Differential nephrotoxicity of cisplatin and a novel series of traditional Chinese medicine-platinum anticancer agents correlates with their chemical reactivity towards sulfur-containing nucleophiles

Anti-Cancer Drugs

Volumn 17, Issue 6, 2006, Pages 673-683

  To, Kenneth K W ^a   Au Yeung, Steve C F ^a   Ho, Yee Ping ^a,b  

^a CHINESE UNIVERSITY OF HONG KONG   (Hong Kong)

^b and Hong Kong Branch of CAS Center for Excellence in Animal Evolution and Genetics   (Hong Kong)

Author keywords

High performance liquid chromatography; Nephrotoxicity; Sulfur containing bionucleophiles; Traditional Chinese medicine platinum compounds

Indexed keywords

ANTINEOPLASTIC AGENT; CARBOPLATIN; CHINESE DRUG; CISPLATIN; CYSTEINE; GLUCOSE; GLUTATHIONE; NORCANTHARIDIN; PLATINUM DERIVATIVE; SODIUM CHLORIDE; SULFUR DERIVATIVE; WATER;

ANIMAL CELL; ARTICLE; CHEMICAL REACTION; CHINESE MEDICINE; CONTROLLED STUDY; CYTOTOXICITY TEST; DRUG ACTIVITY; DRUG CYTOTOXICITY; DRUG HYDROLYSIS; DRUG STABILITY; KIDNEY CELL CULTURE; NEPHROTOXICITY; NONHUMAN; PRIORITY JOURNAL; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; VALIDATION PROCESS;

ANIMALS; ANTINEOPLASTIC AGENTS; CARBOPLATIN; CELLS, CULTURED; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CISPLATIN; KIDNEY; MEDICINE, CHINESE TRADITIONAL; ORGANOPLATINUM COMPOUNDS; PHOSPHOPROTEIN PHOSPHATASE; PHOSPHOPROTEIN PHOSPHATASES; PROTEIN PHOSPHATASE 2; SULFUR; SWINE;

EID: 33747767286     PISSN: 09594973     EISSN: None     Source Type: Journal    
DOI: 10.1097/01.cad.0000217421.14090.e0     Document Type: Article

References (49)

