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 Chemotherapy and Pharmacology

Volumn 51, Issue 6, 2003, Pages 499-504

  Verschraagen, Miranda ^a   Kedde, Marc A ^a   Hausheer, Frederick H ^b   Van Der Vijgh, Wim J F ^a  

^a VU UNIVERSITY MEDICAL CENTER   (Netherlands)

^b BioNumerik Pharmaceuticals Inc   (United States)

Author keywords

BNP7787; Cisplatin; Glutathione; Mesna; Reaction kinetics

Indexed keywords

CISPLATIN; DIETHYLDITHIOCARBAMIC ACID; DIMESNA; DRUG METABOLITE; GLUTATHIONE; GLUTATHIONE DISULFIDE; MESNA; PROTECTIVE AGENT; THIOL DERIVATIVE; THIOSULFATE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; ATOMIC ABSORPTION SPECTROMETRY; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; CHEMOREACTIVITY; DRUG DEGRADATION; DRUG INACTIVATION; DRUG STRUCTURE; HALF LIFE TIME; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NEPHROTOXICITY; NEUROTOXICITY; PRIORITY JOURNAL;

EID: 0038727868     PISSN: 03445704     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00280-003-0610-3     Document Type: Article

References (26)

1. Abe R, Akiyoshi T, Baba T (1990) 'Two-route chemotherapy' using cisplatin and its neutralizing agent, sodium thiosulfate, for intraperitoneal cancer. Oncology 47:422
2. Berry JM, Jacobs C, Sikic B, Halsey J, Borch RF (1990) Modification of cisplatin toxicity with diethyldithiocarbamate. J Clin Oncol 8:1585
3. Boven E, Verschraagen M, Hulscher TM, Erkelens CAM, Hausheer FH, Pinedo HM, Van der Vijgh WJF (2002) BNP7787, a novel protector against platinum-related toxicities, does not affect the efficacy of cisplatin or carboplatin in human tumour xenografts. Eur J Cancer 38:1148
4. Cavalletti E, Cavaletti G, Tredici G, Oggioni N, Spinelli S, Reddy D, Zhao M, Wu M, Hausheer F (1999) Oral and intravenous BNP7787 protects against paclitaxel-mediated neurotoxicity in Wistar rats. Proc Am Assoc Cancer Res 40:398
5. Daley-Yates PT, McBrien DCH (1984) Cisplatin metabolites in plasma, a study of their pharmacokinetics and importance in the nephrotoxic and antitumour activity of cisplatin. Biochem Pharmacol 33:3063
6. Dedon PC, Borch RF (1987) Characterization of the reactions of platinum antitumor agents with biologic and nonbiologic sulfur-containing nucleophiles. Biochem Pharmacol 36:1955
7. Goren MP, Hsu LC, Li JT (I998) Reduction of dimesna to mesna by the isolated perfused rat liver. Cancer Res 58:4358
8. Hausheer FH, Kanter P, Cao S, Haridas K, Seetharamulu P, Reddy D, Petluru P, Zhao M, Murali D, Saxe JD, Yao S, Martinez N, Zukowski A, Rustum YM (1998) Modulation of platinum-induced toxicities and therapeutic index: mechanistic insights and first- and second-generation protecting agents. Semin Oncol 25:584
9. Hausheer F, Cavaletti G, Tredici G, Oggioni N, Spinelli S, Pezzoni G, Manzotti C, Haridas K, Reddy D, Zhao M, Seetharamulu P, Yao S, Pavankumar P, Murali D, Wu M, Saxe J, Cavalletti E (1999) Oral and intravenous BNP7787 protects against platinum neurotoxicity without in vitro or in vivo tumor protection. Proc Am Assoc Cancer Res 40:398
10. Hospers GAP, Eisenhauer EA, De Vries EGE (1999) The sulfhydryl containing compounds WR-2721 and glutathione as radio- and chemoprotective agents. A review, indications for use and prospects. Br J Cancer 80:629
11. Houze P, Gamra S, Madelaine I, Bousquet B, Gourmel B (2001) Simultaneous determination of total plasma glutathione, homocysteine, cysteinylglycine, and methionine by high-performance liquid chromatography with electrochemical detection. J Clin Lab Anal 15:144
12. 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
13. Howell SB, Pfeifle CE, Wung WE, Olshen RA (1983) Intraperitoneal cis-diamminedichloroplatinum with systemic thiosulfate protection. Cancer Res 43:1426
14. Kleinman WA, Richie JP Jr (2000) Status of glutathione and other thiols and disulfides in human plasma. Biochem Pharmacol 60:19
15. Leeuwenkamp OR, Neijt JP, Van der Vijgh WJ, Pinedo HM (1991) Reaction kinetics of cisplatin and its monoaquated species with the modulating agents (di)mesna and thiosulphate. Eur J Cancer 27:1243
16. Long DF, Repta AJ, Sternson LA (1980) The reactivity of cisplatin in plasma. Implications for sample handling in pharmacokinetic studies. Int J Pharm 6:167
17. Nagai N, Okuda R, Kinoshita M, Ogata H (1996) Decomposition kinetics of cisplatin in human biological fluids. J Pharm Pharmacol 48:918
18. Ormstad K, Uehara N (1982) Renal transport and disposition of Na-2-mercaptoethane sulfonate disulfide (dimesna) in the rat. FEBS Lett 150:354
19. Ormstad K, Orrenius S, Låstbom T, Uehara N, Pohl J, Stekar J, Brock N (1983) Pharmacokinetics and metabolism of sodium 2-mercaptoethanesulfonate in the rat. Cancer Res 43:333
20. Ozols RF (1989) Cisplatin dose intensity. Semin Oncol 16:22
21. Qazi R, Chang AYC, Borch RF, Montine T, Dedon P, Loughner J, Bennett JM (1988) Phase I clinical and pharmacokinetic study of diethyldithiocarbamate as a chemoprotector from toxic effects of cisplatin. J Natl Cancer Inst 80:1486
22. Segal E, Le Pecq J-B (1985) Role of ligand exchange processes in the reaction kinetics of the antitumor drug cis-diamminedichloroplatinum (II) with its targets. Cancer Res 45:492
23. Treskes M, Holwerda U, Klein I, Pinedo HM, Van der Vijgh WJF (1991) The chemical reactivity of the modulating agent WR2721 (ethiofos) and its main metabolites with the antitumor agents cisplatin and carboplatin. Biochem Pharmacol 42:2125
24. Van Rijswijk RE, Hoekman K, Burger CW, Verheijen RH, Vermorken JB (1997) Experience with intraperitoneal cisplatin and etoposide and i.v. sodium thiosulphate protection in ovarian cancer patients with either pathologically complete response or minimal residual disease. Ann Oncol 8:1235
25. Verschraagen M, Van der Born K, Zwiers THU, Van der Vijgh WJF (2002) Simultaneous determination of intact cisplatin and its metabolite monohydrated cisplatin in human plasma. J Chromatogr B 772:273
26. Wagner T, Kreft B, Bohlmann G, Schwieder G (1988) Effects of fosfomycin, mesna, and sodium thiosulfate on the toxicity and antitumor activity of cisplatin. J Cancer Res Clin Oncol 114:497