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Interaction of Platinum Antitumor Compounds with DNA

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Book cover Nucleic Acids and Molecular Biology 4

Part of the book series: Nucleic Acids and Molecular Biology ((NUCLEIC,volume 4))

Abstract

The cis and trans isomers of diamminedichloroplatinum(II) (cis- and trans- DDP, Fig. 1) have enjoyed a long history in inorganic chemistry, having first been synthesized and separated in the 19th century. Until recently, however, complexes of the platinum group metals were of little interest to medicinal chemists owing to their reputation as highly toxic compounds. Interest in the biological effects of platinum complexes was greatly stimulated following reports that cis,-[Pt(NH3)2CI4] and related cis-coordinated platinum ammine chloride complexes induced filamentous growth in Escherichia coli, an indication of DNA damage (Rosenberg et al. 1965; Rosenberg et al. 1967; Rosenberg 1980). Subsequent demonstration that cis-DDP exhibited antitumor activity in mice led to clinical trials and eventual FDA approval for its use as an anticancer drug (Rosenberg et al. 1969; Rosenberg 1980).

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Abbreviations

AMP:

2’-deoxyadenosine-5’-monophosphate

bp:

base pair

cis-DDP:

cis-diamminedichloroplatinum(II)

CD:

circular dichroism

CMP:

2’deoxycytosine-5’-monophosphate

D/N:

drug to nucleotide ratio

ΔH*:

enthalpy of activation

ΔS*:

entropy of activation

dA:

2’deoxyadenosine

dC:

2’deoxycytosine

dG:

2’deoxyguanosine

dien:

diethylenetriamine

DNA:

deoxyribonucleic acid

dT:

2’deoxythymidine

en:

ethylenediamine

GMP:

2’deoxy guanosine-5’-monophosphate

NMR:

nuclear magnetic resonance

ppm:

parts per million

RNA:

ribonucleic acid

trans-DDP:

trans-diamminedichloroplatinum(II)

dUMP:

2’deoxyuridine-5’-monophosphate

References

  • Admiraal G, van der Veer JL, de Graaf RAG, den Hartog JHJ, Reedijk J (1987) Intrastrand bis-guanine chelation of d(CpGpG) to cis-platinum: an X-ray single crystal structure analysis. J Am Chem Soc 109: 592–596

    CAS  Google Scholar 

  • Alazard R, Germanier M, Johnson NP (1982) Mechanism of toxicity of platinum(II) compounds in repair-deficient strains of E. coli. Mutat Res 209, 63: 326–337

    Google Scholar 

  • Andrews PA, Murphy MP, Howell SB (1985) Differential potentiation of alkylating and platinating agent cytotoxicity in human ovarian carcinoma cells by glutathione depletion. Cancer Res 46: 6250–6253

    Google Scholar 

  • Appleton TG, Berry RD, Davis CA, Hall JR, Kimlin HA (1984a) Reactions of platinum(II) aqua complexes. 1. Multinuclear (195Pt, 15N, and 31P) NMR study of reactions between the c/s-diamminediaquaplatinum(II) cation and the oxygen-donor ligands hydroxide, Perchlo¬rate, nitrate, sulfate, phosphate, and acetate. Inorg Chem 23: 3514–3531

    Google Scholar 

  • Appleton TG, Hall JR, Ralph SR, Thompson CSM (1984b) Reactions of platinum(II) aqua complexes. 2. 195Pt NMR study of reactions between the tetraaquaplatinum(II) cation and chloride, hydroxide, Perchlorate, nitrate, sulfate, phosphate, and acetate. Inorg Chem 23: 3521–3525

    Google Scholar 

  • Aprile F, Martin DS (1962) Chlorotriammineplatinum(II) ion. Acid hydrolysis and isotopic exchange of chloride ligand. Inorg Chem 1: 551–557

    Google Scholar 

  • Balcarová Z, Brabec V (1986) DNA modified by platinum derivatives cannot adopt the A form. Biochim Biophys Acta 867: 31–35

    PubMed  Google Scholar 

  • Bancroft DP, Lepre CA, Lippard SJ (1990) 195Pt NMR kinetic and mechanistic studies of cis- and trans-diamminedichloroplatinum(II) binding to DNA. J Am Chem Soc (in press)

    Google Scholar 

  • Banerjea D, Basolo F, Pearson RG (1957) Mechanism of substitution reactions of complex ions. XII. Reactions of some platinum(II) complexes with various reactants. J Am Chem Soc 79: 4055–4062

    Google Scholar 

  • Basolo F, Pearson RG (1967) Mechanisms of inorganic reactions, 2nd edn. Wiley, New York

    Google Scholar 

  • Basu AK, Essigmann JM (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 

  • Beck DJ, Popoff S, Sancar A, Rupp WD (1985) Reactions of the UVRABC excision nuclease with DNA damaged by diamminedichloroplatinum(II). Nucleic Acids Res 20: 7395–7412

    Article  Google Scholar 

  • Bedford P, Fichtinger-Schepman AM, Shellard SA, Walker MC, Masters JRW, Hill BT (1988) Differential repair of Pt-DNA adducts in human bladder and testicular tumor continuous cell lines. Cancer Res 48: 3019–3024