1. Howe-Grant ME, Lippard SJ. Aqueous platinum (II) chemistry, binding to biological molecules. In: Sigel H, editor. Metal ions in biological systems 11. New York: Dekker; 1980. pp. 63-125.
2. Appleton TG, Hall JR, Ralph SF, Thompson CSM. NMR study of acid-base equilibria and other reactions of ammineplatinum complexes with aqua and hydroxo ligands. Inorg Chem 1989; 28:1989-1993.
3. Miller SE, House DA. The hydrolysis products of cis- diamminedichloroplatinum(II). 1. The kinetics of formation and anation of the cis-diammine(aqua)chloroplatinum(II) cation in acidic aqueous solution. Inorg Chim Acta 1989; 161:131-137.
4. Miller SE, House DA. 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 1989; 166:189-197.
5. Miller SE, House DA. The hydrolysis products of cis- dichlorodiammineplaltinum(II). 3. Hydrolysis kinetics at physiological pH. Inorg Chim Acta 1990; 173:53-60.
6. Reishus JW, Martin DS. cis-dichloro diammineplatinum(II) acid hydrolysis and isotopic exchange of the chloride ligands. J Am Chem Soc 1961; 83:2457-2462.
7. Pujol M, Girona V, Prat J, Munoz M, De Bolos J. Degradation pathway of carboplatin in aqueous solution. Int J Pharm 1997; 146:263-269.
8. Sherman SE, Lippard SJ. Stuctural aspects of platinum anticancer drug interactions with DNA. Chem Rev 1987; 87:1153-1181.
9. 2]. Science 1982; 218:1075-1082.
10. Johnson NP, Hoeschele JD, Rahn RO. Kinetics analysis of the in vitro binding of radioactive cis- and trans-dichlorodiammine platinum(II) to DNA. Chem Biol Interact 1980; 30:151-169.
11. 195Pt NMR kinetic and mechanistic studies of cis- and trans-diamminedichloroplatinum(II) binding to DNA. J Am Chem Soc 1990; 112:6860-6871.
12. Daley-Yates PT, McBrien DCH. Cisplatin metabolites in plasma, a study of their pharmacokinetics and importance in the nephrotoxic and antitumour activity of cisplatin. Biochem Pharmacol 1984; 33:3063-3070.
13. Dedon PC, Borch RF. Characterization of the reactions of platinum antitumor agents with biologic and nonbiologic sulfur-containing nucleophiles. Biochem Pharmacol 1987; 36:1955-1964.
14. Gonias SL, Pizzo SV. Complexes of serum albumin and cis- dichlorodiammineplatinum(II). The role of cysteine 34 as a nucleophilic entering group and evidence for reaction between bound Pt and a second macromolecule. J Biol Chem 1983; 258:5764-5769.
15. Volckova E, Dudones LP, Bose RN. HPLC determination of binding of cisplatin to DNA in the presence of biological thiols: implications of dominant platinum-thiol binding to its anticancer action. Pharm Res 2002; 19:124-131.
16. Reedijk J. The relevance of hydrogen bonding in the mechanism of action of platinum antitumor compounds. Inorg Chim Acta 1992; 198-200:873-881.
17. 2+ with thioether sulfur and purine nitrogen. J Inorg Biochem 1993; 51:557.
18. Jakupec MA, Galanski M, Keppler BK. The effect of cytoprotective agents in platinum anticancer therapy. Met Ions Biol Syst 2004; 42:179-208.
19. Godwin AK, Meister A, O'Dwyer PJ. High resistance to cisplatin in human ovarian cancer cell lines is associated with marked increase of glutathione synthesis. Proc Natl Acad Sci U S A 1992; 89:3070-3074.
20. Ho YP, To KKW, Au-Yeung SCF, Wang X, Lin G, Han X. Potential new antitumor agents from an innovative combination of demethylcantharidin, a modified traditional Chinese medicine, with a platinum moiety. J Med Chem 2001; 44:2065-2068.
21. To KKW, Wang X, Yu CW, Ho YP, Au-Yeung SCF. Protein phosphatase 2A inhibition and circumvention of cisplatin cross-resistance by novel TCM-platinum anticancer agents containing demethylcantharidin. Bioorg Med Chem 2004; 12:4565-4573.
22. To KKW, Wang X, Ho YP, Au-Yeung SCF. In vitro and in vivo suppression of growth of hepatocellular carcinoma cells by novel traditional Chinese medicine-platinum anti-cancer agents. Anticancer Drugs 2005; 16:825-835.
23. International Conference on Harmonization. Topic Q2B: validation of analytical procedures: methodology. US FDA Federal Register, Vol. 62, March 1997. p. 27463.
24. Altman PL. In: Dittmer DS, editor. Biological handbooks: blood and other body fluids. Washington, DC: Federation of American Societies for Experimental Biology; 1961. p. 75.
