Mechanisms of reaction of L-methionine with carboplatin and oxaliplatin in different media: A comparison with cisplatin

Biopharmaceutics and Drug Disposition

Volumn 20, Issue 2, 1999, Pages 107-116

  Heudi, Olivier ^a   Mercier Jobard, Sophie ^a   Cailleux, Annie ^a   Allain, Pierre ^a  

^a ANGERS UNIVERSITY HOSPITAL   (France)

Author keywords

Carboplatin; Cisplatin; HPLC UV; L methionine; LC MS; Oxaliplatin

Indexed keywords

ANTINEOPLASTIC AGENT; CARBOPLATIN; CISPLATIN; METHIONINE; OXALIPLATIN; PHOSPHATE; PLATINUM DERIVATIVE; SODIUM CHLORIDE; WATER;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPARATIVE STUDY; CONCENTRATION RESPONSE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; ULTRAVIOLET SPECTROSCOPY;

ANTINEOPLASTIC AGENTS; BUFFERS; CARBOPLATIN; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CISPLATIN; DRUG STABILITY; MASS SPECTROMETRY; METHIONINE; ORGANOPLATINUM COMPOUNDS; PHOSPHATES; SPECTROPHOTOMETRY, ULTRAVIOLET; WATER;

EID: 0033037368     PISSN: 01422782     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-081X(199903)20:2<107::AID-BDD161>3.0.CO;2-0     Document Type: Article

References (36)