    PubMed  CAS  Google Scholar 

  • Bellon SF, Lippard SJ (1990) Bending studies of DNA site-specifically modified by cisplatin, trans-diamminedichloroplatinum(II) and cis-[Pt(NH3)2(N3-cytosine)CI]+. Biophys Chem 35: 179–188

    Article  PubMed  CAS  Google Scholar 

  • Bodenner DL, Dedon PC, Keng PC, Borch RF (1986) Effect of diethyldithiocarbamate on cis-diamminedichloroplatinum(II)-induced cytotoxicity, DNA cross-linking, and y-glutamyl transpeptidase inhibition. Cancer Res 46: 2745–2750

    PubMed  CAS  Google Scholar 

  • Böhm S, Oriana S, Spatti GB, Tognella S, Tedeschi M, Zunino F, Di Re F (1988) A clinical study of reduced glutathione as a protective agent against cisplatin-induced toxicity. In: Nicolini M (ed) Platinum and other metal complexes in cancer chemotherapy. Nijhoff, Boston, pp 456–459

    Chapter  Google Scholar 

  • Borch RF, Pleasants ME (1979) The inhibition of cis-platinum nephrotoxicity by diethyldi-thiocarbamate rescue in a rat model. Proc Natl Acad Sci USA 76: 6611–6614

    Article  PubMed  CAS  Google Scholar 

  • Borch RF, Dedon PC, Gringeri A, Montine TJ (1988) Inhibition of platinum drug toxicity by diethyldithiocarbamate. In: Nicolini M (ed) Platinum and other metal coordination complexes in cancer chemotherapy. Nijhoff, Boston, pp 216–227

    Chapter  Google Scholar 

  • Bose RN, Cornelius RD, Viola RE (1986) Multinuclear NMR studies and kinetics of formation of platinum(II)-adenine nucleotide complexes. J Am Chem Soc 108: 4403–4408

    Article  CAS  Google Scholar 

  • Brouwer J, van de Putte P, Fichtinger-Schepman AM, Reedijk J (1981) Base pair substitution hotspots in GAG and GCG nucleotide sequences in E. coli K12 induced by cis-diamminedichloroplatinum(II). Proc Natl Acad Sci USA 78: 7010–7014

    Article  PubMed  CAS  Google Scholar 

  • Bruhn, Toney JH, Lippard SJ (1990) Biological processing of DNA modified by platinum anticancer drugs. In: Lippard SJ (ed) Prog Inorg Chem, vol 39 (in press)

    Google Scholar 

  • Butour JL, Johnson NP (1986) Chemical reactivity of platinum-DNA adducts. Biochemistry 25: 4543–4539

    Article  Google Scholar 

  • Chu GYH, Mansy S, Duncan RE, Tobias RS (1978) Heavy metal nucleotide interactions. II. Stereochemical and electronic effects in the electrophilic attack of cis- and trans-diammineplatinum(II) on 5’-guanosine monophosphate and polyguanylate in aqueous solution. J Am Chem Soc 100: 593–606

    Article  CAS  Google Scholar 

  • Ciccarelli RB, Solomon MJ, Varshavsky A, Lippard SJ (1985) In vivo effects of cis- and trans-diamminedichloroplatinum(II) on SV40 chromosomes: differential repair, DNA-protein crosslinking, and inhibition of replication. Biochemistry 24: 7533–7540

    Google Scholar 

  • Clore GM, Gronenborn AM (1982) Kinetic and structural studies of the intermediates formed in the reactions of 5’-adenosine monophosphate and 5’-guanosine monophosphate with cis-dichlorodiammineplatinum(II) using 1H and 195Pt magnetic resonance spectroscopy. J Am Chem Soc 104: 1369–1375

    Article  CAS  Google Scholar 

  • Cohen GL, Bauer WR, Barton JK, Lippard SJ (1979) Binding of cis- and trans-dichlorodiammineplatinum(II) to DNA: evidence for shortening and unwinding of the double helix. Science 203: 1014–1016

    Article  PubMed  CAS  Google Scholar 

  • Cohen GL, Ledner JA, Bauer WR, Ushay HM, Caravana C, Lippard SJ (1980) Sequence dependent binding of cis-dichlorodiammineplatinum(II) to DNA. J Am Chem Soc 102: 2487–2488

    Article  CAS  Google Scholar 

  • Coley RF, Martin DS (1972) Kinetics and equilibria for the acid hydrolysis of dichloro(ethylenediamine)platinum(II). Inorg Chim Acta 7: 573–577

    Article  Google Scholar 

  • Comess KM, Costello CE, Lippard SJ (1990) Identification and characterization of a novel linkage isomerization in the reaction of trans-diamminedichloroplatinum(II) with 5’- d(TCTACGCGTTCT). Biochemistry 29: 2102–2110

    Article  PubMed  CAS  Google Scholar 

  • Daley-Yates PT, McBrien DCH (1982) The inhibition of renal ATPase by cisplatin and some biotransformation products. Chem-Biol Interact 40: 325–334

    Article  PubMed  CAS  Google Scholar 

  • Dedon PC, Borch RF (1987) Characterization of the reactions of platinum antitumor agents with biologic and non-biologic sulfur-containing nucleophiles. Biochem Pharmacol 36: 1955–1964

