Skip to main content

Part of the book series: Topics in Molecular and Structural Biology ((TMSB))

Abstract

The intracellular chemistry and biological processing of platinum anticancer drugs have been subjects of interest following the discovery of antitumour activity for cis-diamminedichloroplatinum(II) (cis-DDP, or cisplatin, Figure 5.1) (Rosenberg et al. 1965). Although several analogous platinum compounds have received FDA approval in the USA or are in clinical trials (see next chapter), a greater understanding of the molecular mechanism of action of platinum anticancer drugs is essential for the rational design of compounds with broader therapeutic specificity and reduced side-effects. At present, cisplatin is used in the USA for the treatment of metastatic testicular tumours, metastatic ovarian tumours, various head and neck tumours, and advanced bladder cancer. It is particularly effective against testicular cancer, which is the most common form of the disease among males in the 21- to 35-year-old age group. The orderly development of cis-DDP-based combination chemotherapy regimens has led to a present cure rate for testis cancer of approximately 95 per cent (Fox and Loehrer, 1991).

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  • Admiraal, G., Alink, M., Altona, C., Dijt, F. J., van Garderen, C. J., de Graaff, R. A. G. and Reedijk, J. (1992). Conformation of Pt(dien)[d(ApGpA)-N7(2)] in the solid state and in aqueous solution, as determined with single-crystal X-ray diffraction and high-resolution NMR spectroscopy in solution. J. Am. Chem. Soc., 114, 930–938

    Article  CAS  Google Scholar 

  • Akaboshi, M., Kawai, K., Maki, H., Akuta, K., Ujeno, Y. and Miyahara, T. (1992). The number of platinum atoms binding to DNA, RNA and protein molecules of HeLa cells treated with cisplatin at its mean lethal concentration. Jap. J. Cancer Res., 83, 522–526

    Article  CAS  Google Scholar 

  • Anderson, K. S. (1979). Platinum(II) complexes generate frameshift mutations in test strains of Salmonella typhimurium. Mutation Res., 67, 209–214

    Article  Google Scholar 

  • Andrews, P. A. and Howell, S. B. (1990). Cellular pharmacology of cisplatin: Perspectives on mechanisms of acquired resistance. Cancer Cells, 2, 35–43

    PubMed  CAS  Google Scholar 

  • Appleton, T. G., Hall, J. R., Neale, D. W. and Thompson, C. S. M. (1990). Reactions of the cis-diamminediaquaplatinum(II) cation with 2-aminomalonic acid and its homologues, aspartic and glutamic acids. Rearrangements of metastable complexes with carboxylate-bound ligands to N,0-chelates and formation of di- and trinuclear complexes. Inorg. Chem., 29, 3985–3990

    Article  CAS  Google Scholar 

  • Appleton, T. G., Hall, J. R. and Ralph, S. F. (1986). 15N and 195Pt N.M.R. study of the effect of chain length, n, on the reactions of amino acids, +NH,(CH2)„CO2 (n = 1, 2, 3), with platinum(II) ammine complexes. Aust. J. Chem., 39, 1347–1362

    Google Scholar 

  • Arpalahti, J. (1990). Kinetics for pH-dependent complexation of aquated cisdiammineplatinum(II) with inosine and 1-methylinosine. Inorg. Chem., 29, 4598–4602

    Article  CAS  Google Scholar 

  • Arpalahti, J. and Lehikoinen, P. (1990). Kinetics of complexation of aquated Pt(II)(dien) with inosine and 1-methylinosine as a function of pH. Inorg. Chem., 29, 2564–2567

    Article  CAS  Google Scholar 

  • Arpalahti, J. and Lippert, B. (1990). Coordination of aquated cis-platinum(II) diamines to purine nucleosides. Kinetics of complex formation. Inorg. Chem., 29, 104–110

    Article  CAS  Google Scholar 

  • Bancroft, D. P., Lepre, C. A. and Lippard, S. J. (1990). i95Pt NMR kinetic and mechanistic studies of cis- and trans-diamminedichloroplatinum(II) binding to DNA. J. Am. Chem. Soc., 112, 6860–6871

    Google Scholar 

  • Banerjee, S. K., Borden, A., Christensen, R. B., LeClerc, J. E. and Lawrence, C. W. (1990). SOS-dependent replication past a single trans-syn T-T cyclobutane dimer gives a different mutation spectrum and increased error rate compared with replication past this lesion in uninduced cells. J. Bacteriol., 172, 2105–2112

    PubMed  PubMed Central  CAS  Google Scholar 

  • Banjar, Z. M., Hnilica, L. S., Briggs, R. C., Stein, J. and Stein, G. (1984). cis- and trans-Diamminedichloroplatinum(II)-mediated crosslinking of chromosomal non-histone proteins to DNA in HeLa cells. Biochemistry, 23, 1921–1926

    Google Scholar 

  • Basu, A., Teicher, B. A. and Lazo, J. S. (1990). Involvement of protein kinase C in phorbol ester-induced sensitization of HeLa cells to cis-diamminedichloroplatinum(II). J. Biol. Chem., 265, 8451–8457

    PubMed  CAS  Google Scholar 

  • Basu, A. K. and Essigmann, J. M. (1988). Site-specifically modified oligodeoxynucleotides as probes for the structural and biological effects of DNA-damaging agents. Chem. Res. Toxicol, 1, 1–18

    Article  PubMed  CAS  Google Scholar 

  • Baudin, F., Romby, P., Romaniuk, P. J., Ehresmann, B. and Ehresmann, C. (1989). Crosslinking of transcription factor TFIIIA to ribosomal 5S RNA from X. laevis by trans-diamminedichloroplatinum(II). Nucleic Acids Res., 17, 10035–10046

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  • Bellon, S. F., Coleman, J H and Lippard, S. J. (1991). DNA unwinding produced by site-specific intrastrand crosslinks of the antitumor drug cis-diamminedichloro-platinum(II). Biochemistry, 30, 8026–8035

    Article  PubMed  CAS  Google Scholar 

  • Berners-Price, S. J. and Kuchel, P. W. (1990a). Reaction of cis- and trans- [PtC12(NH3)2] with reduced glutathione inside human red blood cells, studied by H and 15N-{1H) DEPT NMR. J. Inorg. Biochem., 38, 327–345

    Google Scholar 

  • Berners-Price, S. J. and Kuchel, P. W. (1990b). Reaction of cis- and trans[PtC12(NH3)2] with reduced glutathione studied by 1H, 13C, 195Pt and 15N-{1H} DEPT NMR. J. Inorg. Biochem., 38, 305–326

    Google Scholar 

  • Bodenner, D. L., Dedon, P. C., Keng, P. C., Katz, J. C. and Borch, R. F. (1986). Selective protection against cis-diamminedichloroplatinum(II)-induced toxicity in kidney, gut, and bone marrow by diethyldithiocarbamate rescue. Cancer Res., 46, 2751–2756

    PubMed  CAS  Google Scholar 

  • Bohr, V. A. (1991). Gene specific DNA repair. Carcinogenesis, 12, 1983–1992

    Article  PubMed  CAS  Google Scholar 

  • Bohr, V. A., Nairn, R. S., Wassermann, K., Jones, J. C., Zhen, W. and May, A. (1991). Studies of preferential DNA repair and strand specificity of DNA repair in the DHFR gene after treatment of hamster cells with UV and chemotherapeutics. Proc. Am. Assoc. Cancer Res., 32, 4

