Skip to main content
SpringerLink
Log in

The Chemistry of Cisplatin in Aqueous Solution

  • Chapter
Platinum-Based Drugs in Cancer Therapy

Part of the book series: Cancer Drug Discovery and Development ((CDD&D))

  • 449 Accesses

Abstract

The antitumor properties of platinum-containing drugs are attributable in large measure to the kinetics of their ligand displacement reactions. As is discussed at length in other contributions to this volume, their primary target is believed to be nitrogen donor atoms in the nucleobases of DNA. The bonds formed between the metal ion and these atoms must be sufficiently long-lived to interfere with the process of cell division, or to trigger the intracellular mechanisms that recognize irreparable damage to a cell. Bonds between the nucleobase nitrogen atoms and platinum(II) clearly fulfil this requirement. Metal ions that form labile bonds with the nucleobase nitrogen atoms cannot act in a similar way and do not give active compounds (1).

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

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 89.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 119.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 169.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Cleare, M. J. and Hoeschele, J. D. (1973) Studies on the antitumor activity of group VIII transition metal complexes. Part I. Platinum (II) complexes. Bioinorg Chem. 2, 187–210.

    Article  CAS  Google Scholar 

  2. Bancroft, D. P., Lepre, C. A., and Lippard, S. J. (1990) 195Pt NMR kinetic and mechanistic studies of cis-and trans-diamminedichloroplatinum(II)binding to DNA. J. Am. Chem. Soc. 112, 6860–6871.

    Google Scholar 

  3. Miller, S. E. and House, D. A. (1991) The hydrolysis products of cis-diammine-dichloroplatinum(II). 5. The anation kinetics of cis-Pt(X)(NH3)2(OH2)+ (X = Cl, OH) with glycine, monohydrogen malonate and chloride. Inorg. Chim. Acta 187, 125–132.

    Article  CAS  Google Scholar 

  4. Frey, U., Ranford, J. D., and Sadler, P. J. (1993) Ring-opening reactions of the anticancer drug carboplatin: NMR characterisation of cis-[Pt(NH3)2(CBDCA-O)(5’GMP-N7)] in solution. Inorg. Chem. 32, 1333–1340.

    Article  CAS  Google Scholar 

  5. Barnham, K. J., Djuran, M. I., Murdoch, P. del S., Ranford, J. D., and Sadler, P. J. (1996) Ring-opened adducts of the anticancer drug carboplatin with sulfur amino acids. Inorg. Chem. 35, 1065–1072.

    Article  CAS  PubMed  Google Scholar 

  6. Lempers, E. L. M. and Reedijk, J. (1991) Interactions of platinum ammine compounds with sulfur-containing biomolecules and DNA fragments. Adv. Inorg. Chem. 37, 175–217.

    Article  CAS  Google Scholar 

  7. Barnham, K. J., Djuran, M. I., Murdoch, P. del S., Ranford, J. D., and Sadler, P. J. (1995) LMethionine increases the reaction of 5’-guanosine monophosphate with the anticancer drug cisplatin: mixed-ligand adducts and reversible methionine binding. J. Chem. Soc. Dalton Trans. 3721–3726.

    Google Scholar 

  8. Heudi, O., Cailleux, A., and Allain, P. (1998) Kinetic studies of the reactivity between cisplatin and its monoaquo species with L-methionine. J. Inorg. Biochem. 71, 61–69.

    Article  CAS  Google Scholar 

  9. van Boom, S. S. G. E. and Reedijk, J. (1993) Unprecedented migration of [Pt(dien)]2+ (dien =1,5,-diamino-3-azapentane) from sulfur to guanosine-N7 in S-guanosyl-L-methionine. J. Chem. Soc. Chem. Commun. 1397–1398.

    Google Scholar 

  10. Appleton, T. G., Hall, J. R., and Ralph, S. F. (1985) Reactions of platinum(II) aqua complexes. 3. Multinuclear (15N 195Pt,’3C and ‘H) NMR study of the reactions of aqua and hydroxo complexes with glycine and (methylimino)diacetic acid. Inorg. Chem. 24 673–677.

