Activation of a camptothecin prodrug by specific carboxylesterases as predicted by quantitative structure-activity relationship and molecular docking studies

Molecular Cancer Therapeutics

Volumn 2, Issue 11, 2003, Pages 1171-1181

  Yoon, Kyoung Jin P ^a   Krull, Erik J ^a   Morton, Christopher L ^a   Bornmann, William G ^c   Lee, Richard E ^b   Potter, Philip M ^a   Danks, Mary K ^a  

^a ST JUDE CHILDREN S RESEARCH HOSPITAL   (United States)

^b UNIVERSITY OF TENNESSEE HEALTH SCIENCE CENTER   (United States)

^c MEMORIAL SLOAN KETTERING CANCER CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CAMPTOTHECIN; CARBOXYLESTERASE; DRUG DERIVATIVE; PRODRUG;

ANIMAL; ARTICLE; BINDING SITE; CELL DIVISION; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECT; HUMAN; IC 50; KINETICS; METABOLISM; QUANTITATIVE STRUCTURE ACTIVITY RELATION; RAT; SYNTHESIS; TUMOR CELL LINE;

ANIMALS; BINDING SITES; CAMPTOTHECIN; CARBOXYLIC ESTER HYDROLASES; CELL DIVISION; CELL LINE, TUMOR; HUMANS; INHIBITORY CONCENTRATION 50; KINETICS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PRODRUGS; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; RATS;

EID: 3242693617     PISSN: 15357163     EISSN: 15388514     Source Type: Journal    
DOI: None     Document Type: Article

References (35)