    Google Scholar 

  • Bowler, B. E. and Lippard, S. J. (1986). Modulation of platinum antitumor drug binding to DNA by linked and free intercalators. Biochemistry, 25, 3031–3038

    Article  PubMed  CAS  Google Scholar 

  • Bradley, L. J. N., Yarema, K. J., Lippard, S. J. and Essigmann, J. M. (1993). Mutagenicity and genotoxicity of the major DNA adduct of the antitumor drug cis-diamminedichloroplatinum(II). Biochemistry, 32, 982–988

    Article  PubMed  CAS  Google Scholar 

  • Bridges, B. A. and Woodgate, R. (1985). Mutagenic repair in Eschericia coli. RecA and umuC,D gene products act at different steps in UV mutagenesis. Proc. Natl Acad. Sci. USA, 82, 4193–4197

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  • Bruhn, S. L., Pil, P. M., Essigmann, J. M., Housman, D. E. and Lippard, S. J. (1992). Isolation and characterization of human cDNA clones encoding a high mobility group box protein that recognizes structural distortions to DNA caused by binding of the anticancer agent cisplatin. Proc. Natl Acad. Sci., USA, 89, 2307–2311

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  • Bruhn, S. L., Toney, J. H. and Lippard, S. J. (1990). Biological processing of DNA modified by platinum compounds. Prog. Inorg. Chem., 38, 477–516

    Article  CAS  Google Scholar 

  • Bubley, G. J., Ashbumer, B. P. and Teicher, B. A. (1991). Spectrum of cisdiamminedichloroplatinum(II) induced mutations in a shuttle vector propagated in human cells. Mol. Carcinogen., 4, 397–406

    Article  CAS  Google Scholar 

  • Buchanan, R. M. and Gralla, J. D. (1990). Cisplatin resistance and mechanism in a viral test system: SV40 isolates that resist inhibition by the antitumor drug have lost regulatory DNA. Biochemistry, 29, 3436–3442

    Article  PubMed  CAS  Google Scholar 

  • Burnout, D., Daune, M. and Fuchs, R. P. P. (1987). Spectrum of cisplatin-induced mutations in Escherichia coli. Proc. Natl Acad. Sci. USA, 84, 3758–3762

    Article  Google Scholar 

  • Burnout, D., Gauthier, C., Chottard, J. C. and Fuchs, R. P. P. (1990). Single d(ApG)/cis-diamminedichloroplatinum(II) adduct-induced mutagenesis in Escherichia coli. Proc. Natl Acad. Sci. USA, 87, 6087–6091

    Article  Google Scholar 

  • Calabresi, P. and Parks, J. R. E. (1985). In Gilman, A. G., Goodman, L. S., Rall, T. W. Murad, F. (Eds.), Goodman and Gilman’s The Pharmacological Basis of Therapeutics, 7th edn. Macmillan, New York, pp. 1290–1291

    Google Scholar 

  • Canon, J.-L., Humblet, Y. and Symann, M. (1990). Resistance to cisplatin: How to deal with the problem? Eur. J. Cancer, 26, 1–3

    Article  PubMed  CAS  Google Scholar 

  • Caradonna, J. P., Lippard, S. J., Gait, M. J. and Singh, M. (1982). The antitumor drug cis-[Pt(NH3)2C12] forms an intrastrand d(GpG) crosslink upon reaction with [d(ApGpGpCpCpT)]2. J. Am. Chem. Soc., 104, 5793–5795

    Article  CAS  Google Scholar 

  • Cariello, N. F., Swenberg, J. A. and Skopek, T. R. (1992). In vitro mutational specificity of cisplatin in the human hypoxanthine guanine phosphoribosyltransferase gene. Cancer Res., 52, 2866–2873

    PubMed  CAS  Google Scholar 

  • Chao, C.-K., Huang, S.-L., Lee, L.-Y and Lin-Chao, S. (1991). Identification of inducible damage-recognition proteins that are overexpressed in HeLa cells resistant to cis- diamminedichloroplatinum(II). Biochem. J., 277, 875–878

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  • Chu, G. and Chang, E. (1988). Xeroderma pigmentosum group E cells lack a nuclear factor that binds to damaged DNA. Science, 242, 564–567

    CAS  Google Scholar 

  • Chu, G. and Chang, E. (1990). Cisplatin-resistant cells express increased levels of a factor that recognizes damaged DNA. Proc. Natl Acad. Sci. USA, 87, 3324–3327

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  • Churchill, M. E. A. and Travers, A. A. (1991). Protein motifs that recognize structural features of DNA. Trends Biochem. Sci., 16, 92–97

    Article  PubMed  CAS  Google Scholar 

  • Ciccarelli, R. B., Solomon, M. J., Varshaysky, A. and Lippard, S. J. (1985). In vivo effects of cis- and trans-diamminedichloroplatinum(II) on SV40 chromosomes: differential repair, DNA-protein cross-linking, and inhibition of replication. Biochemistry, 24, 7533–7540

    PubMed  CAS  Google Scholar 

  • Claereboudt, J., De Spiegeleer, B., Bruijn, E. A. D., Gijbels, R. and Claeys, M. (1989a). Structural characterization of cisplatin analogues by fast atom bombardment (FAB) and laser microprobe mass spectrometry (LAMMA). J. Pharm. Biomed. Anal., 7, 1599–1610

    Article  PubMed  CAS  Google Scholar 

  • Claereboudt, J., Spiegeleer, B. D., Lippert, B., Bruijn, E. A. D. and Claeys, M. (1989b). Fast atom bombardment and tandem mass spectrometry for the structural characterization of cisplatin analogs and bis-nucleobase adducts with cisplatin. Spectrosc. Int. J., 7, 91–112

    CAS  Google Scholar 

  • Comess, K. M., Burstyn, J. N., Essigmann, J. M. and Lippard, S. J. (1992). Replication inhibition and translesion synthesis on templates containing site-specifically placed cis-diamminedichloroplatinum(II) DNA adducts. Biochemistry, 31, 3975–3990

    Article  PubMed  CAS  Google Scholar 

  • Comess, K. M., Costello, C. E. and Lippard, S. J. (1990). Identification and characterization of a novel linkage isomerization in the reaction of transdiamminedichloroplatinum(II) with d(TCTACGCGTTCT). Biochemistry, 29, 2102–2110

    Article  PubMed  CAS  Google Scholar 

  • Comess, K. M. and Lippard, S. J. (1990). Commentary on: Involvement of protein kinase C in phorbol ester-induced sensitization of HeLa cells to cis-diamminedichloroplatinum(II). Chemtracts: Biochemistry and Molecular Biology, 1, 336–337

    CAS  Google Scholar 

  • Corda, Y., Anin, M.-F., Leng, M. and Job, D. (1992). RNA polymerases react differently at d(ApG) and d(GpG) adducts in DNA modified by cisdiamminedichloroplatinum(II). Biochemistry, 31, 1904–1908

    Article  PubMed  CAS  Google Scholar 

  • Corda, Y., Job, C., Anin, M.-F., Leng, M. and Job, D. (1991). Transcription by eucaryotic and procaryotic RNA polymerases of DNA modified at a d(GG) or a d(AG) site by the antitumor drug cis-diamminedichloroplatinum(II). Biochemistry, 30, 222–230