    Google Scholar 

  11. Faggiani, R., Lippert, B., Lock, C. J. L., and Rosenberg, B. (1977) Hydroxo-bridged platinum (II) complexes. 1. Di-µ-hydroxo-bis-[diammineplatinum(II)] nitrate, [(NH3)2Pt(OH)2Pt(NH3)21(NO3)2. J. Am. Chem. Soc. 99, 777–781.

    Article  CAS  Google Scholar 

  12. Lippert, B., Lock, C. J. L., Rosenberg, B., and Zvagulis, M. (1978) Hydroxo-bridged platinum(II) complexes. 4. Crystal structure and vibrational spectra of di-µ-hydroxo-bis[diammineplatinum(II)] carbonate dehydrate, [(NH3)2Pt(OH)2Pt(NH3)2](CO3).2H2O. Inorg. Chem. 17, 2971–2975.

    Google Scholar 

  13. Faggiani, R., Lippert, B., Lock, C. J. L., and Rosenberg, B. (1977) Hydroxo-bridged platinum(II) complexes. 2. Crystallographic characterization and vibrational spectra of cyclotri-µ-hydroxo-tris-[cis-diammineplatinum(II)] nitrate. Inorg. Chem. 16, 1192–1196.

    Google Scholar 

  14. Gill, D. S. and Rosenberg, B. (1982) Synthesis, kinetics and mechanism of formation of polynuclear hydroxo-bridged complexes of (trans-1,2-diamino-cyclohexane)platinum(II)] trisulfate. J. Am. Chem. Soc. 104, 4598–4604.

    Article  CAS  Google Scholar 

  15. Macquet, J. P., Gros, S., and Beauchamp, A. L. (1985) Preparation and crystal structure of the hydroxo-bridged complex bis (cyclo-tri-µ-hydroxo-tris[trans-1,2-diaminocyclohexane) platinum(II)]trisulfate. J. Inorg. Biochem. 25, 197–206.

    Article  CAS  Google Scholar 

  16. Rochon, F. D., Morneau, A., and Melanson, R. (1988) Crystal structure of a hydroxobridged platinum(II) tetramer, cyclo-tetrakis(.t-hydroxo)tetrakis-(ethylenediamine)platinum(II) tetranitrate. Inorg. Chem. 27, 10–13.

    Article  CAS  Google Scholar 

  17. Rochon, F. D., Melanson, R., and Morneau, A. (1992) 195Pt and ‘H NMR study of the products of hydrolysis of Pt(L)X2, where L is an ethylenediamine derivative, and the crystal structure of [Pt(N,N-dimethylenediamine)(.t-OH)]2(NO3)2. Magn. Reson. Chem. 30, 697–706.

    Google Scholar 

  18. Appleton, T. G., Berry, R. D., Davis, C. A., Hall, J. R., and Kimlin, H. A. (1984) Reactions of platinum(II) aqua complexes. 1. Multinuclear (195Pt, ‘5N, and 31P) NMR study of reactions between the cis-diamminediaquaplatinum(II) cation and the oxygen-donor ligands hydroxide, perchlorate, nitrate, sulfate, phosphate, and acetate. Inorg. Chem. 23, 3514–3521.

    Article  CAS  Google Scholar 

  19. Appleton, T. G., Hall, J. R., Ralph, S. F., and Thompson, C. S. M. (1989) NMR study of acid-base equilibria and other reactions of ammineplatinum complexes with aqua and hydroxo ligands. Inorg. Chem. 28„ 1989–1993.

    Google Scholar 

  20. Appleton, T. G., Mathieson, M., Byriel, K. A., and Kennard, C. H. L. (1998) Crystal structure of (µ-acetato-O,O’)(.t-hydroxo)bis(diammine)platinum (II) nitrate. Z. Krist. 213, 247–248.

    CAS  Google Scholar 

  21. Appleton, T. G., Hall, J. R., and Ralph, S. F. (1986) 15N and 195Pt NMR study of the effect of chain length, n, on the reactions of amino acids +NH3(CH2)nCO2- (n=1,2,3) with platinum(II)ammine complexes. Aust. J. Chem. 39, 1347–1362.