    Article  PubMed  CAS  Google Scholar 

  • den Hartog JHJ, Altona C, Chottard JC, Girault JP, Lallemand JY, de Leeuw F, Marcelis ATM, Reedijk J (1982) Conformational analysis of the adduct cis-[Pt(NH3)2{d(GpG)}]+ in aqueous solution. A high field (500–300 MHz) nuclear magnetic resonance investigation. Nucleic Acids Res 10: 4715–4731

    Google Scholar 

  • den Hartog JHJ, Altona C, van Boom JH, van der Marel GA, Haasnoot CAG, Reedijk J (1984a) cis-Diamminedichloroplatinum(II) induced distortion in a double helical DNA fragment. J Am Chem Soc 106: 1528–1530

    Article  Google Scholar 

  • den Hartog JHJ, Altona C, van Boom JH, Reedijk J (1984b) A phosphorus NMR study of the reaction products of cis-diamminedichloroplatinum(II) with a double-helical oligonucleotide and with DNA. FEBS Lett 176: 393–397

    Article  Google Scholar 

  • den Hartog JHJ, Altona C, van Boom JH, van der Marel GA, Haasnoot CAG, Reedijk J (1985a) cis-Diamminedichloroplatinum(II) induced distortion of a single and double-stranded deoxydecanucleosidenonaphosphate studied by nuclear magnetic resonance. J Biomol Struct Dyn 2: 1137–1155

    Google Scholar 

  • den Hartog JHJ, Altona C, van den Elst H, van der Marel GA, Reedijk J (1985b) Unwinding in an undecamer double-helical DNA fragment, after binding of cis-PtCI2(NH3)2 to a d(GTG) sequence. Inorg Chem 24: 983–984

    Article  Google Scholar 

  • Dijt FJ, Canters GW, den Hartog JHJ, Marcelis ATM, Reedijk J (1984) Reaction products of cis-diammineplatinum compounds with 5’-guanosine monophosphate characterized by high frequency proton NMR. J Am Chem Soc 106: 3644–3647

    Article  CAS  Google Scholar 

  • Eastman A (1982a) Separation and characterization of products resulting from the reaction of ds-diamminedichloroplatinum(II) with deoxyribonucleosides. Biochemistry 21: 6732–6736

    Article  PubMed  CAS  Google Scholar 

  • Eastman A (1982b) Comparison of the interaction cis- and trans-diamminedichloroplatinum(II) with DNA by a simple filter binding assay. Biochem Biophys Res Commun 105: 869–875

    Article  PubMed  CAS  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

    Article  PubMed  CAS  Google Scholar 

  • Eastman A (1985) Interstrand crosslinks and sequence specificity in the reaction of cis-dichloro(ethylenediamine)platinum(II) with DNA. Biochemistry 24: 5027–5032

    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 

  • Eastman A (1987a) The formation, isolation, and characterization of DNA adducts produced by anticancer platinum complexes. Pharmacol Ther 34: 155–166

    Article  PubMed  CAS  Google Scholar 

  • Eastman A (1987b) Crosslinking of gutathione to DNA by cancer chemotherapeutic platinum coordination complexes. Chem-Biol Interact 61: 241–248

    Article  PubMed  CAS  Google Scholar 

  • Eastman A, Barry MA (1987) Interaction of trans-diamminediehloroplatinum(II) with DNA: formation of monofunctional adducts and their reaction with glutathione. Biochemistry 26: 3303–3307

    Article  PubMed  CAS  Google Scholar 

  • Eastman A, Jennerwein MM, Nagel DL (1988) Characterization of Afunctional adducts produced in DNA by trans-diamminedichloroplatinum(II). Chem-Biol Interact 67: 71–80

    Article  PubMed  CAS  Google Scholar 

  • Elleman TS, Reishus JW, Martin DS (1957) The acid hydrolysis (aquation) of the trichloroammineplatinate(II) ion. J Am Chem Soc 80: 536–541

    Article  Google Scholar 

  • Fanchiang YT (1986) Reaction intermediates of ds-diammineaqua(hydroxo)platinum(II) with guanosine 5’-monophosphate characterized by proton NMR spectroscopy. J Chem Soc, Dalton Trans 1: 135–140

    Google Scholar 

  • Fichtinger-Schepman AMJ, Lohman PHM, Reedijk J (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: 5345–5357

    Article  PubMed  CAS  Google Scholar 

  • Fichtinger-Schepman AMJ, van der Veer JL, den Hartog JHJ, Lohman PHM, Reedijk J (1985) Adducts of the antitumor drug cis-diamminedichloroplatinum(II) with DNA: formation, identification, and quantitation. Biochemistry 24: 707–713

    Article  PubMed  CAS  Google Scholar 

  • Fichtinger-Schepman AMJ, van Oosterom AT, Lohman PHM, Berends F (1987) cis-Diamminedichloroplatinum(II)-induced DNA adducts in peripheral leukocytes from seven cancer patients. Cancer Res 47: 3000–3004