25. Gstraunthaler G, Pfaller W, Kotanko P. Biochemical characterization of renal epithelial cell exposure (LLC-PK1 and MDCK). Am J Physiol 1985; 248:F536-F544.
26. Mossman T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods 1983; 65:55-63.
27. Sedlak M, Lindsay R. Estimation of total, protein bound and non-protein sulphydryl groups in tissue with Ellman's reagent. Anal Biochem 1968; 25:192-205.
28. Lowry OH, Rosebrough NJ, Farr AL, Randall RJ. Protein measurement with the Folin phenol reagent. J Biol Chem 1951; 193:265-275.
29. Heudi O, Cailleux A, Allain P. Interactions between cisplatin derivatives and mobile phase during chromatographic separation. Chromatographia 1997; 44:19-24.
30. Andersson A, Hedenmalm H, Elfsson B, Ehrsson H. Determination of the acid dissociation constant for cis-diammineaquachloroplatinum(II) ion. A hydrolysis product of cisplatin. J Pharm Sci 1994; 83:859-862.
31. Macka M, Borak J, Semenkova L, Kiss F. Decomposition of cisplatin in aqueous solutions containing chlorides by ultrasonic energy and light. J Pharm Sci 1994; 83:815-818.
32. Rochard E, Barthes D, Courtois P. Stability and compatibility study of carboplatin with three portable infusion pump reservoirs. Int J Pharm 1994; 101:257-262.
33. Benaji B, Dine T, Luyckx M, Brunet C, Goudaliez F, Mallevais ML, et al. Stability and compatibility of cisplatin and carboplatin with PVC infusion bags. J Clin Pharm Ther 1994; 19:95-100.
34. 2(CBDCA-O)(5′-GMP-N7)] in solution. Inorg Chem 1993; 32:1333-1340.
35. Kidani Y, Achiwa K, Ono H, Tomatsu K, Zaikokuj K, Noji M, Tashiro T. Antitumor activities and stability of monochloro (D-glucuronato) (1R,2R-cyclohexanediamine) platinum(II). J Clin Hematol Oncol 1985; 15:35-39.
36. Gust R, Schnurr B, Krauser R, Bernhardt G, Koch M, Schmid M, et al. Stability and cellular studies of [rac-1,2-bis(4-fluorophenyl)-ethyenediamine] [cyclobutane-1,1-dicarboxylato]platinum(II), a novel, highly active carboplatin derivative. J Cancer Res Clin Oncol 1998; 124:585-597.
37. Verschraagen M, Kedde MA, Hausheer FH, van der Vijgh WJF. The chemical reactivity of BNP7787 and its metabolite mesna with the cytostatic agent cisplatin: comparison with the nucleophiles thiosulfate, DDTC, glutathione and its disulfide GSSG. Cancer Chemother Pharmacol 2003; 51:499-504.
38. Prenzler PD, McFadyen WD. Reactions of cisplatin and the cis-diamminediaqua platinum(II) cation with Tris and Hepes. J Inorg Biochem 1997; 68:279-282.
39. Montine TJ, Borch RF. Quiescent LLC-PK1 cells as a model for cis-diamminedichloroplatinum(II) nephrotoxicity and modulation by thiol rescue agents. Cancer Res 1988; 48:6017-6024.
40. Gust R, Schnurr B. Investigations on the stability of carboplatin infusion solutions. Monatshefte Chem 1999; 130:637-644.
41. Siddik ZH, Dible SE, Boxall FE, Harrap KR. Biochemical mechanism of platinum antitumour drugs. In: McBrien DCH, Slater TF, editors. Biochemical mechanisms of platinum antitumour drugs. Oxford: IRL Press; 1980. pp. 191-198.
42. Weiner MW, Jacobs C. Mechanism of cisplatin nephrotoxicity. Fed Proc 1983; 42:2974-2978.
43. Townsend DM, Hanigan MH. Inhibition of gamma-glutamyl transpeptidase or cysteine S-conjugate beta-lyase activity blocks the nephrotoxicity of cisplatin in mice. J Pharmacol Exp Ther 2002; 300:142-148.
44. Townsend DM, Deng M, Zhang L, Lapus MG, Hanigan MH. Metabolism of cisplatin to a nephrotoxin in proximal tubule cells. J Am Soc Nephrol 2003; 14:1-10.
45. Gillard RD, Wilkinson G. Platinum blue and related complexes. J Chem Soc 1964; 152:2835-2837.
46. 2+ moiety to phosphate in aqueous solution. Inorg Chim Acta 1982; 67:L19-L20.
47. 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 1984; 23:3514-3521.
48. Williams PD, Laska DA, Hottendorf GH. Comparative toxicity of aminoglycoside antibiotics in cell cultures derived from human and pig kidney. In vitro Toxicol 1986; 1:23-32.
49. Montine TJ, Borch RF. Role of endogenous sulfur-containing nucleophiles in an in vitro model of cis-diamminedichloroplatinum(II)-induced nephrotoxicity. Biochem Pharmacol 1990; 39:1751-1757.