DNA adducts from chemotherapeutic agents

P.D. Lawley1, D.H. Phillips1
1Haddow Laboratories, Institute of Cancer Research, Cotswold Road, Sutton, Surrey SM2 5NG, UK

Tài liệu tham khảo

Adair, 1931, Experimental and clinical studies on the treatment of cancer by dichloroethyl sulfide (mustard gas), Ann. Surgery, 93, 190, 10.1097/00000658-193101000-00026 Armstrong, 1994, Relation between platinum-DNA adducts and complete remission in adult acute nonlymphocytic leukemia, Leukemia Res., 18, 659, 10.1016/0145-2126(94)90064-7 Arnold, 1958, Synthese und Abbau cytostatisch wirksamer cyclischer N-Phosphamidester des Bis(β-chloroäthyl)amins, Angew. Chem., 70, 539, 10.1002/ange.19580701705 Avery, 1944, Studies on the chemical nature of the substance inducing transformation of pneumococcal types. Induction of transformation by a desoxyribonucleic acid fraction isolated from pneumococcus Type III, J. Exp Med., 79, 137, 10.1084/jem.79.2.137 Bagshawe, 1994, Antibody-directed enzyme pro-drug therapy, Clin. Pharmacother., 27, 368, 10.2165/00003088-199427050-00004 Ball, 1970, DNA repair after mustard gas alkylation by sensitive and resistant Yoshida sarcoma cells in vitro, Chem.-Biol. Interactions, 2, 321, 10.1016/0009-2797(70)90054-2 Ball, 1971, Estimation of interstrand DNA cross-linking resulting from mustard gas alkylation of HeLa cells, Chem.-Biol. Interactions, 4, 797 Bank, 1989, Chlorambucil pharmacokinetics and DNA binding in chronic lymphocytic leukemia lymphocytes, Cancer Res., 49, 554 Bedford, 1988, Differential repair of platinum-DNA adducts in human bladder and testicular tumor continuous cell lines, Cancer Res., 48, 3019 Berends, 1961, On the dimerisation in nucleic acids as a result of ultraviolet irradiation, J. Chem. Phys., 58, 1034 Bergel, 1954, Cyto-active amino-acid and peptide derivatives. Part I. Substituted phenylalanines, J. Chem. Soc., 2409, 10.1039/jr9540002409 Bhat, 1994, Regulation of the formation of the major diethylstilbestrol-DNA adduct and some evidence of its structure, Carcinogenesis, 15, 2137, 10.1093/carcin/15.10.2137 Biedler, 1992, Genetic aspects of multidrug resistance, Cancer, 70, 1799, 10.1002/1097-0142(19920915)70:4+<1799::AID-CNCR2820701623>3.0.CO;2-B Blommaert, 1993, Drug-induced DNA modification in buccal cells of cancer patients receiving carboplatin and cisplatin combination chemotherapy, as determined by an immunocytochemical method: interindividual variation and correlation with disease response, Cancer Res., 53, 5669 Bohr, 1994, Gene-specific damage and repair of DNA adducts and cross-links, 361 Borowy-Borowski, 1990, Recognition between mitomycin C and specific DNA sequences for cross-link formation, Biochemistry, 29, 2999, 10.1021/bi00464a016 Boyce, 1964, Release of ultraviolet light-induced thymine dimers from DNA in E. coli K-12, 51, 293 Brock, 1963, On the activation of cyclophosphamide in vivo and in vitro, Arzneimittel-Forschung, 29, 659 Brookes, 1965, Studies on the mode of action of ibenzmethyzin, 9 Brookes, 1960, The reaction of mustar gas with nucleic acids in vitro and in vivo, Biochem. J., 77, 478, 10.1042/bj0770478 Brookes, 1961, The reaction of mono- and di-functional alkylating agents with nucleic acids, Biochem. J., 80, 496, 10.1042/bj0800496 Brookes, 1964, Evidence for the binding of polynuclear aromatic hydrocarbons to the nucleic acids of mouse skin: relation between carcinogenic power of hydrocarbons and their binding to DNA, Nature (Lond.), 202, 781, 10.1038/202781a0 Brookes, 1965, In vivo reactions of isotopically labelled alkylating agent, 403 Calvert, 1982, Early clinical studies with cis-diammine-1,1-cyclobutane dicarboxylate platinum II, Cancer