Evaluation of a trans configuration for the apoptosis-inducing activity of ceramide

Journal of Lipid Mediators and Cell Signalling

Volumn 16, Issue 3, 1997, Pages 127-137

  Kishida, Etsu ^a   Kasahara, Megumi ^a   Takagi, Yumiko ^a   Matsumura, Masae ^b   Hayashi, Takaomi ^b   Kobayashi, Shu ^b   Masuzawa, Yasuo ^a  

^a HYOGO UNIVERSITY OF TEACHER EDUCATION   (Japan)

^b TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

Apoptosis; Ceramide; Cis isomer of ceramide; Triple bond derivative of ceramide

Indexed keywords

ANTINEOPLASTIC AGENT; CERAMIDE; CERAMIDE DERIVATIVE; DNA; DNA FRAGMENT; SPHINGOSINE DERIVATIVE;

APOPTOSIS; ARTICLE; CELL STRAIN HL 60; CELL STRUCTURE; CIS TRANS ISOMERISM; CONTROLLED STUDY; DRUG CONFORMATION; DRUG POTENCY; DRUG SYNTHESIS; ELECTROPHORESIS; FLUORESCENCE MICROSCOPY; HUMAN; HUMAN CELL; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION;

APOPTOSIS; CELL NUCLEUS; CERAMIDES; DNA FRAGMENTATION; ELECTROPHORESIS, AGAR GEL; HL-60 CELLS; HUMANS; MOLECULAR CONFORMATION; SPHINGOSINE; STEREOISOMERISM; TIME FACTORS;

EID: 0346831352     PISSN: 09297855     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0929-7855(97)00010-2     Document Type: Article

References (33)