    Article  PubMed  CAS  Google Scholar 

  • Costello, C.E., Comess, K. M., Plaziak, A. S., Bancroft, D. P. and Lippard, S. J. (1992). Fast atom bombardment and high performance tandem mass spectrometry of platinum(II) oligodeoxyribonucleotide fragments. Int. J. Mass Spectrom. Ion Processes, 122, 255–279

    Article  CAS  Google Scholar 

  • Dabholkar, M., Parker, R. and Reed, E. (1992). Determinants of cisplatin sensitivity in non-malignant non-drug-selected human T-cell lines. Mutation Res., 274, 45–56

    Article  PubMed  CAS  Google Scholar 

  • deBoer, J. G. and Glickman, B. W. (1989). Sequence specificity of mutation induced by the anti-tumor drug cisplatin in the CHO aprt gene. Carcinogenesis, 10, 1363–1367

    Article  CAS  Google Scholar 

  • Dedon, P. C. and Borch, R. F. (1987). Characterization of the reactions of platinum antitumor agents with biologic and nonbiologic sulfur-containing nucleophiles. Biochem. Pharmacol., 36, 1955–1964

    Article  PubMed  CAS  Google Scholar 

  • DePamphilis, M. L. (1988). Transcriptional elements as components of eukaryotic origins of DNA replication. Cell, 52, 635–638

    Article  PubMed  CAS  Google Scholar 

  • Dieter, I., Lippert, B. Schöllhom, H. and Thewalt, U. (1990). Coordination chemistry of trans-(NH3)2Pt(II) with uracil nucleobases. A comparison with cis-(NH3)2Pt(II). Z. Naturforsch., 45b, 731–740

    Google Scholar 

  • Donahue, B. A., Augot, M., Bellon, S. F., Treiber, D. K., Toney, J. H., Lippard, S. J. and Essigmann, J. M. (1990). Characterization of a DNA damage-recognition protein from mammalian cells that binds specifically to intrastrand d(GpG) and d(ApG) DNA adducts of the anticancer drug cisplatin. Biochemistry, 29, 5872–5880

    Article  PubMed  CAS  Google Scholar 

  • Dynan, W. S. and Tjian, R. (1985). Control of eukaryotic messenger RNA synthesis by sequence-specific DNA-binding proteins. Nature, 316, 774–778

    Article  PubMed  CAS  Google Scholar 

  • Eastman, A. (1986). Reevaluation of interaction of cis-dichloro(ethylenediamine)platinum(II) with DNA. Biochemistry, 25, 3912–3915

    Article  PubMed  CAS  Google Scholar 

  • Enns, R. E. and Howell, S. B. (1992). Isolation of a gene associated with resistance to cisplatin. In Howell, S. B. (Ed.), Platinum and Other Metal Coordination Compounds in Cancer Chemotherapy. Plenum Press, New York, pp. 213–220

    Google Scholar 

  • Fichtinger-Schepman, A. M. J., Baan, R. A. and Berends, F. (1989a). Influence of the degree of DNA modification on the immunochemical determination of cisplatin-DNA adduct levels. Carcinogenesis, 10, 2367–2369

    Article  PubMed  CAS  Google Scholar 

  • Fichtinger-Schepman, A. M. J., Baan, R. A., Luiten-Schuite, A., van Dijk, M. and Lohman, P. H. M. (1985a). Immunochemical quantitation of adducts induced in DNA by cis-diamminedichloroplatinum(II) and analysis of adduct-related DNA unwinding. Chem. -biol. Interact., 55, 275–288

    Article  PubMed  CAS  Google Scholar 

  • Fichtinger-Schepman, A. M. J., Dijt, F. J., Bedford, P., van Oosterom, A. T., Hill, B. T. and Berends, F. (1988). Induction and removal of cisplatin-DNA adducts in human cells in vivo and in vitro as measured by immunochemical techniques. In Methods for Detecting DNA Damaging Agents in Humans. International Agency for Research on Cancer, pp. 321–328

    Google Scholar 

  • Fichtinger-Schepman, A. M. J., Lohman, P. H. M. and Reedijk, J. (1982). Detection and quantitation of adducts formed upon reaction of diamminedichloroplatinum(II) with DNA, by anion-exchange chromatography after enzymatic degradation. Nucleic Acids Res., 10, 5345–5356

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  • Fichtinger-Schepman, A., van Oosterom, A. T., Lohman, P. H. M. and Berends, F. (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 cisdiamminedichloroplatinum(II). Cancer Res., 47, 3000–3004

    Google Scholar 

  • Fichtinger-Schepman, A. M. J., van der Veer, J. L., den Hartog, J. H. J., Lohamn, P. H. M. and Reedijk, J. (1985b). Adducts of the antitumor drug cisdiamminedichloroplatinum(II) with DNA: Formation, identification, and quantitation. Biochemisty, 24, 707–713

    Article  CAS  Google Scholar 

  • Fichtinger-Schepman, A. M. J., van der Velde-Visser, S. D., van DijkKnijnenburg, H. C. M., van Oosterom, A. T., Baan, R. A. and Berends, F. (1990). Kinetics of the formation and removal of cisplatin-DNA adducts in blood cells and tumor tissue of cancer patients receiving chemotherapy: Comparison with in vitro adduct formation. Cancer Res., 50, 7887–7894

    PubMed  CAS  Google Scholar 

  • Fichtinger-Schepman, A. M. J., Vendrik, C. P. J., van Dijk-Knijneburg, W. C. M., de Jong, W. H., van der Minnen, A. C. E., Claessen, A. M. E., van der Velde-Visser, S. D., de Groot, G., Wubs, K. L., Steerenberg, P. A., Schor-nagel, J. H. and Berends, F. (1989b). Platinum concentrations and DNA adduct levels in tumors and organs of cisplatin-treated LOU/M rats inoculated with cisplatin-sensitive or -resistant immunoglobulin M immunocytoma. Cancer Res., 49, 2862–2867

    Google Scholar 

  • Filipski, J., Kohn, K. W. and Bonner, W. M. (1983). Differential crosslinking of histones and non-histones in nuclei by cisPt(II). FEBS Lett., 152, 105–108

    Article  PubMed  CAS  Google Scholar 

  • Fok, E. M. (1990). Computation of kinetics of cis-dichlorodiaminoplatinum(II) hydrolysis. Koordinatsionnaya Khimiya, 16, 1554–1559

    CAS  Google Scholar 

  • Forsti, A., Leppala, S., Takala, M., Laatikainen, R. and Hemminki, K. (1989). Kinetics of reaction of cis-diamminedichloroplatinum(II) with DNA. Pharmacol. Toxicol., 64, 120–125

    Article  PubMed  CAS  Google Scholar 

  • Fox, E. P. and Loehrer, P. J. (1991). Chemotherapy for advanced testicular cancer. Hematology/Oncology Clinics of North America, 5, 1173–1187

    PubMed  CAS  Google Scholar 

  • Frommer, G. and Lippert, B. (1990). Head-tail oriented nucleobases (B = guanine, cytosine) in cis-A2PtB2 resisting cyanide substitution. Implications for the nature of strongly DNA-bound cisplatin. Inorg. Chem., 29, 3259–3260

    Article  CAS  Google Scholar 

  • Ganeva, R. L., Spassovska, N. C. and Genchev, D. D. (1990). The effect of some platinum compounds on the biosynthesis of RNA and its precursors. J. Inorg. Biochem., 40, 13–18

    Article  PubMed  CAS  Google Scholar 

  • Gibbons, G. R., Kaufmann, W. K. and Chaney, S. G. (1991). Role of DNA replication in carrier-ligand-specific resistance to platinum compounds in L1210 cells. Carcinogenesis, 12, 2253–2257