Chemother. Pharmacol., 9, 140, 10.1007/BF00257742 Cole, 1973, Repair of DNA containing interstrand cross-links in Escherichia coli: sequential excision and recombination, 70, 1064 Crathorn, 1966, Mechanism of the cytotoxic action of alkylating agents in mammalian cells and evidence for the removal of alkylated groups from deoxyribonucleic acid, Nature (Lond.), 211, 150, 10.1038/211150a0 den Engelse, 1990, Immunocytochemical analysis of in vivo DNA modification, Mutation Res., 233, 265, 10.1016/0027-5107(90)90169-5 Dabholkar, 1992, Cisplatin-DNA damage and repair in peripheral blood leukocytes in vivo and in vitro, Environ. Health Perspect., 98, 53, 10.1289/ehp.929853 DeVita, 1965, Clinical trials with 1,3-bis(2-chloroethyl)-1-nitrosourea, NSC-409962, Cancer Res., 25, 1876 Dipple, 1971, Reaction of 7-bromomethylbenz[a]anthracene with nucleic acids, nucleotides and nucleosides, Biochemistry, 10, 4323, 10.1021/bi00799a026 Eastman, 1983, Characterization of the adducts produced in DNA by cis-diamminedichloroplatinum(II) and cis-dichloro(ethylenediamine)platinum(II), Biochemistry, 22, 3927, 10.1021/bi00285a031 Emanuel, 1974, Experimental and clinical studies of the antitumor activity of 1-methyl-1-nitrosourea (NSC-23909), Cancer Chemother. Reports, 58, 135 Everett, 1953, Aryl-2-halogenoalkylamines. Part XII. Some carboxylic derivatives of N,N-di-2-chloroethylaniline, J. Chem. Soc., 2386, 10.1039/jr9530002386 Felker, 1993, Treatment of subcutaneous and intracranial brain tumor xenografts with O6-benzylguanine and 1,3-bis(2-chloroethyl)-1-nitrosourea, Cancer Chemother. Pharmacol., 32, 471, 10.1007/BF00685892 Fichtinger-Schepman, 1982, Detection and quantification of adducts formed upon interaction of diamminedichloroplatinum(II) with DNA, by anion-exchange chromatography after enzymatic degradation, Nucleic Acids Res., 10, 5345, 10.1093/nar/10.17.5345 Fichtinger-Schepman, 1986, Interactions of the antitumour drug cisplatin with DNA in vitro and in vivo, 83 Fichtinger-Schepman, 1987, Cis-diamminedichloroplatinum(II)-induced DNA adducts in peripheral leukocytes from seven cancer patients. Quantitative immunochemical detection of the adduct induction and removal after a single dose of cis-diamminedichloroplatnum(II), Cancer Res., 47, 3000 Fichtinger-Schepman, 1990, Kinetics of the formation and removal of cisp;atin-DNA adducts in blood cells and tumor tissue of cancer patients receiving chemotherapy: comparison with in vitro adduct formation, Cancer Res., 50, 7887 Fidder, 1994, Synthesis, characterization, and quantitation of the major adducts formed between sulfur mustard and DNA of calf thymus and human blood, Chem. Res. Toxicol., 7, 199, 10.1021/tx00038a013 Fraval, 1978, Increased sensitivity of u.v.-repair-deficient human cells to DNA-bound platinum products which unlike thymine dimers are not recognized by an endonuclease extracted from micrococcus luteus, Mutation Res., 51, 121, 10.1016/0027-5107(78)90014-3 Geiduschek, 1965, Reversible DNA, 47, 950 Geleziunas, 1991, Increased DNA synthesis and repair-enzyme expression in lymphocytes from patients with chronic lymphocytic leukemia resistant to nitrogen mustards, J. Natl. Cancer Inst., 83, 557, 10.1093/jnci/83.8.557 Gill, 1991, Dose-escalation study of carboplatin (day 1) and cisplatin (day 3): tolerance and relation to leukocyte and buccal cell platinum adducts, Ann. Oncol., 2, 115, 10.1093/oxfordjournals.annonc.a057872 Gilman, 1946, The biological actions and therapeutic applications of the β-chloroethyl amines and sulfides, Science, 103, 409, 10.1126/science.103.2675.409 Goldacre, 1949, Mode of production of chromosome abnormalities by nitrogen mustards: possible