Kinetics of cisplatin and its monohydrated complex with sulfur-containing compounds designed for local otoprotective administration

Experimental Biology and Medicine

Volumn 231, Issue 10, 2006, Pages 1638-1645

  Videhult, Pernilla ^a,b   Laurell, Göran ^b   Wallin, Inger ^a   Ehrsson, Hans ^a,b  

^a KAROLINSKA UNIVERSITY HOSPITAL   (Sweden)

^b KAROLINSKA INSTITUTE   (Sweden)

Author keywords

Antioxidants; cis diamminedichloroplatinum; Hydrated species; Nucleophiles; Ototoxicity

Indexed keywords

ACETYLCYSTEINE; CISPLATIN; DIMETHYLTHIOUREA; MECYSTEINE; METHIONINE; MONOHYDRATED COMPLEX; PLATINUM COMPLEX; SULFUR; THIOSULFATE; UNCLASSIFIED DRUG;

ARTICLE; DRUG DEGRADATION; EAR PROTECTION; LIQUID CHROMATOGRAPHY; PHOTOMETRY;

EID: 33751324545     PISSN: 15353702     EISSN: 15353699     Source Type: Journal    
DOI: 10.1177/153537020623101009     Document Type: Article

References (56)

1. Reedijk J. New clues for platinum antitumor chemistry: kinetically controlled metal binding to DNA. Proc Natl Acad Sci U S A 100:3611-3616, 2003.
2. Andersson A, Fagerberg J, Lewensohn R, Ehrsson H. Pharmacokinetics of cisplatin and its monohydrated complex in humans. J Pharm Sci 85:824-827, 1996.
3. Lempers ELM, Reedijk J. Interactions of platinum amine compounds with sulfur-containing biomolecules and DNA fragments. Adv Inorg Chem 37:175-217, 1991.
4. Mandic A, Hansson J, Linder S, Shoshan MC. Cisplatin induces endoplasmic reticulum stress and nucleus-independent apoptotic signaling. J Biol Chem 278:9100-9106, 2003.
5. Gilmer Knight KR, Kraemer DF, Neuwelt EA. Ototoxicity in children receiving platinum chemotherapy: underestimating a commonly occurring toxicity that may influence academic and social development. J Clin Oncol 23:8588-8596, 2005.
6. Masuda H, Tanaka T, Takahama U. Cisplatin generates superoxide anion by interaction with DNA in a cell-free system. Biochem Biophys Res Commun 203:1175-1180, 1994.
7. Dickey DT, Muldoon LL, Kraemer DF, Neuwelt EA. Protection against cisplatin-induced ototoxicity by N-acetylcysteine in a rat model. Hear Res 193:25-30, 2004.
8. Dickey DT, Wu YJ, Muldoon LL, Neuwelt EA. Protection against cisplatin-induced toxicities by N-acetylcysteine and sodium thiosulfate as assessed at the molecular, cellular, and in vivo levels. J Pharmacol Exp Ther 314:1052-1058, 2005.
9. Ramesh G, Reeves WB. p38 MAP kinase inhibition ameliorates cisplatin nephrotoxicity in mice. Am J Physiol Renal Physiol 289:F166-F174, 2005.
10. Campbell KCM, Rybak LP, Meech RP, Hughes L. D-Methionine provides excellent protection from cisplatin ototoxicity in the rat. Hear Res 102:90-98, 1996.
11. Reser D, Rho M, Dewan D, Herbst L, Li G, Stupak H, Zur K, Romaine J, Frenz D, Goldbloom L, Kopke R, Arezzo J, Van De Water T. L- and D-methionine provide equivalent long term protection against CDDP-induced ototoxicity in vivo, with partial in vitro and in vivo retention of antineoplastic activity. Neurotoxicology 20:731-748, 1999.
12. Li G, Frenz DA, Brahmblatt S, Feghali JG, Ruben RJ, Berggren D, Arezzo J, Van De Water TR. Round window membrane delivery of L-methionine provides protection from cisplatin ototoxicity without compromising chemotherapeutic efficacy. Neurotoxicology 22:163-176, 2001.
13. Howell SB, Taetle R. Effect of sodium thiosulfate on cis- dichlorodiammineplatinum(II) toxicity and antitumor activity in L1210 leukemia. Cancer Treat Rep 64:611-616, 1980.
14. Iwamoto Y, Kawano T, Ishizawa M, Aoki K, Kuroiwa T, Baba T. Inactivation of cis-diamminedichloroplatinum (II) in blood and protection of its toxicity by sodium thiosulfate in rabbits. Cancer Chemother Pharmacol 15:228-232, 1985.
