degree of DNA modification on the immunochemical determination of cisplatin DNA adduct levels. Carcinogenesis (Lond), 10: 2367-70. 1989. Fleisher, J. H.; Lung, C. C.; Meinke, G. C.; Pinnas, J. L. Acetaldehyde-albumin adduct formation possible relevance to an immunologic mechanism in alcoholism. Alcohol, 23: 133-42. 1988.


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DNA-Adduction and Protein Adduct Immunoassays 355

Foiles, P. G.; Akerkar, S. Α.; Chung, F. Application of an immunoassay for cyclic acrolein deoxyguanosine adducts to assess their formation in DNA of Salmonella-Typhimurium under conditions of mutation induction by acrolein. Carcinogenesis (Lond), 10: 87-90. 1989. Foiles, P. G.; Chung, F.; Hecht, S. S. Development of a monoclonal antibody -based immunoassay for cyclic DNA adducts resulting from exposure to crotonaldehyde. Cancer Res., 47: 360-3. 1987.


Foiles, P. G.; Miglietta, L. M.; Akerkar, S. Α.; Everson, R. B.; Hecht, S. S. Detection ofO-6methyldeoxyguanosine in human placental DNA. Cancer Res., 48: 4184-8. 1988. Foiles, P. G.; Trushin, N.; Castonguay, A. Measurement of 0-6methyldeoxyguanosine in DNA methylated by the tobacco-specific carcinogen 4memylnitrosarnino-l-3-pyridyl-l-butanone using a biotin-avidin enzyme-linked immunosorbent assay ELISA. Carcinogenesis (Lond), 6: 989-94. 1985. Foiles, P. G.; Akerkar, S. Α.; Chung, F. L. Application of an immunoassay for cyclic acrolein deoxyguanosine adducts to assess their formation in DNA of Salmonella typhimurium under conditions of mutation induction by acrolein. Carcinogenesis (London), 10: 87-90. 1989. Foiles, P. G.; Chung, F. L.; Hecht, S. S. Development of a monoclonal antibody -based immunoassay for cyclic DNA adducts resulting from exposure to crotonaldehyde. Cancer Res., 47: 360-3. 1987. Fram, R. J.; Woda, Β. Α.; Wilson, J. M.; Robichaud, N. Characterization of acquired resistance to cis diamminedichloroplatinum-Π in human colon carcinoma cells. Cancer Res., 50: 72-7. 1990. Groopman, J.D. DNA adducts of nitropyrene detected by specific antibodies. Res. Report/ Helath Effects Inst., 7: 1-17. 1987. Hsieh, L. L.; Jeffrey, A. M.; Santella, R. M. Monoclonal antibodies to 1 aminopyrene-DNA. Carcinogenesis (Lond), 6: 1289-94. 1985. Hsu, L; Poirier, M.C.;Yuspa, S. H.; Grunberger, D.; Weinstein, I. B.; Yolken, R. H.; Harris, C. C. Measurement of benzo(a)pyrene-DNA adducts by enzyme immunoassays and radioimmunoassay. Cancer Res., 41: 1091-5. 1981. Kriek, E.; Welling, M.; Van der Laken, C. J. Quantitation of carcinogen-DNA adducts by a standardized high-sensitive enzyme immunoassay. IARC Sci. Publ., 59:297-305. 1984. Leadon, S. A. Production of thymine glycols in DNA by radiation and chemical carcinogens as detected by a monoclonal antibody. Brit. J. Cancer Res. Suppl., 8:113-7. 1987. Lee, Β. M.; Santella, R. M. Quantitation of protein adducts as a marker of genotoxic exposure immunologic detection of benzo-a-pyrene-globin adducts in mice. Carcinogenesis (Lond), 9: 1773-8. 1988.


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Lung, C. C.; Fleisher, J. H.; Meinke, G.; Pinnas, J. L. Immunochemical properties of malondialdehyde-protein adducts. J. Immunol. Meth., 128: 127-32. 1990. Marini, S.; Citro, G.; Di Cesare, S.; Zito, R.; Giardina, B. Production and characterization of monoclonal antibodies against DNA single ring diamines adducts. Hybridoma, 7: 193-204. 1988.