role of cross-linking, Nature (Lond.), 163, 667, 10.1038/163667a0 Goldenberg, 1977, Evidence for carrier-mediate transport of melphalan by L5178Y lymphoblasts in vitro, Cancer Res., 37, 755 Gupta-Burt, 1993, Relationship between patient response in ovarian and breast cacer and platinum drug-DNA adduct formation, Cancer Epidemiol., Biomarkers Prevent., 2, 229 Han, 1992, Induction of covalent DNA adducts in rodents by tamoxifen, Cancer Res., 52, 1300 Hansson, 1987, Formation and removal of DNA cross-links induced by melphalan and nitrogen mustard in relation to drug-induced cytotoxicity in human melanoma cells, Cancer Res., 47, 2631 Haque, 1994, Optimization of 32P-postlabelling assays for the quantitation of O6-methyl-and N7-methyldeoxyguanosine-3″-monophosphates in human DNA, Carcinogenesis, 15, 2485, 10.1093/carcin/15.11.2485 Hashimoto, 1985, Chemical modification of DNA with muta-carcinogens. III. Reductive alkylation of DNA with mitomycin C, Environ. Health Perspect., 62, 219, 10.1289/ehp.8562219 Hemminki, 1985, Binding of metabolites of cyclophosphamide to DNA in a rat liver microsomal system and in vivo in mice, Cancer Res., 45, 4237 Hemminki, 1987, DNA-binding products of nornitrogen mustard, a metabolite of cyclophosphamide, Chem.-Biol. Interactions, 61, 75, 10.1016/0009-2797(87)90020-2 Hemminki, 1994, DNA adducts of nitrogen mustards and ethylene imines, 313 Hemminki, 1990, 32P-post-labelling of 7-methyl-dGMP, ring-opened 7-methyl-dGMP and platinated dGpG, Chem.-Biol. Interactions, 74, 45, 10.1016/0009-2797(90)90057-T Henderson, 1993, Platinum chemotherapy during pregnancy for serous cystadenocarcinoma of the ovary, Gynecol. Oncol., 49, 92, 10.1006/gyno.1993.1092 Herron, 1980, Methylated purines in human liver after probable dimethylnitosamine, Cancer Res., 40, 3116 Hopkins, 1991, Sequence preferences of DNA interstrand cross-linking agents: importance of minimal DNA structural reorganization in the cross-linking reactions of mechlorethamine, cisplatin, and mitomycin C, Tetrahedron, 47, 2475, 10.1016/S0040-4020(01)81782-8 Huang, 1994, Substrate spectrum of human exinuclease repair of abasic sites, methylated bases, mismatches, and bulky adducts, 91, 12213 Iyer, 1963, A molecular mechanism of mitomycin action: linking of complementary DNA strands, 50, 355 Iyer, 1964, Mitomycins and porfiromycin: chemical mechanisms of activation and cross-linking of DNA, Science, 145, 55, 10.1126/science.145.3627.55 Jeggo, 1979, Isolation and characterization of E. coli K12 mutants unable to induce the adaptive response to simple alkylating agents, J. Bacteriol., 139, 783, 10.1128/JB.139.3.783-791.1979 Johnson, 1982, Preliminary characterization of the adducts formed between the antitumor compound cis-Pt(NH3)2Cl2 and DNA in vitro, Biochem. Biophys. Res. Commun., 104, 1394, 10.1016/0006-291X(82)91404-8 Karran, 1994, DNA damage tolerance, mismatch repair and genome instability, BioEssays, 16, 833, 10.1002/bies.950161110 Karran, 1980, Escherichia coli mutants deficient in 3-methyladenine-DNA glycosylase, J. Mol. Biol., 140, 101, 10.1016/0022-2836(80)90358-7 Kataoka, 1994, Resistance to antitumor agent-induced apoptosis in a mutant of human myeloid leukemia U937 cells, Exp. Cell Res., 215, 199, 10.1006/excr.1994.1332 Kato, 1988, Modification of DNA by mitomycin C in cancer patients detected by 32P-postlabeling analysis, Mutation Res., 20, 85, 10.1016/0027-5107(88)90167-4 Knox, 1986, Mechanism of cytotoxicity of anticancer platinum drugs: evidence that cis-diamminedichloroplatinum(II) and cis-diammine(1,1-cyclobutanedicarboxylato)platinum(II) differ only in the kinetics of their interaction with DNA, Cancer Res., 46, 1972 