Axial Ligands and Alicyclic Ring Size Modulate the Activity and Biochemical Pharmacology of Ammine/Cycloalkylamine-Platinum(IV) Complexes in Tumor Cells Resistant to cis-Diamminedichloroplatinum(II) or trans-1R-2R-1S,2S-Diaminocyclohexanetetrachloroplatinum(IV)

Cancer Research

Volumn 54, Issue 17, 1994, Pages 4691-4697

  Yoshida, Motofumi ^a   Khokhar, Abdul R ^a   Siddik, Zahid H ^a  

^a UNIVERSITY OF TEXAS MD ANDERSON CANCER CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3 (4,5 DIMETHYL 2 THIAZOLYL) 2,5 DIPHENYLTETRAZOLIUM BROMIDE; ALICYCLIC AMINE; CISPLATIN; CYCLOBUTANE; CYCLOHEXANE; CYCLOPENTANE; CYCLOPROPANE; DNA; GLUTATHIONE; LIGAND; PLATINUM 1,2 DIAMINOCYCLOHEXANE; PLATINUM COMPLEX; TETRAPLATIN;

ANIMAL CELL; ARTICLE; CELL LEVEL; CONTROLLED STUDY; CYTOTOXICITY; DNA ADDUCT; DRUG ACCUMULATION; DRUG DNA BINDING; DRUG RESISTANCE; LEUKEMIA CELL; MOUSE; NONHUMAN; PARTITION COEFFICIENT; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION;

ANIMAL; CISPLATIN; DNA, NEOPLASM; DRUG RESISTANCE; DRUG SCREENING ASSAYS, ANTITUMOR; LEUKEMIA L1210; LIGANDS; ORGANOPLATINUM COMPOUNDS; STRUCTURE-ACTIVITY RELATIONSHIP; SUPPORT, U.S. GOV'T, P.H.S.;

EID: 0027965658     PISSN: 00085472     EISSN: 15387445     Source Type: Journal    
DOI: None     Document Type: Article

References (29)