    Google Scholar 

  22. Appleton, T. G., Hall, J. R., and McMahon, I. J. (1986) Multinuclear NMR study of reactions of methylphosphonic acid, CH3PO3H2 and aminoalkyl-phosphonic acids NH2(CH2)nPO3H2 (n=1,3) with the cis-diamminediaqua-platinum(II) cation and cisdiamminedihydroxoplatinum(II). Inorg. Chem. 25, 720–725.

    Article  CAS  Google Scholar 

  23. Orton, D. M., Gretton, V. A., and Green, M. (1993) Acidity constants for cis-diaquadiammineplatinum(II), the aquated form of cisplatin. Inorg. Chim. Acta 204, 265–266.

    Article  CAS  Google Scholar 

  24. Andersson, A., Hedenmalm, H., Elfsson, B., and Ehrsson, H. (1994) Determination of the acid dissociation constant for cis-diammineaqua-chloroplatinum(II) ion-a hydrolysis product of cisplatin. J. Pharm. Sci. 83, 859–862.

    Article  CAS  PubMed  Google Scholar 

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

    Article  CAS  Google Scholar 

  26. Prenzler, P. D. and McFadyen, W. D. (1997) Reactions of cisplatin and the cis-diamminediaqua platinum(II) cation with Tris and HEPES. J. Inorg. Biochem. 68, 279–282.

    Article  CAS  Google Scholar 

  27. Berners-Price, S. J., Frenkiel, T. A., Frey, U., Ranford, J. D., and Sadler, P. J. (1992) Hydrolysis products of cisplatin: pKa determinations via [’H,15N] NMR Spectroscopy. J. Chem. Soc. Chem. Commun. 789–791.

    Google Scholar 

  28. Martin, R. B. (1983) Hydrolytic equilibria and N7 versus Ni binding in purine nucleosides of cis-diamminedichloroplatinum(II). Am. Chem. Soc. Symp. Ser 208, 231–244.

    Google Scholar 

  29. Jensen, K. A. (1939) The acid strengths of the stereoisomeric diaquo-diammineplato ions. Z. Anorg. Allgem. Chem 242, 87–91.

    Article  CAS  Google Scholar 

  30. Jennerwein, M. and Andrews, P. A. (1995) Effect of intracellular chloride concentration on the cellular pharmacodynamics of cis-diammine-dichloroplatinum(II). Drug Metab. and Dispos. 23, 178–184.

    CAS  Google Scholar 

  31. Miller, S. E. and House, D. A. (1989) The hydrolysis products of cis-diammine-dichloroplatinum(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 

  32. Miller, S. E. and House, D. A. (1989) The hydrolysis products of cis-dichlorodiammineplatinum(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 

  33. Miller, S. E., Gerard, K. J., and House, D. A. (1991) The hydrolysis products of cis-diamminedichloroplatinum(II) 6. A kinetic comparison of the cis-and trans-isomers and other cis-di(amine)di(chloro)platinum(II) compounds. Inorg. Chim. Acta. 190, 135–144.

    Article  CAS  Google Scholar 

  34. Hindmarsh, K., House, D. A., and Turnbull, M. M. (1997) The hydrolysis products of cisdiamminedichloroplatinum(II) 9. Chloride and bromide anation kinetics for some [Pt(II)(N)2(OH2)2]2+ complexes and the structures of [Pt(IV)Br4(N)2] ((N2) = en,tn). Inorg. Chim. Acta 257, 11–18.

    Article  CAS  Google Scholar 

  35. Briere, K. M., Goel, R., Shirazi, F. H., Stewart, D. J., and Smith, I. C. P. (1996) The integrity of cisplatin in aqueous and plasma ultrafiltrate media studied by 195Pt and ‘5N nuclear magnetic resonance. Cancer Chemother. Pharmacol. 37, 518–524.

    CAS  Google Scholar 

  36. Basolo, F., Bailar, J. C., and Tarr, B. R. (1950) The stereochemistry of complex inorganic compounds. X. The stereoisomers of dichlorobis(ethylenediamine)-platinum(IV)chloride. J. Am. Chem. Soc. 72, 2433–2438.

    Article  CAS  Google Scholar 

  37. Glass, G. E., Scwabacher, W. B., and Tobias, R. S. (1968) Oxygen-17 nuclear magnetic resonance studies of the hydration of organometallic cations. Inorg. Chem. 7, 2471–2478.