1. Fillat, C., Carrio, M., Cascante, A., and Sangro, B. Suicide gene therapy mediated by the herpes simplex virus thymidine kinase gene/ganciclovir system: fifteen years of application. Curr. Gene Ther., 3: 13-26, 2003.
2. Shibata, M. A., Morimoto, J., and Otsuki, Y. Suppression of murine mammary carcinoma growth and metastasis by HSVtk/GCV gene therapy using in vivo electroporation. Cancer Gene Ther., 9: 16-27, 2002. (Pubitemid 34052850)
3. Black, M. E., Kokoris, M. S., and Sabo, P. Herpes simplex virus-1 thymidine kinase mutants created by semi-random sequence mutagenesis improve prodrug-mediated tumor cell killing. Cancer Res., 61: 3022-3026, 2001. (Pubitemid 32691949)
4. Wilder, O., Blaese, R. M., and Candotti, F. Enzyme prodrug gene therapy: synergistic use of the herpes simplex virus-cellular thymidine kinase/ganciclovir system and thymidylate synthase inhibitors for the treatment of colon cancer. Cancer Res., 59: 5233-5238, 1999. (Pubitemid 29503987)
5. Corban-Wilhelm, H., Hull, W. E., Becker, G., Bauder-Wust, U., Greulich, D., and Debus, J. Cytosine deaminase and thymidine kinase gene therapy in a dunning rat prostate tumor model: absence of bystander effects and characterization of 5-fluorocytosine metabolism with 19F-NMR spectroscopy. Gene Ther., 9: 1564-1575, 2002. (Pubitemid 35414519)
6. Koyama, F., Sawada, H., Fujii, H., Hirao, T., Ueno, M., Hamada, H., and Nakano, H. Enzyme/prodrug gene therapy for human colon cancer cells using adenovirus-mediated transfer of the Escherichia coli cytosine deaminase gene driven by a CAG promoter associated with 5-fluorocytosine administration. J. Exp. Clin. Cancer Res., 19: 75-80, 2000. (Pubitemid 30305524)
7. Wybranietz, W. A., Gross, C. D., Phelan, A., O'Hare, P., Spiegel, M., Graepler, F., Bitzer, M., Stahler, P., Gregor, M., and Lauer, U. M. Enhanced suicide gene effect by adenoviral transduction of a VP22-cytosine deaminase (CD) fusion gene. Gene Ther., 8: 1654-1664, 2001. (Pubitemid 33085587)
8. Danks, M. K., Morton, C. L., Pawlik, C. A., and Potter, P. M. Overexpression of a rabbit liver carboxylesterase sensitizes human tumor cells to CPT-11. Cancer Res., 58: 20-22, 1998. (Pubitemid 28027709)
9. Potter, P. M., Pawlik, C. A., Morton, C. L., Naeve, C. W., and Danks, M. K. Isolation and partial characterization of a cDNA encoding a rabbit liver carboxylesterase that activates the prodrug irinotecan (CPT-11). Cancer Res., 58: 2646-2651, 1998. (Pubitemid 28275439)
10. Danks, M. K., Morton, C. L., Krull, E. J., Cheshire, P. J., Richmond, L. B., Naeve, C. W., Pawlik, C. A., Houghton, P. J., and Potter, P. M. Comparison of activation of CPT-11 by rabbit and human carboxylesterases for use in enzyme/prodrug therapy. Clin. Cancer Res., 5: 917-924, 1999. (Pubitemid 29180845)
11. Satoh, T., Hosokawa, M., Atsumi, R., Suzuki, W., Hakusui, H., and Nagai, E. Metabolic activation of CPT-11, 7-ethyl-10-[4-(1-piperidino)-1-piperidino] carbonyloxycamptothecin, a novel antitumor agent, by carboxylesterase. Biol. Pharm. Bull., 17: 662-664, 1994. (Pubitemid 24186112)
12. Wagner, L. M., Guichard, S. M., Burger, R. A., Morton, C. L., Straign, C. M., Ashmun, R. A., Harris, L. C., Houghton, P. J., Potter, P. M., and Danks, M. K. Efficacy and toxicity of a virus-directed enzyme prodrug therapy purging method: preclinical assessment and application to bone marrow samples from neuroblastoma patients. Cancer Res., 62: 5001-5007, 2002. (Pubitemid 34984426)
13. Kawato, Y., Aonuma, M., Hirota, Y., Kuga, H., and Sato, K. Intracellular roles of SN-38, a metabolite of the camptothecin derivative CPT-11, in the antitumor effect of CPT-11. Cancer Res., 51: 4187-4191, 1991.
14. Tsuji, T., Kaneda, N., Kado, K., Yokokura, T., Yoshimoto, T., and Tsuru, D. CPT-11 converting enzyme from rat serum: purification and some properties. J. Pharmacobiodyn., 14: 341-349, 1991.
15. Schwer, H., Langmann, T., Daig, R., Becker, A., Aslanidis, C., and Schmitz, G. Molecular cloning and characterization of a novel putative carboxylesterase, present in human intestine and liver. Biochem. Biophys. Res. Commun., 233: 117-120, 1997. (Pubitemid 27215920)
