4-Fluoro-N-butylphenylacetamide: A synthetic phenylacetate derivative that upregulates Bcl-XS, activates caspase cascade and induces apoptosis in human squamous lung cancer CH27 cells

Cancer Letters

Volumn 186, Issue 2, 2002, Pages 211-221

  Chan, Hsu Chin ^a   Kuo, Sheng Chu ^a   Liu, Su Chen ^a   Liu, Chung Hsien ^b   Hsu, Shih Lan ^c  

^a CHINA MEDICAL UNIVERSITY   (Taiwan)

^b CHUNG SHAN MEDICAL UNIVERSITY   (Taiwan)

^c TAICHUNG VETERANS GENERAL HOSPITAL   (Taiwan)

Author keywords

Apoptosis; Bcl XS; Caspase; Phenylacetate derivative

Indexed keywords

4 FLUORO N BUTYLPHENYLACETAMIDE; ACETAMIDE DERIVATIVE; ADENOSINE DIPHOSPHATE RIBOSE; CASPASE; CASPASE 3; CASPASE 9; CASPASE INHIBITOR; CHEMICAL COMPOUND; CYTOCHROME C; DNA FRAGMENT; DNA POLYMERASE; PHENYLACETIC ACID DERIVATIVE; PROTEIN BCL X; UNCLASSIFIED DRUG;

APOPTOSIS; ARTICLE; CANCER GROWTH; CELL PROLIFERATION; CELL STRAIN; CONTROLLED STUDY; CYTOSOL; DNA GEL BLOT ANALYSIS; DRUG EFFECT; GEL ELECTROPHORESIS; HUMAN; HUMAN CELL; HUMAN EXPERIMENT; INHIBITION KINETICS; LUNG SQUAMOUS CELL CARCINOMA; PRIORITY JOURNAL; STAINING; UPREGULATION;

ACETAMIDES; ANTINEOPLASTIC AGENTS; APOPTOSIS; BCL-X PROTEIN; BLOTTING, WESTERN; CARCINOMA, SQUAMOUS CELL; CASPASE 3; CASPASE 9; CASPASES; CELL DEATH; CELL DIVISION; CELL SURVIVAL; CYTOCHROME C GROUP; CYTOSOL; DNA FRAGMENTATION; DOSE-RESPONSE RELATIONSHIP, DRUG; ELECTROPHORESIS, POLYACRYLAMIDE GEL; ENZYME ACTIVATION; HUMANS; IN SITU NICK-END LABELING; LUNG NEOPLASMS; MODELS, CHEMICAL; PHENYLACETATES; PROTO-ONCOGENE PROTEINS C-BCL-2; TIME FACTORS; TUMOR CELLS, CULTURED; UP-REGULATION;

EID: 0037027757     PISSN: 03043835     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0304-3835(02)00352-X     Document Type: Article

References (42)

