Sphinganine 1-phosphate

• CAT Number: R020719
• CAS Number: 19794-97-9
• Molecular Formula: C18H40NO5P
• Molecular Weight: 381.49
• Purity: ≥95%
• Synonyms: [(2S,3R)-2-amino-3-hydroxyoctadecyl] dihydrogen phosphate
• InChI: InChI=1S/C18H40NO5P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(20)17(19)16-24-25(21,22)23/h17-18,20H,2-16,19H2,1H3,(H2,21,22,23)/t17-,18+/m0/s1
• InChIKey: YHEDRJPUIRMZMP-ZWKOTPCHSA-N
• SMILES: CCCCCCCCCCCCCCCC(C(COP(=O)(O)O)N)O

Sphinganine 1-phosphate (D-erythro-Dihydrosphingosine 1-phosphate) is a polar sphingolipid metabolite that regulates cell migration, differentiation, survival and complex physiological processes[1].
Sphinganine 1-phosphate (S1P) is a potent signaling molecule involved in cell stress responses, cancer, angiogenesis and lymphocyte trafficking. Sphinganine 1-phosphate functions primarily by activating a subgroup of the endothelial differentiation gene (EDG) family of G-protein coupled cell surface receptors. Sphinganine 1-phosphate has opposite effects in the regulation of cell metabolism. Sphinganine 1-phosphate regulates skeletal muscle differentiation and regeneration[1].
Sphinganine 1-phosphate (S1P) is involved in cancer. Sphinganine 1-phosphate regulates processes such as inflammation, which can drive tumorigenesis; neovascularization, which provides cancer cells with nutrients and oxygen; and cell growth and survival[1].
Sphinganine-1-Phosphate (1 μM) phosphorylates ERK MAPK, Akt, and HSP27 and induces HSP27 in human renal endothelial cells[2].
Sphinganine 1-phosphate can enhance wound healing in diabetic mice[1].
Sphinganine 1-phosphate provides renal and hepatic protection after liver ischemia and reperfusion (IR) injury in mice through selective activation of S1P1 receptors and pertussis toxin-sensitive G-proteins with subsequent activation of ERK and Akt. Sphinganine 1-phosphate (administered 0.1 mg/kg i.v. immediately before reperfusion and 0.2 mg/kg s.c. 2 h after reperfusion) protects against hepatic and renal injury after liver IR[2].

Reference

[1]. Montserrat Serra, et al. Sphingosine 1-phosphate lyase, a key regulator of sphingosine 1-phosphate signaling and function. Adv Enzyme Regul. 2010;50(1):349-62.
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[2]. Sang Won Park, et al. Sphinganine-1-phosphate protects kidney and liver after hepatic ischemia and reperfusion in mice through S1P1 receptor activation. Lab Invest. 2010 Aug;90(8):1209-24.
 [Content Brief]