The anticancer prodrugs of butyric acid AN-7 and AN-9, possess antiangiogenic properties

Cancer Letters

Volumn 256, Issue 1, 2007, Pages 39-48

  Blank Porat, Diana ^a,b   Gruss Fischer, Tal ^a   Tarasenko, Nataly ^a   Malik, Zvi ^b   Nudelman, Abraham ^b   Rephaeli, Ada ^a  

^a TEL AVIV UNIVERSITY   (Israel)

^b BAR ILAN UNIVERSITY   (Israel)

Author keywords

Angiogenesis; Butyric acid prodrugs; Prostate carcinoma

Indexed keywords

ANGIOGENESIS INHIBITOR; ANGIOGENIC FACTOR; BASIC FIBROBLAST GROWTH FACTOR; BUTYROYLOXYMETHYL DIETHYL PHOSPHATE; EPIDERMAL GROWTH FACTOR RECEPTOR 2; HYPOXIA INDUCIBLE FACTOR 1ALPHA; KI 67 ANTIGEN; PHOSPHATIDYLINOSITOL 3,4,5 TRISPHOSPHATE 3 PHOSPHATASE; PIVALOYLOXYMETHYL BUTYRATE; UNCLASSIFIED DRUG;

ANGIOGENESIS; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIANGIOGENIC ACTIVITY; APOPTOSIS; ARTICLE; CELL MIGRATION; CELL PROLIFERATION; CELL VIABILITY; CONTROLLED STUDY; DOSE RESPONSE; DRUG ACTIVITY; DRUG INHIBITION; DRUG STRUCTURE; HUMAN; HUMAN CELL; IN VITRO STUDY; MALE; MOUSE; NONHUMAN; PRIORITY JOURNAL; PROSTATE CANCER; PROTEIN EXPRESSION;

ANGIOGENESIS INHIBITORS; ANIMALS; ANTINEOPLASTIC AGENTS; APOPTOSIS; BUTYRATES; BUTYRIC ACIDS; CELL PROLIFERATION; ENDOTHELIUM, VASCULAR; FIBROBLAST GROWTH FACTOR 2; HUMANS; HYPOXIA-INDUCIBLE FACTOR 1, ALPHA SUBUNIT; KI-67 ANTIGEN; MALE; MICE; MICE, INBRED BALB C; MICE, NUDE; NEOVASCULARIZATION, PATHOLOGIC; ORGANOPHOSPHORUS COMPOUNDS; PRODRUGS; PROSTATIC NEOPLASMS; PTEN PHOSPHOHYDROLASE; RECEPTOR, ERBB-2; TUMOR CELLS, CULTURED; UMBILICAL VEINS;

MUS; MUS MUSCULUS;

EID: 34548287904     PISSN: 03043835     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.canlet.2007.05.011     Document Type: Article

References (28)