Knox, 1991, The Walker 256 carcinoma: a cell type inherently sensitive only to those difunctional agents that can form DNA interstrand crosslinks, Mutation Res., 255, 227, 10.1016/0921-8777(91)90026-L Koc, 1994, Detection of platinum-DNA adducts in cord blood lymphocytes following in utero platinum exposure, Eur. J. Cancer, 30A, 716 Kohn, 1967, Alkylated DNA: buoyant density changes and modes of decomposition, Biochim. Biophys. Acta, 145, 720, 10.1016/0005-2787(67)90131-1 Kohn, 1965, Cross-linking and repair of DNA in sensitive and resistant strains of E. coli treated with nitrogen mustard, 53, 1154 Kohn, 1966, Interstrand cross-linking of DNA by nitrogen mustard, J. Mol. Biol., 19, 266, 10.1016/S0022-2836(66)80004-9 Kolaric, 1977, Combination chemotherapy with 1-methyl-1-nitrosourea (MNU) and cyclophosphamide in solid tumours, Z. Krebsforschung, 89, 311, 10.1007/BF00283785 Krumbhaar, 1919, The blood and bone marrow in yellow cross gas (mustard gas) poisoning: changes produced in the bone marrow of fatal cases, J. Med. Res., 40, 497 Kyrtopoulos, 1993, Accumulation of O6-methylguanine in human DNA after therapeutic exposure to methylating agents and its relationship with biological effects, Environ. Health Perspect., 99, 143 Lawley, 1984, Carcinogenesis by alkylating agents, Vol. 1, 325 Lawley, 1990, N-Nitroso compounds, 94/1, 409 Lawley, 1965, Molecular mechanism of cytotoxic action of difunctional alkylating agents and of resistance to this action, Nature (Lond.), 206, 480, 10.1038/206480a0 Lawley, 1968, Cytotoxicity of alkylating agents towards sensitive and resistant strains of Escherichia coli in relation to extent and mode of alkylation of cellular macromolecules and repair of alkylation lesions in DNA, Biochem. J., 109, 433, 10.1042/bj1090433 Lawley, 1970, Specific excision of methylation products from DNA of Escherichia coli treated with N-methyl-N″-nitro-N-nitrosoguanidine, Chem.-Biol. Interactions, 2, 154, 10.1016/0009-2797(70)90047-5 Lawley, 1972, Reaction of alkylating mutagens and carcinogens with nucleic acids: detection and estimation of a small extent of methylation at O-6 of guanine in DNA by methyl methanesulfonate in vitro, Chem.-Biol. Interactions, 5, 286, 10.1016/0009-2797(72)90033-6 Lawley, 1973, Methylation of DNA by 3H-14C-methyl-labelled N-methyl-N-nitrosourea: evidence for transfer of the intact methyl group, Chem.-Biol. Interactions, 7, 115, 10.1016/0009-2797(73)90020-3 Lawley, 1970, Methylation of DNA in cultured mammalian cells by N-methyl-N″-nitro-N-nitrosoguanidine: the influence of cellular thiol concentrations on the extent of methylation and the 6-oxygen atom of guanine as a site of methylation, Biochem. J., 116, 693, 10.1042/bj1160693 Lawley, 1969, Inactivation of bacteriophage T7 by mono- and di-functional sulphur mustards in relation to cross-linking and depurination of bacteriophage DNA, J. Mol. Biol., 39, 181, 10.1016/0022-2836(69)90341-6 Lawley, 1986, Repair of chemical carcinogen-induced damage in DNA of human lymphocytes and lymphoid cell lines. Studies on the kinetics of removal of O6-methylguanine and 3-methyladenine, Chem.-Biol. Interactions, 57, 107, 10.1016/0009-2797(86)90053-0 Los, 1991, Cellular pharmacokinetics of carboplatin and cisplatin in relation to their cytotoxic action, Biochem. Pharmacol., 42, 357, 10.1016/0006-2952(91)90723-I Loveless, 1969, Possible relevance of O6-alkylation of deoxyguanosine to mutagenicity and carcinogenicity of nitrosamines and nitrosamides, Nature (Lond.), 223, 206, 10.1038/223206a0 Ludlum, 1986, Nature and biological significance of DNA modification by the haloethylnitrosoureas, 71 Ludlum, 1986, Formation of O6-ethylthioethylguanine in DNA by reaction with sulfur mustard and its apparent lack of repair by O6-alkylguanine alkyltransferase, Carcinogenesis, 7, 1203, 10.1093/carcin/7.7.1203 Ludlum, 1986, Prevention of 1-(3-deoxycytidyl),2-(1-deoxyguanosinyl)ethane cross-link formation in DNA by rat liver O6-alkylguanine-DNA alkyltransferase, Cancer Res., 46, 3353 Ludlum, 1994, Detection of sulfur mustard-induced DNA modifications, Chem.