Activation of clinically used anthracyclines by the formaldehyde-releasing prodrug pivaloyloxymethyl butyrate

Molecular Cancer Therapeutics

Volumn 6, Issue 4, 2007, Pages 1450-1459

  Cutts, Suzanne M ^a   Swift, Lonnie P ^a   Pillay, Vinochani ^a   Forrest, Robert A ^a   Nudelman, Abraham ^c   Rephaeli, Ada ^b   Phillips, Don R ^a  

^a LA TROBE UNIVERSITY   (Australia)

^b TEL AVIV UNIVERSITY   (Israel)

^c BAR ILAN UNIVERSITY   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

ANTHRACYCLINE DERIVATIVE; DAUNORUBICIN; DOXORUBICIN; EPIRUBICIN; EXONUCLEASE; GLYCOPROTEIN P; IDARUBICIN; PIVALOYLOXYMETHYL BUTYRATE; PRODRUG;

ARTICLE; CELL STRAIN MCF 7; DNA ADDUCT; DNA EXTRACTION; DNA SEQUENCE; DRUG POTENTIATION; DRUG STRUCTURE; GENE OVEREXPRESSION; GENOME; GROWTH INHIBITION; MITOCHONDRION; PRIORITY JOURNAL;

ANTHRACYCLINES; ANTINEOPLASTIC AGENTS; APOPTOSIS; BASE PAIRING; BASE SEQUENCE; BLOTTING, SOUTHERN; BUTYRATES; CELL LINE, TUMOR; CROSS-LINKING REAGENTS; DNA ADDUCTS; DRUG INTERACTIONS; FORMALDEHYDE; HUMANS; PRODRUGS;

EID: 34248203689     PISSN: 15357163     EISSN: None     Source Type: Journal    
DOI: 10.1158/1535-7163.MCT-06-0551     Document Type: Article

References (46)