    Google Scholar 

  38. Appleton, T. G. and Hall, J. R. (1970) Complexes with six-membered chelate rings. I. Preparation of platinum(II) and palladium(II) complexes of trimethylene-diamine and some methyl-substituted derivatives. Inorg. Chem. 9, 1800–1806.

    Article  CAS  Google Scholar 

  39. Dhara, S. C. (1970) A rapid method for the synthesis of cis-[Pt(NH3)2C12]. Ind. J. Chem. 8, 193–194.

    Google Scholar 

  40. Boreham, C. J., Broomhead, J. A., and Fairlie, D. P. (1981) A 195Pt and ‘5N NMR study of the anticancer drug, cis-diamminedichloroplatinum(II) and its hydrolysis and oligomerization products. Aust. J. Chem. 34, 659–664.

    Article  CAS  Google Scholar 

  41. O’Halloran, T. V., Lippard, S. J., Richmond, T. J., and Klug, A. (1987) Multiple heavy-atomreagents for molecular X-ray structure determination. Application to the nucleosome core particle. J. Mol. Biol. 194, 705–712.

    Google Scholar 

  42. Lippert, B. Lock, C. J. L., Rosenberg, B., and Zvagulis, M. (1977) cisDinitratodiammineplatinum(II), cis-Pt(NH3)2(NO3)2. Inorg. Chem. 16 1525–1529.

    Google Scholar 

  43. Rochon, F. D. and Melanson, R. (1987) Molecular and crystal structure of a platinum(II) complex with aquo and sulfate ligands: aquo(N,N’-dimethyl-ethylenedeiamine)(sulfato)platinum(II) hydrate. Inorg. Chem. 26, 989–992.

    Article  CAS  Google Scholar 

  44. Harrison, R. C., McAuliffe, C. A., and Zaki, A. M. (1980) An efficient route for the preparation of highly soluble platinum(II) antitumour agents. Inorg. Chim. Acta 46, L15 - L16.

    Article  CAS  Google Scholar 

  45. El-Khateeb, M., Appleton, T. G., Charles, B. G., and Gahan, L. R. (1999) Development of HPLC conditions for valid determination of hydrolysis products of cisplatin. J Pharm. Sci. 88, 319–326.

    Article  CAS  PubMed  Google Scholar 

  46. Gonnet, F., Lemaire, D., Kozelka, J., and Chottard, J.-C. (1993) Isolation of cis[PtC1(NH3)2(H20)](C104), the monohydrated form of the anti-tumour drug cisplatin, using cation-exchange high performance liquid chromatography. J. Chromatogr. 648, 279–282.

    Google Scholar 

  47. Hacker, M. P., Khokhar, A. R., Krakoff, I. H., Brown, D. E, and McCormack, J. (1986) Water-soluble N-substituted iminodiactetate(1,2-diamino-cyclohexane)platinum(II) complexes as potential antitumor agents. J. Cancer. Res. 46, 6250–6254.

    Google Scholar 

  48. Hoeschele, J. D., Farrell, N., Turner, W. R., and Rithner, C. D. (1988) Synthesis and characterisation of diastereomeric (substituted iminodiacetate)(1,2-diaminocyclohexane)platinum(II) complexes. Inorg. Chem. 27, 4106–4113.

    Article  CAS  Google Scholar 

  49. Gandolfi, O., Apfelbaum, H. C., and Blum, J. (1987) Aminomalonate(1,2-diamino-cyclohexane)platinum(II): a competitive antitumour compound with a new class of neutral, chemically stable, water soluble, functionalized platinum(II) complexes. Inorg. Chim. Acta 135, 27–31.

    Article  CAS  Google Scholar 

  50. Gibson, D., Rosenfeld, A., Apfelbaum, H., and Blum, J. (1990) Multinuclear (195Pt, ‘5N, 13C) NMR studies of the reactions between cis-diammine-diaquaplatinum(II) complexes and aminomalonate. Inorg. Chem. 29, 5125–5129.

