An Unexpected Biotransformation Pathway for Tetrachloro-(d,l-trans)-1,2-diaminocyclohexaneplatinum(IV) (Tetraplatin) in the L1210 Cell Line

Cancer Research

Volumn 51, Issue 3, 1991, Pages 969-973

  Chancy, Stephen G ^a   Gibbons, Gregory R ^a   Wyrick, Steven D ^b   Podhasky, Paula ^a  

^a UNIVERSITY OF NORTH CAROLINA SCHOOL OF MEDICINE   (United States)

^b UNIVERSITY OF NORTH CAROLINA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

TETRAPLATIN; TRITIUM;

ANIMAL CELL; ARTICLE; BIOTRANSFORMATION; CONTROLLED STUDY; ISOTOPE LABELING; LEUKEMIA L 1210; MOUSE; NONHUMAN; PRIORITY JOURNAL;

ANIMAL; ANTINEOPLASTIC AGENTS; BIOTRANSFORMATION; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; LEUKEMIA L1210; ORGANOPLATINUM COMPOUNDS; SUPPORT, NON-U.S. GOV'T;

EID: 0026066027     PISSN: 00085472     EISSN: 15387445     Source Type: Journal    
DOI: None     Document Type: Article

References (23)

1. Burchenal, J. H., Kalaher, K., Dew, K., and Lokys, L. Rationale for the development of platinum analogs. Cancer Treat. Rep., 63:1493-1498,1979.
2. Anderson, W. K., Quagliato, D. A., Haugwitz, R. D., Narayanan, V. L., and Wolpert-DeFilippes, M. F. Synthesis, physical properties, and antitumor activity of tetraplatin and related tetrachloroplatinum(IV) stereoisomers of 1,2-diaminocyclohexane. Cancer Treat. Rep., 70:997-1002, 1986.
3. Wilkoff, L. J., Dulmadge, E. A., Trader, M. W., Harrison, S. D., and Griswold, D. P. Evaluation of fra/w-tetrachloro-1,2-diaminocyclohexanepIat-inum(IV) in murine leukemia LI210 resistant and sensitive to cis-diammine-dichloroplatinum(II). Cancer Chemother. Pharmacol., 20:96-100,1987.
4. Behrens, B. C., Hamilton, T. C., Masuda, H., Grotzinger, K. R., Whang-Peng, J., Louie, K. G., Knutsen, T., McKay, W. M., Young, R. C., and Ozols, R. F. Characterization of a aj-diarnminedichloroplatinum(II)-resistant human ovarian cancer cell line and its use in evaluation of platinum analogs. Cancer Res., 47:414-418, 1987.
5. Hills, C. A., Kelland, L. R., Able, G., Siracky, J., Wilson, A. P., and Harrap, K. R. Biological properties of ten ovarian carcinoma cell lines: calibration in vitro against four platinum complexes. Br. J. Cancer, 59:527-534, 1988.
6. Rahman, A., Roh, K. J., Wolpert-DeFilippes, M. F., Goldin, A., Venditta, J. M., and Woolley, P. V. Therapeutic and pharmacological studies of tetrachloro(taui5)l,2-diaminocyclohexaneplatinum(IV), a new platinum analogue. Cancer Res., 48:1745-1752, 1988.
7. Smith, J. H., Smith, M. A., Litterst, C. L., Copley, M. P., Uozumi, J., and Boyd, M. R. Comparative toxicity and renal distribution of the platinum analogs tetraplatin, CHIP, and cisplatin at equimolar doses in the Fischer 344 rat. Fundam. Appl. Toxicol., 10: 45-61, 1988.
8. Smith, M. A., Smith, J. H., Litterst, C. L., Copley, M. P., Uozumi, J., and Boyd, M. R. In vivo biochemical indices of nephrotoxicity of platinum analogs tetraplatin, CHIP, and cisplatin in the Fischer 344 rat. Fundam. Appl. Toxicol., 70:62-72, 1988.
