3102-57-6 Usage
Description
C2 ceramide is a cell-permeable analog of naturally occurring ceramides. It mediates many diverse biological activities, as do natural ceramides. These processes include differentiation of HL-60 cells, induction of apoptosis, activation of protein phosphatase 2A, and inhibition of the mitochondrial respiratory chain. C2 ceramide also enhances the expression of COX-2 in human dermal fibroblasts and stimulates the growth of bovine aortic smooth muscle cells. The ability of C2 ceramide to destabilize membranes may be responsible for its inhibition of platelet aggregation.
Chemical Properties
White Crystalline Solid
Uses
Different sources of media describe the Uses of 3102-57-6 differently. You can refer to the following data:
1. Inhibits cell proliferation and induces monocytic differentiation of HL-60 cells. Activates protein phosphatases
2. A biologically active, cell permeable, but nonphysiologic ceramide analog. It inhibits cell proliferation and induces monocytic differentiation of HL-60 cells and induces apoptosis. It stimulates protein phosphatase 2A and activates MAP Kinase2
Biological Activity
A potent modulator of cell proliferation and differentiation. Activates protein phosphatase-1 (PP1) and -2A (PP2A), as well as ceramide-activated protein phosphatase (CAPP) in vitro .
Biochem/physiol Actions
Cell-permeable, biologically active ceramide. It induces differentiation and apoptosis in cells and has been shown to activate protein phosphatases.
References
1) Minano et al. (2008), C2-ceramide mediates cerebellar granule cells apoptosis by activation of caspases-2, -9, and -3; J. Neurosci. Res., 86 1734
2) Prinetti et al. (1997), Involvement of a ceramide activated protein phosphatase in the differentiation of neuroblastoma Neuro2a cells; FEBS Lett., 414 475
3) Zhang et al. (1997), Kinase suppressor of Ras is ceramide-activated protein kinase; Cell, 89 63
4) Matsuzaka et al. (2016) Characterization and Functional Analysis of Extracellular Vesicles and Muscle-Abundant miRNAs (miR-1, miR-133a, and miR-206) in C2C12 Myocytes and mdx Mice; PLoS One 11(12) e0167811 [Focus Biomolecules Citation]
5) Matsuzaka et al. (2016) Characterization and functional analysis of extracellular vesicles and muscle-abundant miRNA in C2C12 myocytes and Mdx mice; PLoS One 11(12) e0167811 [Focus Biomolecules Citation]
Check Digit Verification of cas no
The CAS Registry Mumber 3102-57-6 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 3,1,0 and 2 respectively; the second part has 2 digits, 5 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 3102-57:
(6*3)+(5*1)+(4*0)+(3*2)+(2*5)+(1*7)=46
46 % 10 = 6
So 3102-57-6 is a valid CAS Registry Number.
InChI:InChI=1/C20H39NO3/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-20(24)19(17-22)21-18(2)23/h15-16,19-20,22,24H,3-14,17H2,1-2H3,(H,21,23)/b16-15+/t19-,20+/m0/s1
3102-57-6Relevant articles and documents
Chiral combinatorial preparation and biological evaluation of unique ceramides for inhibition of sphingomyelin synthase
Koolath, Sajeer,Monde, Kenji,Murai, Yuta,Suga, Yoshiko
supporting information, (2020/02/04)
Enantiomers or diastereomers of chiral bioactive compounds often exhibit different biological and toxicological properties. Here, we report the efficient synthesis of four stereoisomers of sphingosine and derivatization of unique chiral ceramides through a combinatorial chemistry by solid-phase activated resin ester. In addition, to test the effectivity of stereochemistry of ceramide, we demonstrated a cell-based assay of sphingomyelin synthase inhibition in the presence ofchiral unique ceramides, which suggested that libraries of this sort will be a rich source of biologically active synthetic molecules.
Ceramide compound and application
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Paragraph 0036; 0056-0060, (2017/07/06)
The invention relates to a ceramide compound; in the structural general formula, m=2-12; n=0-20. The ceramide compound has significant pseudo neural growth factor activity, and is the small molecule compound capable of passing through blood-brain barrier. The structural general formula is shown as Figure.
Exploring Leishmania major Inositol Phosphorylceramide Synthase (LmjIPCS): Insights into the ceramide binding domain
Mina, John G.,Mosely, Jackie A.,Ali, Hayder Z.,Denny, Paul W.,Steel, Patrick G.
supporting information; experimental part, p. 1823 - 1830 (2011/04/26)
The synthesis of set of ceramide analogues exploring hydrophobicity in the acyl chains and the degree and nature of hydroxylation is described. These have been assayed against the parasitic protozoan enzyme LmjIPCS. These studies showed that whilst the C-3 hydroxyl group was not essential for turnover it provided enhanced affinity. Reflecting the membrane bound nature of the enzyme a long (C13) hydrocarbon ceramide tail was necessary for both high affinity and turnover. Whilst the N-acyl chain also contributed to affinity, analogues lacking the amide linkage functioned as competitive inhibitors in both enzyme and cell-based assays. A model that accounts for this observation is proposed.