Thermal degradation of platinum(IV) precursors to antitumor drugs
First Online: 07 July 2010 DOI:
10.1007/s10973-010-0933-3 Cite this article as: Howell, B.A., Chhetri, P., Dumitrascu, A. et al. J Therm Anal Calorim (2010) 102: 499. doi:10.1007/s10973-010-0933-3 Abstract
Organoplatinum antitumor agents are very effective, broad-spectrum drugs used for the treatment of a variety of cancerous conditions. The two most prominent of these, Cisplatin [
cis-diamminodichloroplatinum(II)] and Carboplatin [diammino(1,1-cyclobutanedicarboxylato)platinum(II)], are large scale commercial successes. The third, Oxaliplatin [(( trans-1,2-diamminocyclohexane)oxalato)platinum(II)], is now commercially available. The administration of all these drugs is accompanied by severe side effects. For Cisplatin, the most debilitating of these is kidney damage and extreme nausea. Several approaches to generate drug-release formulations that might mitigate toxic side effects have been explored. Now, platinum(IV) compounds which are more inert than platinum(II) compounds, and consequently less toxic, but which may be reduced to platinum(II) species within the cell are being evaluated for effectiveness in the treatment of cancer. The thermal stability of several precursors to compounds of this kind has been examined by thermogravimetry. In general, these materials lose ligands sequentially to generate a residue of platinum. This behavior may be generally useful for the characterization of such materials. Keywords Platinum(IV) prodrugs Platinum(II) oxidation Functionalized platinum drugs Ligand lability Thermal stability References
Rosenberg B, VanCamp L, Krigas T. Inhibition of cell division in
by electrolysis products from a platinum electrode. Nature. 1965;205:698–6999.
Rosenberg B, VanCamp L, Grimley EB, Thomson AJ. The inhibition of growth or cell division in Escherichia coli by different ionic species of platinum(IV) complexes. J Biol Chem. 1967;242:1347–52.
Rosenberg B, VanCamp L, Trosco JF, Mansour VH. Platinum compounds: a new class of potent antitumor agents. Nature. 1969;222:385–6.
Rosenberg B. Platinum complexes for the treatment of cancer. In: Spiro TG, editor. Metal ions in biology, vol 1: nuclei acid-metal ion interactions. New York: Wiley; 1980. p. 1–29.
Rosenberg B. Fundamental studies with cisplatin. Cancer. 1985;55:2303–14.
Jamieson ER, Lippard SJ. Structure, recognition, and processing of cisplatin-DNA adducts. Chem Rev. 1999;99:2467–98.
Wong E, Giandomenico CM. Current status of platinum-based antitumor drugs. Chem Rev. 1999;99:2451–66.
Wang D, Lippard SJ. Cellular processing of platinum anticancer drugs. Nat Rev Drug Discovery. 2005;4:307–20.
Dabrowiak JC, Bradner W. Platinum antitumor agents. Prog Med Chem. 1987;24:129158.
Mistry P, Kelland LR, Loh SY, Abel G, Murrer BA, Harrap KR. Comparison of cellular accumulation and cytotoxicity of cisplatin with that of tetraplatin and amminedibutyratodichloro(cyclohexylamine)platinum(IV) (JM221) in human ovarian carcinoma cell lines. Cancer Res. 1992;52(22):6188–93.
McKege M, Kelland L. New platinum drugs. In: Neidle S, Waring M, editors. Molecular aspects of drug-DNA interactions. New York: Macmillan; 1992. p. 169–212.
Jones TW, Chopra S, Kaufman JS, Flamenbaum W, Trump BF.
cis-Diammine-dichloroplatinum(II)-induced acute renal failure in the rat. Correlation of structural and functional alterations. Lab Invest. 1985;52:363–74.
Rosenberg B. Biological effects of platinum compounds. New agents for the control of tumors. Platinum Metals Rev. 1971;15(2):42–51.
Aggrawal SK, Menon GK. Ultrastructural localization of calcium(2
+) and its possible role in the amelioration of kidney toxicity due to cisplatin. J Clin Hematol Oncol. 1981;11:73–84.
Neuse E. Carrier-bound platinum and iron compounds with carcinostatic properties. Polym Adv Technol. 1998;9(10–11):786–93.
Lebwohl D, Canetta R. Clinical development of platinum complexes in cancer therapy: an historical perspective and an update. Eur J Cancer. 1998;34:1522–34.
Jagur-Grodzinski J. Polymers for targeted and/or sustained drug delivery. Polym Adv Technol. 2009;20:595–606.
Hoste K, DeWinne K, Schacht E. Polymeric prodrugs. Int J Pharm. 2004;277(1–2):119–31.