9. Mauldin, S. K., Richard, F. A., Plescia, M., Wyrick, S. D., Sancar, A., and Chaney, S. G. High performance liquid chromatographic separation of platinum complexes containing the 1,2-diaminocyclohexane carrier ligand. Anal. Biochem., 157:129-143,1986.
10. Gibbons, G. R., Wyrick, S., and Chaney, S. G. Rapid reduction of tetrachlo-ro(ttwu)l'2-diaminocyclohexaneplatinum(IV) (tetraplatin) in RPMI-1640 tissue culture medium. Cancer Res., 49:1402-1407,1989.
11. Mauldin, S. K., Husain, I., Sancar, A., and Chaney, S. G. Effects of the bidentate malonate ligand on the utilization and cytotoxicity of platinum compounds in the LI210 cell line. Cancer Res., 46: 2876-2882,1986.
12. Mauldin, S. K., Gibbons, G., Wyrick, S. D., and Chaney, S. G. Intracellular biotransformation of platinum compounds with the 1,2-diaminocyclohexane carrier ligand in the L1210 cell line. Cancer Res., 48:5136-5144, 1988.
13. Mauldin, S. K., Plescia, M., Richard, F. A., Wyrick, S. D., Voyksner, R. D., and Chaney, S. G. Displacement of the bidentate malonate ligand from (d,l-fra/!5-l,2-diaminocyclohexane)malonatoplatinum(II) by physiologically important compounds in vitro. Biochem. Pharmacol., 37:3321-3333, 1988.
14. Langford, C. H., and Gray, H. B. Ligand Substitution Processes. New York: W. A. Benjamin, 1965.
15. Blatter, E. E., Vollono, J. H., Krishman, B. S., and Dabrowiak, J. C. Interaction of the antitumor agents c/s,cw,/ra/i5-Pt,v(NH3)2(OH)2 and c/s,ci5t/rfl/w-PtIV[(CH3)2CHNH2]2Cl2(OH)2 and their reduction products with PM2 DNA. Biochemistry, 23:4817-4820, 1984.
16. van der Veer, J. L., Peters, A. R., and Reedijk, J. Reaction products from platinum(IV) amine compounds and 5'-GMP are mainly bis(5'-GMP)-platinum(II) amine adducts. J. Inorg. Biochem., 26: 137-142,1986.
17. Eastman, A. Glutathione-mediated activation of anticancer platinum(IV) complexes. Biochem. Pharmacol., 36:4177-4178, 1987.
18. Wyrick, S. D., and Chaney, S. G. Tritiated platinum antitumor agents containing the trans-(d,l)~ 1,2-diaminocyclohexane carrier ligand. J. Labelled Compd. Radiopharm., 25:349-357, 1988.
19. Frost, A. A., and Pearson, R. G. Kinetics and Mechanism, Ed. 2, pp. 166-172. New York: John Wiley & Sons, 1961.
20. Mason, W. R. Platinum(II)-catalyzed substitutions of platinum(IV) complexes: Coord. Chem. Rev., 7: 241-255, 1972.
21. Drougge, L., and Elding, L. I. Mechanisms for acceleration of halide anation reactions of platinum(IV) complexes. REOA versus ligand assistance and platinum(II) catalysis without central ion exchange. Inorg. Chim. Acta, 121: 175-183, 1986.
22. Chaney, S. G., Wyrick, S., and Till, G. K. In vitro biotransformations of tetra,ch\oro(d,l-trans) 1,2-diaminocyclohexaneplatinum(IV) (tetraplatin) in rat plasma. Cancer Res., 50:4539-4545,1990.
23. Carfagna, P. F., Poma, A. Wyrick, S. D., Holbrook, D. J., and Chaney, S. G. Comparisons of tetrach\oro(d,l-trans) 1,2-diaminocyclohexaneplati-num(IV) (tetraplatin) biotransformations in the plasma of Fischer 344 rats at therapeutic and toxic doses. Cancer Chemother. Pharmacol., in press, 1991.