    Article  CAS  Google Scholar 

  51. Appleton, T. G., Hall, J. R., Neale, D. W., and Thompson, C. S. M. (1990) Reactions of the cisdiamminediaquaplatinum(II) cation with with 2-amino-malonic acid and its homologues, aspartic and glutamic acids. Rearrangement of metastable complexes with carboxylate-bound ligands to N,O chelates and formation of di-and tri-nuclear complexes. Inorg. Chem. 29, 3985–3990.

    Article  CAS  Google Scholar 

  52. Talebian, A. H., Bensely, D., Ghiorghis, A., Hammer, C. F., Schein, R S., and Green, D. (1991) Asparto(1,2-cyclohexanediamine)platinum(II) complexes: synthesis and characterisation; effects of minor impurities on antitumour activity. Inorg. Chim. Acta 179, 281–287.

    Article  CAS  Google Scholar 

  53. Shooter, K. V., Howse, R., Merrifield, R. K., and Robins, A. B. (1972) Interaction of platinum(II) compounds with bacteriophages. Chem. Biol. Interact. 5, 289–307.

    Article  CAS  PubMed  Google Scholar 

  54. Wood, F. E., Hunt, C. T., and Balch, A. L. (1982) 195Pt and 31P nuclear magnetic resonance studies of the binding of the cis-Pt(NH3)22+ moiety to phosphate in aqueous solution. Inorg. Chim. Acta 67, L19 - L20.

    Google Scholar 

  55. Bose, R. N., Goswani, N., and Moghaddas, S. (1990) Phosphato complexes of platinum(II): phosphorus-31 NMR and kinetics of formation and isomerization studies. Inorg. Chem. 29, 3461–3467.

    Article  CAS  Google Scholar 

  56. Appleton, T. G., Berry, R. D., and Hall, J. R. (1982) ‘Platinum phosphate blues. A comparison with ’amide blues.’ Inorg. Chim. Acta 64, L229 - L233.

    Article  CAS  Google Scholar 

  57. Andersson, A., Fagerberg, J., Lewensohn, R., and Ehrsson, H. (1996) Pharmacokinetics of cisplatin and its monohydrated complex in humans. J. Pharm. Sci. 85, 824–827.

    Article  CAS  PubMed  Google Scholar 

  58. Wenclawiak, B. W. and Wollmann, M. (1996) Separation of platinum(II) anti-tumour drugs by micellar electrokinetic capillary chromatography. J. Chromatogr. A 724, 317–326.

    Article  CAS  Google Scholar 

  59. Shearan, R, Alvarez, J. M. E, Zayed, N., and Smyth, M. R. (1990) High performance liquid chromatography separation of cisplatin and its hydrolysis products on alumina and application to studies of their interaction with cysteine. Biomed. Chromatogr. 4, 78–82.

    Article  CAS  PubMed  Google Scholar 

  60. DeWaal, W. A. J., Maessen, F. J. M. J., and Kraak, J. C. (1987) Analysis of platinum species originating from cis-diamminedichloroplatinum(II) cisplatin in human and rat plasma by high-performance liquid chromatography with on-line inductively coupled plasma atomic emission spectrometric detection. J. Chromatogr. 407, 253–272.

    Article  CAS  Google Scholar 

  61. Heudi, O., Caillieux, A., and Allain, P. (1997) Interactions between cisplatin derivatives and mobile phase during chromatographic separation. Chromatographia 44, 19–24.

    Article  CAS  Google Scholar 

  62. Daley-Yates, P. T. and O’Brien, D. C. H. (1984) Cisplatin metabolites in plasma. A study of their pharmacokinetics and importance in the nephrotoxic and antitumour activity of cisplatin. Biochem. Pharmacol. 33, 3063–3067.

    Article  CAS  PubMed  Google Scholar 

  63. Zhao, Z., Tepperman, K., Dorsey, J. G., and Elder, R. C. (1993) Determination of cisplatin and some possible metabolites by ion-pairing chromatography with inductively coupled plasma mass spectroscopic determination. J. Chromatogr. Biomed. Applic. 615, 83–89.

    Article  CAS  Google Scholar 

  64. Berners-Price, S. J. and Sadler, P. J. (1996) Coordination chemistry of metallodrugs-insights into biological speciation from NMR spectroscopy. Coord. Chem. Rev. 151, 1–40.

