A mechanistic and kinetic study of the E-ring hydrolysis and lactonization of a novel phosphoryloxymethyl prodrug of camptothecin

Pharmaceutical Research

Volumn 20, Issue 7, 2003, Pages 1031-1038

  Hanson, Bradley A ^a,b   Schowen, Richard L ^a   Stella, Valentino J ^a  

^a UNIVERSITY OF KANSAS   (United States)

^b PFIZER INC   (United States)

Author keywords

Camptothecin; Hydrolysis; Kinetic solvent isotope effects; Lactonization; Phosphoryloxymethyl (POM) prodrug; Stability

Indexed keywords

ACETIC ACID; BUFFER; CAMPTOTHECIN; CARBOXYLIC ACID; LACTONE; PHOSPHATE; PRODRUG; WATER;

ACIDITY; ALKALINITY; ARTICLE; CATALYSIS; CHEMISTRY; CONCENTRATION RESPONSE; DRUG SOLUBILITY; DRUG STRUCTURE; EQUILIBRIUM CONSTANT; HYDROLYSIS; KINETICS; MECHANICS; PH; PRIORITY JOURNAL; RADIATION DETECTION; REACTION ANALYSIS; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ULTRAVIOLET RADIATION;

CAMPTOTHECIN; HYDROLYSIS; LACTONES; MECHANICS; PRODRUGS;

EID: 0038198601     PISSN: 07248741     EISSN: None     Source Type: Journal    
DOI: 10.1023/A:1024410322870     Document Type: Article

References (35)