    PubMed  CAS  Google Scholar 

  • Fichtinger-Schepman AMJ, Dijt FT, de Jong WH, van Oosterom AT, Berends F (1988) In vivo cis-diammmedichloroplatinum(II) adduct formation and removal as measured by immunochemical techniques. In: Nicolini M (ed) Platinum and other metal coordination complexes in cancer chemotherapy. Nijhoff, Boston, pp 33–46

    Google Scholar 

  • Filipski J, Kohn KW, Prather R, Bonner WM (1979) Thiourea reverses crosslinks and restores biological activity in DNA treated with dichlorodiamminoplatinum(II). Science 204: 181–183

    Article  PubMed  CAS  Google Scholar 

  • Filipski J, Kohn KW, Bonner WM (1980) The nature of inactivating lesions produced by platinum(II) complexes in phage λ DNA. Chem-Biol Interact 32: 321–330

    Article  PubMed  CAS  Google Scholar 

  • Fouts CS, Reily MD, Marzili LG, Zon G (1987) 31P NMR investigation of fourteen self-complementary oligodeoxyribunocleotides (8-mer to 14-mer) treated with platinum complexes. Inorg Chim Acta 137: 1–13

    Article  Google Scholar 

  • Fouts CS, Marzili LG, Byrd RA, Summers MF, Zon G, Shinozuka K (1988) HMQC and 1H and 31P NMR studies of platinum amine adducts of tetradeoxyribonucleotides. Relationship between 31P shift and potential hydrogen-bonding interactions in pGpG moieties cross-linked by platinum. Inorg Chem 27: 366–376

    Article  CAS  Google Scholar 

  • Fraval HNA, Rawlings CJ, Roberts JJ (1978) Increased sensitivity of UV-repair deficient human cells to DNA bound platinum products which unlike thymine dimers are not recognized by an endonuclease extracted from M. Luteus. Mutat Res 51: 121–132

    Article  PubMed  CAS  Google Scholar 

  • Gibson D, Lippard SJ (1987) Synthesis and NMR structural studies of the adduct of trans-diamminedichloroplatinum(II) with the DNA fragment d(GCG). Inorg Chem 26: 2275–2279

    Article  CAS  Google Scholar 

  • Gralla JD, Sesse-Dwight S, Poljak LG (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 

  • Guarino AM, Miller DS, Arnold ST, Pritchard JB, Davis RD, Urbanek MA, Miller TJ, Litterst CL (1979) Platinate toxicity: past, present, and prospects. Cancer Treat Rep 63: 1475–1483

    PubMed  CAS  Google Scholar 

  • Hamilton TC, Winkler MA, Louie KG, Batist G, Behrens BC, Tsuruo T, Grotzinger KR, McKoy WM, Young RC, Ozols RF (1985) Augmentation of adriamycin, melphalan, and cisplatin cytotoxicity in drug-resistant and sensitive human ovarian cell lines by buthionine sulfoximine mediated glutathione depletion. Biochem Pharmacol 34: 2583–2586

    Article  PubMed  CAS  Google Scholar 

  • Harder HC (1975) Renaturation effects of cis and trans platinum II and IV compounds on calf thymus DNA. Chem-Biol Interact 10: 27–32

    Article  PubMed  CAS  Google Scholar 

  • Harder HC, 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

    Google Scholar 

  • Harder HC, Smith RG, Leroy AF (1976) Template primer inactivation by cis- and trans-dichlorodiammineplatinum(II) for human DNA polymerase a, β, and Rauscher murine leukemia virus reverse transcriptase, as a mechanism of toxicity. Cancer Res 36: 3821–3829

    PubMed  CAS  Google Scholar 

  • Heiger-Bernays WJ, Essigmann JM, Lippard SJ (1990) Effects of the antitumor drug cis-diamminedichloroplatinum(II) and related platinum complexes on eukaryotic DNA replication. Biochemistry 29 (in press)

    Google Scholar 

  • Hemminki K. Thilly WG (1988) Binding of cisplatin to specific sequences of human DNA in vitro. Mutat Res 202: 133–138

    Google Scholar 

  • Hollis LS, Amundsen AR, Stern EW (1989) Chemical and biological properties of a new series of cis-diammineplatinum(II) antitumor agents containing three nitrogen donors: cis- [Pt(NH3)2(N-donor)CI]+. J Med Chem 32: 128–136

    Article  PubMed  CAS  Google Scholar 

  • Hospers GAP, Mulder NH, de Jong B, de Ley L, Uges DR, Fichtinger-Schepman AMJ, Scheper RJ, de Vries EG (1988) Characterization of a human small cell lung carcinoma cell line with acquired resistance to ds-diamminedichloroplatinum(II) in vitro. Cancer Res 48: 6803–6807

    CAS  Google Scholar 

  • Houssier C, Macquet MN, Fredericq E (1983) Denaturation level of DNA-Pt complexes evidenced by Tb3+ fluorescence enhancement and electric dichroism. Biochim Biophys Acta 739: 312–316

    PubMed  CAS  Google Scholar 

  • Howe-Grant ME, Lippard SJ (1980) Aqueous platinum(II) chemistry; binding to biological molecules. In: Sigel H (ed) Metal ions in biological systems, vol 2. Marcel Dekker, New York