-Biol. Interactions, 91, 39, 10.1016/0009-2797(94)90005-1 Marcelis, 1983, Binding of platinum compounds to nucleic acids with respect to the anti-tumor activity of cis-diamminedichloroplatinum(II) and derivatives, Rec. Trav. Chim. Pays Bas, 102, 121, 10.1002/recl.19831020301 Marnett, 1994, DNA adducts of α,β-unsaturated aldehydes and dicarbonyl compounds, 151 McDiarmid, 1991, Evidence for acrolein-modified DNA in peripheral blood leukocytes of cancer patients treated with cyclophosphamide, Mutation Res., 248, 93, 10.1016/0027-5107(91)90091-2 McElwain, 1979, Marrow autotransplantation accelerates haematological recovery in patients with malignant melanoma treated with high dose melphalan, Br. J. Cancer, 40, 72, 10.1038/bjc.1979.142 Millar, 1987, Comparison of melphalan toxicity in human lymphocytic cells and Chinese hamster cells in vitro: the relationship between DNA-DNA crosslink formation and clonogenic survival, Carcinogenesis, 8, 1225, 10.1093/carcin/8.9.1225 Millar, 1989, Melphalan transport into human malignant lymphoid cells differs from the murine equivalent in vitro, Br. J. Cancer, 59, 710, 10.1038/bjc.1989.149 Mirkes, 1992, Identifiication of cyclophosphamide-DNA adducts in rat embryos exposed in vitro to 4-hydroperoxycyclophosphamide, Chem. Res. Toxicol., 5, 382, 10.1021/tx00027a010 Mitchell, 1992, Effect of O6-benzylguanine on the sensitivity of human tumor xenografts to 1,3-bis(2-chloroethyl)-1-nitrosourea and on DNA inter-strand cross-link formation, Cancer Res., 52, 1171 Mol, 1993, Quantification of sulfur-mustard-induced cross-links and single-strand breaks in cultured human epidermal keratinocytes, Mutation Res., 294, 235, 10.1016/0921-8777(93)90006-3 Motzer, 1994, Platinum-DNA adducts assayed in leukocytes of patients with germ cell tumors measured by atomic absorbance spectrometry and enzyme-linked immunosorbent assay, Cancer, 73, 2843, 10.1002/1097-0142(19940601)73:11<2843::AID-CNCR2820731130>3.0.CO;2-D Mustonen, 1991, Measurement by 32P-postlabelling of 7-methylguanine levels in white blood cell DNA of healthy individuals and cancer patients treated with dacarbazine and procarbazine. Human data and method development for 7-alkylguanines, Carcinogenesis, 12, 1423, 10.1093/carcin/12.8.1423 Ojwang, 1989, Synthesis of a duplex oligonucleotide containing a nitrogen mustard interstrand DNA-DNA cross-link, Cancer Res., 49, 6529 Olsson, 1980, Repair of alkylated DNA in Escherichia coli, J. Biol. Chem., 255, 10569, 10.1016/S0021-9258(19)70341-X Osborne, 1993, Alkylation of DNA by melphalan with special reference to adenine derivatives and adenine-guanine cross-linking, Chem.-Biol. Interactions, 89, 49, 10.1016/0009-2797(93)03197-3 Osborne, 1995, Alkylation of DNA by the nitrogen mustard bis(2-chloroethyl)methylamine, Chem. Res. Toxicol., 8, 316, 10.1021/tx00044a018 Osborne, 1995, Products from alkylation of DNA in cells by melphalan: human soft tissue sarcoma cell line RD and Escherichia coli WP2, Chem.