Abstract
A few selected medicinal drugs, diamminedichloroplatinum (II) componds, mitomycin C, psoralens, and diethylstilbestrol are briefly reviewed with respect to the formation and biological significance of their DNA adducts. Different types of adducts, e.g., DNA intrastrand crosslinks, DNA interstrand crosslinks, or monoadducts appear to represent the critical DNA lesions of the different drugs, accounting for cytotoxicity and carcinogenicity. Thus, these examples serve to illustrate the complexity of DNA adduct formation and its biological sequelae.
Key words: DNA adducts, Cis-platinum, Mitomycin C, Psoralens, Diethylstilbestrol
References
- Blackburn GM, Thompson MH, King HWS (1976) Binding of diethylstilboestrol to deoxyribonucleic acid by rat liver microsomal fractions in vitro and in mouse foetal cells in culture. Biochem J 158:643–646 [DOI] [PMC free article] [PubMed] [Google Scholar]
- Bredberg A, Lambert B, Soderhall S (1982) Induction and repair of psoralen cross-links in DNA of normal human and xeroderma pigmentosum fibroblasts. Mutat Res 93:221–234 [DOI] [PubMed] [Google Scholar]
- Cleaver JE, Killpack S, Gruenert DC (1985) Formation and repair of psoralen-DNA adducts and pyrimidine dimers in human DNA and chromatin. Environ Health Perspect 62:127–134 [DOI] [PMC free article] [PubMed] [Google Scholar]
- Eastman A (1983) Characterization of the adducts produced in DNA by cis-diamminedichloroplatinum (II) and cis-dichloro(ethylenediamine)platinum(II). Biochemistry 22:3927–3933 [DOI] [PubMed] [Google Scholar]
- Eastman A (1984) Characterization of the interaction of cis-dichloro(ethylendiammine) platinum(II) with the DNA of sensitive and resistent L1210 cells. Proc Am Assoc Cancer Res 25:367 [Google Scholar]
- Epe B, Metzler M (1985) Nature of the macromolecular binding of diethylstibestrol to DNA and protein following oxidation by peroxidase/hydrogen peroxide. Chem Biol Interact 56:351–361 [DOI] [PubMed] [Google Scholar]
- Epe B, Schiffmann D, Metzler M (1986) Possible role of oxygen radicals in cell transformation by diethylstilbestrol and related compounds. Carcinogenesis 7:1329–1334 [DOI] [PubMed] [Google Scholar]
- Hashimoto Y, Shudo K (1985) Chemical modification of DNA with mutacarcinogens. III. Reductive alkylation of DNA with mitomycin C. Environ Health Perspect 62:219–222 [DOI] [PMC free article] [PubMed] [Google Scholar]
- Hashimoto Y, Shudo K, Okamoto T (1982) Structures of modified nucleotides isolated from calf thymus DNA alkylated with reductively activated mitocycin C. Tetrahedron Lett 23:677–680 [Google Scholar]
- Hashimoto Y, Shudo K, Okamoto T (1983) Modification of deoxyribonucleic acid with reductively activated mitomycin C. Structures of modified nucleotides. Chem Pharm Bull 31:861–869 [DOI] [PubMed] [Google Scholar]
- Hemminki K, Ludlum DB (1984) Covalent modification of DNA by antineoplastic agents. J Natl Cancer Inst 73:1021–1028 [PubMed] [Google Scholar]
- IARC Monographs on the evaluation of the carcinogenic risk of chemicals to humans (1979) vol 21: sex hormones(II). International Agency for Research on Cancer, Lyon (France)
- Kanne D, Straub K, Rapoport H, Hearst JE (1982) Psoralen-deoxyriboucleic acid photoreaction. Characterization of the monoaddition products from 8-methoxypsoralen and 4,5′,8-trimethylpsoralen. Biochemistry 21:861–871 [DOI] [PubMed] [Google Scholar]
