| Identification | Back Directory | [Name]
C8 D-threo Ceramide (d18:1/8:0) | [CAS]
175892-43-0 | [Synonyms]
C8 D-threo Ceramide (d18:1/8:0)
Octanamide, N-[(1R,2R,3E)-2-hydroxy-1-(hydroxymethyl)-3-heptadecen-1-yl]- | [Molecular Formula]
C26H51NO3 | [MDL Number]
MFCD08703023 | [MOL File]
175892-43-0.mol | [Molecular Weight]
425.69 |
| Hazard Information | Back Directory | [Description]
C8 D-threo Ceramide is a bioactive sphingolipid and cell-permeable analog of naturally occurring ceramides.1 It is cytotoxic to U937 cells (IC50 = 17 μM) and induces nuclear DNA fragmentation 5- to 6-fold more potently than C8 ceramide .1,2 C8 D-threo Ceramide is a substrate for E. coli diacylglycerol kinase.1 It activates ceramide-activated protein kinase (CAPK) in U937 cells. C8 D-threo Ceramide also enhances V. cholerae cytolysin pore formation in liposome lipid membranes, as measured by calcein release, with a 50% release dose (RD50) value of ~5 μg/ml.3
| [References]
1. Karasavvas, N., Erukulla, R.K., Bittman, R., et al. 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 Eur. J. Biochem. 236(2),729-737(1996).
2. Chang, Y.-T., Choi, J., Ding, S., et al. The synthesis and biological characterization of a ceramide library J. Am. Chem. Soc. 124(9),1856-1857(2002).
3. Zitzer, A., Bittman, R., Verbicky, C.A., et al. Coupling of cholesterol and cone-shaped lipids in bilayers augments membrane permeabilization by the cholesterol-specific toxins streptolysin O and Vibrio cholerae cytolysin J. Biol. Chem. 276(18),14628-14633(2001). |
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