Stereospecific induction of apoptosis in U937 cells by N-octanoyl-sphingosine stereoisomers and N-octyl-sphingosine: The ceramide amide group is not required for apoptosis

European Journal of Biochemistry

Volumn 236, Issue 2, 1996, Pages 729-737

  Karasavvas, Nicos ^a   Erukulla, Ravi Kumar ^a   Bittman, Robert ^a   Lockshin, Richard ^b   Zakeri, Zahra ^a  

^a CITY UNIVERSITY OF NEW YORK   (United States)

^b ST JOHN'S UNIVERSITY   (United States)

Author keywords

Apoptosis; Ceramide analogs; Ceramide stereoisomers; Signal transduction; Sphingolipids

Indexed keywords

CERAMIDE; SPHINGOSINE DERIVATIVE;

ANIMAL CELL; APOPTOSIS; ARTICLE; CONTROLLED STUDY; GENE ACTIVATION; NONHUMAN; PRIORITY JOURNAL; SIGNAL TRANSDUCTION; STEREOCHEMISTRY;

APOPTOSIS; CELL DIVISION; CERAMIDES; DNA DAMAGE; HUMANS; SPHINGOSINE; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; TUMOR CELLS, CULTURED;

ANIMALIA;

EID: 0030000464     PISSN: 00142956     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1432-1033.1996.00729.x     Document Type: Article

References (36)