    Google Scholar 

  • Howell SB, Taetle R (1980) Effect of sodium thiosulfate on cis-dichlorodiammineplatinum(II) toxicity and antitumor activity in L1210 leukemia. Cancer Treat Rep 64: 611–616

    PubMed  CAS  Google Scholar 

  • Johnson NP, Hoeschle JD, Rahn RO (1980) Kinetic analysis of the in vitro binding of radioactive cis- and trans-dichlorodiammineplatinum(II) to DNA. Chem-Biol Interact 30: 151–169

    Article  PubMed  CAS  Google Scholar 

  • Johnson NP, Macquet JP, Weibers JL, Monsarrat B (1982) Structures of adducts formed between [Pt(dien)Cl]Cl and DNA in vitro. Nucleic Acids Res 10: 5255–5271

    Article  PubMed  CAS  Google Scholar 

  • Johnson NP, Lapetoule P, Razaka H, Villani G (1985a) Biological and biochemical effects of DNA damage caused by platinum compounds. In: McBrien DCH, Slater TF (eds) Biochemical mechanisms of platinum antitumor drugs. IRL, Oxford, pp 1–28

    Google Scholar 

  • Johnson NP, Mazard AM, Escalier J, Macquet JP (1985b) Mechanism of the reaction between cis-[Pt(NH3)2Cl2] and DNA in vitro. J Am Chem Soc 107: 6376–6380

    Article  CAS  Google Scholar 

  • Johnson NP, Lapetoule P, Razaka H, Butour JL (1988) Kinetics of formation of genotoxic platinum-DNA lesions in vivo. In: Nicolini M (ed) Platinum and other metal complexes in cancer chemotherapy. Nijhoff, Boston, pp 5–15

    Google Scholar 

  • Kelman AD, Buchbinder M (1978) Platinum-DNA crosslinking: platinum antitumor drug interactions with native lambda bacteriophage DNA studied using a restriction endonuclease. Biochimie 60: 893–899

    Article  CAS  Google Scholar 

  • Knox RJ, Friedlos F, Lydall DA, Roberts JJ (1986) Mechanism of cytotoxicity of anticancer platinum drugs: evidence that cis-diamminedichloroplatinum(II) and cis-diammine(1, 1-cyclobutanedicarboxylate)platinum(II) differ only in the kinetics of their interaction with DNA. Cancer Res 46: 1972–1979

    CAS  Google Scholar 

  • Kosower NS, Kosower EM (1978) The glutathione status of cells. Int Rev Cytol 54: 109–119

    Article  PubMed  CAS  Google Scholar 

  • Kozelka J, Archer S, Petsko GA, Lippard SJ (1987) Molecular mechanics modeling of oligonucleotide adducts of the antitumor drug cis-diamminedichloroplatinum(II). Biopolymers 26: 1245–1271

    Article  PubMed  CAS  Google Scholar 

  • Langford CH, Gray HB (1966) Ligand substitution processes. WA Benjamin, London

    Google Scholar 

  • Lepre CA, Strothkamp KG, Lippard SJ (1987) Synthesis and 1H 1NMR spectroscopic characterization of trans-[Pt(NH3)2{d(AGGCCT) N7-A(l), N7-G(3)}]. Biochemistry 26: 5651–5657

    Article  PubMed  CAS  Google Scholar 

  • Lepre CA, Chassot L, Costello C, Lippard SJ (1990) Synthesis and characterization of trans-[Pt(NH3)2Cl2] adducts of [d(CCTCGAGTCTCC)·d(GGAGACTCGAGG)]. Biochemistry 29: 811–823

    Article  PubMed  CAS  Google Scholar 

  • Lim MC, Martin RB (1976) The 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 SJ (1982) New chemistry of an old molecule: cis-[Pt(NH3)2Cl2]. Science 218: 1075–1082

    Article  PubMed  CAS  Google Scholar 

  • Lippert B (1988) Modelling platinum-nucleic acids interactions coordination chemistry with biological aspects. Gazz Chim Ital 118: 153–165

    CAS  Google Scholar 

  • Loehrer PJ, Einhorn LH (1984) Cisplatin. Ann Intern Med 100: 704–713 Macquet JP, Butour JL (1978a) Modifications of DNA secondary structure upon platinum binding: a proposed model. Biochemie 60: 901–914

    Google Scholar 

  • Macquet JP, Butour JL (1978b) A circular dichroism study of DNA-platinum complexes. Eur J Biochem 83: 375–387

    Article  PubMed  CAS  Google Scholar 

  • Macquet JP, Theophanides T (1975) DNA-platinum interactions in vitro with trans- and cis-Pt(NH3)2Cl2. Bioinorg Chem 5: 59–66

    Article  PubMed  CAS  Google Scholar 

  • Malfoy B, Hartmann B, Leng M (1981) The B→Z transition of poly (dG-dC)·poly(dG-dC) modified by some platinum derivatives. Nucleic Acids Res 9: 5659–5669

    Article  PubMed  CAS  Google Scholar 

  • Malinge JM, Leng M (1988) Reactivity of monofunctional cis-platinum adducts as a function of DNA sequence. Nucleic Acids Res 16: 7663–7672

    PubMed  CAS  Google Scholar 

  • Mansy S, Rosenberg B, Thomson AJ (1978) Binding of cis- and trans-dichlorodiammineplatinum(II) to nucleosides. 1. Location of binding sites J Am Chem Soc 95: 1633–1640

