860652P
Avanti
C8 Ceramide-1-Phosphate (d17:1/8:0)
Avanti Research™ - A Croda Brand 860652P, powder
Synonym(s):
N-octanoyl-ceramide-1-phosphate (C17 base) (ammonium salt)
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About This Item
Empirical Formula (Hill Notation):
C25H53N2O6P
CAS Number:
Molecular Weight:
508.67
UNSPSC Code:
12352211
NACRES:
NA.25
Recommended Products
form
powder
packaging
pkg of 1 × 1 mg (860652P-1mg)
manufacturer/tradename
Avanti Research™ - A Croda Brand 860652P
lipid type
sphingolipids
shipped in
dry ice
storage temp.
−20°C
SMILES string
CCCCCCCCCCCC/C=C/[C@@]([H])(O)[C@@]([H])(NC(CCCCCCC)=O)COP([O-])(O)=O.[NH4+]
General description
C8 Ceramide-1-Phosphate (d17:1/8:0) is a novel bioactive sphingolipid. It is formed by the phosphorylation of C8-ceramide or N-octanoyl-D-erythro-sphingosine (C17 base) catalyzed by ceramide kinase (CERK). C1P is a sphingolipid analog of phosphatidate.
Biochem/physiol Actions
Ceramide 1-phosphate (C1P) acts as a mitogenic agent. It exhibits antiapoptotic and prosurvival properties. C1P stimulates inflammatory response and facilitates phagocytosis. It also has an ability to negatively regulate tumor necrosis factor-α (TNFα) production induced by lipopolysaccharide. C1P is reputed to be a second lipid messenger of agonist-stimulated sphingomyelin metabolism.
Packaging
5 mL Amber Glass Screw Cap Vial (860652P-1mg)
Legal Information
Avanti Research is a trademark of Avanti Polar Lipids, LLC
Storage Class
11 - Combustible Solids
wgk_germany
WGK 3
Certificates of Analysis (COA)
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Szczepan Józefowski et al.
Journal of immunology (Baltimore, Md. : 1950), 185(11), 6960-6973 (2010-11-03)
LPS is a constituent of cell walls of Gram-negative bacteria that, acting through the CD14/TLR4 receptor complex, causes strong proinflammatory activation of macrophages. In murine peritoneal macrophages and J774 cells, LPS at 1-2 ng/ml induced maximal TNF-α and MIP-2 release
V T Hinkovska-Galcheva et al.
The Journal of biological chemistry, 273(50), 33203-33209 (1998-12-05)
Ceramide, a product of agonist-stimulated sphingomyelinase activation, is known to be generated during the phagocytosis of antibody-coated erythrocytes by polymorphonuclear leukocytes. Agonist-stimulated formation of ceramide-1-phosphate is now shown to occur in 32PO4-labeled neutrophils. Ceramide-1-phosphate is formed by a calcium-dependent ceramide
Antonio Gómez-Muñoz et al.
Journal of lipid research, 45(1), 99-105 (2003-10-03)
It was reported previously that ceramide-1-phosphate (Cer-1-P) is mitogenic for fibroblasts (Gómez-Muñoz, A., P. A. Duffy, A. Martin, L. O'Brien, H-S. Byun, R. Bittman, and D. N. Brindley. 1995. Mol. Pharmacol. 47: 883-889; Gómez-Muñoz, A., L. M. Frago, L. Alvarez
A Gomez-Muñoz et al.
Molecular pharmacology, 47(5), 833-839 (1995-05-01)
Ceramide and ceramide-1-phosphate are sphingolipid analogues of diacylglycerol and phosphatidate, respectively, and they are putative second messengers of agonist-stimulated sphingomyelin metabolism. The interactions of exogenous cell-permeable ceramides and ceramide-1-phosphates in modifying DNA synthesis and signal transduction were investigated in Rat-1
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