Khandare J, Minko T. Polymer-drug conjugates: progress in polymeric prodrugs. Prog Polym Sci. 2006;31(4):359–97.
Duncan R. Polymer conjugates as anticancer nanomedicines. Nat Rev Cancer. 2006;6(9):688–701.
Duncan R. The dawning era of polymer therapeutics. Nat Rev Drug Discov. 2003;2(5):347–60.
Batz H-G. Polymeric drugs. Adv Polym Sci. 1977;23:25–53.
Langer R. Drug delivery and targeting. Nature. 1998;392(6679, Suppl):5–10.
Langer R. Drug delivery: drugs on target. Science. 2001;293(5527):58–9.
Allen TM, Cullis PR. Drug delivery systems: entering the mainstream. Science. 2004;303(5665):1818–22.
Tomalia DA, Dewald JR, Hall M, Martin SJ, Smith PB. Preprint. 1st SPSJ International Polymer Conference, Kyoto, Japan 1984. p. 65.
Tomalia DA, Baker H, Dewald JR, Hall M, Kallos G, Martin S, Roeck J, Ryder J, Smith PB. A new class of polymers: starburst-dendritic macromolecules. Polym J. 1985;17(1):117–32.
Tomalia DA. Starburst/cascade dendrimers: fundamental building blocks for a new nanoscopic chemistry set. Aldrichim Acta. 1993;26(4):91–101.
Tomalia DA, Frechet JMJ, editors. Dendrimers and other dendritic polymers. New York: Wiley; 2001.
Tomalia DA, Reyna LA. Dendrimers as multi-purpose nanodevices for oncology drug delivery and diagnostic imaging. Biochem Soc Trans. 2007;35(1):61–7.
Tomalia DA. Birth of a new macromolecular architecture: dendrimers as quantized building blocks for nanoscale synthetic organic chemistry. Aldrichim Acta. 2004;37(2):39–57.
Howell BA, Fan D, Rakesh L. Nanoscale dendrimer-platinum conjugates as multivalent antitumor drugs. In: Abd-El-Aziz AS, Carraher CE, Pittman CU, Zeldin M, editors. Inorganic and organometallic macromolecules: design and applications. New York: Springer Science; 2008. p. 269–94.
Kim T-W, Chung PW, Slowing II, Tsunoda M, Yeung ES, Lin VS-Y. Structurally ordered mesoporous carbon nanoparticles as transmembrane delivery vehicle in human cancer cells. Nano Lett. 2008;8(11):3724–7.
Prato M, Kostarelos K, Bianco A. Functionalized carbon nanotubes in drug design and discovery. Acc Chem Res. 2008;41(1):60–8.
Liu Z, Winters M, Holodniy M, Dai HJ. siRNA delivery into human T cells and primary cells with carbon-nanotube transporters. Angew Chem Int Ed. 2007;46(12):2023–7.
Liu Z, Cai W, He L, Nakayama N, Chen K, Sun X, Chen X, Dai H. In vivo biodistribution and highly efficient tumour targeting of carbon nanotubes in mice. Nature Nanotech. 2007;2(1):47–52.
Dhar S, Liu Z, Thomale J, Dai H, Lippard SJ. Targeted single-wall carbon nanotube-mediated Pt(IV) prodrug delivery using folate as a homing device. J Am Chem Soc. 2008;130(34):11467–76.
Feazell RP, Nakayama-Ratchford N, Dai H, Lippard SJ. Soluble single-walled carbon nanotubes as longboat delivery systems for platinum(IV) anticancer drug design. J Am Chem Soc. 2007;129(27):8438–9.
Hall MD, Dillon CT, Zhang M, Beale P, Cai Z, Lai B, Stampfl APJ, Hambley TW. The cellular distribution and oxidation state of platinum(II) and platinum(IV) antitumour complexes in cancer cells. J Biol Inorg Chem. 2003;8(7):726–32.
Ang WH, Pilet S, Scopelliti R, Buss F, Juilleavat-Jeannevet L, Dyson PJ. Synthesis and characterization of platinum(IV) anticancer drugs with functionalized aromatic carboxylate ligands: Influence of the ligands on drug efficacies and uptake. J Med Chem. 2005;48(25):8060–9.
Barnes KR, Kutikov A, Lippard SJ. Synthesis, characterization, and cytotoxicity of a series of estrogen-tethered platinum(IV) complexes. Chem Biol. 2004;11(4):557–64.
Rieter WJ, Pott KM, Taylor KML, Lin W. Nanoscale coordination polymers for platinum-based anticancer drug delivery. J Am Chem Soc. 2008;130(35):11584–5.
Kay H, Palmer JW, Stanko JA. US Patent 0080131 A1, 2005.
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