15. Goel R, Cleary SM, Horton C, Kirmani S, Abramson I, Kelly C, Howell SB. Effect of sodium thiosulfate on the pharmacokinetics and toxicity of cisplatin. J Natl Cancer Inst 81:1552-1560, 1989.
16. Ekborn A, Laurell G, Johnstrom P, Wallin I, Eksborg S, Ehrsson H. D-Methionine and cisplatin ototoxicity in the guinea pig: D-methionine influences cisplatin pharmacokinetics. Hear Res 165:53-61, 2002.
17. Choe WT, Chinosornvatana N, Chang KW. Prevention of cisplatin ototoxicity using transtympanic N-acetylcysteine and lactate. Otol Neurotol 25:910-915, 2004.
18. Laurell G, Teixeira M, Sterkers O, Bagger-Sjoback D, Eksborg S, Lidman O, Ferrary E. Local administration of antioxidants to the inner ear. Kinetics and distribution. Hear Res 173:198-209, 2002.
19. Wimmer C, Mees K, Stumpf P, Welsch U, Reichel O, Suckfull M. Round window application of D-methionine, sodium thiosulfate, brain-derived neurotrophic factor, and fibroblast growth factor-2 in cisplatin-induced ototoxicity. Otol Neurotol 25:33-40, 2004.
20. Ehrsson HC, Wallin IB, Andersson AS, Edlund PO. Cisplatin, transplatin, and their hydrated complexes: separation and identification using porous graphitic carbon and electrospray ionization mass spectrometry. Anal Chem 67:3608-3611, 1995.
21. Lim MC, Martin RB. The nature of cis amine Pd(II) and antitumor cis amine Pt(II) complexes in aqueous solutions. J Inorg Nucl Chem 38:1911-1914, 1976.
22. Ehrsson H, Wallin I. Liquid chromatographic determination of oxaliplatin in blood using post-column derivatization in a microwave field followed by photometric detection. J Chromatogr B 795:291-294, 2003.
23. Andersson A, Ehrsson H. Determination of cisplatin and cis-diammineaquachloroplatinum(II) ion by liquid chromatography using post-column derivatization with diethyldithiocarbamate. J Chromatogr B 652:203-210, 1994.
24. Elferink F, van der Vijgh WJF, Klein I, Pinedo HM. Interaction of cisplatin and carboplatin with sodium thiosulfate: reaction rates and protein binding. Clin Chem 32:641-645, 1986.
25. Nagai N, Okuda R, Kinoshita M, Ogata H. Decomposition kinetics of cisplatin in human biological fluids. J Pharm Pharmacol 48:918-924, 1996.
26. Dedon PC, Borch RF. Characterization of the reactions of platinum antitumor agents with biologic and nonbiologic sulfur-containing nucleophiles. Biochem Pharmacol 36:1955-1964, 1987.
27. Miller SE, House DA. The hydrolysis products of cis- dichlorodiammineplatinum(II) 3. Hydrolysis kinetics at physiological pH. Inorg Chim Acta 173:53-60, 1990.
28. Daley-Yates PT, McBrien DCH. The inhibition of renal ATPase by cisplatin and some biotransformation products. Chem Biol Interact 40:325-334, 1982.
29. Hannemann J, Duwe J, Baumann K. Iron- and ascorbic acid-induced lipid peroxidation in renal microsomes isolated from rats treated with platinum compounds. Cancer Chemother Pharmacol 28:427-433, 1991.
30. Kohl HH, Friedman ME, Melius P, Mora EC, McAuliffe CA. Enhanced inhibition of both cellular protein synthesis and malate dehydrogenase by aged aquoplatinum(II) complexes. Chem Biol Interact 24:209-215, 1979.
31. Yachnin JR, Wallin I, Lewensohn R, Sirzen F, Ehrsson H. The kinetics and cytotoxicity of cisplatin and its monohydrated complex. Cancer Lett 132:175-180, 1998.
32. Zheng H, Fink D, Howell SB. Pharmacological basis for a novel therapeutic strategy based on the use of aquated cisplatin. Clin Cancer Res 3:1157-1165, 1997.
33. 2+, and the hydrolysis product of cisplatin in the rat. Cancer Chemother Pharmacol 29:29-32, 1991.
34. Ekborn A, Lindberg A, Laurell G, Wallin I, Eksborg S, Ehrsson H. Ototoxicity, nephrotoxicity and pharmacokinetics of cisplatin and its monohydrated complex in the guinea pig. Cancer Chemother Pharmacol 51:36-42, 2003.