1. Prestayko, A. W., D'Aoust, J. C., Issell, B. F., and Crooke, S. T., Cisplatin (cis-diamminedichloroplatinum II). Cancer Treat. Rev. 6: 17-39, 1979.
2. Schilder, R. J., and Ozols, R. F., New therapies for ovarian cancer. Cancer Invest. 10: 307-315, 1992.
3. Harrap, K. R., Preclinical studies identifying carboplatin as a viable cisplatin alternative. Cancer Treat. Rev. 12 (Suppl. A): 21-33, 1985.
4. Andrews, P. A., and Howell, S. B., Cellular pharmacology of cisplatin: perspectives on mechanisms of acquired resistance. Cancer Cells, 2: 35-43, 1990.
5. Timmer-Bosscha, H. Mulder, N. H., and de Vries, E.G.E. Modulation of cis-diamminedichloroplatinum(II) modulation: a review. Br. J. Cancer, 66: 415-425, 1992.
6. Burchenal, J. H., Kalaher, K. O'Toole, T. and Chisholm, J. Lack of cross-resistance between certain platinum coordination compounds in mouse leukemia. Cancer Res. 37: 3455-3457, 1977.
7. Christian, M. C., The current status of new platinum analogs. Semin. Oncol. 19: 720-733, 1992.
8. Kelland, L. R., Murrer, B. A., Abel, G. Giandomenico, C. M., Mistry, P. and Harrap, K. R., Ammine/amine platinum(TV) dicarboxylates: a novel class of platinum complex exhibiting selective cytotoxicity to intrinsically cisplatin-resistant human ovarian carcinoma cell lines. Cancer Res. 52: 822-828, 1992.
9. Al-Baker, S. Siddik, Z. H., and Khokhar, A. R., Synthesis and characterization of new antitumor trans-R,R-, trans-S.S- and cis-1, 2-diaminocyclohexane platinum(IV) complexes. J. Coord. Chem. 31: 109-116, 1994.
10. Khokhar, A. R., Al-Baker, S. and Siddik, Z. H., Synthesis and antitumor activity of 1, 2-diaminocyclohexane platinum(IV) complexes. J. Inorg. Biochem. 54: 39-47, 1994.
11. Siddik, Z. H., Al-Baker, S. Burditt, T. L., and Khokhar, A. R., Differential antitumor activity and toxicity of isomeric 1, 2-diaminocyclohexane platinum (II) complexes. J. Cancer Res. Clin. Oncol. 120: 12-16, 1993.
12. Kido, Y. Khokhar, A. R., Al-Baker, S. and Siddik, Z. H., Modulation of cytotoxicity and cellular pharmacology of 1, 2-diaminocyclohexane platinum(IV) complexes mediated by axial and equatorial ligands. Cancer Res. 53: 4567-4572, 1993.
13. Vollano, J. F., Al-Baker, S. Dabrowiak, J. C., and Schurig, J. E., Comparative antitumor studies on platinum(II) and platinum(IV) complexes containing 1, 2-diaminocyclohexane. J. Med. Chem. 30: 716-719, 1987.
14. Khokhar, A. R., Deng, Y. Al-Baker, S. Yoshida, M. and Siddik, Z. H., Synthesis and antitumor activity of ammine/amine platinum(II) and (IV) complexes. J. Inorg. Biochem. 57: 677-687, 1993.
15. Eastman, A. and Illenye, S. Murine leukemia L1210 cell lines with different patterns of resistance to platinum coordination complexes. Cancer Treat. Rep. 68: 1189-1190, 1984.
16. Richon, V. M., Schultz, N. and Eastman, A. Multiple mechanisms of resistance to cis-diamminedichloroplatinum(II) in murine leukemia L1210 cells. Cancer Res. 47: 2056-2061, 1987.
17. Eastman, A. Glutathione-mediated activation of anticancer platinum(IV) complexes. Biochem. Pharmacol. 36: 4177-4178, 1987.
18. Carmichael, J. DeGraff, W. Gazdar, A. Minna, J. and Mitchell, J. Evaluation of a tetrazolium-based semi-automatic colorimetric assay: Assessment of chemosensitivity testing. Cancer Res. 47: 936-942, 1987.
19. Kido, Y. Khokhar, A. R., and Siddik, Z. H., Differential cytotoxicty, uptake and DNA binding of tetraplatin and analogous isomers in sensitive and resistant cancer cells. Anticancer Drugs, 4: 251-258, 1993.
20. Siddik, Z. H., Boxall, F. E., and Harrap, K. R., Flameless atomic absorption spectrophotometric determination of platinum in tissues solubilized in hyaminehydroxide. Anal. Biochem. 163: 21-26, 1987.
21. Siddik, Z. H., and Newman, R. A., Use of platinum as a modifier in the sensitive detection of tellurium in biological samples. Anal. Biochem. 172: 190-1%, 1988.
22. Lowry, O. H., Rosebrough, N. J., Farr, A. L., and Randall, R. J., Protein measurement with the Folin phenol reagent. J. Biol. Chem. 193: 265-275, 1951.
23. Maniatis, T. Fritsch, E. F., and Sambrook, J. Molecular Cloning: A Laboratory Manual. Cold Spring Harbor, NY: Cold Spring Harbor Laboratory, 1982.
24. Leo, A. Hansch, C. and Elkins, D. Partition coefficients and their uses. Chem. Rev. 71: 525-616, 1971.
25. Roberts, J. J., Knox, R. J., Friedlos, F. and Lydall, D. A., DNA as a target for the cytotoxic and antitumour action of platinum co-ordination complexes: comparative in vitro and in vivo studies of cisplatin and carboplatin. In: D.C.H. McBrien and T.F. Slater (eds.), Biochemical Mechanisms of Platinum Antitumour Drugs, pp. 29-64. Oxford: IRL Press, 1986.
26. Blatter, E. E., Vollano, J. F., Krishnan, B. S., and Dabrowiak, J. C., Interaction of the antitumor agents cis,cis,trims-PtIV(NH3)2Cl2(OH)2 and cis, cis, trans-PtIV[(CH3)2CHNH2]2Cl2(OH)2 and their reduction products with PM2 DNA. Biochemistry, 23: 4817-4820, 1984.
27. Pendyala, L. Arakali, A. V., Sansone, P. Cowens, J. W., and Creaven, P. J., DNA binding of iproplatin and its divalent metabolite cis-dichloro-bis-isopropylamine platinum(II). Cancer Chemother. Pharmacol. 27: 248-250, 1990.
28. Gibbons, G. R., Wyrick, S. and Chaney, S. G., Rapid reduction of tetrachloro(D, L-trans)1, 2-diaminocyclohexaneplatinum(IV) (tetraplatin) in RPMI 1640 tissue culture medium. Cancer Res. 49: 1402-1407, 1989.
29. Chaney, S. G., Wyrick, S. and Till, G. K., In vitro biotransformation of tetrachloro(D,L-trans)l, 2-diaminocyclohexaneplatinum(IV) (tetraplatin) in rat plasma. Cancer Res. 50: 4539-4545, 1990.