Morita, T.; Ikeda, S.; Minoura, Y.; Kojima, M.; Tada, M. Polyclonal antibodies to DNA modified with 4 nitroquinoline 1-oxide application for the detection of 4 nitroquinoline 1-oxide-DNA adducts in-vivo. Jpn. J. Cancer Res. (GANN), 79: 195-203. 1988. Nakayama, J.; Yuspa, S. H.; Poirier, M. C. Benzo-a-pyrene-DNA adduct formation and removal in mouse epidermis in-vivo and in-vitro relationships of DNA binding to initiation of skin carcinogenesis. Cancer Res., 44: 4087-95. 1984. Nehls, P.; Rajewsky, M. F. Monoclonal antibody-based immunoassay for the determination of cellular enzymatic activity for repair ofspecificcarcinogen-DNA adducts O-6 alkylguanine. Carcinogenesis (Lond), 11: 81-8. 1990. Nehls, P.; Rajewsky, M. F. Monoclonal antibody-based immunoassay for the determination of cellular enzymic activity for repair of specific carcinogen-DNA adducts (O-6-alkylguanine). Carcinogenesis (Lond), 11: 81-7. 1990. Nemoto, N.; Nakatsuru, Y.; Nakagawa, K.; Tazawa, Α.; Ishikawa, T. Immunohistochemical detection of anti-racemic-trans-7 8 dihydroxy-9 10-epoxy-7 8 9 l0-tetrahydrobenzo-a-pyrene-bound adduct in nuclei of cultured hela cells and mouse lung tissue. J. Cancer Res. Clin. Oncol., 114: 225-30. 1988. Newman, M. J.; Light, Β. Α.; Weston, Α.; Tollurud, D.; Clark, J. L.; Mann, D. L.; Blackmon, J. P.; Harris, C. C. Detection and characterization of human serum antibodies to polycyclic aromatic hydrocarbon diol-epoxide DNA adducts . J. Clin. Invest., 82: 145-53. 1988. Paules, R. S.; Poirier, M. C.; Mass, M. J.; Yuspa, S. H.; Kaufman, D. G. Quantitation by electron microscopy of the binding of highly specific antibodies to benzo-a-pyrene DNA adducts. Carcinogenesis (Lond), 6: 193-8. 1985. Perera, F. P.; Hemminki, K.; Young, T. L.; Brenner, D.; Kelly, G.; Santella, R. M. Detection of polycyclic aromatic hydrocarbon-DN A adducts in white blood cells of foundry workers. Cancer Res., 48: 2288-91. 1988. Perera, F.; Mayer, J.; Jaretzki, Α.; Hearne, S.; Brenner, D.; Young, T. L.; Fischman, Η. K.; Grimes, M.; Grantham, S.; Et, A. Axomparison of DNA adducts and sister chromatid exchange in lung cancer cases and controls. Cancer Res., 49: 4446-51. 1989. Perera, F. P.; Poirier, M.C.;Yuspa, S. H.; Nakaymama, J.; Jaretzki, Α.; Curnen, M. M.; Knowles, D. M.; Weinstein, I. B. A pilot project in molecular cancer epidemiology determination of benzo-a-pyrene DNA adducts in animal and human tissues by immunoassays. Carcinogenesis (Lond), 3: 1405-10. 1982.


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DNA-Adduction and Protein Adduct Immunoassays357

Perera, F.; Santella, R.; Poirier, M. Biomonitoring of workers exposed to carcinogens: Immunoassays to benzo-a-pyrene-DNA adducts as a prototype. J. Occup. Med,. 28: 1117-23. 1986. Perera, F. P.; Santella, R. M.; Brenner, D.; Poirier, M. C.; Munshi, Α. Α.; Fischman, Η. Κ.; Van Ryzin, J. DNA adducts protein adducts and sister chromatid exchange in cigarette smokers and nonsmokers. J. Natl. Cancer Inst, 79: 449-56. 1987.