1. Jemal A., Sieg R., Ward E., Murray T., Xu J., Smigal C., and Thun M.J. Cancer statistics. CA Cancer J. Clin. 56 (2006) 106-130
2. Gelmann E.P. Molecular biology of the androgen receptor. J. Clin. Oncol. 20 (2002) 3001-3015
3. Yuan X., Li T., Wang H., Zhang T., Barua M., Borgesi R.A., Bubley G.J., Lu M.L., and Balk S.P. Androgen receptor remains critical for cell-cycle progression in androgen-independent CWR22 prostate cancer cells. Am. J. Pathol. 169 (2006) 682-696
4. Rosato R.R., and Grant S. Histone deacetylase inhibitors in cancer therapy. Cancer Biol. Ther. 2 (2003) 30-37
5. Zhang Z., Karam J., Frenkel E., Sagalowsky A., and Hsieh J.T. The application of epigenetic modifiers on the treatment of prostate and bladder cancer. Urol. Oncol. 24 (2006) 152-160
6. Rephaeli A., Zhuk R., and Nudelman A. Butyric acid prodrugs from bench to bedside: synthetic design, mechanisms of action and clinical applications. Drug Develop. Res. 50 (2000) 379-391
7. Nudelman A., Levovich I., Cutts S.M., Phillips D.R., and Rephaeli A. The role of intracellularly released formaldehyde and butyric acid, in the anticancer activity of acyloxyalkyl esters. J. Med. Chem. 48 (2005) 1042-1054
8. Nudelman A., Gnizi E., Kats Y., Azulai R., Cohen-Ohana M., Zhuk R., Sampson S.R., Langzam L., Fibach E., Prus E., Pugach V., and Rephaeli A. Prodrugs of butyric acid. Novel derivatives possessing increased aqueous solubility and potential for treating cancer and blood diseases. Eur. J. Med. Chem. 36 (2001) 63-74
9. Engel D., Nudelman A., Levovich I., Gruss-Fischer T., Entin-Meer M., Phillips D.R., Cutts S.M., and Rephaeli A. Mode of interaction between AN-7 and doxorubicin in MCF-7 and resistant MCF-7/Dx cell lines. J. Cancer Res. Clin. Oncol. 132 (2006) 673-683
10. Patnaik A., Rowinsky K., Villalona M.A., Hammond L.A., Britten C.D., Siu L.L., Goetz A., Felton S.A., Burton S., Valone F.H., and Eckhardt S.G. A phase I study of pivaloyloxymethyl butyrate, a prodrug of the differentiating agent butyric acid, in patients with advanced solid malignancies. Clin. Cancer Res. 8 (2002) 2142-2148
11. Reid T., Valone F., Lipera W., Irwin D., Paroly W., Natale R., Sreedharan S., Keer H., Lum B., Scappaticci F., and Bhatnagar A. Phase II trial of the histone deacetylase inhibitor Pivaloyloxymethyl butyrate (Pivanex, AN-9) in advanced non-small cell lung cancer. Lung Cancer 45 (2004) 381-386
12. Rephaeli A., Entin-Meer M., Engel D., Tarasenko N., Gruss-Fischer T., Bruachman I., Phillips D.R., Cutts S.M., Haas-Kogan D.A., and Nudelman A. The selectivity and anti-metastatic activity of oral bioavailable butyric acid prodrugs. Invest. New Drugs 24 (2006) 383-392
13. Rephaeli A., Blank-Porat D., Tarasenko N., Entin-Meer M., Levovich I., Cutts S.M., Phillips D.R., Malik Z., and Nudelman A. In vivo and in vitro antitumor activity of butyroyloxymethyl-diethyl phosphate (AN-7), a histone deacetylase inhibitor, in human prostate cancer. Int. J. Cancer 116 (2005) 226-235
14. Entin-Meer M., Rephaeli A., Yang X., Nudelman A., Vanden Berg S.R., and Haas-Kogan D.A. Butyric acid prodrugs are histone deacetylase inhibitors that show antineoplastic activity and radiosensitizing capacity in the treatment of malignant gliomas. Mol. Cancer Ther. 4 (2005) 1952-1961
15. Nudelman A., Ruse M., Aviram A., Rabizadeh E., Shaklai M., Zimrah Y., and Rephaeli A. Novel anticancer prodrugs of butyric acid. J. Med. Chem. 35 (1992) 687-694
16. Malinda K.M., Sidhu G.S., Mani H., Banaudha K., Maheshwari R.K., Goldstein A.L., and Kleinman H.K. Thymosin beta 4 accelerates wound healing. J. Invest. Dermatol. 113 (1999) 364-368
17. Schweigerer L., Neufeld G., Friedman J., et al. Capillary endothelial cells express basic fibroblast growth factor, a mitogen that promotes their own growth. Nature 325 (1987) 257-259
18. Robertson N.E., Discafani C.M., Downs E.C., Hailey J.A., Sarre O., Runkle Jr. R.L., Popper T.L., and Plunkett M.L. A quantitative in vivo mouse model used to assay inhibitors of tumor-induced angiogenesis. Cancer Res. 51 (1991) 1339-1344
19. McCaffrey T.A., Agarwal L.A., and Weksler B.B. A rapid fluorometric DNA assay for the measurement of cell density and proliferation in vitro. In Vitro Cell Dev. Biol. 24 (1988) 247-252
20. Pilkington G.J., Bjerkvig R., de Ridder L., and Kaaijk P. In vitro and in vivo models for the study of brain tumor invasion. Anticancer Res. 17 (1997) 4107-4109
21. Di Lorenzo G., Autorino R., De Laurentiis M., Cindolo L., D'Armiento M., Bianco A.R., and de Placido S. HER-2/neu receptor in prostate cancer development and progression to androgen independence. Tumori 90 (2004) 163-170
22. Chakravarti A., and Zhai G.G. Molecular and genetic prognostic factors of prostate cancer. World J. Urol. 21 (2003) 265-274
23. Mulholland D.J., Dedhar S., Wu H., and Nelson C.C. PTEN and GSK3β: key regulators of progression to androgen-independent prostate cancer. Oncogene 25 (2006) 329-337
24. Kwabi-Addo B., Ozen M., and Ittmann M. The role of fibroblast growth factors and their receptors in prostate cancer. Endocr. Relat. Cancer 11 (2004) 709-724
25. Brahimi-Horn C., and Pouyssegur J. The role of the hypoxia-inducible factor in tumor metabolism growth and invasion. Bull. Cancer 93 (2006) E73-E80
26. Condon M.S. The role of the stromal microenvironment in prostate cancer. Sem. Cancer Biol. 15 (2005) 132-137
27. Berger R., Lin D.I., Nieto M., Sicinska E., Garraway L.A., Adams H., Signoretti S., Hahn W.C., and Loda M. Androgen-dependent regulation of Her-2/neu in prostate cancer cells. Cancer Res. 66 (2006) 5723-5728
28. Wen Y., Hu M.C., Makino K., Spohn B., Bartholomeusz G., Yan D.H., and Hung M.C. HER-2/neu promotes androgen-independent survival and growth of prostate cancer cells through the Akt pathway. Cancer Res. 60 (2000) 6841-6845