    Google Scholar 

  • Marcelis ATM, van Kralingen CG, Reedijk J (1980) Interactions of cis- and trans-diammine compounds with 5’-guanosine monophosphate and 5’-deoxyguanosine monophosphate. A proton NMR investigation. J Inorg Biochem 13: 213–222

    Google Scholar 

  • Marcelis ATM, Erkelens C, Reedijk J (1984) The interaction of aquated platinum(II) compounds with purine mononucleotides. Inorg Chim Acta 91: 129–135

    Article  CAS  Google Scholar 

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

    Article  PubMed  CAS  Google Scholar 

  • Marzilli LG, Reily MD, Heyl BL, McMurray CT, Wilson WD (1984) Evidence for similar structural changes on binding of platinum antitumor agents to DNA and nucleosomes. FEBS Lett 176: 389–392

    Article  PubMed  CAS  Google Scholar 

  • Mazeau K, Vovelle F, Rahmouni A, Leng M, Ptak M (1989) Structure of the intrastrand cis-[Pt(NH3)2{d(GCG)}] adduci in a dodecanucleotide duplex. II. A molecular mechanics modelling study. Anti-Cancer Drug Design 4: 63–78

    Google Scholar 

  • Millar DP, Ho KM, Aroney MJ (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 KJ, Taylor ER, Basch H, Krauss M, Stevens WJ (1985) A theoretical model for the binding of cis-Pt(NH3)2+2 to DNA. J Biomol Struct Dyn 2: 1157–1170

    PubMed  CAS  Google Scholar 

  • Miller SK, Marzilli LG (1985) Interaction of platinum antitumor agents with guanine nucleosides and nucleotides. Inorg Chem 24: 2421–2425

    Article  CAS  Google Scholar 

  • Naser LJ, Pinto AL, Lippard SJ, Essigmann JM (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 

  • Norman RE, Sadler PJ (1988) 14N NMR studies of amine release from platinum antitumor drugs: models and human blood plasma.

    Google Scholar 

  • Inorg Chem 27: 3583–3587

    Google Scholar 

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

    Article  PubMed  CAS  Google Scholar 

  • Pinto AL, Lippard SJ (1985a) Binding of the antitumor drug cis-diamminedichloroplatinum(II) (cisplatin) to DNA. Biochim Biophys Acta 780: 167–180

    PubMed  CAS  Google Scholar 

  • Pinto AL, Lippard SJ (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  CAS  Google Scholar 

  • Plooy ACM, van Dijk M, Lohman PHM (1984) Induction and repair of DNA crosslinks 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 

  • Popoff SC, Beck DJ, Rupp WD (1987) Repair of plasmid DNA damaged in vitro with cis- or trans-diamminedichloroplatinum(II) in E. coli. Mutat Res 183: 129–137

    PubMed  CAS  Google Scholar 

  • Ptak M, Rahmouni A, Mazeau K, Thuong NT, Leng M (1989) Structure of the intrastrand cis-[Pt(NH3)2(d(GCG)}] adduct in a dodecanucleotide duplex. I. A 1H and 31P NMR study. Anti-Cancer Drug Design 4: 53–61

    PubMed  CAS  Google Scholar 

  • Pullman A, Pullman B (1981) Molecular electrostatic potential of the nucleic acids. Q Rev Biophys 14: 289–380

    Article  PubMed  CAS  Google Scholar 

  • Razaka H, Villani G, Hoffman JS, Defais M, Johnson NP (1988) Enhanced mutagenesis during post-treatment incubation of E. coli treated with cis-diamminedichloroplatinum(II). Mutat Res 209: 63–66

    Article  PubMed  CAS  Google Scholar 

  • Reed E, Ozols RF, Tarone R, Yuspa SH, Poirier MC (1987) Platinum-DNA adducts in leukocyte DNA correlate with disease response in ovarian cancer patients receiving platinum-based chemotherapy. Proc Natl Acad Sci USA 84: 5024–5028

    Article  PubMed  CAS  Google Scholar 

  • Reedijk J (1987) The mechanism of action of platinum antitumor drugs. Pure Appl Chem 59: 181–192

    Article  CAS  Google Scholar 

  • Reily MD, Marzilli LG (1985) 31P and 1H NMR spectroscopic studies of platinum adducts of poly(I)·poly(C). The antitumor agent cis-Pt(NH3)2Cl2 forms an N7, N7 bis-adduct. J Am Chem Soc 107: 4916–4924

    Google Scholar 

  • Reslova-Vasilukova S (1974) Indirect induction of prophage lambda by cis-dichlorodiammineplatinum(II) treatment. In: Conners TA, Roberts JJ (eds) Recent results in cancer research, vol 48. Springer, Berlin Heidelberg New York, pp 105–106

    Google Scholar 

  • Rice JA, Crothers DM, Pinto AL, Lippard SJ (1988) The major adduct of the antitumor drug cis-diamminedichloroplatinum(II) with DNA bends the duplex by ~ 40° toward the major groove. Proc Natl Acad Sci USA 85: 4158–4161

