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C2 Ceramide

BML-SL100

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Cell-permeable ceramide analog

N-Acetylsphingosine is a biologically active, cell-permeable ceramide analog. It inhibits cell proliferation and induces monocytic differentiation of HL-60 cells and induces apoptosis. It stimulates protein phosphatase 2A4, activates MAP kinase and SAP kinase and induces PKCδ and ε translocation. Physiological levels of C2 ceramide, produced by the action of a PAF:sphingosine CoA-independent transacetylase, have been detected in HL-60 cells.

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Product Details

Alternative Name	N-Acetyl-D-erythro-sphingosine
Appearance	White solid.
CAS	3102-57-6
Couple Target	Jnk, MAPK, Serine/threonine-protein phosphatase
Couple Type	Activator
Formula	C₂₀H₃₉NO₃
MW	341.5
Purity	≥98% (TLC)
Solubility	Soluble in 100% ethanol (>25mg/ml) or DMSO (>50mg/ml).
Technical Info / Product Notes	C2 ceramide may precipitate from aqueous media, particularly those lacking serum or serum albumin, at concentrations ~20µM or higher. To avoid this problem, a 1:1 complex of C2 Ceramide with BSA may be prepared as follows: Dissolve C2 ceramide to 200mM (68.3mg/ml) in anhydrous DMSO. Dissolve fatty acid-free BSA in water to 66mg/ml (1mM). Dilute the ceramide/DMSO stock 200-fold into the BSA solution, with constant stirring. A precipitate will form at first, but will dissolve after ~30 minutes of stirring at room temperature. Alternatively, a solution of C2 Ceramide/BSA may be prepared directly, without making a DMSO stock: 1) prepare a 20% w/v stock of BSA in water (3mM); 2) use the BSA stock to dissolve the solid C2 Ceramide at 1.02mg/ml (3mM). Complete dissolution of the ceramide may require more than 1 hour of stirring at room temperature.

Handling & Storage

Use/Stability	As indicated on product label or CoA when stored as recommended. Stable for at least 1 year after receipt when stored, as supplied, at -20°C. Stock solutions are stable for up to 3 months at -20°C.
Long Term Storage	-20°C
Shipping	Ambient Temperature

Regulatory Status	RUO – Research Use Only

A sphingolipid rheostat controls apoptosis versus apical cell extrusion as alternative tumour-suppressive mechanisms: Armistead, J., Höpfl, S., et al.; Cell Death Dis. 15, 746 (2024), Abstract
Inactivation of potassium channels by ceramide in rat pancreatic β-cells: T.Q. Acosta, et al.; Arch. Biochem. Biophys. 735, 109520 (2023), Abstract
Acid sphingomyelinase promotes SGK1-dependent vascular calcification: T. Luong, et al.; Clin. Sci. 135, 515 (2021), Abstract — Full Text
Cellular stress promotes NOD1/2-dependent inflammation via the endogenous metabolite sphingosine-1-phosphate: Pei, G., Zyla, J., et al.; EMBO J. 40, e106272 (2021), Abstract
An Endothelial-to-Adipocyte Extracellular Vesicle Axis Governed by Metabolic State: Crewe, C., Joffin, N., et al.; Cell 175, 695 (2018), Abstract
Short-chain C2 ceramide induces heme oxygenase-1 expression by upregulating AMPK and MAPK signaling pathways in rat primary astrocytes: J.S. Jung, et al.; Neurochem. Int. 94, 9 (2016), Application(s): Cell culture, Abstract
Exogenous C2 Ceramide Suppresses Matrix Metalloproteinase Gene Expression by Inhibiting ROS Production and MAPK Signaling Pathways in PMA-Stimulated Human Astroglioma Cells: J. S. Jung, et al.; Int. J. Mol. Sci. 17, e477 (2016), Application(s): Cell culture, Abstract — Full Text
The TrkA receptor mediates experimental thermal hyperalgesia produced by nerve growth factor: Modulation by the p75 neurotrophin receptor: A. Khodorova, et al.; Neuroscience 340, 384 (2016), Abstract
Bone morphogenic protein (BMP) signaling up-regulates neutral sphingomyelinase 2 to suppress chondrocyte maturation via the Akt protein signaling pathway as a negative feedback mechanism: Kakoi, H., Maeda, S., et al.; J. Biol. Chem. 289, 8135 (2014), Abstract
Dynamic GLUT4 sorting through a syntaxin-6 compartment in muscle cells is derailed by insulin resistance-causing ceramide: Foley, K. P., Klip, A., et al.; Biol. Open 3, 314 (2014), Application(s): In Vitro, Abstract

Last modified: May 29, 2024

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C2 Ceramide

BML-SL100

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