- Liehr, JG, DaGue BB, Ballatore AM, Henkin J (1983) Diethylstilbestrol (DES) quinone: A reactive intermediate in DES metabolism. Biochem Pharmacol 32:3711–3718 [DOI] [PubMed] [Google Scholar]
- Liehr JG, Randerath K, Randerath E (1985) Target organ-specific covalent DNA damage preceding diethylstilbestrol-induced carcinogenesis. Carcinogenesis 6:1067–1069 [DOI] [PubMed] [Google Scholar]
- Liehr JG, Avitts TA, Randerath E, Randerath K (1986) Estrogen-induced endogenous DNA adduction: possible mechanism of hormonal cancer. Proc Natl Acad Sci 83:5301–5305 [DOI] [PMC free article] [PubMed] [Google Scholar]
- Lown JW (1977) Interactions of selected antitumor antibiotics with nucleic acids. In: van Temelen EE (ed) Bioorganic chemistry, vol 3. Academic Press, New York, pp 95–121 [Google Scholar]
- Lutz WK (1979) In vivo covalent binding of organic chemicals to DNA as a quantitative indicator in the process of chemical carcinogenesis. Mutat Res 65:289–356 [DOI] [PubMed] [Google Scholar]
- Lutz WK, Jaggi W, Schlatter C (1982) Covalent binding of diethylstibestrol to DNA in rat and hamster liver and kidney. Chem Biol Interact 42:251–257 [DOI] [PubMed] [Google Scholar]
- Metzler M (1984) Biochemical toxicology of diethylstilbestrol. In: Hodgson E, Bend JR, Philpot RM (eds) Reviews in biochemical toxicology. Elsevier Science Publishing Company Inc, New York, pp 191–220 [Google Scholar]
- Metzler M, McLachlan JA (1978) Peroxidase-mediated oxidation, a possible pathway for metabolic activation of diethylstilbestrol. Biochem Biophys Res Comm 85:874–884 [DOI] [PubMed] [Google Scholar]
- Pathak MA, Joshi PC (1984) Production of active oxygen species (1O2 and O2−) by psoralens and ultraviolet radiation (320–400 nm). Biochim Biophys Acta 798:115–126 [DOI] [PubMed] [Google Scholar]
- Peckler S, Graves B, Kanne D, Rapoport H, Hearst JE, Kim SH (1982) Structure of a psoralen-thymine monoadduct formed in photoreaction with DNA. J Mol Biol 162:157–172 [DOI] [PubMed] [Google Scholar]
- Pinto AL, Lippard SJ (1985) Binding of the antitumor drug cis-diaminedichloro-platinum(II) to DNA. Biochim Biophys Acta 780:167–180 [DOI] [PubMed] [Google Scholar]
- Plooy ACM, van Diik M, Lohman PHM (1984) Induction and repair of DNA cross-links in Chinese hamster ovary cells treated with various platinum coordination compounds in relation to platinum binding to DNA, cytotoxicity, mutagenicity, and antitumor activity. Cancer Res 44:2043–2051 [PubMed] [Google Scholar]
- Poirier MC, Reed E, Zwelling LA, Ozols RF, Litterst CL, Yuspa SH (1985) Polyclonal antibodies to quantitate cis-diamminedichloroplatinum(II)-DNA adducts in cancer patients and animald models. Environ Health Perspect 62:89–94 [DOI] [PMC free article] [PubMed] [Google Scholar]
- Randerath K, Randerath E, Agrawal HP, Gupta RC, Schurdak ME, Reddy MV (1985) Postlabeling methods for carcinogen-DNA adduct analysis. Environ Health Perspect 62:57–65 [DOI] [PMC free article] [PubMed] [Google Scholar]
- Song PS, Tapley KI (1979) Photochemistry and photobiology of psoralens. Photochem Photobiol 29:1177–1197 [DOI] [PubMed] [Google Scholar]
- Straub K, Kanne D, Hearst JE, Rapoport H (1981) Isolation and characterization of pyrimidine-psoralen photoadducts from DNA. J Am Chem Soc 103:2347–2355 [Google Scholar]
- Tomasz M, Lipman R, Snyder JK, Nakanishi K (1983) Full structure of a mitomycin C dinuclotide phosphate adduct. Use of differential FT-IR spectroscopy in microscale structural studies. J Am Chem Soc 105:2059–2063 [Google Scholar]