    Article  PubMed  CAS  Google Scholar 

  • Godwin, A. K., Meister, A., Odwyer, P. J., Huang, C. S., Hamilton, T. C. and Anderson, M. E. (1992). High resistance to cisplatin in human ovarian cancer cell lines is associated with marked increase of glutathione synthesis. Proc. Natl Acad. Sci. USA, 89, 3070–3074

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  • Gralla, J. D., Sasse-Dwight, S. and Poljak, L. G. (1987). Formation of blocking lesions at identical DNA sequences by the nitrosourea and platinum classes of anticancer drugs. Cancer Res., 47, 5092–5096

    PubMed  CAS  Google Scholar 

  • Green, M. and Miller, J. M. (1987). A cyclic nucleobase phosphate: Fast atom bombardment studies on a 1: 1 mixture of cis-[Pt(NH3)2(OH)21(CF3SO3)2 and guanosine 5’-monophosphoric acid. J. Chem. Soc., Chem. Commun., 1864–1865

    Google Scholar 

  • Greene, M. H. (1992). Is cisplatin a human carcinogen. J. Nat! Cancer Inst., 84, 306–312

    Article  PubMed  CAS  Google Scholar 

  • Haneda, H., Katabami, M., Miyamoto, H., Isobe, H., Shimizu, T., Ishiguro, A., Moriuti, T., Takasaki, Y. and Kawakami, Y. (1991). The relationship of the proliferating cell nuclear antigen protein to cis-DDP resistance of a murine leukemia cell line P388/CDDP. Oncology, 48, 234–238

    Article  PubMed  CAS  Google Scholar 

  • Hansson, J. and Wood, R. D. (1989). Repair synthesis by human cell extracts in DNA damaged by cis- and trans-diamminedichloroplatinum(H). Nucleic Acids Res., 17, 8073–8091

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  • Harder, H. C. and Rosenberg, B. (1970). Inhibitory effects of antitumor platinum compounds on DNA, RNA and protein synthesis in mammalian cells in vitro. Int. J. Cancer, 6, 207–216

    Article  PubMed  CAS  Google Scholar 

  • Harrison, S. C. (1991). A structural taxonomy of DNA-binding domains. Nature, 353, 715–719

    Article  PubMed  CAS  Google Scholar 

  • Heiger-Bemays, W. J., Essigmann, J. M. and Lippard, S. J. (1990). Effect of the antitumor drug cis-diamminedichloroplatinum(II) and related platinum complexes on eukaryotic DNA replication. Biochemistry, 29, 8461–8466

    Article  Google Scholar 

  • Hemminiki, K. and Thilly, W. G. (1988). Binding of cisplatin to specific sequences of human DNA in vitro. Mutation Res., 202, 133–138

    Article  Google Scholar 

  • Hoffmann, J.-S., Hubscher, U., Michot, B. and Villani, G. (1991). Interaction of cis-diamminedichloroplatinum(II) with single-stranded DNA in the presence or absence of Escherichia coli single-stranded binding protein. Biochem. Pharma-col., 42, 1393–1398

    Article  CAS  Google Scholar 

  • Hoffmann, J.-S., Johnson, N. P. and Villani, G. (1989). Conversion of monofunctional DNA adducts of cis-diamminedichloroplatinum(II) to bifunctional lesions. J. Biol. Chem., 264, 15130–15135

    PubMed  CAS  Google Scholar 

  • Hollander, M. C. and Fornace, A. J., Jr. (1989). Induction of fos RNA by DNA-damaging agents. Cancer Res., 49, 1687–1692

    PubMed  CAS  Google Scholar 

  • Howe-Grant, M. and Lippard, S. J. (1980). Aqueous platinum(II) chemistry; Binding to biological molecules. Metal Ions Biol. Syst., 11, 63–125

    CAS  Google Scholar 

  • Howell, S. B., Pfeifle, C. E., Wing, W. E. and Olshen, R. A. (1983). Intraperitoneal cis-diamminedichloroplatinum(II) with systemic thiosulfate protection. Cancer Res., 43, 1426–1431

    PubMed  CAS  Google Scholar 

  • Howle, J. A. and Gale, G. R. (1970). cis-DDP: Persistent and selective inhibition of deoxyribonucleic acid synthesis in vivo. Biochem. Pharmacol. 19 2757–2762

    Article  PubMed  CAS  Google Scholar 

  • Iakovidis, A., Hadjiliadis, N., Dahan, F., Laussac, J.-P. and Lippert, B. (1990). Complete displacement of N,O bound amino acids (amacH) in cis-[(NH3)2Pt(amac)]NO3 chelates by 9-methylguanine (9-MeGH) and 9-methyladenine (9-MeA). The crystal structure of cis-[(NH3)2Pt(9-MeA-N7)2](NO3)2.1.5 H2O. Inorg. Chim. Acta, 175, 57–63

    Article  CAS  Google Scholar 

  • Inagaki, K., Alink, M., Nagai, A., Kidani, Y. and Reedijk, J. (1990). Unusual isomerization reaction of a platinum-dinucleotide compound. Inorg. Chem., 29, 2183–2185

    Article  CAS  Google Scholar 

  • Inagaki, K., Tomita, A. and Kidani, Y. (1988). Studies on the reaction products of antitumor platinum complexes with d(ApG), d(GpA) and d(pGpA). 2’-Deoxy sugar is favorable for G-N7, A-N1 chelation. Bull. Chem. Soc. Jpn, 61, 2825–2831

    Article  CAS  Google Scholar 

  • Isonishi, S., Andrews, P. and Howell, S. (1990). Increased sensitivity to cisdiamminedichloroplatinum(II) in human ovarian carcinoma cells in response to treatment with 12-O-Tetradecanoylphorbol 13-acetate. J. Biol. Chem., 265, 3623–3627

    PubMed  CAS  Google Scholar 

  • Isonishi, S., Hom, D. K., Thiebaut, F. B., Mann, S. C., Andrews, P. A., Basu, A., Lazo, J. S., Eastman, A. and Howell, S. B. (1991). Expression of the c-Ha-ras oncogene in mouse NIH-3T3 cells induces resistance to cisplatin. Cancer Res., 51, 5903–5909

    PubMed  CAS  Google Scholar 

  • Jäckel, M. and Köpf-Maier, P. (1991). Influence of cisplatin on cell-cycle progression in xenografted human head and neck carcinomas. Cancer Chemother. Pharmacol., 27, 464–471

    Article  PubMed  Google Scholar 

  • Johnson, N. P., Hoeschele, J. D., Rahn, R. O., O’Neill, J. P. and Hsie, A. W. (1980). Mutagenicity, cytotoxicity, and DNA binding of platinum(II) chloro-amines in Chinese hamster ovary cells. Cancer Res., 40, 1463–1468

    PubMed  CAS  Google Scholar 

  • Johnson, N. P., Macquet, J. P., Wiebers, J. L. and Monsarrat, B. (1982). Structures of the adducts formed between [Pt(dien)Cl]Cl and DNA in vitro. Nucleic Acids Res., 10, 5255–5271

    Article  PubMed  CAS  Google Scholar 

  • Johnson, N. P., Mazard, A. M., Escalier, J. and Macquet, J. P. (1985). Mechanism of the reaction between cis-[PtC12(NH3)2] and DNA in vitro. J. Am. Chem. Soc., 107, 6376–6380