1. Anonymous. Analysis in cancer incidence and mortality - Taiwan, 1999 (Chinese). Epidemiol. Bull. 16:2000;389-391.
2. Chen Y., Perng R.P., Yang K.Y., Lin W.C., Wu H.W., Tsai C.M., Whang-Peng J. Phase II study of tamoxifen, ifosfamide, epirubicin and cisplatin combination chemotherapy in patients with non-small cell lung cancer failing previous chemotherapy. Lung Cancer. 29:2000;139-146.
3. Gorospe M., Shack S., Guyton K.Z., Samid D., Holbrook N.J. Up-regulation and functional role of p21Waf1/Cip1 during growth arrest of human breast carcinoma MCF-7 cells by phenylacetate. Cell Growth Diff. 7:1996;1609-1615.
4. Samid D., Ram Z., Hudgins W.R., Shack S., Liu L., Walbridge S., Oldfield E.H., Myers C.E. Selective activity of phenylacetate against malignant gliomas: resemblance to fetal brain damage in phenylketonuria. Cancer Res. 54:1994;891-895.
5. Samid D., Yeh A., Prasanna P. Induction of erythroid differentiation and fetal hemoglobin production in human leukemic cells treated with phenylacetate. Blood. 80:1992;1576-1581.
6. Samid D., Shack S., Myers C.E. Selective growth arrest and phenotypic reversion of prostate cancer cells in vitro by nontoxic pharmacological concentrations of phenylacetate. J. Clin. Invest. 91:1993;2288-2295.
7. Thibault A., Cooper M.R., Figg W.D., Venzon D.J., Sartor A.O., Tompkins A.C., Weinberger M.S., Headlee D.J., McCall N.A., Samid D. A phase I and pharmacokinetic study of intravenous phenylacetate in patients with cancer. Cancer Res. 54:1994;1690-1694.
8. Thibault A., Samid D., Cooper M.R., Figg W.D., Tompkins A.C., Patronas N., Headlee D.J., Kohler D.R., Venzon D.J., Myers C.E. Phase I study of phenylacetate administered twice daily to patients with cancer. Cancer. 75:1995;2932-2938.
9. Adam L., Crepin M., Savin C., Israel L. Sodium phenylacetate induces growth inhibition and Bcl-2 down-regulation and apoptosis in MCF7ras cells in vitro and in nude mice. Cancer Res. 55:1995;5156-5160.
10. Ponzoni M., Bocca P., Chiesa V., Decensi A., Pistoia V., Raffaghello L., Rozzo C., Montaldo P.G. Differential effects of N-(4-hydroxyphenyl) retinamide and retinoic acid on neuroblastoma cells: apoptosis versus differentiation. Cancer Res. 55:1995;853-861.
11. Raff M.C. Social controls on cell survival and cell death. Nature (Lond.). 356:1992;397-400.
12. Haldar S., Negrini M., Monne M., Sabbioni S., Croce C.M. Down-regulation of bcl-2 by p53 in breast cancer cells. Cancer Res. 54:1994;2095-2097.
13. Wyllie A.H. Apoptosis: cells death in tissue regulation. J. Pathol. 153:1987;313-316.
14. Dive C., Hickman J.A. Drug-target interactions: only the first step in the commitment to a programmed cell death? Br. J. Cancer. 64:1991;192-196.
15. Lowe S.W., Ruley H.E., Jacks T., Housman D.E. p53-dependent apoptosis modulates the cytotoxicity of anticancer agents. Cell. 74:1993;957-967.
16. Brusilow S.W., Danney M., Waber L.J., Batshaw M., Burton B., Levitsky K., Roth L., McKeethren C., Ward J. Treatment of episodic hyperammonemia in children with inborn errors of urea synthesis. N. Engl. J. Med. 310:1984;1630-1634.
17. Wang J.L., Liu D., Zhang Z.J., Shan S., Han X., Srinivasula S.M., Croce C.M., Alnemri E.S., Huang Z. Structure-based discovery of an organic compound that binds Bcl-2 protein and induces apoptosis of tumor cells. Proc. Natl Acad. Sci. USA. 97:2000;7124-7129.
18. Uehara T., Kikuchi Y., Nomura Y. Caspase activation accompanying cytochrome c release from mitochondria is possibly involved in nitric oxide-induced neuronal apoptosis in SH-SY5Y cells. J. Neurochem. 72:1999;196-205.
19. Samid D., Shack S., Sherman L.T. Phenylacetate: a novel nontoxic inducer of tumor cell differentiation. Cancer Res. 52:1992;1988-1992.
20. Ferrandina G., Melichar B., Loercher A., Verschraegen C.F., Kudelka A.P., Edwards C.L., Scambia G., Kavanagh J.J., Abbruzzese J.L., Freedman R.S. Growth inhibitory effects of sodium phenylacetate (NSC 3039) on ovarian carcinoma cells in vitro. Cancer Res. 57:1997;4309-4315.
21. Antonsson B., Martinou J.C. The Bcl-2 protein family. Exp. Cell. Res. 256:2000;50-57.