1. B. Rosenberg, L. Van Camp and T. Krigas, Inhibition of cell division in Escherichia coli by electrolysis products from platinum electrode. Nature, 205, 698-699 (1965).
2. B. Rosenberg, Anticancer activity of cis-dichlorodiammineplatinum(II) and some relevant chemistry. Cancer Treat. Rep., 63, 1433-1438 (1979).
3. S.J. Dufful and B.A. Robinson, Clinical pharmacokinetics and dose optimisation of carboplatin: a review. Clin. Pharmacokinet., 33, 161-183 (1997).
4. C. Louvet and A. de Gramont, Place et intérêt de l'oxaliplatine dans les cancers colorectaux métastasés. Rev. Méd. Interne., 18, 368s-371s (1997).
5. P.C. Dedon and R.F. Borch, Characterization of the reactions of platinum antitumor agents with biologic and non biologic sulfur-containing nucleophiles. Biochem. Pharmacol., 36, 1955-1964 (1987).
6. P. Pil and S.J. Lippard, Cisplatin related drugs. Encycl. Cancer, 1, 392-410 (1997).
7. L.A. Zwelling and K.W. Kohn, Mechanism of action of cis-dichlorodiammineplatinum(II). Cancer Treat. Rep., 63, 1439-1444 (1979).
8. W.J.F. Van der Vigh and I. Klein, Protein binding of five platinum compounds comparison of two ultrafiltration systems. Cancer Chemother. Pharmacol., 18, 129-132 (1986).
9. A.J. Repta and D.F. Long, Reactions of cisplatin with human plasma and plasma fractions In Cisplatin Current Status and New Developments, A.W. Prestayko, ST. Crooke and S.K. Carter (Eds), Academic Press, New York, 1980, pp. 285-304.
10. N. Nagai, R. Okuda, M. Kinoshita and H. Ogata, Decomposition kinetics of cisplatin in human biological fluids. J. Pharm. Pharmacol., 48, 918-924 (1996).
11. F. Tosetti, M. Rocco, R.A. Fulco, S. Chiara, M. Bruzzone, E. Campora and M. Esposito, Serial determination of platinum, content and free sulfhydryl levels in plasma of patients treated with cisplatin or carboplatin. Anticancer Res., 8, 381-386 (1988).
12. O. Heudi, A. Cailleux, and P. Allain, Kinetic studies of the reactivity between cisplatin and its monoaquo species with L-methionine. J. Inorg. Biochem., 71, 61-69 (1998).
13. R.N. Bose, S.K. Ghosh and S. Moghaddas, Kinetic analysis of the cis-diamminedichloroplatinum(II)-cysteine reaction: implications to the extent of platinum-DNA binding. J. Inorg. Biochem., 65, 199-205 (1997).
14. R.J. Knox, F. Friedlos, D.A. Lydall and J. Roberts, Mechanism of cytotoxicity of anticancer platinum drugs: evidence that cis-diamminedichloroplatinum(II) and cis-diammine-(1,1-cyclobutanedicarboxylato) platinum(II) differ only in the kinetics of their interaction with DNA. Cancer Res., 46, 1972-1979 (1986).
15. 14C-carboplatin. Cancer Chemother. Pharmacol., 20, 271-276 (1987).
16. C.P. Saris, P.J.M. Van de Vaart, R.C. Rietbroek and F.A. Blommaert, In vitro formation of DNA adducts by cisplatin, lobaplatin and oxaliplatin in calf thymus DNA in solution and in cultured human cells. Carcinogenesis, 17, 2763-2769 (1996).
17. L. Pendyala and P.J. Creaven, In vitro cytotoxicity, protein binding, red cell partitioning, and biotransformation of oxaliplatin. Cancer Res., 53, 5970-5976 (1993).
18. P.T. Daley-Yates and D.C.H. McBrien, The inhibition of renal ATPase by cisplatin and some biotransformation products. Chem. Biol. Interact., 40, 325-334 (1982).
19. O. Heudi, A. Cailleux and P. Allain, Interactions between cisplatin derivatives and mobile phase during chromatographic separation. Chromatographia, 44, 19-24 (1997).
20. 2(CBDCA-O)(5′-GMP-N7)] in solution. Inorg. Chem., 32, 1333-1340 (1993).
21. B.J. Corden, Reaction of platinum(II) antitumor agents with sulfhydral compounds and the implications for nephrotoxicity. Inorg. Chim. Acta., 137, 125-130 (1987).
22. Z. Zhao, K, Tepperman, J.G. Dorsey and R.C. Elder, Determination of cisplatin and some possible metabolites by ion-paring chromatography with inductively coupled plasma mass spectrometric detection. J. Chromatogr. Biomed. Appl., 615, 83-89 (1993).
23. R.E. Norman, J.D. Ranford and P.J. Sadler, Studies of platinum(II) methionine complexes: metabolites of cisplatin. Inorg. Chem., 31, 877-888 (1992).
24. A. Bemareggi, L. Torti, R.M. Facino, M. Carini, G. Depta, B. Casetta, N. Farrell, S Spadacini, R. Ceserani and S. Tognella, Characterization of cisplatin-glutathione adducts by liquid chromatography-mass spectrometry. Evidence for their formation in vitro but not in vivo after concomitant administration of cisplatin and glutathione to rats and cancer patients. J. Chromatogr. B., 609, 247-263 (1995).
25. 2 moiety to the phosphate in aqueous solution. Inorg. Chem. Acta, 67, L19-L20 (1982).
26. F.E. Efferink, W.J.F. Van der Vigh, I. Klein and H.M. Pinedo, Interaction of cisplatin and carboplatin with sodium thiosulfate: reaction rates and protein binding. Clin. Chem., 32, 641-645 (1986).
27. 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 (1994).
28. R. Carballar, M. Munoz, M. Pujol, J Prat, V. Cirona and J. de Bolos, Stability study of carboplatin in aqueous solution and under illumination by high-performance liquid chromatography. Biomed. Chromatogr., 11, 119-120 (1997).
29. Y.W. Cheung, J.C. Cradock, B.R. Vishnuvajjala and K.P. Flora, Stability of cisplatin, iproplatin, carboplatin, and tetraplatin in commonly used intravenous solutions. Am. J. Hosp. Pharm., 44, 124-130 (1987).
30. I.S. Krull, X.D. Ding, S. Baverman, C. Selavka, F. Hocheberg and L.A. Sternson, Trace analysis for platinum anti-cancer drugs via LCEC. J. Chromatogr. Sci., 21, 166-173 (1983).
31. K.J. Barnham, M.I. Djuran, P. del S. Murdoch, J.D. Ranford and P.J. Sadler, Ring-opened adducts of the anticancer drug carboplatin with sulfur amino acids. Inorg. Chem., 35, 1065-1072 (1996).
32. W.P. Petros, S.G. Chaney, D.C. Smith, J. Fangmeier, M. Sakata, T.D. Brown and D.L. Trump, Pharmacokinetic and biotransformation studies of ormaplatinin conjunction with a phase I trial. Cancer Chemother. Pharmacol., 33, 347-354 (1994).
33. 2]: metabolite of the anticancer drug cisplatin. Inorg. Chem., 32, 2249-2255 (1993).
34. W.W. Alden and A.J. Repta, Exacerbation of cisplatin induced nephrotoxicity by methionine. Chem. Biol. Interact., 48, 121-124 (1984).
35. C.M. Riley, L.A. Sternson, A.J. Repta and S.A. Slyter, Monitoring the reactions of cisplatin with nucleotides and methionine by reversed-phase high-performance liquid chromatography using cationic and anionic pairing ions. Anal. Biochem., 130, 203-214 (1983).
36. D. Screnci, H.M. Er, T.W. Hambley, W. Galettis, W. Brouwer and M.J. McKeage, Stereoselective peripheral sensory neurotoxicity of diaminocyclohexane platinum enantiomers related to ormaplatin and oxaliplatin. Br. J. Cancer, 76, 502-510 (1997).