AN-113, a novel prodrug of 4-phenylbutyrate with increased anti-neoplastic activity in glioma cell lines

Cancer Letters

Volumn 253, Issue 2, 2007, Pages 205-214

  Entin Meer, Michal ^a   Rephaeli, Ada ^b   Yang, Xiaodong ^a   Nudelman, Abraham ^c   Nudelman, Ayelet ^c   Haas Kogan, Daphne Adele ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b TEL AVIV UNIVERSITY   (Israel)

^c BAR ILAN UNIVERSITY   (Israel)

Author keywords

H2AX; AN 113; Glioma; HDAC inhibitor; Radiation potentiation

Indexed keywords

1 (4 PHENYLBUTYROYLOXYETHYL) PIVALATE; 2,2 DIMETHYLPROPIONYLOXYMETHYL 4 PHENYLBUTYRATE; 4 PHENYLBUTYRIC ACID; AN 111; AN 113; AN 183; BUTYROYLOXYMETHYL 4 PHENYLBUTYRATE; CASPASE 8; CASPASE 8 INHIBITOR; HISTONE DEACETYLASE INHIBITOR; PRODRUG; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; ASTROCYTE; BLOOD BRAIN BARRIER; CELL CYCLE; CELL PROLIFERATION; CHEMICAL STRUCTURE; CONTROLLED STUDY; DRUG DOSE ESCALATION; DRUG EFFECT; DRUG POTENCY; FLOW CYTOMETRY; GLIOMA CELL; HUMAN; HUMAN CELL; IN VITRO STUDY; NERVE CELL CULTURE; PRIORITY JOURNAL; RADIATION DOSE;

ANTINEOPLASTIC AGENTS; ASTROCYTES; BLOOD-BRAIN BARRIER; BRAIN NEOPLASMS; CELL LINE, TUMOR; CELL PROLIFERATION; GLIOMA; HISTONE DEACETYLASES; HUMANS; PHENYLBUTYRATES; PRODRUGS;

EID: 34347341518     PISSN: 03043835     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.canlet.2007.01.022     Document Type: Article

References (28)

