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Synthetic Products
Sphingolipids
Sphingosylphosphorylcholine
Lysosphingomyelin
Purity >99%

 


Product Name
Product Number
 
Sphingosylphosphorylcholine
860600

Sphingosylphosphorylcholine (SPC), or lysosphingomyelin, is a sphingolipid metabolite and putative second messenger important in several intracellular and intercellular events
and has been implicated in regulation of cell growth, differentiation, and programmed cell death. SPC increased intracellular calcium concentration and nitric oxide production in endothelial cells in situ causing endothelium-dependent vasorelaxation of bovine coronary arteries.1 SPC also may regulate calcium release from the sarcoplasmic reticulum by modifying the gating kinetics of the cardiac ryanodine receptor.2 Stimulation of cardiac myocytes with SPC led to an increase in the total amount of protein, an accelerated rate of total protein synthesis, and a decrease in protein degradation, suggesting that SPC may play a critical role in the development of cardiac hypertrophy.3 Patients with atopic dermatitis abnormally expressed sphingomyelin deacylase in their epidermis resulting in elevated levels of SPC rather than ceramide. SPC enhanced the expression of intercellular adhesion molecule-1 (ICAM-1), and transforming necrosis factor-alpha (TNF-alpha) levels significantly increased in the medium of cultured human keratinocytes. Also, SPC induced a rapid activation of mitogen-activated protein kinase in keratinocytes. These finding suggest that SPC plays an important role in the inflammatory process of epidermis in skin diseases, such as atopic dermatitis, with high expression of sphingomyelin deacylase.4 Finally, a study of brain lipids in patients with the sphingomyelinase-deficient types of Niemann-Pick disease demonstrated the abnormal accumulation of SPC occurs only in the brain of neuronopathic type A patients but not in the non-neuronopathic type B patients. Elevated levels of SPC were observed in the brains of type A patients while type B patients showed no significant increase of SPC in brain lipids. Both type A and B patients exhibited abnormally high levels of SPC in liver and spleen, establishing the integrity of brain tissue in type B Niemann-Pick disease and suggesting that SPC could play a role in the pathophysiology of brain dysfunction in the neuronopathic type A.5

Source: Synthesized from D-erythro-Sphingosine
Physical State: Powder
Chemical Purity: >99%, by TLC and NMR.
References:
  1. Mogami, K.; Mizukami, Y.; Todoroki-Ikeda, N.; Ohmura, M.; Yoshida, K.; Miwa, S.; Matsuzaki, M.; Matsuda, M., and Kobayashi, S. (1999 Sep 3). Sphingosylphosphorylcholine induces cytosolic Ca2+ elevation in endothelial cells in situ and causes endothelium-dependent relaxation through nitric oxide production in bovine coronary artery. FEBS Lett; 457(3):375-80.

  2. Uehara, A.; Yasukochi, M.; Imanaga, I., and Berlin, J. R. (1999 Nov 5). Effect of sphingosylphosphorylcholine on the single channel gating properties of the cardiac ryanodine receptor. FEBS Lett; 460(3):467-71.

  3. Sekiguchi, K.; Yokoyama, T.; Kurabayashi, M.; Okajima, F., and Nagai, R. (1999 Nov 26). Sphingosylphosphorylcholine induces a hypertrophic growth response through the mitogen-activated protein kinase signaling cascade in rat neonatal cardiac myocytes. Circ Res; 85(11):1000-8.

  4. Imokawa, G.; Takagi, Y.; Higuchi, K.; Kondo, H., and Yada, Y. (1999 Jan). Sphingosylphosphorylcholine is a potent inducer of intercellular adhesion molecule-1 expression in human keratinocytes. J Invest Dermatol; 112(1):91-6.

  5. Rodriguez-Lafrasse, C. and Vanier, M. T. (1999 Feb). Sphingosylphosphorylcholine in Niemann-Pick disease brain: accumulation in type A but not in type B. Neurochem Res; 24(2):199-205.
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