1. J. Fassberg and V. J. Stella. A kinetic and mechanistic study of the hydrolysis of camptothecin and some analogues. J. Pharm. Sci. 81:676-684 (1992).
2. M. E. Wall, M. C. Wani, C. E. Cook, K. H. Palmer, A. T. McPhail, and G. A. Sim. Plant antitumor agents. I. The isolation and structure of camptothecin, a novel alkaloidal leukemia and tumor inhibitor from Camptotheca acuminata. J. Am. Chem. Soc. 88:3888-3890 (1966).
3. M. C. Wani and M. E. Wall. Plant antitumor agents. II. The structure of two new alkaloids from Camptotheca acuminata. J. Org. Chem. 34:1364-1367 (1969).
4. J. A. Adamovics and C. R. Hutchinson. Prodrug analogues of the antitumor alkaloid camptothecin. J. Med. Chem. 22:310-314 (1979).
5. M. C. Wani, P. E. Ronman, J. T. Lindley, and M. E. Wall. Plant antitumor agents. 18. Synthesis and biological activity of camptothecin analogues. J. Med. Chem. 23:554-560 (1980).
6. M. C. Wani, A. W. Nicholas, and M. E. Wall. Plant antitumor agents. 23. Synthesis and antileukemic activity of camptothecin analogues. J. Med. Chem. 29:2358-2363 (1986).
7. M. C. Wani, A. W. Nicholas, G. Manikumar, and M. E. Wall. Plant antitumor agents. 25. Total synthesis and antileukemic activity of ring A substituted camptothecin analogues. Structure-activity correlations. J. Med. Chem. 30:1774-1779 (1987).
8. W. Eng, L. Faucette, R. K. Johnson, and R. Sternglanz. Evidence that DNA topoisomerase I is necessary for the cytotoxic effects of camptothecin. Mol. Pharmacol. 34:755-760 (1988).
9. C. Jaxel, K. W. Kohn, M. C. Wani, M. E. Wall, and Y. Pommier. Structure-activity study of the actions of camptothecin derivatives on mammalian topoisomerase I: Evidence for a specific receptor site and a relation to antitumor activity. Cancer Res. 49:1465-1469 (1989).
10. Y. Hsiang, L. F. Liu, M. E. Wall, M. C. Wani, A. W. Nicholas, G. Manikumar, S. Kirschenbaum, R. Silber, and M. Potmesil. DNA topoisomerase I-mediated DNA cleavage and cytotoxicity of camptothecin analogues. Cancer Res. 49:4385-4389 (1989).
11. R. P. Hertzberg, M. J. Caranfa, and S. M. Hecht. On the mechanism of topoisomerase I inhibition by camptothecin: Evidence for binding to an enzyme-DNA complex. Biochemistry 28:4629-4638 (1989).
12. Y. Hsiang, M. G. Lihou, and L. F. Liu. Arrest of replication forks by drug-stabilized topoisomerase I-DNA cleavable complexes as a mechanism of cell killing by camptothecin. Cancer Res. 49:5077-5082 (1989).
13. M. Bjornsti, P. Benedetti, G. A. Viglianti, and J. C. Wang. Expression of human DNA topoisomerase I in yeast cells lacking yeast DNA topoisomerase I: Restoration of sensitivity of the cells to the antitumor drug camptothecin. Cancer Res. 49:6318-6323 (1989).
14. M. Gupta, A. Fujimori, and Y. Pommier. Eurkaryotic DNA topoisomerase I. Biochim. Biophys. Acta 1262:1-14 (1995).
15. J. C. Wang. DNA topoisomerases. Annu. Rev. Biochem. 65:635-692 (1996).
16. C. Jaxel, G. Capranico, D. Kerrigan, K. W. Kohn, and Y. Pommier. Effect of local DNA sequence on topoisomerase I cleavage in the presence or absence of camptothecin. J. Biol. Chem. 266:20418-20423 (1991).
17. Y, Pommier, G. Kohlhagen, K. W. Kohn, F. Leteurtre, M. C. Wani, and M. E. Wall. Interaction of an alkylating camptothecin derivative with a DNA base at topoisomerase I-DNA cleavage sites. Proc. Natl. Acad. Sci. USA 92:8861-8865 (1995).
18. J. A. Gottlieb and J. K. Luce. Treatment of malignant melanoma with camptothecin (NSC-100880). Cancer Chemother. Rep. 56:103-105 (1972).
19. F. M. Muggia, P. J. Creaven, H. H. Hansen, M. H. Cohen, and O. S. Selawry. Phase 1 clinical trial of weekly and daily treatment with camptothecin (NSC-100880): Correlation with preclinical studies. Cancer Chemother. Rep. 56:515-521 (1972).
20. P. J. Creaven, L. M. Allen, and F. M. Muggia. Plasma camptothecin (NSC-100880) levels during a 5-day course of treatment: Relation to dose and toxicity. Cancer Chemother. Rep. 56:573-578 (1972).
21. M. E. Wall and M. C. Wani. Antineoplastic agents from plants. Annu. Rev. Pharmacol. Toxicol. 17:117-132 (1977).
22. R. P. Hertzberg, M. J. Caranfa, K. G. Holden, D. R. Jakas, G. Gallagher, M. R. Mattern, S. M. Mong, J. O. Bartus, R. K. Johnson, and W. D. Kingsbury. Modification of hydroxy lactone ring of camptothecin; inhibition of topoisomerase I and biological activity. J. Med. Chem. 32:715-720 (1989).
23. M. Safadi, R. Olizai, and V. J. Stella. Phosphoryloxymethyl carbamates and carbonates - Novel water-soluble prodrugs for amines and hindered alcohols. Pharm. Res. 10:1350-1355 (1993).
24. J. P. Krise, J. Zygmunt, G. I. Georg, and V. J. Stella. Novel prodrug approach for tertiary amines: Synthesis and preliminary evaluation of N-phosphonooxymethyl prodrugs. J. Med. Chem. 42:3094-3100 (1999).
25. J. P. Krise, S. Narisawa, and V. J. Stella. A novel prodrug approach for tertiary amines. 2. Physiochemical and in vitro enzymatic evaluation of selected N-phosphonooxymethyl prodrugs. J. Pharm. Sci. 88:922-927 (1999).
26. J. P. Krise, S. Narisawa, and V. J. Stella. A novel prodrug approach for tertiary amines. 3. In vivo evaluation of two N-phosphonooxymethyl prodrugs in rats and dogs. J. Pharm. Sci. 88:928-932 (1999).
27. M. E. Wall. Plant antitumor agents. 5. Alkaloids with antitumor activity. In K. Mothes, K. Schrieber and H. R. Schulte (eds.), International Symposium on Biochemistry and Physiology of the Alkaloids, Academie-Verlag, Berlin, 1969, pp. 77-87.
28. A. W. Nicholas, M. C. Wani, G. Manikumar, M. E. Wall, K. W. Kohn, and Y. Pommier. Plant antitumor agents. 29. Synthesis and biological activity of ring D and ring E modified analogues of camptothecin. J. Med. Chem. 33:972-978 (1990).
29. V. J. Stella, J. J. Zygmunt, I. G. Georg and M. S. Safadi. Water soluble prodrugs of hindered alcohols. United States Patent 6,204,257, March 20, 2001.
30. K. B. Schowen and R. L. Schowen. Solvent isotope effects on enzyme systems. Methods Enzymol. 87C:551-606 (1982).
31. M. J. Kaufman. Rate and equilibrium constants for acid-catalyzed lactone hydrolysis of HMG-CoA reductase inhibitors. Int. J. Pharm. 66:97-106 (1990).
32. J. Emsley and D. Hall. Reaction mechanisms. In J. Emsley (ed.), The Chemistry of Phosphorus: Environmental, Organic, Inorganic, Biochemical, and Spectroscopic Aspects, John Wiley & Sons, New York, 1976, pp. 232.
33. W. D. Kumler and J. J. Eiler. The acid strength of mono and diesters of phosphoric acid: The n-alkyl esters from methyl to butyl, the esters of biological importance and the natural guanidine phosphoric acids. J. Am. Chem. Soc. 65:2355 (1943).
34. W. P. Jencks. and J. Regenstein. Physical and Chemical Data. In G. D. Fasman (ed.), Handbook of Biochemistry and Molecular Biology, CRC Press, Cleveland, 1976, pp. 310-342.
35. Y. Pocker and E. Green. Hydrolysis of D-glucono-δ-lactone. I. General acid-base catalysis, solvent deuterium isotope effects, and transition state characterization. J. Am. Chem. Soc. 95:113-119 (1973).