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Selectivity of ceramide-mediated biology. Lack of activity of erythro-dihydroceramide.
Open accessAbstract
Ceramide is emerging as a putative second messenger mediating effects of extracellular agents on cell growth and differentiation (Okazaki, T., Bielawska, A., Bell, R. M., and Hannun, Y. (1990) J. Biol. Chem. 265, 15822-15831) and programed cell death (Obeid, L. M., Linardic, C. M., Karolak, L. A., and Hannun, Y. A. (1993) Science 259, 1769-1771). In this study, the eight stereoisomers of C2-ceramide and dihydroceramide were synthesized, and their cellular activity was investigated. The four stereoisomers of C2-ceramide were active in inhibition of cell growth and induction of apoptosis with modest differences in potency. On the other hand, with C2-dihydroceramide only the threo compounds were active in these assays whereas the erythro compounds were totally inactive. Thus, of the two naturally occurring molecules, the analog of D-erythro-ceramide (with the 4-5 trans double bond) was active, whereas the analog of D-erythro-dihydroceramide was inactive. These results demonstrate the specificity of ceramide action and suggest that the introduction of the double bond is critical for imparting the biochemical and biological activity of ceramide.
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Cited by
Ceramide in apoptosis: an overview and current perspectives
Pettus, B. J., Chalfant, C. E., & Hannun, Y. A. (2002) · Biochimica et Biophysica Acta (BBA) - Molecular and Cell Biology of Lipids · doi:10.1016/s1388-1981(02)00331-1 · Cited by 788
Self-citationMerrill Jr., A. H., Sullards, M. C., Allegood, J. C., Kelly, S., & Wang, E. (2005) · Methods · doi:10.1016/j.ymeth.2005.01.009 · Cited by 594
Ceramide Activates the Stress-activated Protein Kinases
Westwick, J. K., Bielawska, A. E., Dbaibo, G., Hannun, Y. A., & Brenner, D. A. (1995) · Journal of Biological Chemistry · doi:10.1074/jbc.270.39.22689 · Cited by 303
Self-citationIdentification and Characterization of a Sphingolipid Δ4-Desaturase Family
Ternes, P., Franke, S., Zähringer, U., Sperling, P., & Heinz, E. (2002) · Journal of Biological Chemistry · doi:10.1074/jbc.m202947200 · Cited by 293
Role of ceramide-activated protein phosphatase in ceramide-mediated signal transduction.
Wolff, R. A., Dobrowsky, R. T., Bielawska, A., Obeid, L. M., & Hannun, Y. A. (1994) · Journal of Biological Chemistry · doi:10.1016/s0021-9258(17)32212-3 · Cited by 285
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Metadata
- Authors
- Bielawska, A., Crane, H. M., Liotta, D., Obeid, L. M., & Hannun, Y. A.
- Venue
- Journal of Biological Chemistry
- Publisher
- Elsevier BV
- Published
- 1993-12
- Volume
- 268
- Issue
- 35
- Pages
- 26226-26232
- ISSN
- 0021-9258 (ISSN-L)
- OpenAlex
- W1536767595
- Cited by
- 309
- References
- 0
- FWCI
- 5.00
- Type
- journal article
- Language
- en
- Open access
- hybrid
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- Bielawska, A., Crane, H. M., Liotta, D., Obeid, L. M., & Hannun, Y. A. (1993). Selectivity of ceramide-mediated biology. Lack of activity of erythro-dihydroceramide. Journal of Biological Chemistry. https://doi.org/10.1016/s0021-9258(19)74304-x
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