1. Kim, M.-Y., Linardic, C., Obeid, L. & Hannun, Y. A. (1991) Identification of sphingomyelin turnover as an effector mechanism for the action of tumor necrosis factor α and γ-interferon, J. Biol. Chem. 266, 484-489.
2. Mathias, S., Younes, A., Kan, C.-C., Orlow, I., Joseph, C. & Kolesnick, R. N. (1993) Activation of the sphingomyelin signaling pathway in intact EL4 cells and in a cell-free system by IL-1 β, Science 259, 519-522.
3. Raines, M. A., Kolesnick, R. N. & Golde, D. W. (1993) Sphingomyelinase and ceramide activated mitogen- activated protein kinase in myeloid HL-60 cells, J. Biol. Chem. 268, 14572-14575.
4. Dobrowsky, R. T. & Hannun, Y. A. (1992) Ceramide stimulates a cytosolic protein phosphatase, J. Biol. Chem. 267, 5048-5051.
5. Mathias, S., Dressler, K. A. & Kolesnick, R. N. (1991) Characterization of a ceramide-activated protein kinase: Stimulation by tumor necrosis factor α, Proc. Natl Acad. Sci. USA 88, 10009-10013.
6. 3-induced HL-60 cell differentiation, J. Biol. Chem. 265, 15823-15831.
7. Obeid, L. M., Linardic, C. M., Karolak, L. A. & Hannun, Y. A. (1993) Programmed cell death induced by ceramide, Science 259, 1769-1771.
8. Jarvis, W. D., Kolesnick, R. N., Fornari, F. A., Traylor, R. S., Gewirtz, D. A. & Grant, S. (1994) Induction of apoptotic DNA damage and cell death by activation of the sphingomyelin pathway, Proc. Natl Acad. Sci. USA 91, 73-77.
9. Fishbein, J. D., Dobrowsky, R. T., Bielawska, A., Garrett, S. & Hannun, Y. A. (1993) Ceramide-mediated growth inhibition and CAPP are conserved in Saccharomyces cerevisiae, J. Biol. Chem. 268, 9255-9261.
10. Bielawska, A., Crane, H. M. Liotta, D., Obeid, L. M. & Hannun, Y. A. (1993) Selectivity of ceramide-mediated biology, J. Biol. Chem. 268, 26226-26232.
11. Rivas, C. I., Golde, D. W., Vera, J. C. & Kolesnick, R. N. (1994) Involvement of the sphingomyelin pathway in autocrine tumor necrosis factor signaling for human immunodeficiency virus production in chronically infected HL-60 cells, Blood 83, 2191-2197.
12. Corver, J., Moesby, L., Erukulla, R. K., Reddy, K. C., Bittman, R. & Wilschut, J. (1995) Sphingolipid-dependent fusion of Semliki Forest virus with cholesterol-containing liposomes requires both the 3-hydroxyl group and the double bond of the sphingolipid backbone, J. Virol. 69, 3220-3223.
13. Wiegmann, K., Schütze, S., Machleidt, T., Witte, D. & Krönke, M. (1994) Functional dichotomy of neutral and acidic sphingomyelinases in tumor necrosis factor signaling, Cell 78, 1005-1015.
14. Ridgway, N. D. & Merriam, D. L. (1995) Metabolism of short-chain ceramide in Chinese hamster ovary (CHO) cells, Biochim. Biophys. Acta 1256, 57-70.
15. Younes, A., Kahn, D. W., Besterman, J. M., Bittman, R., Byun, H.-S. & Kolesnick, R. N. (1992) Ceramide is a competitive inhibitor of diacylglycerol kinase in vitro and in intact human leukemia (HL-60) cells, J. Biol. Chem. 267, 842-847.
16. Abe, A., Wu, D., Shayman, J. A. & Radin, N. S. (1992) Metabolic effects of short-chain ceramide and glucosylceramide on sphingolipids and protein kinasc C, Eur. J. Biochem. 210, 765-773.
17. Bielawska, A., Linardic, C. M. & Hannun, Y. A. (1992) Ceramide-mediated biology, J. Biol. Chem. 267, 18493-18497.
18. Wolff, R. A., Dobrowsky, R. T., Bielawska, A., Obeid, L. M. & Hannun, Y. A. (1994) Role of ceramide-activated protein phosphatase in ceramide-mediated signal transduction, J. Biol. Chem. 269, 19605-19609.
19. Wyllie, A. H. (1987) Apoptosis: cell death in tissue regulation, J. Pathol. 153, 313-316.
20. Arens, M. J., Morris, R. G. & Wyllie, A. H. (1990) Apoptosis: the role of the endonuclease, Am. J. Pathol. 136, 593-608.
21. Bittman, R. (1993) Chemical preparation of glycerolipids: A review of recent syntheses, in Phospholipids handbook (Ceve, G., ed.) pp. 141-232, Marcel Dekker, New York.
22. Garner, P. & Park, J. M. (1991) 1,1,-Dimethylethyl (S)- or (R)-4-formyl-2,2-dimethyl-3-oxazolidinecarboxylate: A useful serinai derivative, Org. Synth. 70, 18-26.
23. Herold, P. (1988) Synthesis of D-erythro- and D-threo-sphingosine derivatives from L-serine, Helv. Chim. Acta 71, 354-362.
24. Garner, P., Park, J. M. & Malecki, E. (1988) A stereodivergent synthesis of D-erythro-sphingosine and D-threo-sphingosine from L-serine, J. Org. Chem. 53, 4395-4398.
25. Slotte, J. P., Östman, A.-L., Kumar, E. R. & Bittman, R. (1993) Cholesterol interacts with lactosyl and maltosyl cerebrosides hut not with glucosyl or galactosyl cerebrosides in mixed monolayers, Biochemistry 32, 7886-7892.
26. Miyashita, T. & Reed, J. C. (1993) Bcl-2 oncoprotein blocks chemotherapy-induced apoptosis in a human leukemia cell line, Blood 81, 151-157.
27. Oberhammer, F. A., Pavelka, M., Sharma, S., Tiefenbacher, R., Purchio, A. F., Bursch, W. & Hermann, S.-R. (1992) Induction of apoptosis in cultured hepatocytes and in regressing liver by transforming growth factor β1, Proc. Natl Acad. Sci. USA 89, 5408-5412.
28. Sambrook, J., Fritsch, E. F. & Maniatis, T. (1989) Molecular cloning:a laboratory manual, 2nd edn. Cold Spring Harbor Laboratory Press, Cold Spring Harbor NY.
29. Tilly, J. L., Kowalski, K. I., Johnson, A. L. & Hsueh, A. J. W. (1991) Involvement of apoptosis in ovarian follicular atresia and postovulatory regression, Endocrinology 129, 2799-2801.
30. Zakeri, Z. F., Quaglino, D., Latham, T. & Lockshin, R. A. (1993) Delayed internucleosomal DNA fragmentation in programmed cell death, FASEB J. 7, 470-478.
31. Liu, J., Mathias, S., Yang, Z. & Kolesnick, R. N. (1994) Renaturation and tumor necrosis factor-α stimulation of a 97-kDa ceramide-activated protein kinase, J. Biol. Chem. 269, 3047-3052.
32. Preiss, J., Loomis, C. R., Bishop, W. R., Stain, R., Niedel, J. E. & Bell, R. M. (1986) Quantitative measurement of sn-1,2-diacylglycerols present in platelets, hepatocytes, and ras- and sis-transformed normal rat kidney cells, J. Biol. Chem. 261, 8597-8600.
33. Wright, S. A., Zheng, H., Zhong, J., Torti, F.-M. & Larrick, J. W. (1993) Role of protein phosphorylation in TNF-induced apoptosis: Phosphatase inhibitors synergise with TNF to activate DNA fragmentation in normal as well as TNF-resistant U937 variants, J. Cell. Biochem. 53, 222-233.
34. Hannun, Y. A., Obeid, L. M. & Wolff, R. A. (1993) The novel second messenger ceramide: Identification, mechanism of action, and cellular activity, Adv. Lipid Res. 25, 43-64.
35. Müller, G., Ayoub, M. Storz, P., Rennecke, J., Fabbro, D. & Pfizenmaier, K. (1995) PKC ζ is a molecular switch in signal transduction of TNF-α, bifunctionally regulated by ceramide and arachidonic acid, EMBO J. 4, 1961-1969.
36. Gulbins, E., Coggeshall, M. K., Baier, G., Telford, D., Langlet, C., Bitterlich B.-G., Berard B.-N., Burn, P., Wittinghofer, A. & Altman, A. (1994) Direct stimulation of Vav guanine nucleotide exchange activity for ras by phorbol esters and diglycerides, Mol. Cell. Biol. 14, 4749-4758.