16. Humerickhouse, R., Lohrbach, K., Li, L., Bosron, W. F., and Dolan, M. E., Characterization of CPT-11 hydrolysis by human liver carboxylesterase isoforms hCE-1 and hCE-2. Cancer Res., 60: 1189-1192, 2000. (Pubitemid 30151980)
17. Rivory, L. P., Chatelut, E., Canal, P., Mathieu-Boue, A., and Robert, J. Kinetics of the in vivo interconversion of the carboxylate and lactone forms of irinotecan (CPT-11) and of its metabolite SN-38 in patients. Cancer Res., 54: 6330-6333, 1994.
18. Wood, J. L., Fortunak, J. M., Mastrocola, A. R., Mellinger, M., and Burk, P. L. An efficient conversion of camptothecin to 10-hydroxycamptothecin. J. Org. Chem., 60 (17): 1995.
19. Yoon, K. J., Morton, C. L., Potter, P. M., Danks, M. K., and Lee, R. E. Synthesis and evaluation of esters and carbamates to identify critical functional groups for esterase-specific metabolism. Bioorg. Med. Chem., 11: 3237-3244, 2003. (Pubitemid 36801991)
20. Jones, G., Willett, P., Glen, R. C., Leach, A. R., and Taylor, R. Development and validation of a genetic algorithm for flexible docking. J. Mol. Biol., 267: 727-748, 1997. (Pubitemid 27170693)
21. Bencharit, S., Morton, C. L., Howard-Williams, E. L., Danks, M. K., Potter, P. M., and Redinbo, M. R. Structural insights into CPT-11 activation by mammalian carboxylesterases. Nat. Struct. Biol., 9: 337-342, 2002. (Pubitemid 34462550)
22. Connolly, M. L. Analytical molecular surface calculation. J. Appl. Crystallogr., 16: 548-558, 1983.
23. SYBYL, Version 6.8. St. Louis, MO: Tripos Associates, 2001.
24. Clark, M., Cramer, R. D., III, and Van Opdenbosch, N. The tripos force field. J. Comput. Chem., 10: 982-1012, 1989.
25. Stewart, J. J. MOPAC: a semiempirical molecular orbital program. J. Comput. Aided Mol. Des., 4: 1-105, 1990.
26. Cramer, R. D., Patterson, D. E., and Bunce, J. D. Comparative molecular field analysis (CoMFA). I. Effect of shape on binding of steroids to carrier proteins. J. Am. Chem. Soc., 110: 5959-5967, 1988.
27. Kliebe, G., Abraham, U., and Mietzner, T. Molecular similarity indices in a comparative analysis (CoMSIA) of drug molecules to correlate and predict their biological activity. J. Med. Chem., 37: 4130-4146, 1994. (Pubitemid 24379702)
28. Bush, B. L. and Nachbar, R. B., Jr. Sample-distance partial least squares: PLS optimized for many variables, with application to CoMFA. J. Comput. Aided Mol. Des., 7: 587-619, 1993.
29. Collantes, E. R., Xing, L., Miller, P. C., Welsh, W. J., and Profeta, S. Comparative molecular field analysis as a tool to evaluate mode of action of chemical hybridization agents. J. Agric. Food Chem., 47: 5245-5251, 1999. (Pubitemid 30016969)
30. Potter P. M., Wolverton, J. S., Morton, C. L., Wierdl, M., and Danks, M. K. Cellular localization domains of a rabbit and human carboxylesterase: influence on irinotecan (CPT-11) metabolism by the rabbit enzyme. Cancer Res., 58: 3627-3632, 1998. (Pubitemid 28376561)
31. Watkins, R. M., Morton, C. L., Weeks, J. K., Oliver, L., Wierdl, M., Danks, M. K., and Potter, P. M. Structural constraints affect the metabolism of 7-ethyl-10-[4-(1-piperidino)-1-piperidino]carbonyloxycamptothecin (CPT-11) by carboxylesterases. Mol. Pharmacol., 60: 355-362, 2001. (Pubitemid 32678301)
32. Guichard, S. M., Morton, C. L., Krull, E. J., Stewart, C. F., Danks, M. K., and Potter, P. M. Conversion of the CPT-11 metabolite APC to SN-38 by rabbit liver carboxylesterase. Cancer Res., 4: 3089-3094, 1998. (Pubitemid 29001486)
33. Morton, C. L. and Potter, P. M. Comparison of Escherichia coli, Saccharomyces cerevisiae, Pichia pastoris, Spodoptera frugiperda, and COS7 cells for recombinant gene expression. Application to a rabbit liver carboxylesterase. Mol. Biotechnol., 16: 193-202, 2000. (Pubitemid 32217198)
34. Huang, T. L., Szekacs, A., Uematsu, T., Kuwano, E., Parkinson, A., and Hammock, B. D. Hydrolysis of carbonates, thiocarbonates, carbamates, and carboxylic esters of α-naphthol, β-naphthol, and ρ-nitrophenol by human, rat, and mouse liver carboxylesterases. Pharm. Res., 10: 639-648, 1993. (Pubitemid 23152306)
35. Huang, T. L., Shiotsuki, T., Uematsu, T., Borhan, B., Li, Q. X., and Hammock, B. D. Structure-activity relationships for substrates and inhibitors of mammalian liver microsomal carboxylesterases. Pharm. Res., 13: 1495-1500, 1996. (Pubitemid 26356951)