1. Kristeleit R., Stimson L., Workman P., and Aherne W. Histone modification enzymes: novel targets for cancer drugs. Expert. Opin. Emerg. Drugs 9 (2004) 135-154
2. Vigushin D.M., and Coombes R.C. Histone deacetylase inhibitors in cancer treatment. Anticancer Drugs 13 (2002) 1-13
3. Lin H.Y., Chen C.S., Lin S.P., Weng J.R., and Chen C.S. Targeting histone deacetylase in cancer therapy. Med. Res. Rev. 26 (2006) 397-413
4. Carducci M.A., Nelson J.B., Chan-Tack K.M., Ayyagari S.R., Sweatt W.H., Campbell P.A., et al. Phenylbutyrate induces apoptosis in human prostate cancer and is more potent than phenylacetate. Clin. Cancer Res. 2 (1996) 379-387
5. Gore S.D., SamidL D., and Weng J. Impact of the putative differentiating agents sodium phenylbutyrate and sodium phenylacetate on proliferation, differentiation, and apoptosis of primary neoplastic myeloid cells. Clin. Cancer Res. 3 (1997) 1755-1762
6. Melchior S.W., Brown L.G., Figg W.D., Quinn J.E., Santucci R.A., Brunner J., et al. Effects of phenylbutyrate on proliferation and apoptosis in human prostate cancer cells in vitro and in vivo. Int. J. Oncol. 14 (1999) 501-508
7. Pelidis M.A., Carducci M.A., and Simons J.W. Cytotoxic effects of sodium phenylbutyrate on human neuroblastoma cell lines. Int. J. Oncol. 12 (1998) 889-893
8. Gilbert J., Baker S.D., Bowling M.K., Grochow L., Figg W.D., Zabelina Y., et al. A phase I dose escalation and bioavailability study of oral sodium phenylbutyrate in patients with refractory solid tumor malignancies. Clin. Cancer Res. 7 (2001) 2292-2300
9. Baker M.J., Brem S., Daniels S., Sherman B., and Phuphanich S. Complete response of a recurrent, multicentric malignant glioma in a patient treated with phenylbutyrate. J. Neurooncol. 59 (2002) 239-242
10. Entin-Meer M., Rephaeli A., Yang X., Nudelman A., VandenBerg 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
11. 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
12. Murphy S. Generation of astrocytes cultures from normal and neoplastic central nervous system. In: Conn P.M. (Ed). Methods in Neurosciences vol. 2 (1990), Academic press, San Diego 33-47
13. Coleman M.L., Sahai E.A., Yeo M., Bosch M., Dewar A., and Olson M.F. Membrane blebbing during apoptosis results from caspase-mediated activation of ROCK I. Nat. Cell Biol. 3 (2001) 339-345
14. Noh E.J., and Lee J.S. Functional interplay between modulation of histone deacetylase activity and its regulatory role in G2-M transition. Biochem. Biophys. Res. Commun. 310 (2003) 267-273
15. Redon C., Pilch D., Rogakou E., Sedelnikova O., Newrock K., and Bonner W. Histone H2A variants H2AX and H2AZ. Curr. Opin. Genet. Dev. 12 (2002) 162-169
16. Camphausen K., Burgan W., Cerra M., Oswald K.A., Trepel J.B., Lee M.J., et al. Enhanced radiation-induced cell killing and prolongation of gammaH2AX foci expression by the histone deacetylase inhibitor MS-275. Cancer Res. 64 (2004) 316-321
17. Burger P.C., Dubois P.J., Schold Jr. S.C., Smith Jr. K.R., Odom G.L., Crafts D.C., et al. Computerized tomographic and pathologic studies of the untreated, quiescent, and recurrent glioblastoma multiforme. J. Neurosurg. 58 (1983) 159-169
18. Miller A.C., Whittaker T., Thibault A., and Samid D. Modulation of radiation response of human tumour cells by the differentiation inducers, phenylacetate and phenylbutyrate. Int. J. Radiat. Biol. 72 (1997) 211-218
19. Reid T., Valone F., Lipera W., Irwin D., Paroly W., Natale R., et al. 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
20. Patnaik A., Rowinsky E.K., Villalona A., Hammond L.A., Britten C.D., Siu L.L., 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. 8 (2002) 2142-2148
21. Peixoto P., and Lansiaux A. Histone-deacetylases inhibitors: from TSA to SAHA. Bull. Cancer 93 (2006) 27-36
22. Prakash F.B., Meyer S.M., Wozniak A., Heilbrun L.K., Flaherty L., Zalupski M., et al. Chronic oral administration of CI-994: a phase 1 study. Invest. New Drugs 19 (2001) 1-11
23. Saito A., Yamashita T., Mariko Y., Nosaka Y., Tsuchiya K., Ando T., et al. A synthetic inhibitor of histone deacetylase, MS-27-275, with marked in vivo antitumor activity against human tumors. Proc. Natl. Acad. Sci. USA 96 (1999) 4592-4597
24. J.L. Marshall, N. Rizvi, J. Kauh, W. Dahut, M. Figuera, M.H. Kang, et al., A phase I trial of depsipeptide (FR901228) in patients with advanced cancer, J. Exp. Ther. Oncol. 2 (2002) 325-332.
25. Komatsu T.K., Tsukamoto Y.M., Kato T., Nishino N., Sato S., Yamori T., et al. Cyclic hydroxamic-acid-containing peptide 31, a potent synthetic histone deacetylase inhibitor with antitumor activity. Cancer Res. 61 (2001) 4459-4466
26. Munshi A., Kurland J.F., Nishikawa T., Tanaka T., Hobbs M.L., Tucker S.L., et al. Histone deacetylase inhibitors radiosensitize human melanoma cells by suppressing DNA repair activity. Clin. Cancer Res. 11 (2005) 4912-4922
27. Chinnaiyan P., Vallabhaneni G., Armstrong E., Huang S.M., and Harari P.M. Modulation of radiation response by histone deacetylase inhibition. Int. J. Radiat. Oncol. Biol. Phys. 62 (2005) 223-229
28. Akimoto T. Potentiation of radiation-induced cell killing by histone deacetylase inhibitor. Nippon Rinsho 62 (2004) 1348-1354