1. Minotti G, Menna P, Salvatorelli E, Cairo G, Gianni L. Anthracyclines: molecular advances and pharmacologic developments in antitumor activity and cardiotoxicity. Pharmacol Rev 2004;3:185-229.
2. DeVita VT, Hellman S, Rosenberg SA, editors. Principles and practice of oncology. 6th ed. Philadelphia: Lippincott Williams and Wilkins; 2001.
3. Hortobagyi GN. Anthracyclines in the treatment of cancer. An overview. Drugs 1997;54 Suppl 4:1-7.
4. Arcamone F, Cassinelli G, Fantini G, et al. Adriamycin, 14-hydroxydaunomycin, a new antitumor antibiotic from S. peucetius var. caesius. Biotechnol Bioeng 2000;67:704-13.
5. Arcamone F. Adriamycin and its analogs. Tumori 1984;70:113-9.
6. Weiss RB. The anthracyclines: will we ever find a better doxorubicin? Semin Oncol 1992;19:670-86.
7. Bakker M, van der Graaf WTA, Groen HJM, Smit EF, De Vries EGE. Anthracyclines-pharmacology and resistance, a review. Curr Pharmaceut Design 1995;1:133-44.
8. Sordet O, Khan QA, Kohn KW, Pommier Y. Apoptosis induced by topoisomerase inhibitors. Curr Med Chem Anti-Cancer Agents 2003;3: 271-90.
9. Gewirtz DA. A critical evaluation of the mechanisms of action proposed for the antitumor effects of the anthracycline antibiotics adriamycin and daunorubicin. Biochem Pharmacol 1999;57:727-41.
10. Phillips DR, Cullinane C. Adriamycin. In: Creighton TE, editor. Encyclopedia of molecular biology, vol. 1. New York: John Wiley and Sons; 1999. p. 68-72.
11. Taatjes DJ, Guadiano G, Resing K, Koch TH. Redox pathway leading to the alkylation of DNA by the anthracycline, antitumor drugs adriamycin and daunomycin. J Med Chem 1997;40:1276-86.
12. Wang AH, Gao YG, Liaw YC, Li YK. Formaldehyde cross-links daunorubicin and DNA efficiently: HPLC and X-ray diffraction studies. Biochemistry 1991;30:3812-5.
13. Zeman SM, Phillips DR, Crothers DM. Characterization of covalent adriamycin-DNA adducts. Proc Natl Acad Sci U S A 1998;95: 11561-5.
14. Cutts SM, Parker BS, Swift LP, Kimura K-1, Phillips DR. Structural requirements for the formation of anthracycline-DNA adducts. Anticancer Drug Design 2000; 15:373-86.
15. Fenick DJ, Taatjes DJ, Koch TH. Doxoform and daunoform: anthracycline-formaldehyde conjugates toxic to resistant tumor cells. J Med Chem 1997;40:2452-61.
16. Taatjes DJ, Fenick DJ, Koch TH. Epidoxoform: a hydrolytically more stable anthracycline-formaldehyde conjugate toxic to resistant tumor cells. J Med Chem 1998;41:1306-14.
17. Taatjes DJ, Koch TH. Nuclear targeting and retention of anthracycline antitumor drugs in sensitive and resistant tumor cells. Curr Med Chem 2001;8:15-29.
18. Dernell WS, Powers BE, Taatjes DJ, Cogan P, Gaudiano G, Koch TH. Evaluation of the epidoxorubicin-formaldehyde conjugate, epidoxoform, in a mouse mammary carcinoma model. Cancer Invest 2002;20: 713-24.
19. Burke PJ, Koch TH. Design, synthesis, and biological evaluation of doxorubicin-formaldehyde conjugates targeted to breast cancer cells. J Med Chem 2004;47:1193-206.
20. Cogan PS, Koch TH. Rational design and synthesis of androgen receptor-targeted nonsteroidal anti-androgen ligands for the tumor-specific delivery of a doxorubicin-formaldehyde conjugate. J Med Chem 2003;46: 5258-70.
21. Nudelman A, Ruse M, Aviram A, et al. Novel anticancer prodrugs of butyric acid 2. J Med Chem 1992;35:687-94.
22. Rephaeli A, Rabizadeh E, Aviram A, Shaklai M, Ruse M, Nudelman A. Derivatives of butyric acid as potential anti-neoplastic agents. Int J Cancer 1991;49:66-72.
23. Patnaik A, Rowinsky EK, Villalona MA, et al. A phase I study of pivaloyloxymethyl butyrate, a prodrug of the differentiating agent butyric acid, in patients with advanced solid malignancies. Clin Cancer Res 2002; 8:2142-8.
24. Kasukabe T, Rephaeli A, Honma Y. An anti-cancer derivative of butyric acid (pivalyloxmethyl buterate) and daunorubicin cooperatively prolong survival of mice inoculated with monocytic leukaemia cells. Br J Cancer 1997;75:850-4.
25. Niitsu N, Kasukabe T, Yokoyama A, et al. Anticancer derivative of butyric acid (pivalyloxymethyl butyrate) specifically potentiates the cytotoxicity of doxorubicin and daunorubicin through the suppression of microsomal glycosidic activity. Mol Pharmacol 2000;58:27-36.