    Article  CAS  Google Scholar 

  • Jones, J. C., Zhen, W., Reed, E., Parker, R. J., Sancar, A. and Bohr, V. A. (1991). Gene-specific formation and repair of cisplatin intrastrand adducts and intrastrand cross-links in Chinese hamster ovary cells. J. Biol. Chem., 266, 7101–7107

    PubMed  CAS  Google Scholar 

  • Jones, M. M. and Beaty, J. A. (1991). Rate of displacement of guanosine by cyanide from cis-diamminebis(guanosine)platinum(II) chloride determined by using 13C NMR. Inorg. Chem., 30, 1584–1587

    Article  CAS  Google Scholar 

  • Kashani-Sabet, M., Wang, W. and Scanlon, K. J. (1990). Cyclosporin A suppresses cisplatin-induced c-fos gene expression in ovarian carcinoma cells. J. Biol. Chem., 265, 11285–11288

    PubMed  CAS  Google Scholar 

  • Kasselouri, S., Laussac, J.-P. and Hadjiliadis, N. (1989). trans-Ternary complexes of Pd(II) with nucleosides and dipeptides. Models for trans-DDP-DNA-protein crosslinks. Inorg. Chim. Acta, 166, 239–248

    Article  CAS  Google Scholar 

  • Kawai, K., Kamatani, N., Georges, E. and Ling, V. (1990). Identification of a membrane glycoprotein overexpressed in murine lymphoma sublines resistant to cis-diamminedichloroplatinum(II). J. Biol. Chem., 265, 13137–13142

    PubMed  CAS  Google Scholar 

  • Keck, M. V. and Lippard, S. J. (1992). Unwinding of supercoiled DNA by platinum-ethidium and related complexes. J. Am. Chem. Soc., 114, 3386–3390

    Article  CAS  Google Scholar 

  • Kelland, L. R., Mistry, P., Abel, G., Freidlos, F., Loh, S. Y., Roberts, J. J. and Harrap, K. R. (1992). Establishment and characterization of an in vitro model of acquired resistance to cisplatin in a human testicular nonseminatous germ cell line. Cancer Res., 52, 1710–1716

    PubMed  CAS  Google Scholar 

  • Kelley, S. and Rozencweig, M. (1989). Resistance to platinum compounds: Mechanisms and beyond. Eur. J. Cancer Clin. Oncol., 25, 1135–1140

    Article  PubMed  CAS  Google Scholar 

  • Kelley, S. L., Basu, A., Teicher, B. A., Hacker, M. P., Hamer, D. H. and Lazo, J. S. (1988). Overexpression of metallothionein confers resistance to anticancer drugs. Science, 241, 1813–1815

    Article  PubMed  CAS  Google Scholar 

  • Kline, T. P., Marzilli, L. G., Live, D. and Zon, G. (1989). Investigations of platinum amine induced distortions in single- and double-stranded oligodeoxyribonucleotides. J. Am. Chem. Soc., 111, 7057–7068

    Article  CAS  Google Scholar 

  • Krizanovic, O., Pesch, F. J. and Lippert, B. (1989). Nucleobase displacement from trans-diamine-platinum(II) complexes. A rationale for the inactivity of transDDP as an antitumor agent? Inorg. Chim. Acta, 165, 145–146

    Article  CAS  Google Scholar 

  • Langford, C. H. and Gray, H. B. (1965). Ligand Substitution Processes. W. A. Benjamin, New York

    Google Scholar 

  • Lemaire, M.-A., Schwartz, A., Rahmouni, A. R. and Leng, M. (1991). Interstrand crosslinks are preferentially formed at the d(GC) sites in the reaction between cis-diamminedichloroplatinum(II) and DNA. Proc. Natl Acad. Sci. USA, 88, 1982–1985

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  • Lempers, E. L. M. and Reedijk, J. (1990a). Characterization of products from [PtCI(dien)]CI and S-adenosyl-L-homocysteine. Evidence for a pH-dependent migration of the platinum moiety from the sulfur atom to the amine group and vice versa. Inorg. Chem., 29, 1880–1884

    Article  CAS  Google Scholar 

  • Lempers, E. L. M. and Reedijk, J. (1990b). Reversibility of binding of cisplatin-methionine in proteins by diethyldithiocarbamate or thiourea: A study with model adducts. Inorg. Chem., 29, 217–222

    Article  CAS  Google Scholar 

  • Leopold, W. R., Miller, E. C. and Miller, J. A. (1979). Carcinogenicity of antitumor cis-platinum(II) coordination complexes in the mouse and rat. Cancer Res., 39, 913–918

    PubMed  CAS  Google Scholar 

  • Lepre, C. A., Chassot, L., Costello, C. E. and Lippard, S. J. (1990). Synthesis and characterization of trans-[Pt(NH3)2C12] adducts of d(CCTCGAGTCTCC).d(GGAGACTCGAGG). Biochemistry, 29, 811–823

    Article  PubMed  CAS  Google Scholar 

  • Lim, M. C. and Martin, R. B. (1976). Nature of cis-amine Pd(II) and antitumor cis-amine Pt(II) complexes in aqueous solutions. J. Inorg. Nucl. Chem., 38, 1911–1914

    Article  CAS  Google Scholar 

  • Lippard, S. J. and Hoeschele, J. D. (1979). Binding of cis- and transdichlorodiammineplatinum(II) to the nucleosome core. Proc. Natl Acad. Sci. USA, 76, 6091–6095

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  • Lippert, B. (1989). Platinum nucleobase chemistry. Prog. Inorg. Chem., 37, 1–97

    Article  CAS  Google Scholar 

  • Litterst, C. L. (1984). In Hacker, M. P., Douple, E. B. and Krakoff, I. H. (Eds), Platinum Coordination Complexes in Cancer Chemotherapy. Martinus Nijhoff, Dordrecht, p. 78

    Google Scholar 

  • Litterst, C. L., Gram, T. E., Dedrich, R. L., Leroy, A. F. and Guarino, A. M. (1976). Distribution and disposition of platinum following intravenous administration of cis-diamminedichloroplatinum(II) to dogs. Cancer Res., 36, 2340–2344

    PubMed  CAS  Google Scholar 

  • Litterst, C. L., LeRoy, A. F. and Guarino, A. M. (1979). Disposition and distribution of platinum following parenteral administration of cis-dichlorodi-ammineplatinum(II) to animals. Cancer Treat. Rep., 63, 1485–1492

    PubMed  CAS  Google Scholar 

  • Loehrer, P. J. and Einhorn, L. H. (1984). Cisplatin. Ann. Intern. Med., 100, 704–713

    Article  PubMed  CAS  Google Scholar 

  • McCloskey, J. A. (1982). In Alderweireldt, F. C. and Esmans, E. L. (Eds), Nucleosides, Nucleotides, and Their Biological Applications. University of Antwerp, Belgium, pp. 47–67

    Google Scholar 

  • May, A., Nairn, R. S., Okumoto, D. S., Wassermann, K., Stevnsner, T., Jones, J. C. and Bohr, V. A. (1993). Repair of individual DNA strands in the hamster dihydrofolate reductase gene after treatment with ultraviolet light, alkylating agents, and cisplatin. J. Biol. Chem., 268, 1650–1657

    PubMed  CAS  Google Scholar 

  • Malinge, J.-M., Schwartz, A. and Leng, M. (1987). Characterization of the ternary complexes formed in the reaction of cis-diamminedichloroplatinum(II), ethidium bromide and nucleic acids. Nucleic Acids Res., 15, 1779–1797