Perera, F. P.; Poirier, M. C.; Yuspa, S. H.; Nakayama, J.; Jaretzki, Α.; Curnen, M. M.; Knowles, D. M.; Weinstein, I. B. A pilot project in molecular cancer epidemiology: determination of benzo-a-pyrene-DNA adducts in animal and human tissues by immunoassays. Carcinogenesis (Lond), 3: 1405-10. 1982. Poirier, M. C. Antibodies to carcinogen DNA adducts . J. Natl. Cancer Inst., 67: 515-20. 1981. Poirier, M. C.; Lippard, S. J.; Zwelling, L. Α.; Ushay, Η. M.; Kerrigan, D.; Thill, C. C.; Santella, R. M.; Grunberger, D.; Yuspa, S. H. Antibodies elicited against cis-diammine-dichloro-platinum-II-modified-DNA are specific for cis-diammine -dichloro-platinum-II-DNA adducts formed in-vivo and in-vitro. Proc. Natl. Acad. Sci. U S A, 79: 6443-7. 1982. Poirier, M. C.; Stanley, J. R.; Beckwith, J. B.; Weinstein, I. B.; Yuspa, S. H. Indirect immuno fluorescent localization of benzo-a-pyrene adducted to nucleic-acids in cultured mouse keratinocyte nuclei. Carcinogenesis (Lond), 3: 345-8. 1982. Poirier, M. C. Antibodies to carcinogen-DNA adducts. J. Natl. Cancer Inst., 67: 515-9. 1981. Poirier, M. C.; Liou, S. H.; Reed, E.; Strickland, P. T.; Tockman, M. S. Determination of carcinogen-DNA adducts by immunoassay. J. UOEH, 11: 35367. 1989. Poirier, M.C.;Nakayama, J.; Perera, F. P.; Weinstein, I. B.; Yuspa, S. H. Identification of carcinogen-DNA adducts by immunoassays. Environ. Sci. Res., 29:427-40. 1983. Poirier, M. C.; Stanley, J. R.; Beckwith, J. B.; Weinstein, I. B.; Yuspa, S. H. Indirect immunofluorescent localization of benzo-a-pyrene adducted to nucleic acids in cultured mouse keratinocyte nuclei. Carcinogenesis (Lond), 3: 345-8. 1982. Poirier, M. C.; True, Β.; Laishes, Β. A. Determination of 2-acetylaminofluorene adducts by immunoassay. Environ. Health Perspect., 49: 93-9. 1983. Potter, D. W.; Pumford, N. R.; Hinson, J. Α.; Benson, R. W.; Roberts, D. W. Epitope characterization of acetaminophen bound to protein and nonprotein sulfhydryl groups by an ELISA. J. Pharmacol. Exp. Ther., 248: 182-9. 1989. Pumford, N. R.; Hinson, J. Α.; Potter, D. W.; Rowland, K. L.; Benson, R. W.; Roberts , D. W. Immunochemical quantitation of 3-cystein-S-yl-acetaminophen adducts in serum and liver proteins of acetaminophen-treated mice. J. Pharmacol. Exp. Ther., 248: 190-6. 1989.


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Rajagopalan, R.; Melamede, R. J.; Laspia, M. F.; Erlanger, B. F.; Wallace, S. S. Properties of antibodies to thymine glycol, a product of the radiolysis of DNA. Rad. Res., 97:499-510. 1984. Reed, E.; Litterst, C. L.; Thill, C. C.; Yuspa, S. H.; Poirier, M. C. Cis diamminedichloroplatinum-II-DNA adduct formation in renal gonadal and tumor tissues of male and female rats. Cancer Res., 47: 718-22. 1987.


