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Chemical Compound Review

C2-ceramide     N-[(E,2S,3R)-1,3- dihydroxyoctadec-4-en-2...

Synonyms: C2ceramide, C2 ceramide, C2-cer, AC1NUZJL, CHEMBL105867, ...
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Disease relevance of Acetyl ceramide


Psychiatry related information on Acetyl ceramide


High impact information on Acetyl ceramide

  • The effects of C2-ceramide on DNA fragmentation were prevented by the protein kinase C activator phorbol 12-myristate 13-acetate, which suggests the existence of two opposing intracellular pathways in the regulation of apoptosis [7].
  • Other stimuli such as C2-ceramide were capable of inducing rapid apoptosis in OLs [8].
  • We found that submicromolar concentrations of C2-ceramide induced IL-6 gene expression and protein production as effectively as IL-1 beta [9].
  • Finally, all CD95-sensitive cell lines tested could be induced to undergo apoptosis after exposure to cell-permeant C2-ceramide [10].
  • This effect was mimicked by sphingomyelinase, but not by phospholipase A2 or phospholipase C. C2-ceramide induced IL-8 gene transcription mainly through activation of NF-kappaB because mutation of the NF-kappaB-binding site completely abrogated the induction of luciferase activity [11].

Chemical compound and disease context of Acetyl ceramide


Biological context of Acetyl ceramide


Anatomical context of Acetyl ceramide


Associations of Acetyl ceramide with other chemical compounds


Gene context of Acetyl ceramide

  • Furthermore, TNF alpha, sphingomyelinase, and C2-ceramide induce c-jun, a gene that is stimulated by the ATF-2 and c-Jun transcription factors [29].
  • While PMA activated extracellular signal-regulated kinase (ERK), a downstream kinase of Raf-MEK signaling, C2-ceramide activated c-Jun NH2-terminal kinase (JNK), an anchor kinase of stress-induced signaling [3].
  • ERK activation was enhanced by C2-ceramide plus PMA stimulation, whereas the activation of JNK was aborted [3].
  • Further, JNK/SAPK activity is stimulated 2.7- and 2.8-fold, respectively, in cells exposed to C2-ceramide (5 microM) or TNF alpha (10 ng/ml) [29].
  • In contrast, the related mitogen-activated protein kinases ERK1 and ERK2 are weakly stimulated following TNF alpha treatment (1.5-fold) and are inhibited by C2-ceramide treatment [29].

