Cytotoxicity and acid ceramidase inhibitory activity of 2-substituted aminoethanol amides

Chemistry and Physics of Lipids

Volumn 156, Issue 1-2, 2008, Pages 33-40

  Bedia, Carmen ^a   Canals, Daniel ^a   Matabosch, Xavier ^a   Harrak, Youssef ^a   Casas, Josefina ^a   Llebaria, Amadeu ^a   Delgado, Antonio ^a,b   Fabriás, Gemma ^a  

^a INSTITUTE OF ADVANCED CHEMISTRY OF CATALONIA IQAC CSIC   (Spain)

^b UNIVERSITY OF BARCELONA   (Spain)

Author keywords

Apoptosis; Cancer; Ceramide; Farber disease; Sphingolipids

Indexed keywords

ACYLSPHINGOSINE DEACYLASE; AMIDE; CERAMIDE; N (1 HYDROXYOCTADEC 3 EN 2 YL)PIVALOYLAMIDE; SPHINGOSINE; UNCLASSIFIED DRUG;

APOPTOSIS; ARTICLE; CELL LYSATE; CHEMICAL STRUCTURE; CONCENTRATION RESPONSE; CONTROLLED STUDY; CYTOTOXICITY; FLOW CYTOMETRY; HUMAN; HUMAN CELL; IC 50; LD 50; PRIORITY JOURNAL; SYNTHESIS;

ACID CERAMIDASE; AMIDES; APOPTOSIS; ENZYME INHIBITORS; ETHANOLAMINES; HUMANS; INHIBITORY CONCENTRATION 50; KINETICS; SPHINGOLIPIDS; TIME FACTORS; TUMOR CELLS, CULTURED;

EID: 55049124638     PISSN: 00093084     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chemphyslip.2008.07.012     Document Type: Article

References (47)