-Biol. Interactions, 97, 287, 10.1016/0009-2797(95)03623-T Pai, 1992, Therapy of patients with metastatic breast cancer with 5-fluoruracil, leucovorin and carboplatin, Anti-Cancer Drugs, 3, 463, 10.1097/00001813-199210000-00003 Pegg, 1992, Repair of DNA containing O6-alkylguanine, FASEB J., 6, 2302, 10.1096/fasebj.6.6.1544541 Plooy, 1984, Induction and repair of DNA cross-links in Chinese hamster ovary cells treated with various platium coordination compounds in relation to platinum binding to DNA, cytotoxicity, mutagenicity, and antitumor activity, Cancer Res., 44, 2043 Poirier, 1982, Antibodies elicited against cis-diamminedichloroplatinum(II)-DNA adducts formed in vivo and in vitro, 79, 6443 Poirier, 1987, DNA adducts of cisplatin in nucleated peripheral blood cells and tissues of cancer patients, Prog. Exp. Tumor Res., 31, 104, 10.1159/000413907 Poirier, 1988, DNA adducts of cisplatin and carboplatin in tissues of cancer patients, 313 Poirier, 1993, Platinum-DNA interactions in human tissues measured by cisplatin DNA enzyme-linked immunosorbent assay and atomic absorbance spectroscopy, Environ. Health Persepct., 99, 149, 10.1289/ehp.9399149 Preussmann, 1969, Mechanism of carcinogenesis with 1-aryl-3,3-dialkyltriazenes. Enzymatic dealkylation by rat liver microsomal fraction in vitro, Biochem. Pharmacol., 18, 1, 10.1016/0006-2952(69)90002-1 Reddy, 1987, 32P-Analysis of DNA adducts in somatic and reproductive tissues of rats treated with the anticancer antibiotic, mitomycin C, Mutation Res., 179, 75, 10.1016/0027-5107(87)90043-1 Reed, 1991, Alkylating agents and platinum: is clinical resistance simply a tumor cell phenomenon?, Current Opininon in Oncology, 3, 1055, 10.1097/00001622-199112000-00014 Reed, 1986, Quantitation of cisplatin-DNA-intrastrand adducts in testicular and ovarian cancer patients receiving cisplatin chemotherapy, J. Clin. Invest., 77, 545, 10.1172/JCI112335 Reed, 1988, Quantitation of platinum-DNA binding after therapeutic levels of drug exposure — a novel use of graphite furnace spectrometry, Atomic Spectroscopy, 9, 93 Reed, 1990, Characterization of the DNA damage recognized by an antiserum elicited against cis-diamminedichloroplatinum(II)-modified DNA, Carcinogenesis, 11, 2117, 10.1093/carcin/11.12.2117 Reid, 1969, The response of mammalian cells to alkylating agents II. On the mechanism of the removal of sulfur-mustard-induced crosslinks, Biochim. Biophys. Acta, 179, 179, 10.1016/0005-2787(69)90134-8 Rink, 1993, Covalent structure of a nitrogen-mustard-induced DNA interstrand crosslink: an N7-to-N7 linkage of deoxyguanosine residues at the duplex sequence 5″-d(GNC), J. Am. Chem. Soc., 115, 2551, 10.1021/ja00060a001 Roberts, 1982, The frequency of interstrand cross-links in DNA following reaction of cis-diamminedichloroplatinum(II) with cells in culture or DNA in vitro: stability of DNA cross-links and their repair, Chem.-Biol. Interactions, 39, 181, 10.1016/0009-2797(82)90120-X Roberts, 1972, Cross-linking of complementary strands of DNA in mammalian cells by antitumour platinum compounds, Nature (Lond.), 235, 282, 10.1038/235282a0 Roberts, 1979, The mechanism of action of antitumor platinum compounds, Prog. Nucleic Acid Res. Mol. Biol., 22, 71, 10.1016/S0079-6603(08)60799-0 Roberts, 1971, Evidence for the inactivation and repair of the mammalian DNA template after alkylation by mustard gas and half mustard gas, Eur. J. Cancer, 7, 515, 10.1016/0014-2964(71)90056-9 Roberts, 1971, Quantitative aspects of the repair of alkylated DNA in cultured mammalian cells I. The effect on HeLa and Chinese hamster cell survival of alkylation of cellular macromolecules, Chem.