Date published: 2025-12-2

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3-O-Methylsphingomyelin

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Application:
3-O-Methylsphingomyelin is a novel selective inhibitor of neutral sphingomyelinase
Purity:
98%
Molecular Weight:
604.85
Molecular Formula:
C32H65N2O6P
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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3-O-Methylsphingomyelin is a modified form of sphingomyelin, a type of sphingolipid found in animal cell membranes. Sphingomyelin is a significant component of the myelin sheath, which insulates axons and allows for efficient transmission of electrical signals in neurons. It is also found in various other cell types and has roles in cellular signaling and apoptosis. 3-O-Methylsphingomyelin is a novel selective inhibitor of N-SMase (neutral sphingomyelinase), (Ki=37 muM) that is cell-permeable and does not inhibit acid sphingomyelinase. N-SMase is an enzyme responsible for hydrolyzing sphingomyelin to ceramide and phosphorylcholine. Ceramide is a bioactive lipid involved in a variety of cellular processes including cell cycle arrest, apoptosis, and inflammation. By selectively inhibiting N-SMase and not acid sphingomyelinase, 3-O-Methylsphingomyelin offers targeted modulation of sphingolipid metabolism.


3-O-Methylsphingomyelin References

  1. The role of neutral sphingomyelinase produced ceramide in lipopolysaccharide-mediated expression of inducible nitric oxide synthase.  |  Won, JS., et al. 2004. J Neurochem. 88: 583-93. PMID: 14720208
  2. Sphingomyelins suppress the targeted disruption of lysosomes/endosomes by the photosensitizer NPe6 during photodynamic therapy.  |  Caruso, JA., et al. 2005. Biochem J. 392: 325-34. PMID: 15943580
  3. Aryl hydrocarbon receptor modulation of tumor necrosis factor-alpha-induced apoptosis and lysosomal disruption in a hepatoma model that is caspase-8-independent.  |  Caruso, JA., et al. 2006. J Biol Chem. 281: 10954-67. PMID: 16446372
  4. IL-1beta-induced iNOS expression, NO release and loss in metabolic cell viability are resistant to inhibitors of ceramide synthase and sphingomyelinase in INS 832/13 cells.  |  Veluthakal, R., et al. 2006. JOP. 7: 593-601. PMID: 17095838
  5. De novo C16- and C24-ceramide generation contributes to spontaneous neutrophil apoptosis.  |  Seumois, G., et al. 2007. J Leukoc Biol. 81: 1477-86. PMID: 17329567
  6. A novel non-transcriptional pathway mediates the proconvulsive effects of interleukin-1beta.  |  Balosso, S., et al. 2008. Brain. 131: 3256-65. PMID: 18952671
  7. TNF-α- and tumor-induced skeletal muscle atrophy involves sphingolipid metabolism.  |  De Larichaudy, J., et al. 2012. Skelet Muscle. 2: 2. PMID: 22257771
  8. Endogenous interleukin-1β in neuropathic rats enhances glutamate release from the primary afferents in the spinal dorsal horn through coupling with presynaptic N-methyl-D-aspartic acid receptors.  |  Yan, X., et al. 2013. J Biol Chem. 288: 30544-30557. PMID: 24003233
  9. Disulfide-containing high mobility group box-1 promotes N-methyl-D-aspartate receptor function and excitotoxicity by activating Toll-like receptor 4-dependent signaling in hippocampal neurons.  |  Balosso, S., et al. 2014. Antioxid Redox Signal. 21: 1726-40. PMID: 24094148
  10. New oleyl glycoside as anti-cancer agent that targets on neutral sphingomyelinase.  |  Romero-Ramírez, L., et al. 2015. Biochem Pharmacol. 97: 158-72. PMID: 26206186
  11. Membrane lipid raft homeostasis is directly linked to neurodegeneration.  |  Moll, T., et al. 2021. Essays Biochem. 65: 999-1011. PMID: 34623437
  12. Vascular smooth muscle cell senescence accelerates medin aggregation via small extracellular vesicle secretion and extracellular matrix reorganization.  |  Whitehead, M., et al. 2023. Aging Cell. 22: e13746. PMID: 36433666
  13. Multi-locus deletion mutation induced by silver nanoparticles: Role of lysosomal-autophagy dysfunction.  |  Si, B., et al. 2023. Ecotoxicol Environ Saf. 257: 114947. PMID: 37105094
  14. Interaction of sphingomyelinase with sphingomyelin analogs modified at the C-1 and C-3 positions of the sphingosine backbone.  |  Lister, MD., et al. 1995. Biochim Biophys Acta. 1256: 25-30. PMID: 7742352

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

3-O-Methylsphingomyelin, 1 mg

sc-205580
1 mg
$126.00

3-O-Methylsphingomyelin, 5 mg

sc-205580A
5 mg
$520.00