1. Batra S., Reynolds C.P., and Maurer B.J. Fenretinide cytotoxicity for Ewing's sarcoma and primitive neuroectodermal tumor cell lines is decreased by hypoxia and synergistically enhanced by ceramide modulators. Cancer Res. 64 (2004) 5415-5424
2. Bedia C., Casas J., Garcia V., Levade T., and Fabrias G. Synthesis of a novel ceramide analogue and its use in a high-throughput fluorogenic assay for ceramidases. ChemBiochem 8 (2007) 642-648
3. Bedia C., Triola G., Casas J., Llebaria A., and Fabrias G. Analogs of the dihydroceramide desaturase inhibitor GT11 modified at the amide function: synthesis and biological activities. Org. Biomol. Chem. 3 (2005) 3707-3712
4. Bielawska A., Bielawski J., Szulc Z.M., Mayroo N., Liu X., Bai A., Elojeimy S., Rembiesa B., Pierce J., Norris J.S., and Hannun Y.A. Novel analogs of d-e-MAPP and B13. Part 2: Signature effects on bioactive sphingolipids. Bioorg. Med. Chem. 16 (2007) 1032-1045
5. Crawford K.W., Bittman R., Chun J., Byun H.S., and Bowen W.D. Novel ceramide analogues display selective cytotoxicity in drug-resistant breast tumor cell lines compared to normal breast epithelial cells. Cell. Mol. Biol. 49 (2003) 1017-1023
6. Chavez J.A., Holland W.L., Bar J., Sandhoff K., and Summers S.A. Acid ceramidase overexpression prevents the inhibitory effects of saturated fatty acids on insulin signaling. J. Biol. Chem. 280 (2005) 20148-20153
7. Dagan A., Wang C., Fibach E., and Gatt S. Synthetic, non-natural sphingolipid analogs inhibit the biosynthesis of cellular sphingolipids, elevate ceramide and induce apoptotic cell death. Biochim. Biophys. Acta 1633 (2003) 161-169
8. Eliyahu E., Park J.H., Shtraizent N., He X., and Schuchman E.H. Acid ceramidase is a novel factor required for early embryo survival. FASEB J. 21 (2007) 1403-1409
9. Elojeimy S., Holman D.H., Liu X., El-Zawahry A., Villani M., Cheng J.C., Mahdy A., Zeidan Y., Bielwaska A., Hannun Y.A., and Norris J.S. New insights on the use of desipramine as an inhibitor for acid ceramidase. FEBS Lett. 580 (2006) 4751-4756
10. Elojeimy S., Liu X., McKillop J.C., El-Zawahry A.M., Holman D.H., Cheng J.Y., Meacham W.D., Mahdy A.E., Saad A.F., Turner L.S., Cheng J.T.A.D., Dong J.Y., Bielawska A., Hannun Y.A., and Norris J.S. Role of acid ceramidase in resistance to FasL: therapeutic approaches based on acid ceramidase inhibitors and fasl gene therapy. Mol. Ther. 15 (2007) 1259-1263
11. Eto M., Bennouna J., Hunter O.C., Hershberger P.A., Kanto T., Johnson C.S., Lotze M.T., and Amoscato A.A. C16 ceramide accumulates following androgen ablation in LNCaP prostate cancer cells. Prostate 57 (2003) 66-79
12. Granot T., Milhas D., Carpentier S., Dagan A., Segui B., Gatt S., and Levade T. Caspase-dependent and -independent cell death of Jurkat human leukemia cells induced by novel synthetic ceramide analogs. Leukemia 20 (2006) 392-399
13. Grijalvo S., Bedia C., Triola G., Casas J., Llebaria A., Teixido J., Rabal O., Levade T., Delgado A., and Fabrias G. Design, synthesis and activity as acid ceramidase inhibitors of 2-oxooctanoyl and N-oleoylethanolamine analogues. Chem. Phys. Lipids 144 (2006) 69-84
14. Grijalvo S., Matabosch X., Llebaria A., and Delgado A. A Straightforward protocol for the solution-phase parallel synthesis of ceramide analogues. Eur. J. Org. Chem. (2008) 150-155
15. Hara S., Nakashima S., Kiyono T., Sawada M., Yoshimura S., Iwama T., Banno Y., Shinoda J., and Sakai N. p53-Independent ceramide formation in human glioma cells during gamma-radiation-induced apoptosis. Cell Death Differ. 11 (2004) 853-861
16. Holman D.H., Turner L.S., El-Zawahry A., Elojeimy S., Liu X., Bielawski J., Szulc Z.M., Norris K., Zeidan Y.H., Hannun Y.A., Bielawska A., and Norris J.S. Lysosomotropic acid ceramidase inhibitor induces apoptosis in prostate cancer cells. Cancer Chemother. Pharmacol. 61 (2008) 231-242