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  • Marrot, L. and Leng, M. (1989). Chemical probes of the conformation of DNA modified by cis-diamminedichloroplatinum(II). Biochemistry, 28, 1454–1461

    Article  PubMed  CAS  Google Scholar 

  • Martin, L. B., III, Schreiner, A. F. and van Breemen, R. B. (1991). Characterization of cisplatin adducts of oligonucleotides by fast atom bombardment mass spectrometry. Anal. Biochem., 193, 6–15

    Google Scholar 

  • Masuda, H., Tanaka, T., Matsuda, H. and Kusaba, I. (1990). Increased removal of DNA-Marilyn platinum in a human ovarian cancer cell line resistant to cisdiamminedichloroplatinum(II). Cancer Res., 50, 1863–1866

    PubMed  CAS  Google Scholar 

  • Mellon, I. M. and Hanawalt, P. C. (1989). Induction of the Eschericia coli lactose operon selectively increases repair of its transcribed DNA strand. Nature, 342, 95–98

    Article  PubMed  CAS  Google Scholar 

  • Mellon, I. M., Spivak, G. S. and Hanawalt, P. C. (1987). Selective removal of transcription-blocking DNA damage from the transcribed strand of the mammalian DHFR gene. Cell, 51, 241–249

    Article  PubMed  CAS  Google Scholar 

  • Millar, D. P., Ho, K. M. and Aroney, M. J. (1988). Modification of DNA dynamics by platinum drug binding: A time-dependent fluorescence depolarization study of the interaction of cis- and trans-diamminedichloroplatinum(II) with DNA. Biochemistry, 27, 8599–8606

    Article  PubMed  CAS  Google Scholar 

  • Miller, C. A., III, Cohen, M. D. and Costa, M. (1991). Complexing of actin and other nuclear proteins to DNA by cis-diamminedichloroplatinum(II) and chromium compounds. Carcinogenesis, 12, 269–276

    Article  PubMed  CAS  Google Scholar 

  • Miller, S. E. and House, D. A. (1989a). The hydrolysis products of cisdiamminedichloroplatinum(II). 1. The kinetics of formation and anation of the cis-diammine(aqua)chloroplatinum(II) cation in acidic aqueous solution. Inorg. Chim. Acta, 161, 131–137

    Article  CAS  Google Scholar 

  • Miller, S. E. and House, D. A. (1989b). The hydrolysis products of cisdichlorodiammineplatinum(II). 2. The kinetics of formation and anation of the cis-diamminedi(aqua)platinum(II) cation. Inorg. Chim. Acta, 166, 189–197

    Article  CAS  Google Scholar 

  • Miller, S. E. and House, D. A. (1990). The hydrolysis products of cisdichlorodiammineplatinum(II). 3. Hydrolysis kinetics at physiological pH. Inorg. Chim. Acta, 173, 53–60

    Article  CAS  Google Scholar 

  • Mis, J. R. A. and Kunz, B. A. (1990). Analysis of mutations induced in the SUP4-o gene of Saccharomyces cerevisiae by cis-diammine dichloroplatinum(II). Carcinogenesis, 11, 633–638

    Article  PubMed  CAS  Google Scholar 

  • Miyazaki, M., Kohno, K., Saburi, Y., Matsuo, K., Ono, M., Kuwano, M., Tsuchida, S., Sato, K., Sakai, M. and Muramatsu, M. (1990). Drug resistance to cis-diamminedichloroplatinum(II) in Chinese hamster ovary cell lines transfected with glutathione S-transferase PI gene. Biochem. Biophys. Res. Commun., 166, 1358–1364

    Article  PubMed  CAS  Google Scholar 

  • Mukundan, S., Jr., Xu, Y., Zon, G. and Marzilli, L. G. (1991). Heteronuclear 13C–1H NMR investigation of the effects on an oligodeoxyribonucleotide of intrastrand crosslinking by a Pt anticancer drug. A large shift of C3’ accompanies an S to N conformation change. J. Am. Chem. Soc., 113, 3021–3027

    Article  CAS  Google Scholar 

  • Naser, L. J., Pinto, A. L., Lippard, S. J. and Essigmann, J. M. (1988). Chemical and biological studies of the major DNA adduct of cis-diamminedichloroplatinum(II), cis-[Pt(NH3)2{d(GpG)}], built into a specific site in a viral genome. Biochemistry, 27, 4357–4367.

    Article  PubMed  CAS  Google Scholar 

  • Ogawa, M., Gale, G. R. and Keim, S. S. (1975). Effects of cis-diamminedichloroplatinum (NSC 119875) on murine and human hemopoietic precursor cells. Cancer Res., 35, 1398–1401

    PubMed  CAS  Google Scholar 

  • Page, J. D., Husain, I., Sancar, A. and Chaney, S. G. (1990). Effect of the diaminocyclohexane carrier ligand on platinum adduct formation, repair, and lethality. Biochemistry, 29, 1016–1024

    Article  PubMed  CAS  Google Scholar 

  • Parker, R. J., Gill, I., Tarone, R., Vionnet, J. A., Grunberg, S., Muggia, F. M. and Reed, E. (1991). Platinum-DNA damage in leukocyte DNA of patients receiving carboplatin and cisplatin chemotherapy, measured by atomic absorption spectrometry. Carcinogenesis, 12, 1253–1258

    Google Scholar 

  • Patel D. J. (1992). Covalent carcinogenic guanine-modified DNA lesions: Solution structures of adducts and crosslinks. Current Opinion Struct. Biol., 2, 345–353

    Article  CAS  Google Scholar 

  • Patton, T. F., Himmelstein, K. J., Belt, R., Bannister, S. J., Sternson, L. A. and Repta, A. J. (1978). Plasma levels and urinary excretion of filterable platinum species following bolus injection and iv infusion of cis-dichlorodiammineplatinum(II) in Man. Cancer Treat. Rep., 62, 1359–1362

    PubMed  CAS  Google Scholar 

  • Peerey, L. M. and Kostic, N. M. (1987). Transition-metal compounds as new reagents for selective cross-linking of proteins. Synthesis and characterization of 2 bis(cytochrome c) complexes of platinum. Inorg. Chem., 26, 2079–2083

    Article  CAS  Google Scholar 

  • Pesch, F. J., Preut, H. and Lippert, B. (1990). Mixed nucleobase, amino acid complexes of Pt(II). Preparation and X-ray structure of trans-[(CH3NH2)2Pt(1MeC-N 3)(gly-N)]NO3.2H2O and its precursor trans-[(CH3NH2)2Pt(1-MeC-N 3)Cl]Cl•H2O. Inorg. Chim. Acta, 169, 195–200

    Article  CAS  Google Scholar 

  • Pil, P. M. and Lippard, S. J. (1992). Specific binding of chromosomal protein HMG 1 to DNA damaged by the anticancer drug cisplatin. Science, 256, 234–237

    Article  PubMed  CAS  Google Scholar 

  • Pinto, A. L. and Lippard, S. J. (1985a). Binding of the antitumor drug cisdiamminedichloroplatinum(II) (cisplatin) to DNA. Biochem. Biophys. Acta, 780, 167–180

    PubMed  CAS  Google Scholar 

  • Pinto, A. L. and Lippard, S. J. (1985b). Sequence-dependent termination of in vitro DNA synthesis by cis- and trans-diamminedichloroplatinum(II). Proc. Natl Acad. Sci. USA, 82, 4616–4619