22. Zou H., Henzel W.J., Liu X., Lutschg A., Wang X. Apaf-1, a human protein homologous to C. elegans CED-4, participates in cytochrome c-dependent activation of caspase-3. Cell. 90:1997;405-413.
23. Li P., Nijhawan D., Budihardjo I., Srinivasula S.M., Ahmad M., Alnemri E.S., Wang X. Cytochrome c and dATP-dependent formation of Apaf-1/caspase-9 complex initiates an apoptotic protease cascade. Cell. 91:1997;479-489.
24. Li F., Srinivasan A., Wang Y., Armstrong R.C., Tomaselli K.J., Fritz L.C. Cell-specific induction of apoptosis by microinjection of cytochrome c. Bcl-xL has activity independent of cytochrome c release. J. Biol. Chem. 272:1997;30299-30305.
25. Nieves-Neira W., Pommier Y. Apoptotic response to camptothecin and 7-hydroxystaurosporine (UCN-01) in the 8 human breast cancer cell lines of the NCI Anticancer Drug Screen: multifactorial relationships with topoisomerase I, protein kinase C, Bcl-2, p53, MDM-2 and caspase pathways. Int. J. Cancer. 82:1999;396-404.
26. Thibault A., Samid D., Cooper M.R., Figg W.D., Tompkins A.C., Patronas N. Phase I trial of phenylacetate administered twice daily to patients with cancer. Cancer. 75:1995;2932-2938.
27. Vaux D.L., Korsmeyer S.J. Cell death in development. Cell. 96:1999;245-254.
28. Susin S.A., Lorenzo H.K., Zamzami N., Marzo I., Brenner C., Larochette N., Prevost M.C., Alzari P.M., Kroemer G. Mitochondrial release of caspase-2 and -9 during the apoptotic process. J. Exp. Med. 189:1999;381-393.
29. Kluck R.M., Bossy-Wetzel E., Green D.R., Newmeyer D.D. The release of cytochrome c from mitochondria: a primary site for Bcl-2 regulation of apoptosis. Science. 275:1997;1132-1136.
30. Yang J., Liu X., Bhalla K., Kim C.N., Ibrado A.M., Cai J., Peng T.I., Jones D.P., Wang X. Prevention of apoptosis by Bcl-2: release of cytochrome c from mitochondria blocked. Science. 275:1997;1129-1132.
31. Yang E., Korsmeyer S.J. Molecular thanatopsis: a discourse on the BCL2 family and cell death. Blood. 88:1996;386-401.
32. Boise L.H., Gonzalez-Garcia M., Postema C.E., Ding L., Lindsten T., Turka L.A., Mao X., Nunez G., Thompson C.B. bcl-x, a bcl-2-related gene that functions as a dominant regulator of apoptotic cell death. Cell. 74:1993;597-608.
33. L and Bcl-2. EMBO J. 16:1997;968-977.
34. Minn A.J., Boise L.H., Thompson C.B. Bcl-X(S) antagonizes the protective effects of Bcl-x(L). J. Biol. Chem. 271:1996;6306-6312.
35. Ealovega M.W., McGinnis P.K., Sumantran V.N., Clarke M.F., Wicha M.S. Bcl-Xs gene therapy induces apoptosis of human mammary tumors in nude mice. Cancer Res. 56:1996;1965-1969.
36. Jia L., Macey M.G., Yin Y., Newland A.C., Kelsey S.M. Subcellular distribution and redistribution of Bcl-2 family proteins in human leukemia cells undergoing apoptosis. Blood. 93:1999;2353-2359.
37. Hockenbery D.M., Oltvai Z.N., Yin X.M., Milliman C.L., Korsmeyer S.J. Bcl-2 functions in an antioxidant pathway to prevent apoptosis. Cell. 75:1993;241-251.
38. Krajewski S., Tanaka S., Takayama S., Schibler M.J., Fenton W., Reed J.C. Investigation of the subcellular distribution of the bcl-2 oncoprotein: residence in the nuclear envelope, endoplasmic reticulum, and outer mitochondrial membranes. Cancer Res. 53:1993;4701-4714.
39. Gonzalez-Garcia M., Perez-Ballestero R., Ding L., Duan L., Boise L.H., Thompson C.B., Nunez, G. bcl-XL is the major bcl-x mRNA form expressed during murine development and its product localizes to mitochondria. Development. 120:1994;3033-3042.
40. Fulda S., Friesen C., Los M., Scaffidi C., Mier W., Benedict M., Nunez G., Krammer P.H., Peter M.E., Debatin K.M. Betulinic acid triggers CD95 (APO-1/Fas)- and p53-independent apoptosis via activation of caspases in neuroectodermal tumors. Cancer Res. 57:1997;4956-4964.
41. Friesen C., Herr I., Krammer P.H., Debatin K.M. Involvement of the CD95 (APO-1/FAS) receptor/ligand system in drug-induced apoptosis in leukemia cells. Nat. Med. 2:1996;574-577.
42. Fulda S., Sieverts H., Friesen C., Herr I., Debatin K.M. The CD95 (APO-1/Fas) system mediates drug-induced apoptosis in neuroblastoma cells. Cancer Res. 57:1997;3823-3829.