26. Cutts SM, Rephaeli A, Nudelman A, Hmelnitsky I, Phillips DR. Molecular basis for the synergistic interaction of adriamycin with the formaldehyde-releasing prodrug pivaloyloxymethyl butyrate (AN-9). Cancer Res 2001;61:8194-202.
27. Swift LP, Rephaeli A, Nudelman A, Phillips DR, Cutts SM. Doxorubicin-DNA adducts induce a non-topoisomerase II-mediated form of cell death. Cancer Res 2006;66:4863-71.
28. Swift LP, Cutts SM, Rephaeli A, Nudelman A, Phillips DR. Activation of adriamycin by the pH-dependent formaldehyde-releasing prodrug hexamethylenetetramine. Mol Cancer Ther 2003;2:189-98.
29. Cutts SM, Swift LP, Rephaeli A, Nudelman A, Phillips DR. Recent advances in understanding and exploiting the activation of anthracyclines by formaldehyde. Curr Med Chem Anti-Canc Agents 2005;5: 431-47.
30. Cutts SM, Nudelman A, Rephaeli A, Phillips DR. The power and potential of doxorubicin-DNA adducts. IUBMB Life 2005;57:73-81.
31. Zhen W, Evans MK, Haggerty CM, Bohr VA. Deficient gene specific repair of cisplatin-induced lesions in xeroderma pigmentosum and Fanconi's anemia cell lines. Carcinogenesis 1993;14:919-24.
32. Vos JM. Analysis of psoralen monoadducts and interstrand crosslinks in defined genomic sequences. In: Friedberg EC, Hanawalt PC, editors. DNA repair: a laboratory manual of research procedures, vol. 3. New York: Marcel Dekker; 1988. p. 367-98.
33. Cutts SM, Swift LP, Rephaeli A, Nudelman A, Phillips DR. Sequence specificity of adriamycin-DNA adducts in human tumor cells. Mol Cancer Ther 2003;2:661-70.
34. Maxam AM, Gilbert W. A new method for sequencing DNA. Proc Natl Acad Sci U S A 1977;74:560-4.
35. Malorni W, Fais S, Fiorentini C. Morphological aspects of apoptosis. In: Watson J, editor. Purdue Cytometry CD-ROM Series, vol. 4. West Lafayette: Purdue University Cytometry Laboratories; 1997.
36. Cullinane C, Cutts SM, Panousis C, Phillips DR. Interstrand crosslinking by adriamycin in nuclear and mitochondrial DNA of MCF-7 cells. Nucleic Acids Res 2000;28:1019-25.
37. Binaschi M, Capranico G, Dal Bo L, Zunino F. Relationship between lethal effects and topoisomerase II-mediated double-stranded DNA breaks produced by anthracyclines with different sequence specificity. Mol Pharmacol 1997;51:1053-9.
38. Wielinga PR, Westerhoff HV, Lankelma J. The relative importance of passive and P-glycoprotein mediated anthracycline efflux from multidrug-resistant cells. Eur J Biochem 2000;267:649-57.
39. Mulder HS, Dekker H, Pinedo HM, Lankelma J. The P-glycoprotein-mediated relative decrease in cytosolic free drug concentration is similar for several anthracyclines with varying lipophilicity. Biochem Pharmacol 1995;50:967-74.
40. Garnier-Suillerot A, Marbeuf-Gueye C, Salerno M, et al. Analysis of drug transport kinetics in multidrug-resistant cells: implications for drug action. Curr Med Chem 2001;8:51-64.
41. Bennis S, Faure P, Chapey C, et al. Cellular pharmacology of lipophilic anthracyclines in human tumor cells in culture selected for resistance to doxorubicin. Anticancer Drugs 1997;8:610-7.
42. Bogush T, Robert J. Comparative evaluation of the intracellular accumulation and DNA binding of idarubicin and daunorubicin in sensitive and multidrug-resistant human leukaemia K562 cells. Anticancer Res 1996; 16:365-8.
43. Broxterman HJ, Sonneveld P, van Putten WJ, et al. P-glycoprotein in primary acute myeloid leukemia and treatment outcome of idarubicin/ cytosine arabinoside-based induction therapy. Leukemia 2000;14: 1018-24.
44. Taatjes DJ, Fenick DJ, Koch TH. Nuclear targeting and nuclear retention of anthracycline-formaldehyde conjugates implicates DNA covalent bonding in the cytotoxic mechanism of anthracyclines. Chem Res Toxicol 1999; 12:588-96.
45. Podell ER, Harrington DJ, Taatjes DJ, Koch TH. Crystal structure of epidoxorubicin-formaldehyde virtual crosslink of DNA and evidence for its formation in human breast-cancer cells. Acta Crystallogr D Biol Crystallogr 1999;55:1516-23.
46. Cutts SM, Nudelman A, Pillay V, et al. Formaldehyde-releasing prodrugs in combination with doxorubicin can overcome cellular drug resistance. Oncol Res 2005;15:199-213.