17. Huang Y., Tanimukai H., Liu F., Iqbal K., Grundke-Iqbal I., and Gong C.X. Elevation of the level and activity of acid ceramidase in Alzheimer's disease brain. Eur. J. Neurosci. 20 (2004) 3489-3497
18. Kanto T., Kalinski P., Hunter O.C., Lotze M.T., and Amoscato A.A. Ceramide mediates tumor-induced dendritic cell apoptosis. J. Immunol. 167 (2001) 3773-3784
19. Koch J., Gartner S., Li C.M., Quintern L.E., Bernardo K., Levran O., Schnabel D., Desnick R.J., Schuchman E.H., and Sandhoff K. Molecular cloning and characterization of a full-length complementary DNA encoding human acid ceramidase. Identification of the first molecular lesion causing Farber disease. J. Biol. Chem. 271 (1996) 33110-33115
20. Liu X., Elojeimy S., El-Zawahry A.M., Holman D.H., Bielawska A., Bielawski J., Rubinchik S., Guo G.W., Dong J.Y., Keane T., Hannun Y.A., Tavassoli M., and Norris J.S. Modulation of ceramide metabolism enhances viral protein apoptin's cytotoxicity in prostate cancer. Mol. Ther. 14 (2006) 637-646
21. Liu X., Elojeimy S., Turner L.S., Mahdy A.E., Zeidan Y.H., Bielawska A., Bielawski J., Dong J.Y., El-Zawahry A.M., Guo G.W., Hannun Y.A., Holman D.H., and Rubinchik S. Acid ceramidase inhibition: a novel target for cancer therapy. Front. Biosci. 13 (2008) 2293-2298
22. Liu X., Zeidan Y.H., Elojeimy S., Holman D.H., El-Zawahry A.M., Guo G.W., Bielawska A., Bielawski J., Szulc Z., Rubinchik S., Dong J.Y., Keane T.E., Tavassoli M., Hannun Y.A., and Norris J.S. Involvement of sphingolipids in apoptin-induced cell killing. Mol. Ther. 14 (2006) 627-636
23. Merrill Jr. A.H., Sullards M.C., Allegood J.C., Kelly S., and Wang E. Sphingolipidomics: high-throughput, structure-specific, and quantitative analysis of sphingolipids by liquid chromatography tandem mass spectrometry. Methods (2005) 207-224 207-224
24. Mimeault M., Pommery N., and Henichart J.P. Synergistic antiproliferative and apoptotic effects induced by epidermal growth factor receptor and protein kinase a inhibitors in human prostatic cancer cell lines. Int. J. Cancer 106 (2003) 116-124
25. Mimeault M., Pommery N., Wattez N., Bailly C., and Henichart J.P. Anti-proliferative and apoptotic effects of anandamide in human prostatic cancer cell lines: implication of epidermal growth factor receptor down-regulation and ceramide production. Prostate 56 (2003) 1-12
26. Monick M.M., Mallampalli R.K., Bradford M., McCoy D., Gross T.J., Flaherty D.M., Powers L.S., Cameron K., Kelly S., Merrill Jr. A.H., and Hunninghake G.W. Cooperative prosurvival activity by ERK and Akt in human alveolar macrophages is dependent on high levels of acid ceramidase activity. J. Immunol. 173 (2004) 123-135
27. Morales A., Paris R., Villanueva A., Llacuna L., Garcia-Ruiz C., and Fernandez-Checa J.C. Pharmacological inhibition or small interfering RNA targeting acid ceramidase sensitizes hepatoma cells to chemotherapy and reduces tumor growth in vivo. Oncogene 26 (2006) 905-916
28. Mormeneo D., Casas J., Llebaria A., and Delgado A. Synthesis and preliminary antifungal evaluation of a library of phytosphingolipid analogues. Org. Biomol. Chem. 5 (2007) 3769-3777
29. Munoz-Olaya J.M., Matabosch X., Bedia C., Egido-Gabas M., Casas J., Llebaria A., Delgado A., and Fabrias G. Synthesis and biological activity of a novel inhibitor of dihydroceramide desaturase. ChemMedChem 3 (2008) 946-953
30. Musumarra G., Barresi V., Condorelli D.F., and Scire S. A bioinformatic approach to the identification of candidate genes for the development of new cancer diagnostics. Biol. Chem. 384 (2003) 321-327
31. Okino N., He X., Gatt S., Sandhoff K., Ito M., and Schuchman E.H. The reverse activity of acid ceramidase. J. Biol. Chem. 278 (2003) 29948-29953