    CAS  Google Scholar 

  65. Barnham, K. J., Berners-Price, S. J., Guo, Z., Murdoch, P. del S., and Sadler, P. J. (1996) NMR spectroscopy of platinum drugs: from DNA to body fluids, in Platinum and Other Metal Coordination Compounds in Cancer Chemotherapy 2 ( Pinedo, H. M. and J. H. Schmogale, eds.), Plenum, New York, pp. 1–16.

    Google Scholar 

  66. Norman, R. E. and Sadler, P. J. (1988) 14N NMR studies of amine release from anticancer drugs: models and human blood plasma. Inorg. Chem. 27, 3583–3587.

    Google Scholar 

  67. Bell, J. D., Norman, R. E., and Sadler, P. J. (1987) Coordination chemistry in biological media: reactions of antitumour Pt(II) and Au(III) complexes with cell culture media. J. Inorg. Biochem. 31, 241–246.

    Article  CAS  PubMed  Google Scholar 

  68. Ranford, J. D., Sadler, P. J., Balmanno, K., and Newell, D. R. (1991) ‘H NMR studies of human urine: urinary elimination of the anticancer drug carboplatin. Magn. Reson. Chem. 29, S125–129.

    Google Scholar 

  69. Piotto, M., Saudek, V., and Sklenar, V. (1992) Gradient-tailored excitation for single-quantum NMR spectroscopy of aqueous solutions. J. Biomol. NMR 2, 661–665.

    Article  CAS  PubMed  Google Scholar 

  70. Berners-Price, S. J. and Kuchel, P. W. (1990) The reaction of cis-and trans-[PtC12(NH3)21 with reduced glutathione inside human red blood cells studied by ‘H and 15N-(’H) DEPT NMR. J. Inorg. Biochem. 38, 327–345.

    Google Scholar 

  71. Macdonald, F. and Sadler, P. J. (1986) 195Pt NMR spectroscopy: applications to the study of anticancer drugs, in Biochemical Mechanisms of Platinum Antitumour Drugs (McBrien, D. C. H. and T. F. Slater, eds.), IRL, Oxford, pp. 361–381.

    Google Scholar 

  72. Rosenberg, B. (1978) Platinum complex-DNA interactions and anticancer activity. Biochimie 60, 859–867.

    Article  CAS  Google Scholar 

  73. Appleton, T. G., Hall, J. R., and Ralph, S. F. (1985) 15N and 795Pt NMR spectra of platinum ammine complexes: trans and cis-influence series based on 195Pt-’5N coupling constants and 15N chemical shifts. Inorg. Chem. 24, 4685–4693.

    Google Scholar 

  74. Stonehouse, J., Shaw, G. L., Keeler, J., and Laue, E. D. (1994) Minimizing sensitivity losses in gradient-selected 15N-’H HSQC spectra of proteins. J. Magn. Reson. Series A 107, 174–184.

    Article  Google Scholar 

  75. Barnham, K. J., Berners-Price, S. J., Frenkiel, T. A., and Sadler, P. J. (1995) Platination pathways for reactions of cisplatin with GG single-stranded and double-stranded decanucleotides. Angew. Chem. Int. Ed. 34, 1874–1877.

    Google Scholar 

  76. Berners-Price, S. J., Barnham, K. J., Frey, U., and Sadler, P. J. (1996) Kinetic analysis of the stepwise platination of single-and double-stranded GG oligonucleotides with cisplatin and cis-[PtCI(H2O)(NH3)21+. Chem. Eur. J. 2, 1283–1291.

    Google Scholar 

  77. Reeder, F., Guo, Z., Murdoch, P. del S., Corazza, A., Hambley, T. W., Berners-Price, S. J., Chottard, J.-C., and Sadler, R. J. (1997) Platination of a GG single-and double-stranded 14-mer oligonucleotide with diaqua cisplatin followed by NMR and HPLC. Influence of the platinium ligands and base sequence on 5’-G versus 3’-G platination selectivity. Eue J. Biochem. 249, 370–382.

