Computational consideration of cisplatin hydrolysis and acid dissociation in aqueous media: Effect of total drug concentrations

International Journal of Pharmaceutics

Volumn 246, Issue 1-2, 2002, Pages 95-104

  Yotsuyanagi, Toshihisa ^a   Usami, Makiko ^a   Noda, Yasuhiro ^a   Nagata, Mariko ^a  

^a NAGOYA CITY UNIVERSITY   (Japan)

Author keywords

Cisplatin; Dissociation in aqueous media; Generalized Newton method; Mathematical model; Simulation

Indexed keywords

CISPLATIN; HYDROCHLOROTHIAZIDE;

AQUEOUS SOLUTION; ARTICLE; CONCENTRATION RESPONSE; DISSOCIATION; DRUG EFFECT; DRUG HYDROLYSIS; MATHEMATICAL MODEL; PH; PRIORITY JOURNAL; PUBLISHING; SIMULATION;

ANTINEOPLASTIC AGENTS; CISPLATIN; DRUG STABILITY; HYDROGEN-ION CONCENTRATION; HYDROLYSIS; MODELS, CHEMICAL; SODIUM CHLORIDE; SOLUBILITY; WATER;

EID: 0037057322     PISSN: 03785173     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0378-5173(02)00382-4     Document Type: Article

References (29)

1. Alberts B., Bray D., Lewis J., Raff M., Roberts K., Watson J.D. Molecular Biology of the Cell. second ed. 1989;300-301 Garland Publishing, New York.
2. Appleton T.G., Hall J.R., Ralph S.F., Thompson C.S.M. NMR-study of acid-base equilibria and other reaction of ammineplatinum complexes with aqua and hydroxo ligands. Inorg. Chem. 28:1989;1989-1993.
3. 15N NMR study of anticancer drug, cis-diamminedichloroplatinum(II), and its hydrolysis and oligometrization products. Aust. J. Chem. 34:1981;659-664.
4. Bose R.N., Cornelius R.D., Viola R.E. Multinuclear NMR studies and the kinetics of formation of platinum(II)-adenine nucleoside complexes. J. Am. Chem. Soc. 108:1986;4403-4408.
5. Chen D., Ohta N., Ukai M., Masuda M., Yotsuyanagi T. Binding and aggregation of human γ-globulin by cis-diamminedichloroplatinum(II) through disulfide bond. Bull. Chem. Pharm. 17:1994;1561-1566.
6. Goswami, N., Bennett-Slavin, L.L., Bose, R.N., 1989. New insights into the mechanism of the cis-platin-guanosine 5′-monophosphate reaction. J. Chem. Soc., Chem. Commun., 132-133.
7. Hahn M., Kleine M., Sheldrick W.S. Interaction of cisplatin with methionine and histidine containing peptides: competition between backbone binding, macrochelation and peptide cleavage. J. Biol. Inorg. Chem. 6:2001;556-566.
8. Heudi O., Mercier-Jobard S., Cailleux A., Allain P. Mechanism of reaction of L-methionine with carboplatin and oxaliplatin in different media: a comparison with cisplatin. Biopharm. Drug Dispos. 20:1999;107-116.
9. Heudi O., Brisset H., Cailleux A., Allain P. Chemical instability and methods for measurement of cisplatin adducts formed by interactions with cysteine and glutathione. Int. J. Clin. Pharmacol. Ther. 39:2001;344-349.
10. Jensen K.A. Uber die konstitution eininger platinammine. Z. Anorg. Allgem. Chem. 229:1936;252-264.
11. Jensen K.A. Uber die säuresträken der stereoisomern diaquodiammin-platoinen. Z. Anorg. Allgem. Chem. 242:1939;87-91.
12. Johnson N.P., Hoeschele J.D., Rahn R.O. Kinetic analysis of the in vitro binding of radioactive cis and trans-dichlorodiammineplatinum(II) to DNA. Chem. Biol. Interact. 30:1980;151-169.
13. Lee K.W., Martin D.S. Jr. Cis-dichlorodiammineplatinum(II), aquation equilibria and isotopic exchange of chloride ligands with free chloride and tetrachloroplatinate(II). Inorg. Chim. Acta. 17:1976;105-110.
14. Long D.F., Patton T.F., Repta A.J. Platinum levels in human erythrocytes following intravenous administration of cisplatin: importance of erythrocytes as a distribution site for platinum species. Biopharm. Drug Dispos. 2:1981;137-146.
15. Lyss A.P. Perry M.C., Enzymes and Random Synthetics, Cisplatin. The Chemotherapy Source Book. 1992;405-409 Williams & Wilkins, Baltimore.
16. Martin A. Physical Pharmacy, Physical Chemical Principles in the Pharmaceutical Sciences. 1993;160-161 Lea & Febiger, Philadelphia.
17. Miller S.E., House D.A. 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. 161:1989a;131-137.
18. Miller S.E., House D.A. The hydrolysis products of cis-dichlorodiammine-platinum(II) 2. The kinetics of formation and anation of the cis-diamminedi(aqua) chloroplatinum (II) cation. Inorg. Chim. Acta. 166:1989b;189-197.
19. Miller S.E., House D.A. The hydrolysis products of cis-dichlorodiammine-platinum (II) 3. Hydrolysis kinetics at physiological pH. Inorg. Chim. Acta. 173:1990;53-60.
20. Perumareddi J.R., Adamson A.W. Photochemistry of complex ions. V. The photochemistry of some square-planar platinum(II) complexes. J. Phys. Chem. 72:1968;414-420.
21. Reedijk J. Why does cisplatin reach guanine-N7 with competing S-donor ligands available in the cell. Chem. Rev. 99:1999;2499-2510.
22. Reishus J.W., Martin D.S. cis-Dichlorodiammineplatinum(II). Acid hydrolysis and isotopic exchange of the chloride ligands. J. Am. Chem. Soc. 83:1961;2457-2462.
23. Shearan P., Alvarez J.M.F., Zayed N., Smyth M.R. High-performance liquid chromatographic separation of cisplatin and its hydrolysis products on alumina and application to studies of their interaction with cysteine. Biomed. Chromatogr. 4:1990;73-82.
24. Shiraishi, K., 2001. DECIMAL BASIC (based on ISO FULL BASIC language system), http://hp.vector.co.ip/authors/VA0008683/index.htm.
25. Stanek G. Scientific computing. Zwillinger D., CRC Standard Mathematical Tables and Formulae. 30th ed. 1996;690-692 CRC Press, Boca Raton, FL.
26. Stokes R.H., Robinson R.A. Ionic hydration and activity in electrolyte solutions. J. Am. Chem. Soc. 70:1948;1870-1878.
27. Sundquist W.I., Lippard S.J. The coordination chemistry of platinum anticancer drugs and related compounds with DNA. Coord. Chem. Rev. 100:1990;293-322.
28. Zenker A., Galanski M., Bereuter T.L., Keppler B.K., Linder W. Kinetics of binding properties of 5′-GMP with cisplatin under simulated physiological conditions by capillary electrophoresis. J. Chromatogr. B. 745:2000;211-219.
29. Zheng H., Fink D., Howell S.B. Pharmacological basis for a novel therapeutic strategy based on the use of aquatod cisplatin. Clin. Cancer Res. 3:1997;1157-1165.