35. 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 33:3063-3070, 1984.
36. 195Pt NMR kinetic and mechanistic studies of cis- and trans-diamminedichloroplatinum(II) binding to DNA. J Am Chem Soc 112:6860-6871, 1990.
37. Segal E, Le Pecq JB. Role of ligand exchange processes in the reaction kinetics of the antitumor drug cis-diamminedichloroplatinum(II) with its targets. Cancer Res 45:492-498, 1985.
38. Corden BJ. Reaction of platinum(II) antitumor agents with sulfhydral compounds and the implications for nephrotoxicity. Inorg Chim Acta 137:125-130, 1987.
39. Dabrowiak JC, Goodisman J, Souid AK. Kinetic study of the reaction of cisplatin with thiols. Drug Metab Dispos 30:1378-1384, 2002.
40. Heudi O, Cailleux A, Allain P. Kinetic studies of the reactivity between cisplatin and its monoaquo species with L-methionine. J Inorg Biochem 71:61-69, 1998.
41. Leeuwenkamp OR, Neijt JP, van der Vijgh WJF, Pinedo HM. Reaction kinetics of cisplatin and its monoaquated species with the modulating agents (di)mesna and thiosulphate. Eur J Cancer 27:1243-1247, 1991.
42. + (X=Cl, OH) with glycine, monohydrogen malonate and chloride. Inorg Chim Acta 187:125-132, 1991.
43. Ohta N, Inagaki K, Muta H, Yotsuyanagi T, Matsuo T. Reaction of oxidized glutathione with cis- and trans-diamminedichloroplatinum(II) and their aquated complexes through the disulfide bond. Int J Pharm 161:15-21, 1998.
44. 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 83:859-862, 1994.
45. Parnes LS, Sun AH, Freeman DJ. Corticosteroid pharmacokinetics in the inner ear fluids: an animal study followed by clinical application. Laryngoscope 109:1-17, 1999.
46. Wang J, Lloyd Faulconbridge RV, Fetoni A, Guitton MJ, Pujol R, Puel JL. Local application of sodium thiosulfate prevents cisplatin-induced hearing loss in the guinea pig. Neuropharmacology 45:380-393, 2003.
47. Tabuchi K, Tsuji S, Fujihira K, Oikawa K, Hara A, Kusakari J. Outer hair cells functionally and structurally deteriorate during reperfusion. Hear Res 173:153-163, 2002.
48. Tabuchi K, Tsuji S, Ito Z, Hara A, Kusakari J. Does xanthine oxidase contribute to the hydroxyl radical generation in ischemia and reperfusion of the cochlea? Hear Res 153:1-6, 2001.
49. El-Khateeb M, Appleton TG, Gahan LR, Charles BG, Berners-Price SJ, Bolton AM. Reactions of cisplatin hydrolytes with methionine, cysteine, and plasma ultrafiltrate studied by a combination of HPLC and NMR techniques. J Inorg Biochem 77:13-21, 1999.
50. Townsend DM, Marto JA, Deng M, Macdonald TJ, Hanigan MH. High pressure liquid chromatography and mass spectrometry characterization of the nephrotoxic biotransformation products of cisplatin. Drug Metab Dispos 31:705-713, 2003.
51. Feghali JG, Liu W, Van De Water TR. L-N-acetyl-cysteine protection against cisplatin-induced auditory neuronal and hair cell toxicity. Laryngoscope 111:1147-1155, 2001.
52. Alden WW, Repta AJ. Exacerbation of cisplatin-induced nephrotoxicity by methionine. Chem Biol Interact 48:121-124, 1984.
53. Sterkers O, Saumon G, Tran Ba Huy P, Ferrary E, Amiel C. Electrochemical heterogeneity of the cochlear endolymph: effect of acetazolamide. Am J Physiol 246:F47-F53, 1984.
54. Salt AN, Ma Y. Quantification of solute entry into cochlear perilymph through the round window membrane. Hear Res 154:88-97, 2001.
55. Laurell G, Andersson A, Engstrom B, Ehrsson H. Distribution of cisplatin in perilymph and cerebrospinal fluid after intravenous administration in the guinea pig. Cancer Chemother Pharmacol 36:83-86, 1995.
56. Tanaka F, Whitworth CA, Rybak LP. Round window pH manipulation alters the ototoxicity of systemic cisplatin. Hear Res 187:44-50, 2004.