Reed, E.; Ozols, R. F.; Tarone, R.; Yuspa, S. H.; Poirier, M. C. Platinum-DNA adducts in leukocyte DNA correlate with disease response in ovarian cancer patients receiving platinum-based chemotherapy. Proc. Natl. Acad. Sci. U S A, 84: 5024-8. 1987. Reed, E.; Yuspa, S. H.; Zwelling, L. Α.; Ozols, R. F.; Poirier, M. C. Quantitation of cis diamminedichloroplatinum-Π cisplatin DNA-intrastrand adducts in testicular and ovarian cancer patients receiving cisplatin chemotherapy. J. Clin. Invest., 77: 545-50. 1986. Rio, P.; Bazgar, S.; Leng, M. Detection of N-hydroxy-2-acetylamino fluorene DNA adducts in rat liver measured by radioimmunoassay. Carcinogenesis (Lond), 3:225-8. 1982. Roberts, D. W.; Benson, R. W.; Groopman, J. D.; Flammang, T. J.; Nagle, W. Α.; Moss, A. J.; Kadlubar, F. F. Immunochemical quantification of DNA adducts derived from the human bladder carcinogen 4-aminobiphenyl. Cancer Res., 48: 6636-42. 1988. Roberts, D. W.; Benson, R. W.; Flammang, T. J.; Kudlubar, F. F. Development of an avidin-biotin amplified enzyme-linked immunoassay for detection of DNA adducts of the human bladder carcinogen 4-aminobiphenyl. Basic Life Sci., 38: 479-88. 1986. Roberts, D. W.; Pumford, N. R.; Potter, D. W.; Benson, R. W.; Hinson, J. A. A sensitive immunochemical assay for acetaminophen-protein adducts. J. Pharmacol. Exp. Ther., 241:527-33. 1987. Saffhill, R.; Boyle, J. M. Detection of carcinogen DNA adducts by radioimmunoassay. Br. J. Cancer, 44: 275. 1981. Santella, R. M. Monitoring human exposure to carcinogens by DNA adduct measurement. Cell Biol. Toxicol., 4: 511-6. 1988. Santella, R. M.; Lin, C. D.; Cleveland, W. L.; Weinstein, I. B. Monoclonal antibodies to DNA modified by a benzo-a-pyrene diol epoxide. Carcinogenesis (Lond), 5: 373-8. 1984. Santella, R. M.; Lin, C. D.; Dharmaraja, N. Monoclonal antibodies to a benzo-a -pyrene diol epoxide modified protein. Carcinogenesis (Lond), 7: 441-4. 1986. Santella, R. M.; Weston, Α.; Perera, F. P.; Tivers, G. T.; Harris, C. C.; Young, T. L.; Nguyen, D.; Lee, B. M.; Poirier, M. C. Interlaboratory comparison of antisera and immunoassays for benzo-a-pyrene-diol-epoxide-I-modified DNA. Carcinogenesis (Lond), 9: 1265-70. 1988.


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DNA-Adduction and Protein Adduct Immunoassays359

Shamsuddin, A. K. M.; Gan, R. Immunocytochemical localization of benzo-a -pyrene-DNA adducts in human tissues. Hum. Pathol., 19: 309-15. 1988. Shamsuddin, A. K. M.; Sinopoli, N. T.; Hemminki, K.; Boesch, R. R.; Harris, C. C. Detection of benzo-a-pyrene DNA adducts in human white blood cells. Cancer Res., 45: 66-8. 1985. Shuker, D. E. G. Detection of adducts arising from human exposure to N-nitroso compounds. Cancer Surv., 8: 475-88. 1989.


Stein, A. M.; Gratzner, H. G.; Stein, J. H.; Mccabe, M. M. High avidity monoclonal antibody to imidazolering-opened7 methylguanine. Carcinogenesis (Lond), 10: 927-32. 1989. Sundquist, W. L; Lippard, S. J.; Stollar, B. D. Monoclonal antibodies to DNA modified with cis or trans diamminedichloroplatinum-II. Proc. Natl. Acad. Sci. U S A, 84:8225-9. 1987. Tada, M.; Aoki, H.; Kojima, M.; Morita, T.; Shirai, T.; Yamada, H.; Ito, N. Preparation and characterization of antibodies against 3,2-dimethyl-4 -aminobiphenyl-modified DNA. Carcinogenesis(Lond), 10: 1397-402. 1989. Talbot, B.; Desnoyers, S.; Castonguay, A. Immunoassays for proteins alkylated by nicotine-derived N-nitrosamines. Arch. Toxicol., 64: 360-4. 1990. Tierney, B.; Benson, Α.; Garner, R. C. Immunoaffinity chromatography of carcinogen DNA adducts with polyclonal antibodies directed against benzo-a -pyrene-diol-epoxide DNA. J. Natl. Cancer Inst., 77: 261-8. 1986. Tilby, M. J.; Lawley, P. D.; Farmer, P. B. Alkylation of DNA by melphalan in relation to immunoassay of melphalan DNA adducts characterization of mono -alkylated and cross-linked products from reaction of melphalan with deoxy-GMP and GMP. Chem-Biol. Interact, 73: 183-94. 1990. Tromberg, B. J.; Sepaniak, M. J.; Alarie, J. P.; Vo-Dinh, T.; Santella, R. M. Development of antibody-based fiber-optic sensors for detection of a benzo-a-pyrene metabolite. Anal. Chem., 60: 1901-8. 1988. Van Der Laken, C. J.; Hagenaars, A. M.; Hermsen, G.; Kriek, E.; Kuipers, A. J.; Nagel, J.; Scherer, E.; Welling, M. Measurement of O-6-ethyldeoxyguanosine and N-deoxyguanosin-8-yl-N-acetyl-2-aminofluorene in DNA by high sensitive enzyme immunoassays. Carcinogenesis (Lond), 3: 569-72. 1982. Van Schooten, F. J.; Kreik, E.; Hillebrand, M. J. X.; Van Leeuwen, F. E. Reactivity of antibodies to DNA modified by benzo-a-pyrene is dependent on the level of modification Iimplications for quantitation of benzo-a-pyrene-DNA adducts in-vivo. Eur. J. Cancer Clin. Oncol., 23: 1809. 1987. Van Schooten, F. J.; Kriek, E.; Steenwinkel M-J, S. T.; Noteborn, H. P. J.; Hillebrand, M. J. X.; Van Leeuwen, F. E. The binding efficiency of polyclonal and monoclonal antibodies to DNA modified with benzo-a-pyrenediol epoxide is dependent on the level of modification implications for quantitation of benzo-a pyrene-DNA adducts in-vivo. Carcinogenesis (Lond), 8: 1263-70. 1987.