Analytical, diagnostic and therapeutic context of Acetyl ceramide


  1. C2-ceramide signaling in glioma cells: synergistic enhancement of CD95-mediated, caspase-dependent apoptosis. Wagenknecht, B., Roth, W., Gulbins, E., Wolburg, H., Weller, M. Cell Death Differ. (2001) [Pubmed]
  2. Ceramide formation leads to caspase-3 activation during hypoxic PC12 cell death. Inhibitory effects of Bcl-2 on ceramide formation and caspase-3 activation. Yoshimura, S., Banno, Y., Nakashima, S., Takenaka, K., Sakai, H., Nishimura, Y., Sakai, N., Shimizu, S., Eguchi, Y., Tsujimoto, Y., Nozawa, Y. J. Biol. Chem. (1998) [Pubmed]
  3. The mitogen-activated protein kinase pathway inhibits ceramide-induced terminal differentiation of a human monoblastic leukemia cell line, U937. Ragg, S.J., Kaga, S., Berg, K.A., Ochi, A. J. Immunol. (1998) [Pubmed]
  4. Suppression of Cancer Cell Migration and Invasion by Protein Phosphatase 2A through Dephosphorylation of {micro}- and m-Calpains. Xu, L., Deng, X. J. Biol. Chem. (2006) [Pubmed]
  5. Prevalence of necrosis in C2-ceramide-induced cytotoxicity in NB16 neuroblastoma cells. Ramos, B., Lahti, J.M., Claro, E., Jackowski, S. Mol. Pharmacol. (2003) [Pubmed]
  6. Short-chain ceramide regulates hepatic methionine adenosyltransferase expression. Frago, L.M., Pañeda, C., Fabregat, I., Varela-Nieto, I. J. Hepatol. (2001) [Pubmed]
  7. Programmed cell death induced by ceramide. Obeid, L.M., Linardic, C.M., Karolak, L.A., Hannun, Y.A. Science (1993) [Pubmed]
  8. Multiple sclerosis: Fas signaling in oligodendrocyte cell death. D'Souza, S.D., Bonetti, B., Balasingam, V., Cashman, N.R., Barker, P.A., Troutt, A.B., Raine, C.S., Antel, J.P. J. Exp. Med. (1996) [Pubmed]
  9. Ceramide induces interleukin 6 gene expression in human fibroblasts. Laulederkind, S.J., Bielawska, A., Raghow, R., Hannun, Y.A., Ballou, L.R. J. Exp. Med. (1995) [Pubmed]
  10. Apoptotic signaling through CD95 (Fas/Apo-1) activates an acidic sphingomyelinase. Cifone, M.G., De Maria, R., Roncaioli, P., Rippo, M.R., Azuma, M., Lanier, L.L., Santoni, A., Testi, R. J. Exp. Med. (1994) [Pubmed]
  11. Helicobacter pylori-dependent ceramide production may mediate increased interleukin 8 expression in human gastric cancer cell lines. Masamune, A., Shimosegawa, T., Masamune, O., Mukaida, N., Koizumi, M., Toyota, T. Gastroenterology (1999) [Pubmed]
  12. Role of enhanced ceramide generation in DNA damage and cell death in chemical hypoxic injury to LLC-PK1 cells. Ueda, N., Kaushal, G.P., Hong, X., Shah, S.V. Kidney Int. (1998) [Pubmed]
  13. Inhibition of skin carcinomas but not papillomas by sphingosine, N-methylsphingosine, and N-acetylsphingosine. Birt, D.F., Merrill, A.H., Barnett, T., Enkvetchakul, B., Pour, P.M., Liotta, D.C., Geisler, V., Menaldino, D.S., Schwartzbauer, J. Nutrition and cancer. (1998) [Pubmed]
  14. L1-CAM in a membrane-bound or soluble form augments protection from apoptosis in ovarian carcinoma cells. Stoeck, A., Gast, D., Sanderson, M.P., Issa, Y., Gutwein, P., Altevogt, P. Gynecol. Oncol. (2007) [Pubmed]
  15. Effect of Ca2+-dependent cell death on the release of herpes simplex virus. Yura, Y., Matsumoto, R., Sumi, T., Kusaka, J. Arch. Virol. (2003) [Pubmed]
  16. Pituitary adenylate cyclase-activating polypeptide prevents the effects of ceramides on migration, neurite outgrowth, and cytoskeleton remodeling. Falluel-Morel, A., Vaudry, D., Aubert, N., Galas, L., Benard, M., Basille, M., Fontaine, M., Fournier, A., Vaudry, H., Gonzalez, B.J. Proc. Natl. Acad. Sci. U.S.A. (2005) [Pubmed]
  17. Defective apoptotic signal transduction pathway downstream of caspase-3 in human B-lymphoma cells: A novel mechanism of nuclear apoptosis resistance. Kawabata, Y., Hirokawa, M., Kitabayashi, A., Horiuchi, T., Kuroki, J., Miura, A.B. Blood (1999) [Pubmed]
  18. Suppression of Bcl-2 messenger RNA production may mediate apoptosis after ionizing radiation, tumor necrosis factor alpha, and ceramide. Chen, M., Quintans, J., Fuks, Z., Thompson, C., Kufe, D.W., Weichselbaum, R.R. Cancer Res. (1995) [Pubmed]