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  • Pinto, A. L., Naser, L. J., Essigmann, J. M. and Lippard, S. J. (1986). Site-specifically platinated DNA, a new probe of the biological activity of platinum anticancer drugs. J. Am. Chem. Soc., 108, 7405

    Article  CAS  Google Scholar 

  • Pizzo, S. V., Roche, P. A., Feldman, S. R. and Gonias, S. L. (1986). Further characterization of the platinum-reactive component of the a2-macroglobulinreceptor recognition site. Biochem. J., 238, 217–225

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  • Pizzo, S. V., Swaim, M. W., Roche, P. A. and Gonias, S. L. (1988). Selectivity and stereospecificity of the reactions of dichlorodiammineplatinum(II) with three purified plasma proteins. J. Inorg. Biochem., 33, 67–76

    Article  PubMed  CAS  Google Scholar 

  • Plaziak, A. S., Costello, C. E., Comess, K. M., Bancroft, D. P. and Lippard, S. J. (1990). High performance tandem mass spectrometry of platinated oligonucleotide fragments. In Proceedings of the 38th ASMS Conference on Mass Spectrometry and Allied Topics, Tucson, Arizona, pp. 792–793

    Google Scholar 

  • Plooy, A. C. M., van Dijk, M. and Lohman, P. H. M. (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  CAS  Google Scholar 

  • Poirier, M. C., Egorin, M. J., Fichtinger-Schepman, A. M. J., Yuspa, S. H. and Reed, E. (1988). DNA adducts of cisplatin and carboplatin in tissues of cancer patients. In Bartsch, H., Hemminki, K. and O’Neil, I. K. (Eds), Methods for Detecting DNA Damaging Agents in Humans: Applications in Cancer Epidemiology and Prevention. IARC Scientific Publications, Lyon, pp. 313–320

    Google Scholar 

  • Poirier, M. C., Reed, E., Litterst, C. L., Katz, D. and Guptaburt, S. (1992). Persistence of platinum-ammine-DNA adducts in gonads and kidneys of rats and multiple tissues from cancer patients. Cancer Res., 52, 149–153

    PubMed  CAS  Google Scholar 

  • Popoff, S. C., Beck, D. J. and Rupp, W. D. (1987). Repair of plasmid DNA damaged in vitro with cis- or trans-diamminedichloroplatinum(II) in Escherichia coli. Mutation Res., 183, 129–137

    PubMed  CAS  Google Scholar 

  • Ptak, M., Rahmouni, A., Mazeau, K., Thuong, N. T. and Leng, M. (1989). Structure of the intrastrand cis-[Pt(NH3)2{d(GpCpG)}] adduct in a dodecanucleotide duplex I. A 1H and 31P n.m.r. study. Anti-cancer Drug Design, 4, 53–61

    PubMed  CAS  Google Scholar 

  • Ratilla, E. M. A., Scott, B. K., Moxness, M. S. and Kostic, N. M. (1990). Terminal and new bridging coordination of methylguanidine, arginine, and canavanine to platinum(II). The first crystallographic study of bonding between a transition metal and a guanidine ligand. Inorg. Chem., 29, 918–926

    Article  CAS  Google Scholar 

  • Roberts, J. J. and Friedlos, F. (1987). Differential toxicity of cis- and transdiamminedichloroplatinum(II) toward mammalian cells: Lack of any difference in the rates of loss of their DNA-bound adducts. Cancer Res., 47, 31–36

    PubMed  CAS  Google Scholar 

  • Robichaud, A., Mehra, M.-C., Jankowski, C., Virelizier, H., Butour, J.-L. and Johnson, N. P. (1989). Study of platination of nucleic acids using atomic absorption and mass spectrometry. Spectroscopy Lett., 22, 59–68

    Article  CAS  Google Scholar 

  • Roos, I. A. G., Thomson, A. J. and Eagles, J. (1974). Mass spectrometric studies of the interaction of platinum complexes with nucleoside analogues. Chem.-biol. Interact., 8, 421–427

    Article  PubMed  CAS  Google Scholar 

  • Rosenberg, B., Van Camp, L. and Krigas, T. (1965). Inhibition of cell division in Escherichia coli by electrolysis products from a platinum electrode. Nature, 205 698

    Article  PubMed  CAS  Google Scholar 

  • Royer-Pokora, B., Gordon, L. K. and Haseltine, W. A. (1981). Use of exonuclease III to determine the site of stable lesions in defined sequences of DNA: the cyclobutane pyrimidine dimer and cis- and trans-dichlorodiammineplatinum(II) examples. Nucleic Acids Res., 9, 4595–4609

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  • Sancar, A. and Sancar, G. B. (1988). DNA repair enzymes. Ann. Rev. Biochem., 57, 29–67

    Article  PubMed  CAS  Google Scholar 

  • Santos, R. A., Tang, P. and Harbison, G. S. (1989). Determination of the DNA sugar pucker using 13C NMR spectroscopy. Biochemistry, 28, 9372–9378

    Article  PubMed  CAS  Google Scholar 

  • Schilder, R., Hall, L., Monks, A., Handel, L., Fornace, A., Jr., Ozols, R., Fojo, A. and Hamilton, T. C. (1990). Metallothionein gene expression and resistance to cisplatin in human ovarian cancer. Int. J. Cancer, 45, 416–422

    Article  PubMed  CAS  Google Scholar 

  • Schwarts, A., Marrot, L. and Leng, M. (1989). Conformation of DNA modified at a d(GG) or a d(AG) site by the antitumor drug cis-diamminedichloroplatinum(II). Biochemistry, 28, 7975–7979

    Article  Google Scholar 

  • Schwartz, A., Marrot, L. and Leng, M. (1989). Conformation of DNA modified at a d(GG) or a d(AG) site by the antitumor drug cis-diamminedichloroplatinum(II). Biochemistry, 28, 7975–7979

    Article  PubMed  CAS  Google Scholar 

  • Selby, C. P. and Sancar, A. (1990). Transcription preferentially inhibits nucleotide excision repair of the template DNA strand in vitro. J. Biol. Chem., 265, 21330–21336

    PubMed  CAS  Google Scholar 

  • Selby, C. P. and Sancar, A. (1991). Gene- and strand-specific repair in vitro: Partial purification of a transcription-repair coupling factor. Proc. Natl Acad. Sci. USA, 88, 8232–8236

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  • Shellard, S. A., Hosking, L. K. and Hill, B. T. (1991). Anomalous relationship between cisplatin sensitivity and the formation and removal of platinum-DNA adducts in two human ovarian carcinoma cell lines in vitro. Cancer Res., 51, 4557–4564

    PubMed  CAS  Google Scholar 

  • Sherman, S. E. and Lippard, S. J. (1987). Structural aspects of platinum anticancer drug interactions with DNA. Chem. Rev., 87, 1153–1181

    Article  CAS  Google Scholar 

  • Sip, M., Schwartz, A., Voyelle, F., Ptak, M. and Leng, M. (1992). Distortions induced in DNA by cis-platinum interstrand adducts. Biochemistry, 31, 2508–2513

    Article  PubMed  CAS  Google Scholar 

  • Struik, A. F., Zuiderwijk, C. T. M., Vanboom, J. H., Elding, L. I. and Reedijk, J. (1991). Guanine-06 methylation reduces the reactivity of d(GpG) toward platinum complexes. J. Inorg. Biochem., 44, 249–260