-Biol. Interactions, 3, 29, 10.1016/0009-2797(71)90024-X Roberts, 1986, The unique sensitivity of Walker rat tumour cells to difunctional agents is associated with a failure to recover from inhibition of DNA synthesis and increased chromosome damage, Mutation Res., 166, 169, 10.1016/0167-8817(86)90015-5 Robinson, 1985, Verapamil potentiation of melphalan cytotoxicity and cellular uptake in murine fibrosarcoma and bone marrow, Br. J. Cancer., 52, 813, 10.1038/bjc.1985.264 Rosenberg, 1985, Fundamental studies with cisplatin, Cancer, 55, 2303, 10.1002/1097-0142(19850515)55:10<2303::AID-CNCR2820551002>3.0.CO;2-L Rosenberg, 1965, Inhibition of cell division in Escherichia coli by electrolysis products from a platinum electrode, Nature (Lond.), 205, 698, 10.1038/205698a0 Rydberg, 1982, Nonenzymatic methylation of DNA by the intracellular methyl group donor S-adenosyl-l-methionine is a potentially mutagenic reaction, EMBO J., 1, 211, 10.1002/j.1460-2075.1982.tb01149.x Santella, 1988, Detection and quantification of 8-methoxypsoralen-DNA adducts, 333 Selby, 1987, Multiple myeloma treated with high dose intravenous melphalan, Br. J. Haematol., 66, 55, 10.1111/j.1365-2141.1987.tb06890.x Selby, 1988, The development of high dose melphalan and of autologous bone marrow transplantation in the treatment of multiple myeloma: Royal Marsden and St Bartholomew's Hospital studies, Hematol. Oncol., 6, 173, 10.1002/hon.2900060218 Setlow, 1964, The disappearance of thymine dimers from DNA: an error-correcting mechanism, 51, 226 Shealy, 1962, Imidazoles. I. Coupling reactions of 5-diazoimidazole-4-carboxamide, J. Org. Chem., 27, 2150, 10.1021/jo01053a060 Shields, 1990, Combined high-performance liquid chromatography/32P-postlabeling assay of N7-methyldeoxyguanosine, Cancer Res., 50, 6580 Shooter, 1972, The interaction of platinum II compounds with bacteriophages T7 and R17, Chem.-Biol. Intetactions, 5, 289, 10.1016/0009-2797(72)90069-5 Skibba, 1971, Methylation of nucleic acids and urinary excretion of 14C-labeled 7-methylguanine in rats and man after administration of 4(5)-(3,3,-dimethyl-1-triazeno)imidazole 5(4)-carboxamide, Toxicol. Appl. Pharmacol., 18, 707, 10.1016/S0041-008X(71)80026-1 Souliotis, 1991, In vivo formation and repair of O6-methylguanine in human leukocyte DNA after intravenous exposure to dacarbazine, Carcinogenesis, 12, 285, 10.1093/carcin/12.2.285 Souliotis, 1992, Measurement of O6-methylguanine-type adducts in DNA and O6-alkylguanine-DNA-alkyltransferase repair activity in normal and neoplastic human tissues, Comp. Biochem. Physiol., 101B, 269 Stephens, 1986, Emergence of nitrosourea resistant sublines of Lewis lung tumour following MeCCNU treatment in vivo, Br. J. Cancer, 53, 237, 10.1038/bjc.1986.41 Strandberg, 1982, The significance of DNA crosslinking to cis-diammine-dichloroplatinum(II)-induced cytotoxicity in sensitive and resistant lines of murine leukemia L1210 cells, Chem.-Biol. Interactions., 39, 169, 10.1016/0009-2797(82)90119-3 Strauss, 1991, The ‘A rule’ of mutagen specificity: a consequence of DNA polymerase bypass of non-instructional lesions?, BioEssays, 13, 79, 10.1002/bies.950130206 Strauss, 1992, The origin of point mutations in human tumor cells, Cancer Res., 52, 249 Takeshima, 1994, p53 Mutations in lung cancers from Japanese mustard gas workers, Carcinogenesis, 15, 2075, 10.1093/carcin/15.10.2075 Tattersall, 1978, Pharmacokinetics of melphalan following oral or intravenous administration in patients with malignant disease, Eur. J. Cancer, 14, 507, 10.1016/0014-2964(78)90253-0 Teng, 1989, DNA sequence specificity of mitomycin cross-linking, Biochemistry, 28, 3901, 10.1021/bi00435a041 Terheggen, 1991, Formation of interaction products of carboplatin with DNA in vitro and in cancer patients, Br. J. Cancer, 63, 195, 10.1038/bjc.1991.48 Tilby, 1987, Immunological detection of DNA damage caused by melphalan using monoclonal antibodies, Cancer Res., 47, 1542 Tilby, 1990, Alkylation of DNA by melphalan in relation to immunoassay of melphalan-DNA adducts: characterization of monoalkylated and crosslinked products from reaction of melphalan with dGMP and GMP, Chem.