    CAS  Google Scholar 

  78. Davies, M. S., Berners-Price, S. J., and Hambley, T. W. (1998) Rates of platination of double stranded AG and GA containing oligonucleotides: insights into why cisplatin binds to AG but not GA Sequences in DNA. J. Am. Chem. Soc. 120, 11380–11390.

    Article  CAS  Google Scholar 

  79. Barton, S. J., Barnham, K. J., Habtemariam, A., Sue, R. E., and Sadler, P. J. (1998) pK„ values of aqua ligands of platinum(II) anticancer complexes: [1H,15N] and 195Pt NMR studies of cis-and trans-[PtC12(NH3)(cyclohexamine)]. Inorg. Chim. Acta 273, 8–13.

    Google Scholar 

  80. Guo, Z., Chen, Y., Zang, E., and Sadler, P. J. (1997) [1H,15N] nuclear magnetic resonance studies of [Pt(dien)Cl]+ (dien = diethylenetriamine): hydrolysis and reactions with nucleotides. J. Chem. Soc. Dalton Trans. 4107–4111.

    Google Scholar 

  81. Barnham, K. J., Frey, U., Murdoch, P. del S., Ranford, J. D., and Sadler, P. J. (1994) [Pt(CBDCA-O)(NH3)2(L-methionine-S)]: ring-opened adduct of the anticancer drug carboplatin (“paraplatin”). Detection of a similar complex in urine by NMR spectroscopy. J. Am. Chem. Soc. 116, 11175–11176.

    Google Scholar 

  82. Grinberg, A. A., Stetsenko, A. I., Mitkinova, N. D., and Tikhonova, L. S. (1971) Acid properties of aqua complexes of platinum(II). Russ. J. Inorg. Chem. 16, 137. (Zh. Neorg. Khim. 116 1264–1266 ).

    Google Scholar 

  83. LeRoy, A. F., Lutz, R. J., Dedrick, R. L., Litterst, C. L., and Gaurino, A. M. (1979) Pharmacokinetic study of cis-dichlorodiammineplatinum(II) (DDP) in the beagle dog: thermodynamic and kinetic behaviour of DDP in the biologic milieu. Cancer Treat. Rep. 63, 59–71.

    CAS  Google Scholar 

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

    CAS  Google Scholar 

  85. Lee, K. W. and Martin, D. S. Jr. (1976) cisDichlorodiammineplatinum(II) aquation equilibria and isotopic exchange of chloride ions with free chloride and tetrachloroplatinate(II). Inorg. Chim. Acta 17, 105–110.

    Google Scholar 

  86. Lim, M. C. and Martin, R. B. (1976) The nature of cis amine Pd(II) and antitumour cis amine Pt(II) complexes in aqueous solutions. J. Inorg. Nucl. Chem. 38, 1911–1914.

    Article  CAS  Google Scholar 

  87. Ismail, I. M. and Sadler, P. J. (1983) 195Pt and ‘5N NMR studies of antitumor complexes. Am. Chem. Soc. Symp. Ser. 209, 171–190.

    Google Scholar 

Download references

Authors
  1. Susan J. Berners-Price
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Trevor G. Appleton
    View author publications

    You can also search for this author in PubMed Google Scholar

Editor information

Editors and Affiliations

  1. CRC Centre for Cancer Therapeutics, The Institute of Cancer Research, UK

    Lloyd R. Kelland

  2. Department of Chemistry, Virginia Commonwealth University, USA

    Nicholas P. Farrell

Rights and permissions

Reprints and permissions

Copyright information

© 2000 Springer Science+Business Media New York

About this chapter

Cite this chapter

Berners-Price, S.J., Appleton, T.G. (2000). The Chemistry of Cisplatin in Aqueous Solution. In: Kelland, L.R., Farrell, N.P. (eds) Platinum-Based Drugs in Cancer Therapy. Cancer Drug Discovery and Development. Humana Press, Totowa, NJ. https://doi.org/10.1007/978-1-59259-012-4_1

Download citation

  • DOI: https://doi.org/10.1007/978-1-59259-012-4_1

  • Publisher Name: Humana Press, Totowa, NJ

  • Print ISBN: 978-1-61737-091-5

  • Online ISBN: 978-1-59259-012-4

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation