Description
C6 ceramide is a cell-permeable analog of naturally occurring ceramides. With a longer carbon chain than C2 ceramide, it is somewhat more hydrophobic, and may more closely mimic the effects of natural ceramides. C6 ceramide mediates many diverse biological activities including apoptosis, activation of protein phosphatase 2A, and inhibition of the mitochondrial respiratory chain. It also enhances the expression of COX-2 in rat granulosa cells and stimulates the growth of bovine aortic smooth muscle cells. C6 ceramide acts in neuronal axons to inhibit neurite growth.
Chemical Properties
Off White Powder
Uses
C6 Ceramide (d18:1/6:0) has been used as a chemotherapeutic agent to test its anti-tumor effect in breast cancer cells and ovarian cancer cell lines. It has also been used to test chemo-sensitization effects in cancer cells.
Uses
A biologically active, cell permeable, but nonphysiologic ceramide analog. It stimulates protein phosphatase 2A at concentrations as low as 10 nM and activiates MAP kinase. It induces apoptosis and inhibits glycoproptein traffic by the secretory pathway.
Definition
ChEBI: N-(hexanoyl)sphing-4-enine is an N-acylsphingosine consisting of sphing-4-enine bearing a hexanoyl group on nitrogen. It is functionally related to a sphing-4-enine.
General Description
Biologically active, cell-permeable, non-physiological ceramide analog. Induces a dramatic arrest in the G
0/G
1 phase of the cell cycle. Activates MAP kinase. Activates protein phosphatase 2A (PP2A) at 10 nM. Inhibits diacylglycerol accumulation and phospholipase D (PLD) activation in fibroblasts. Induces apoptosis in MOLT-4 leukemia cells.
Biochem/physiol Actions
C6 Ceramide (d18:1/6:0) is involved in inhibiting proliferation and inducing apoptosis. When used in combination with acid ceramidase inhibitor DM102, [(2R,3Z)-N-(1-hydroxyoctadec-3-en-2-yl)pivaloylamide], it favors cell death in human breast cancer cells lines. C6 Ceramide may serve as an adjunct in chemotherapy. It elicits anti-tumor effects via AKT (serine/threonine-specific protein kinase) dephosphorylation and α-tubulin acetylation.
References
[1] R T DOBROWSKY Y A H. Ceramide stimulates a cytosolic protein phosphatase.[J]. The Journal of Biological Chemistry, 1992, 267 8: 5048-5051.
[2] R T DOBROWSKY. Ceramide activates heterotrimeric protein phosphatase 2A.[J]. The Journal of Biological Chemistry, 1993, 268 21: 15523-15530.
[3] P SANTANA. Interleukin-1 beta stimulates sphingomyelin hydrolysis in cultured granulosa cells: evidence for a regulatory role of ceramide on progesterone and prostaglandin biosynthesis.[J]. Endocrinology, 1996, 137 6: 2480-2489. DOI:
10.1210/endo.137.6.8641202[4] E I DE CHAVES. Elevation of ceramide within distal neurites inhibits neurite growth in cultured rat sympathetic neurons.[J]. The Journal of Biological Chemistry, 1997, 272 5: 3028-3035. DOI:
10.1074/jbc.272.5.3028