360


Wallin, H.; Jeffre, A. M.; Santella, R. M. Investigation of benzo-a-pyrene-globin adducts. Cancer Lett., 35: 139-46. 1987. Wani, Α. Α.; D'ambrosio, S. M. Immunological quantitation of 0-4 ethylthymidine in alkylated DNA repair of minor miscoding base in human cells. Carcinogenesis (Lond), 8: 1137-44. 1987. Wani, Α. Α.; Sullivan, J. K.; Lebowitz, J. Immunoassays for carbodiimide modified DNA-detection of unpairing transitions in supercoiled cole 1 DNA. Nucleic Acids Res., 17: 9957-78. 1989.


Weston, Α.; Newman, M.; Vahakangas, K.; Rowe, M.; Trivers, G. E.; Mann, D. L.; Harris, C. C. Measurement of carcinogen-macromolecular adducts and serum antibodies recognizing DNA adducts in biological specimens from people exposed to chemical carcinogens. Environ. Sci. Res., 36: 91-101. 1987. Weston, Α.; Newman, M. J.; Mann, D. L.; Brooks, B. R. Molecular mechanics and antibody binding in the structural analysis of polycyclic aromatic hydrocarbon diol-epoxide DNA adducts. Carcinogenesis (Lond), 11: 859-64. 1990. Weston, Α.; Rowe, M.; Poirier, M.; Trivers, G.; Vahakangas, Κ.; Newman, M.; Haugen, Α.; Manchester, D.; Mann, D.; Harris, C. The application of immunoassays and fluorometry to the detection of polycyclic hydrocarbon -macromolecular adducts and anti-adduct antibodies in humans. Int Arch. Occup. Environ. Health, 60: 157-62. 1988. Wild, C. P.; Jiang, Y.; Sabbioni, G.; Chapot, B.; Montesano, R. Evaluation of methods for quantitation of aflatoxin albumin adducts and their application to human exposure assessment. Cancer Res., 50: 245-51. 1990. Wilson, V. L.; Weston, Α.; Manchester, D. K.; Trivers, G. E.; Roberts, D. W.; Kadlubar, F. F.; Wild, C. P.; Montesano, R.; Willey, J. C.; Et, A. Alkyl and aryl carcinogen adducts detected in human peripheral lung. Carcinogenesis (Lond), 10: 2149-54. 1989. Wogan, G.N. Markers of exposure to carcinogens. Environ. Health Perspect, 81: 9-18. 1989. Yang, X. Y.; Delohery, T.; Santella, R. M. Flow cytometric analysis of 8 -methoxypsoralen-DNA photoadducts in human keratinocytes. Cancer Res., 48: 7013-7. 1988. Yang, X. Y.; Deleo, V.; Santella, R. M. Immunological detection and visualization of 8-methoxypsoralen-DNA photoadducts. Cancer Res., 47: 2451-5. 1987. Yang, X. Y.; Gasparro, F. P.; Deleo, V. Α.; Santella, R. M. 8-methoxypsoralen -DNA adducts in patients treated with 8-methoxypsoralen and UV-A light. J. Invest. Dermatol., 92: 59-63. 1989. Young, T. L.; Santella, R. M. Development of techniques to monitor for exposure to vinyl chloride monoclonal antibodies to ethenoadenosine and ethenocytidine. Carcinogenesis (Lond), 9: 589-92. 1988.


APPENDIX 3 DNA-ADDUCTION AND PROTEIN-ADDUCT

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