1. 2 production and sphingomyelin metabolism: Evidence for the regulation of cyclooxygenase gene expression by sphingosine and ceramide. J Biol Chem. 267:1992;20044-20050.
2. Bielawska A., Linardic C.M., Hannun Y.A. Ceramide-mediated biology: Determination of structural and stereospecific requirements through the use of N-acyl-phenylaminoalcohol analogs. J Biol Chem. 267:1992;18493-18497.
3. Bielawska A., Crane H.M., Liotta D., Obeid L.M., Hannun Y.L. Selectivity of ceramide-mediated biology: Lack of activity of erythro-dihydroceramide. J Biol Chem. 268:1993;26226-26232.
4. Bose R., Verheij M., Haimovitz-Friedman A., Scotto K., Fuks Z., Kolesnick R. Ceramide synthase mediates daunorubicin-induced apoptosis: An alternative mechanism for generating death signals. Cell. 82:1995;405-414.
5. Cesarone C.F., Bolognesi C., Santi L. Improved microfluorometric DNA determination in biological material using 33258 Hoechst. Anal Biochem. 100:1979;188-197.
6. Chang Y., Abe A., Shayman J.A. Ceramide formation during heat shock: A potential mediator of αB-crystallin transcription. Proc Natl Acad Sci USA. 92:1995;12275-12279.
7. Cifone M.G., Maria R.D., Roncaioli P., Rippo M.R., Azuma M., Lanier L.L., Santoni A., Testi R. Apoptotic signalling through CD95 (Fas/Apo-1) activates an acidic sphingomyelinase. J Exp Med. 177:1993;1547-1552.
8. Dressler K.A., Mathias S., Kolesnick R.N. Tumor necrosis factor-c activates the sphingomyelin signal transduction pathway in a cell-free system. Science. 255:1992;1715-1718.
9. Haimovitz-Friedman A., Kan C., Ehleiter D., Persaud R.S., McLoughlin M., Fuks Z., Kolesnick R.N. lonizing radiation acts on cellular membranes to generate ceramide and initiate apoptosis. J Exp Med. 180:1994;525-535.
10. Hannun Y.A. The sphingomyelin cycle and the second messenger function of ceramide. J Biol Chem. 269:1994;3125-3128.
11. Hickman J.A. Apoptosis induced by anticancer drugs. Cancer Metastasis Rev. 11:1992;121-139.
12. Kim M., Linardic C., Obeid L., Hannun Y. Identification of sphingomyeiin turnover as an effector mechanism for the action of tumor necrosis factor α and γ interferon: Specific role in cell differentiation. J Biol Chem. 266:1991;484-489.
13. Kobayashi S., Hayashi T., Kawasuji T. Enantioselective syntheses of erythro-sphingosine and phytosphingosine from simple achiral aldehydes using catalytic asymmetric aldol reactions as key steps. Tetrahedron Lett. 35:1994;9573-9576.
14. Kolesnick R., Golde D.W. The sphingomyelin pathway in tumor necrosis factor and interleukin-1 signalling. Cell. 77:1994;325-328.
15. Kolesnick R., Fuks Z. Ceramide: A signal for apoptosis or mitogenesis? J Exp Med. 181:1995;1949-1952.
16. Labarca C., Paigen K. A simple, rapid, end sensitive DNA assay procedure. Anal Biochem. 102:1980;344-352.
17. Lapidot Y., Rappoprt S., Wolman Y. Use of esters of N-hydroxysuccinimide in the synthesis of N-acylamino acids. J Lipid Res. 8:1967;142-145.
18. Laulederkind S.J.F., Bielawska A., Raghow R., Hannun Y.A., Ballou L.R. Ceramide induces interleukin 6 gene expression in human fibroblasts. J Exp Med. 182:1995;599-604.
19. 2-ceramide. J Biol Chem. 270:1995;12808-12813.
20. Ling Y., Priebe W., Perez-Soler R. Apoptosis induced by anthracycline antibiotics in P388 parent and multidrug-resistant cells. Cancer Res. 53:1993;1845-1852.
21. Liu J., Mathias S., Yang Z., Kolesnick R.N. Renaturation and tumor necrosis factor-α stimulation of α97-kDa ceramide-activated protein kinase. J Biol Chem. 269:1994;3047-3052.
22. Lozano J., Berra E., Municio M.M., Diaz-Meco M.T., Dominguez I., Sanz L., Moscat J. Protein kinase Cζ isoform is critical for κB-dependent promoter activation by sphingomyelinase. J Biol Chem. 269:1994;19200-19202.
23. Meikrantz W., Schlegel R. Apoptosis and the cell cycle. J Cell Biochem. 58:1995;160-174.
24. Obeid L.M., Hannun Y.A. Ceramide: A stress signal and mediator of growth suppression and apoptosis. J Cell Biochem. 58:1995;191-198.
25. Ohta H., Yatomi Y., Sweeney E.A., Hakomori S., Igarshi Y. A possible role of sphingosine in induction of apoptosis by tumor necrosis factor-α in human neutrophils. FEBS Lett. 355:1994;267-270.
26. Ohta H., Sweeney E.A., Masamune A., Yatomi Y., Hakomori S., Igarashi Y. Induction of apoptosis by sphingosine in human leukemic HL-60 cells: A possible endogenous modulator of apoptotic DNA fragmentation occurring during phorbol ester-induced differentiation. Cancer Res. 55:1995;691-697.
27. 3-induced HL-60 cell differentiation. J Biol Chem. 265:1990;15823-15831.
28. Raines M.A., Kolesnick R.N., Golde D.W. Sphingomyelinase and ceramide activate mitogen-activated protein kinase in myeloid HL-60 cells. J Biol Chem. 268:1993;14572-14575.
29. Sawai H., Okazaki T., Yamamoto H., Okano H., Takeda Y., Tashima M., Sawada H., Okuma M., Ishikura H., Umehara H., Domae N. Requirement of AP-1 for ceramide-induced apoptosis in human leukemTa HL-60 cells. J Biol Chem. 270:1995;27326-27331.
30. Schütze S., Potthoff K., Machleidt T., Berkovic D., Wiegmann K., Kronke M. TNF activates NF-KB by phosphatidylcholine-specific phospholipase C-induced `acidic' sphingomyelin breakdown. Cell. 71:1992;765-776.
31. Strum J.C., Small G.W., Pauig S.B., Daniel L.W. 1-D-Arabinofuranosylcytosine stimulates ceramide and diglyceride formation in HL-60 cells. J Biol Chem. 269:1994;15493-15497.
32. Westwick J.K., Bielawska A.E., Dbaibo G., Hannun A., Brenner D.A. Ceramide activates the stress-activated protein kinases. J Biol Chem. 270:1995;22689-22692.
33. Yao B., Zhang Y., Delikat S., Mathias S., Basu S., Kolesnick R. Phosphorylation of Raf by ceramide-activated protein kinase. Nature. 378:1995;307-310.