    Article  PubMed  CAS  Google Scholar 

  • Richon VM, Schulte N, Eastman A (1987) Multiple mechanisms of resistance to cis-diamminedichloroplatinum(II) in murine leukemia L1210 cells. Cancer Res 47: 2056–2061

    PubMed  CAS  Google Scholar 

  • Roberts JJ, Friedlos F (1987) Quantitative estimation of cisplatin-induced DNA interstrand crosslinks and their repair in mammalian cells: relationship to toxicity. Pharmacol Ther 34: 215–246

    Article  PubMed  CAS  Google Scholar 

  • Rosenberg B (1980) Platinum complexes for the treatment of cancer. In: Spiro TG (ed) Nucleic acid-metal-ion interactions, chap 1. John Wiley, New York (Metal ions in biology, vol 1 )

    Google Scholar 

  • Rosenberg B, van Camp L, Krigas T (1965) Inhibition of cell division in E. coli by electrolysis products from a platinum electrode. Nature 205: 698–699

    Article  PubMed  CAS  Google Scholar 

  • Rosenberg B, van Camp L, Grimely EB, Thomson AJ (1967) The inhibition of growth or cell division in E. coli by different ionic species of Pt(IV) complexes. J Biol Chem 242: 1347–1352

    PubMed  CAS  Google Scholar 

  • Rosenberg B, van Camp L, Trosko JE, Mansour VH (1969) Platinum complexes: a new class of potent antitumor agents. Nature 222: 385–386

    Article  PubMed  CAS  Google Scholar 

  • Royer-Pokora B, Gordon LK, Haseltine WA (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  CAS  Google Scholar 

  • Sarrazin M, Peyrot V, Briand C (1986) NMR studies of the interaction of cis-diamminedichloroplatinum(II) and corresponding hydrolysis products with adenosine phosphates. Inorg Chim Acta 124: 87–96

    Article  CAS  Google Scholar 

  • Schaller W, Reisner H, Holler E (1987) Kinetic investigation of the DNA platination reaction: evidence for a transient adduct between deoxyribonucleic acid and cis-platinum(II). Biochemistry 26: 943–950

    Article  PubMed  CAS  Google Scholar 

  • Schaller W, Reisner H, Holler E (1987) Kinetic investigation of the DNA platination reaction: evidence for a transient adduct between deoxyribonucleic acid and cis-platinum(II). Biochemistry 26: 943–950

    Article  PubMed  CAS  Google Scholar 

  • Scovell WM, Capponi VJ (1984) S1 nuclease sensitivity to cis- and trans-diamminedichloroplatinum(II) modified DNAs: influence of ( G + C) content and nucleotide sequence. Biochem Biophys Res Commun 124: 367–374

    Google Scholar 

  • Segal E, Le Pecq JB (1985) Role of ligand exchange processes in the reaction kinetics of the antitumor drug cis-diamminedichloroplatinum(II) with its targets. Cancer Res 45: 492–498

    PubMed  CAS  Google Scholar 

  • Sherman SE, Lippard SJ (1987) Structural aspects of platinum anticancer drug interactions with DNA. Chem Rev 87: 1153–1181

    Article  CAS  Google Scholar 

  • Sherman SE, Gibson D, Wang AHJ, Lippard SJ (1985) X-ray structure of the major adduct of the anticancer drug cisplatin with DNA: cis-[Pt(NH3)2{d(pGpG)}]. Science 230: 412–417

    Article  PubMed  CAS  Google Scholar 

  • Sherman SE, Gibson D, Wang AHJ, Lippard SJ (1988) Crystal and molecular structure of cis-[Pt(NH3)2{d(pGpG)}], the principal adduct formed by cis-diamminedichloroplatinum(II) with DNA. J Am Chem Soc 110: 7368–7381

    Article  CAS  Google Scholar 

  • Srivastava RC, Froehlich J, Eichhorn GL (1978) The effect of platinum binding on the structure of DNA and its function in RNA synthesis. Biochimie 60: 879–891

    Article  CAS  Google Scholar 

  • Sundquist WI, Lippard SJ (1986) Binding of cis- and trans-diamminedichloroplatinum(II) to deoxyribonucleic acid exposes nucleosides as measured immunochemically with anti-nucleoside antibodies. Biochemistry 25: 1520–1524

    Article  PubMed  CAS  Google Scholar 

  • Sundquist WI, Bancroft DP, Chassot L, Lippard SJ (1988) DNA promotes the reaction of cis-diamminedichloroplatinum(II) with the exocyclic amino groups of ethidium bromide. J Am Chem Soc 110: 8559–8560

    Article  CAS  Google Scholar 

  • Teo B-K, Eisenberger P, Reed J, Barton JK, Lippard SJ (1978) Study of the binding of cis- and trans-dichlorodiammineplatinum(II) to calf thymus DNA by EXAFS spectroscopy. J Am Chem Soc 100: 3225–3227

    Article  CAS  Google Scholar 

  • Tirmenstein MA, Reed DJ (1988) The glutathione status of rat kidney nuclei following administration of buthionine sulfoximine. Biochem Biophys Res Commun 155: 956–961

    Article  PubMed  CAS  Google Scholar 

  • Tucker MA, Colvin CB, Martin DS (1964) Substitution reactions of trichloroammineplatinate(II) ion and the trans effect. Inorg Chem 3: 1373–1383