-Biol. Interactions, 73, 183, 10.1016/0009-2797(90)90002-5 Tilby, 1993, Application of a sensitive immunoassay to the study of DNA adducts formed in peripheral blood mononuclear cells of patients undergoing high-dose melphalan therapy, Eur. J. Cancer, 29A, 681, 10.1016/S0959-8049(05)80346-6 Tilby, 1995, A monoclonal antibody that recognises alkali-stabilized melphalan-DNA adducts and its application in immunofluorescence microscopy, Carcinogenesis, 16, 1895, 10.1093/carcin/16.8.1895 Tomasz, 1994, DNA adducts of the mitomycins, 349 Tong, 1980, Crosslinking of DNA by busulfan: formation of diguaninyl derivatives, Biochim. Biophys. Acta, 608, 174, 10.1016/0005-2787(80)90145-8 Tong, 1982, Modifications of DNA by different haloethylnitrosoureas, Cancer Res., 42, 4460 van Delft, 1991, The isolation of monoclonal antibodies selected for the detection of imidazole ring-opened N7-ethylguanine in purified DNA and in cells in situ. Cross-reactions with methyl, 2-hydroxyethyl and sulphur mustard adducts, Carcinogenesis, 12, 1041, 10.1093/carcin/12.6.1041 van Delft, 1992, Determination of N7-methylguanine in DNA of white blood cells from cancer patients treated with dacarbazine, Carcinogenesis, 13, 1257, 10.1093/carcin/13.7.1257 van der Schans, 1994, Immunochemical detection of adducts of sulfur mustard to DNA of calf thymus and human white blood cells, Chem. Res. Toxicol., 7, 408, 10.1021/tx00039a019 Venitt, 1968, Interstrand cross-links in DNA of Escherichia coli B/r and Bs−1 and their removal by the resistant strain, Biochem. Biophys. Res. Commun., 31, 355, 10.1016/0006-291X(68)90483-X Venitt, 1993, Carcinogenic and genotoxic effects of antineoplastic agents, 27 Vistica, 1979, Concentrative uptake of melphalan, a cancer chemotherapeutic agent which is transported by the leucine-preferring carrier system, Biochem. Biophys. Res. Commun., 86, 929, 10.1016/0006-291X(79)91801-1 Wakaki, 1958, Isolation of new fractions of antitumor mitomycins, Antibiotics and Chemotherapy, 8, 228 Walton, 1993, Constitutive expression of human bcl-2 modulates nitrogen mustard and camptothecin induced apoptosis, Cancer Res., 53, 1853 Warren, 1980, Removal of alkylation products from DNA of E. coli cells treated with the carcinogens N-ethyl-N-nitrosourea and N-methyl-N-nitrosourea: influence of growth conditions and DNA repair defects, Carcinogenesis, 1, 67, 10.1093/carcin/1.1.67 Watson, 1953, Molecular structure of nucleic acids. A structure for deoxyribose nucleic acids, Nature (Lond.), 171, 737, 10.1038/171737a0 Watson, 1953, Genetical implications of the structure of deoxyribose nucleic acid, Nature (Lond.), 171, 964, 10.1038/171964b0 Weidner, 1989, Determination at single nucleotide resolution of the sequence specificity of DNA interstrand crosslinking agents in DNA fragments, J. Am. Chem. Soc., 111, 9270, 10.1021/ja00208a043 White, 1992, Genotoxic potential of tamoxifen and analogues in female Fischer F344n rats, DBA2 and C57B16 mice and in human MCL-5 cells, Carcinogenesis, 13, 2197, 10.1093/carcin/13.12.2197 Yang, 1987, Immunological detection and visualization of 8-methoxypsoralen-DNA photoadducts, Cancer Res., 47, 2451 Yang, 1989, 8-Methoxypsoralen-DNA adducts in patients treated with 8-methoxypsoralen and ultraviolet A light, J. Invest. Dermatol., 92, 59, 10.1111/1523-1747.ep13071224 Zwelling, 1979, DNA-protein and DNA interstrand crosslinking by cis- and trans-platinum(II) diamminedichloride in L 1210 mouse leukemia cells and relation to cytotoxicity, Cancer Res., 39, 365