| Identification | Back Directory | [Name]
C6 Biotin Ceramide (d18:1/6:0) | [CAS]
192070-02-3 | [Synonyms]
C6 Biotin Ceramide (d18:1/6:0) | [Molecular Formula]
C34H62N4O5S | [MDL Number]
MFCD19705498 | [MOL File]
192070-02-3.mol | [Molecular Weight]
638.94 |
| Hazard Information | Back Directory | [Description]
C6 Ceramide-biotin is an affinity probe that allows C2 ceramide (d18:1/2:0) to be detected or immobilized through interaction with the biotin ligand. C6 Ceramide-biotin has been used to detect ceramide binding partners, such as inhibitor 2 of protein phosphatase 2A (I2PP2A), in vitro and in situ.1 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.2 C6 ceramide mediates many diverse biological activities including apoptosis, activation of PP2A, and inhibition of the mitochondrial respiratory chain.2,3,4,5 It also enhances the expression of COX-2 in rat granulosa cells and stimulates the growth of bovine aortic smooth muscle cells.6,7 C6 ceramide acts in neuronal axons to inhibit neurite growth.8
| [References]
1. Mukhopadhyay, A., Saddoughi, S.A., Song, P., et al. Direct interaction between the inhibitor 2 and ceramide via sphingolipid-protein binding is involved in the regulation of protein phosphatase 2A activity and signaling FASEB J. 23(3),751-763(2009).
2. Dobrowsky, R.T., and Hannun, Y.A. Ceramide stimulates a cytosolic protein phosphatase J. Biol. Chem. 267(8),5048-5051(1992).
3. Cai, Z., Bettaieb, A., El Mahdani, N., et al. Alteration of the sphingomyelin/ceramide pathway is associated with resistance of human breast carcinoma MCF7 cells to tumor necrosis factor-α-mediated cytotoxicity J. Biol. Chem. 272(11),6918-6926(1997).
4. Dobrowsky, R.T., Kamibayashi, C., Mumby, M.C., et al. Ceramide activates heterotrimeric protein phosphatase 2A J. Biol. Chem. 268(21),15523-15530(1993).
5. Gudz, T.I., Tserng, K.Y., and Hoppel, C.L. Direct inhibition of mitochondrial respiratory chain complex III by cell-permeable ceramide J. Biol. Chem. 272(39),24154-24158(1997).
6. Santana, P., Llanes, L., Hernandez, I., et al. Interleukin-1β stimulates sphingomyelin hydrolysis in cultured granulosa cells: Evidence for a regulatory role of ceramide on progesterone and prostaglandin biosynthesis Endocrinology 137(6),2480-2489(1996).
7. Augé, N., Andrieu, N., Nègre-Salvayre, A., et al. The sphingomyelin-ceramide signaling pathway is involved in oxidized low density lipoprotein-induced cell proliferation J. Biol. Chem. 271(32),19251-19255(1996).
8. Posse de Chaves, E.I., Bussière, M., Vance, D.E., et al. Elevation of ceramide within distal neurites inhibits neurite growth in cultured rat sympathetic neurons J. Biol. Chem. 272(4),2038-3035(1997). |
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