    Article  CAS  Google Scholar 

  • Tucker MA, Colvin CB, Martin DS (1964) Substitution reactions of trichloroammineplatinate(II) ion and the trans effect. Inorg Chem 3: 1373–1383

    Article  CAS  Google Scholar 

  • Ushay HM (1984) The interaction of platinum antitumor complexes with DNA: reactivity of complexes, unwinding of superhelical DNA, restriction enzyme inhibition, and conformational changes. Ph. D. dissertation, Columbia University, New York

    Google Scholar 

  • Ushay HM, Tullius TD, Lippard SJ (1981) Inhibition of the Bam HI cleavage and unwinding of pBR322 DNA by the antitumor drug cis-diamminedichloroplatinum(II). Biochemistry 22: 3927–3933

    Google Scholar 

  • Ushay HM, Santella RM, Caradonna JP, Grunberger D, Lippard SJ (1982) Binding of [(dien)PtCl]Cl to poly(dG-dC)·poly(dG-dC) facilitates the B→Z conformational transition. Nucleic Acids Res 10: 3573–3589

    Article  PubMed  CAS  Google Scholar 

  • van der Veer JL, Ligtvoet GJ, van den Elst H, Reedijk J (1986a) trans-Diamminedichloroplatinum(II) can chelate d(GTG) via both guanines in a similar fashion as the cis isomer. J Am Chem Soc 108: 3860–3862

    Article  Google Scholar 

  • van der Veer JL, van den Elst H, den Hartog JHJ, Fichtinger-Schepman AMJ, Reedijk J (1986b) Reaction of the antitumor drug cis-diamminedichloroplatinum(II) with the trinucleotide d(GAG): identification of two main products and kinetic aspects of their formation. Inorg Chem 25: 4657–4663

    Article  Google Scholar 

  • van Garderen CJ, van den Elst H, van Boom JH, Reedijk J (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  Google Scholar 

  • van Hemelryck B, Guittet E, Chottard G, Girault JP, Huynh-Dinh T, Lallemand JY, Igolen J, Chottard JC (1984) A d(GpG) platinated oligonucleotide can form a duplex with a complementary strand. J Am Chem Soc 106: 3037–3039

    Article  Google Scholar 

  • van Hemelryck B, Guittet E, Chottard G, Girault JP, Herman F, Huynh-Dinh T, Lallemand JY, Igolen J, Chottard JC (1986) A high melting cis-[Pt(NH3)2{d(GpG)}] adduct of a decanucleotide duplex. Biochem Biophys Res Commun 130: 758–763

    Article  Google Scholar 

  • van Hemelryck B, Girault JP, Chottard G, Valadon P, Laoui A, Chottard JC (1987) Sequence dependent platinum chelation by ApG and GpA reacting with cis-diamminedichloroplatinum(II) and its diaqua derivative. Inorg Chem 26: 787–793

    Article  Google Scholar 

  • Villani G, Hübscher U, Butour JL (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 polymerases α. Nucleic Acids Res 16: 4407–4418

    Article  PubMed  CAS  Google Scholar 

  • Vrána O, Brabec V, Kleinwächter V (1986) Polarographic studies on the conformation of some platinum complexes: relations to antitumor activity. Anticancer Drug Design 1: 95–109 Wilson WD, Heyl BL, Reddy R, Marzilli L (1982) Diamagnetic metal species that induce pronounced changes in the 31P NMR spectrum of DNA. Inorg Chem 21: 2527–2528

    Google Scholar 

  • Wing RM, Pjura P, Drew HR, Dickerson RE (1984) The primary mode of binding of cisplatin to a B-DNA dodecamer: CGCGAATTCGCG. EMBO J 3: 1201–1206

    Google Scholar 

  • Zunino F, Tofanetti O, Besati A, Cavalletti E, Savi G (1983) Protective effect of reduced glutathione against cis-dichlorodiammineplatinum(II)-induced nephrotoxicity and lethal toxicity. Tumori 69: 105–111

    PubMed  CAS  Google Scholar 

  • Zwelling LA, Anderson T, Kohn KW (1979) DNA-protein and DNA interstrand cross-linking by cis- and trans-platinum(II)diamminedichloride in L1210 mouse leukemia cells and relation to cytotoxicity. Cancer Res 39: 365–369

    PubMed  CAS  Google Scholar 

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  1. Department of Chemistry, Massachussets Institute of Technology, Cambridge, MA, 02139, USA

    S. J. Lippard

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  1. C. A. Lepre
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  1. Abteilung Chemie, Max-Planck-Institut für experimentelle Medizin, Hermann-Rein-Straße 3, D-3400, Göttingen, Germany

    Fritz Eckstein

  2. Biochemistry Department, University of Dundee, GB-Dundee, DD1 4HN, UK

    David M. J. Lilley

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Lepre, C.A., Lippard, S.J. (1990). Interaction of Platinum Antitumor Compounds with DNA. In: Eckstein, F., Lilley, D.M.J. (eds) Nucleic Acids and Molecular Biology 4. Nucleic Acids and Molecular Biology, vol 4. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-84150-7_2

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