  19. The growth arrest and downregulation of c-myc transcription induced by ceramide are related events dependent on p21 induction, Rb underphosphorylation and E2F sequestering. Alesse, E., Zazzeroni, F., Angelucci, A., Giannini, G., Di Marcotullio, L., Gulino, A. Cell Death Differ. (1998) [Pubmed]
  20. Damage-induced neuronal endopeptidase (DINE) is a unique metallopeptidase expressed in response to neuronal damage and activates superoxide scavengers. Kiryu-Seo, S., Sasaki, M., Yokohama, H., Nakagomi, S., Hirayama, T., Aoki, S., Wada, K., Kiyama, H. Proc. Natl. Acad. Sci. U.S.A. (2000) [Pubmed]
  21. Herpes simplex virus 1 induces and blocks apoptosis at multiple steps during infection and protects cells from exogenous inducers in a cell-type-dependent manner. Galvan, V., Roizman, B. Proc. Natl. Acad. Sci. U.S.A. (1998) [Pubmed]
  22. Ceramide mediates the rapid phase of febrile response to IL-1beta. Sanchez-Alavez, M., Tabarean, I.V., Behrens, M.M., Bartfai, T. Proc. Natl. Acad. Sci. U.S.A. (2006) [Pubmed]
  23. Control of ceramide-induced apoptosis by IGF-1: involvement of PI-3 kinase, caspase-3 and catalase. Kondo, T., Kitano, T., Iwai, K., Watanabe, M., Taguchi, Y., Yabu, T., Umehara, H., Domae, N., Uchiyama, T., Okazaki, T. Cell Death Differ. (2002) [Pubmed]
  24. Integrins alpha(v)beta3 and alpha(v)beta5 are expressed by endothelium of high-risk neuroblastoma and their inhibition is associated with increased endogenous ceramide. Erdreich-Epstein, A., Shimada, H., Groshen, S., Liu, M., Metelitsa, L.S., Kim, K.S., Stins, M.F., Seeger, R.C., Durden, D.L. Cancer Res. (2000) [Pubmed]
  25. Functional expression of Fas and Fas ligand on human gut lamina propria T lymphocytes. A potential role for the acidic sphingomyelinase pathway in normal immunoregulation. De Maria, R., Boirivant, M., Cifone, M.G., Roncaioli, P., Hahne, M., Tschopp, J., Pallone, F., Santoni, A., Testi, R. J. Clin. Invest. (1996) [Pubmed]
  26. Apoptosis caused by oxidized LDL is manganese superoxide dismutase and p53 dependent. Kinscherf, R., Claus, R., Wagner, M., Gehrke, C., Kamencic, H., Hou, D., Nauen, O., Schmiedt, W., Kovacs, G., Pill, J., Metz, J., Deigner, H.P. FASEB J. (1998) [Pubmed]
  27. Interaction of ceramides, sphingosine, and sphingosine 1-phosphate in regulating DNA synthesis and phospholipase D activity. Gómez-Muñoz, A., Waggoner, D.W., O'Brien, L., Brindley, D.N. J. Biol. Chem. (1995) [Pubmed]
  28. Ceramide inhibits IgE-mediated activation of phospholipase D, but not of phospholipase C, in rat basophilic leukemia (RBL-2H3) cells. Nakamura, Y., Nakashima, S., Ojio, K., Banno, Y., Miyata, H., Nozawa, Y. J. Immunol. (1996) [Pubmed]
  29. Ceramide activates the stress-activated protein kinases. Westwick, J.K., Bielawska, A.E., Dbaibo, G., Hannun, Y.A., Brenner, D.A. J. Biol. Chem. (1995) [Pubmed]
  30. Role of c-jun expression increased by heat shock- and ceramide-activated caspase-3 in HL-60 cell apoptosis. Possible involvement of ceramide in heat shock-induced apoptosis. Kondo, T., Matsuda, T., Kitano, T., Takahashi, A., Tashima, M., Ishikura, H., Umehara, H., Domae, N., Uchiyama, T., Okazaki, T. J. Biol. Chem. (2000) [Pubmed]
  31. Ceramide mediates insulin resistance by tumor necrosis factor-alpha in brown adipocytes by maintaining Akt in an inactive dephosphorylated state. Teruel, T., Hernandez, R., Lorenzo, M. Diabetes (2001) [Pubmed]
  32. Sphingosine 1-phosphate inhibits activation of caspases that cleave poly(ADP-ribose) polymerase and lamins during Fas- and ceramide-mediated apoptosis in Jurkat T lymphocytes. Cuvillier, O., Rosenthal, D.S., Smulson, M.E., Spiegel, S. J. Biol. Chem. (1998) [Pubmed]
  33. Regulatory role of ceramide in interleukin (IL)-1 beta-induced E-selectin expression in human umbilical vein endothelial cells. Ceramide enhances IL-1 beta action, but is not sufficient for E-selectin expression. Masamune, A., Igarashi, Y., Hakomori, S. J. Biol. Chem. (1996) [Pubmed]
  34. The protective effect of ceramide in immature rat brain hypoxia-ischemia involves up-regulation of bcl-2 and reduction of TUNEL-positive cells. Chen, Y., Ginis, I., Hallenbeck, J.M. J. Cereb. Blood Flow Metab. (2001) [Pubmed]
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