32. Park J.H., and Schuchman E.H. Acid ceramidase and human disease. Biochim. Biophys. Acta 1758 (2006) 2133-2138
33. Raisova M., Goltz G., Bektas M., Bielawska A., Riebeling C., Hossini A.M., Eberle J., Hannun Y.A., Orfanos C.E., and Geilen C.C. Bcl-2 overexpression prevents apoptosis induced by ceramidase inhibitors in malignant melanoma and HaCaT keratinocytes. FEBS Lett. 516 (2002) 47-52
34. Saad A.F., Meacham W.D., Bai A., Anelli V., Elojeimy S., Mahdy A.E., Turner L.S., Cheng J., Bielawska A., Bielawski J., Keane T.E., Obeid L.M., Hannun Y.A., Norris J.S., and Liu X. The Functional effects of acid ceramidase overexpression in prostate cancer progression and resistance to chemotherapy. Cancer Biol. Ther. 6 (2007) 1455-1460
35. Samsel L., Zaidel G., Drumgoole H.M., Jelovac D., Drachenberg C., Rhee J.G., Brodie A.M., Bielawska A., and Smyth M.J. The ceramide analog, B13, induces apoptosis in prostate cancer cell lines and inhibits tumor growth in prostate cancer xenografts. Prostate 58 (2004) 382-393
36. Seelan R.S., Qian C., Yokomizo A., Bostwick D.G., Smith D.I., and Liu W. Human acid ceramidase is overexpressed but not mutated in prostate cancer. Genes Chromosomes Cancer 29 (2000) 137-146
37. Selzner M., Bielawska A., Morse M.A., Rudiger H.A., Sindram D., Hannun Y.A., and Clavien P.A. Induction of apoptotic cell death and prevention of tumor growth by ceramide analogues in metastatic human colon cancer. Cancer Res. 61 (2001) 1233-1240
38. Strelow A., Bernardo K., Adam-Klages S., Linke T., Sandhoff K., Kronke M., and Adam D. Overexpression of acid ceramidase protects from tumor necrosis factor-induced cell death. J. Exp. Med. 192 (2000) 601-612
39. Sugita M., Dulaney J.T., and Moser H.W. Ceramidase deficiency in Farber's disease (lipogranulomatosis). Science 178 (1972) 1100-1102
40. Taguchi M., Goda K., Sugimoto K., Akama T., Yamamoto K., Suzuki T., Tomishima Y., Nishiguchi M., Arai K., Takahashi K., and Kobori T. Biological evaluation of sphingomyelin analogues as inhibitors of sphingomyelinase. Bioorg. Med. Chem. Lett. 13 (2003) 3681-3684
41. Taguchi M., Sugimoto K., Goda K., Akama T., Yamamoto K., Suzuki T., Tomishima Y., Nishiguchi M., Arai K., Takahashi K., and Kobori T. Sphingomyelin analogues as inhibitors of sphingomyelinase. Bioorg. Med. Chem. Lett. 13 (2003) 1963-1966
42. Thon L., Mathieu S., Kabelitz D., and Adam D. The murine TRAIL receptor signals caspase-independent cell death through ceramide. Exp. Cell Res. 312 (2006) 3808-3821
43. Thon L., Mohlig H., Mathieu S., Lange A., Bulanova E., Winoto-Morbach S., Schutze S., Bulfone-Paus S., and Adam D. Ceramide mediates caspase-independent programmed cell death. FASEB J. 19 (2005) 1945-1956
44. Tsuboi K., Sun Y.X., Okamoto Y., Araki N., Tonai T., and Ueda N. Molecular characterization of N-acylethanolamine-hydrolyzing acid amidase, a novel member of the choloylglycine hydrolase family with structural and functional similarity to acid ceramidase. J. Biol. Chem. 280 (2005) 11082-11092
45. Usta J., El Bawab S., Roddy P., Szulc Z.M., Hannun Y.A., and Bielawska A. Structural requirements of ceramide and sphingosine based inhibitors of mitochondrial ceramidase. Biochemistry 40 (2001) 9657-9668
46. Villorbina G., Canals D., Carde L., Grijalvo S., Pascual R., Rabal O., Teixido J., Fabrias G., Llebaria A., Casas J., and Delgado A. Solid-phase synthesis of a combinatorial library of dihydroceramide analogues and its activity in human alveolar epithelial cells. Bioorg. Med. Chem. 15 (2006) 50-62
47. Zeidan Y.H., Pettus B.J., Elojeimy S., Taha T., Obeid L.M., Kawamori T., Norris J.S., and Hannun Y.A. Acid ceramidase but not acid sphingomyelinase is required for TNFα-induced PGE2 production. J. Biol. Chem. 281 (2006) 24695-24703