    Article  PubMed  CAS  Google Scholar 

  • Szymkowski, D. E., Yarema, K., Essigmann, J. M., Lippard, S. J. and Wood, R. D. (1993). An intrastrand d(GpG) platinum crosslink in duplex M13 DNA is refractory to repair by human cell extracts. Proc. Natl Acad. Sci. USA, 89, 10772–10776

    Article  Google Scholar 

  • Taylor, J. and O’Day, C. L. (1990). cis-syn Thymine dimers are not absolute blocks to replication by DNA polymerase I of Escherichia coli in vitro. Biochemistry 29,1624–1632

    Google Scholar 

  • Teicher, B. A., Herman, T. S., Holden, S. A., Wang, Y., Pfeffer, M. R., Crawford, J. W. and Frei, E., III (1990). Tumor resistance to alkylating agents conferred by mechanisms operative only in vivo. Science, 247, 1457–1462

    PubMed  CAS  Google Scholar 

  • Terheggen, P. M. A. B., Emondt, J. Y., Root, B. G. J., Schrier, P. I., Den Engelse, L. and Begg, A. C. (1990). Correlation between cell killing by cisdiamminedichloroplatinum(II) in six mammalian cell lines and binding of a cis-diamminedichloroplatinum(II)-DNA antiserum. Cancer Res., 50, 3556–3561

    PubMed  CAS  Google Scholar 

  • Terheggen, P. M. A. B., Root, B. G. J., Lempers, E. L. M., van Tellingen, O., Begg, A. C. and den Engelse, L. (1991). Antibodies against cisplatin-modified DNA and cisplatin-modified (di)nucleotides. Cancer Chemother. Pharmacol., 28, 185–191

    Article  PubMed  CAS  Google Scholar 

  • Terleth, C., van de Putte, P. and Brouwer, J. (1991). New Insights in DNA Repair: Preferential Repair of Transcriptionally Active DNA. Mutagenesis, 6, 103–111

    Article  PubMed  CAS  Google Scholar 

  • Tilby, M. J., Johnson, C., Knox, R. J., Cordell, J., Roberts, J. J. and Dean, C. J. (1991). Sensitive detection of DNA modifications induced by cisplatin and carboplatin in vitro and in vivo using a monoclonal antibody. Cancer Res., 51, 123–129

    PubMed  CAS  Google Scholar 

  • Toney, J. H., Donahue, B. A., Kellett, P. J., Bruhn, S. L., Essigmann, J. M. and Lippard, S. J. (1989). Isolation of cDNAs encoding a human protein that binds selectively to DNA modified by the anticancer drug cis-diamminedichloroplatinum(II). Proc. Natl Acad. Sci. USA, 86, 8328–8332

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  • Tullius, T. D. and Lippard, S. J. (1981). cis-Diamminedichloroplatinum(II) binds in a unique manner to oligo(dG)-Oligo(dC) sequences in DNA — A new assay using exonuclease III. J. Am. Chem. Soc., 103, 4620–4622

    Google Scholar 

  • Tullius, T. D. and Lippard, S. J. (1982). Ethidium bromide changes the nuclease-sensitive DNA binding sites of the antitumor drug cis-diamminedichloroplatinum(II). Proc. Natl Acad. Sci. USA, 79, 3489–3492

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  • Urata, H. and Akagi, M. (1989). Mechanism of the reversal reaction of platinated DNA with thiourea studied by platinated 5’-GMP. Biochem. Biophys. Res. Commun., 161, 819–824

    Article  PubMed  CAS  Google Scholar 

  • Urata, H., Fujikawa, K., Tamura, M. and Akagi, M. (1990). Stability of platinated oligonucleotide duplexes containing a base pair mismatch at the site complementary to the platination site. J. Am. Chem. Soc., 112, 8611–8612

    Article  CAS  Google Scholar 

  • Urata, H., Ueno, M., Yamasaki, F. and Akagi, M. (1991). Interstrand crosslinking of the hexadeoxynucleotide d(TACGTA) upon reaction with transdiamminedichloroplatinum(II). Biochem. Biophys. Res. Commun., 175, 537–542

    Article  PubMed  CAS  Google Scholar 

  • van Garderen, C. J., Altona, C. and Reedijk, J. (1988). Alterations in the d(CpGpT) structure in solution as a result of [platinum chloro(diethylenetriamine]+ binding. Eur. J. Biochem., 178, 115–121

    Article  PubMed  CAS  Google Scholar 

  • van Garderen, C. J., Altona, C. and Reedijk, J. (1990). Conformational changes in a single- and double-stranded nonanucleotide upon complexation of a monofunctional platinum compound as studied by 111 NMR, 31P NMR, and CD methods. Inorg. Chem., 29, 1481–1487

    Article  CAS  Google Scholar 

  • van Garderen, C. J., Bloemink, M. J., Richardson, E. and Reedijk, J. (1991). Formation and structure of the reaction products of PtC12(en) with d(pGpG) and d(GpG); preference for d(GpG) chelation after phosphate dehydronation. J. Inorg. Biochem., 42, 199–205

    Article  CAS  Google Scholar 

  • van Garderen, C. J., van den Elst, H., van Boom, J. H., Reedijk, J. and van Houte, L. P. A. (1989). A double-stranded DNA fragment shows a significant decrease in double-helix stability after binding of monofunctional platinum amine compounds. J. Am. Chem. Soc., 111, 4123–4125

    Article  CAS  Google Scholar 

  • Villani, G., Hübscher, U. and Butour, J. L. (1988). Sites of termination of in vitro DNA synthesis on cis-diamminedichloroplatinum(II) treated single-stranded DNA: A comparison between E. coli DNA polymerase I and eucaryotic DNA polymerase a. Nucleic Acid Res., 16, 4407–4418

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  • Visse, R., de Ruijter, M. Brouwer, J., Brandsma, J. A. and van de Putte, P. (1991). uvr Excision repair protein complex of Eschericia coli binds to the convex side of a cisplatin-induced kink in the DNA. J. Biol. Chem., 266, 7609–7617

    Google Scholar 

  • Vrieling, H., van Rooijen, M. L., Groen, N. A., Zdzienicka, Z., Simons, J. W. I. M., Lohman, P. H. M., and van Zeeland, A. A. (1989). DNA Strand Specificity for UV-induced Mutations in Mammalian Cells. Mol. Cell. Biol., 9, 1277–1283

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  • Walker, G. C. (1984). Mutagenesis and inducible responses to deoxyribonucleic acid damage in Escherichia coli. Microbiol. Rev., 48, 60–93

    PubMed  CAS  Google Scholar 

Download references

Authors

Editor information

Editors and Affiliations

Copyright information

© 1993 The contributors

About this chapter

Cite this chapter

Comess, K.M., Lippard, S.J. (1993). Molecular Aspects of Platinum-DNA Interactions. In: Neidle, S., Waring, M.J. (eds) Molecular Aspects of Anticancer Drug-DNA Interactions. Topics in Molecular and Structural Biology. Palgrave, London. https://doi.org/10.1007/978-1-349-12356-8_5

Download citation

  • DOI: https://doi.org/10.1007/978-1-349-12356-8_5

  • Publisher Name: Palgrave, London

  • Print ISBN: 978-1-349-12358-2

  • Online ISBN: 978-1-349-12356-8

  • eBook Packages: EngineeringEngineering (R0)

Publish with us

Policies and ethics