An affinity probe for C6 ceramide binding partners
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C6 Biotin Ceramide (d18:1/6:0)

Item No. 9000415

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3aS,4S,6aR)-hexahydro-N-[6-[[(1S,2R,3E)-2-hydroxy-1-(hydroxymethyl)-3-heptadecen-1-yl]amino]-6-oxohexyl]-2-oxo-1H-thieno[3,4-d]imidazole-4-pentanamide
CAS Number
192070-02-3
Synonyms
  • Biotin Ceramide (d18:1/6:0)
  • Biotin Cer(d18:1/6:0)
  • C6 Ceramide-biotin
  • N-C6:0-biotin-D-erythro-Ceramide
  • N-hexanoyl-biotin-D-erythro-Sphingosine
Molecular Formula
C34H62N4O5S
Formula Weight
638.9
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: Soluble
SMILES
CCCCCCCCCCCCC/C=C/[C@@H](O)[C@@H](NC(CCCCCNC(CCCC[C@H]1[C@]2([H])[C@](NC(N2)=O)([H])CS1)=O)=O)CO
InChi Code
InChI=1S/C34H62N4O5S/c1-2-3-4-5-6-7-8-9-10-11-12-13-15-20-29(40)27(25-39)36-32(42)23-16-14-19-24-35-31(41)22-18-17-21-30-33-28(26-44-30)37-34(43)38-33/h15,20,27-30,33,39-40H,2-14,16-19,21-26H2,1H3,(H,35,41)(H,36,42)(H2,37,38,43)/b20-15+/t27-,28-,29+,30-,33-/m0/s1
InChi Key
AWBCMSFWIASOLO-MDSNSZKOSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $722

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    Product Description

    C6 Ceramide-biotin is an affinity probe that allows C2 ceramide (d18:1/2:0) (Item No. 62525) 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 (Item No. 62510), 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 [Matreya, LLC. Catalog No. 2081]

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description 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. The FASEB Journal 23(3), 751-763 (2009).

    2. Dobrowsky, R.T., and Hannun, Y.A. Ceramide stimulates a cytosolic protein phosphatase. The Journal of Biological Chemisty 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. The Journal of Biological Chemisty 272(11), 6918-6926 (1997).

    4. Dobrowsky, R.T., Kamibayashi, C., Mumby, M.C., et al. Ceramide activates heterotrimeric protein phosphatase 2A. The Journal of Biological Chemisty 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. The Journal of Biological Chemisty 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. The Journal of Biological Chemisty 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. The Journal of Biological Chemisty 272(4), 2038-3035 (1997).