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Sphinganine (d18:0)

(Synonyms: D-赤式-C18-二氢-D-神经鞘氨醇) 目录号 : GC40794

Sphingolipid pathway intermediate

Sphinganine (d18:0) Chemical Structure

Cas No.:764-22-7

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5mg
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10mg
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25mg
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50mg
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产品描述

Sphinganine (d18:0) is a precursor of ceramide and sphingosine as well as a substrate of sphingosine kinases, which generate sphinganine-1-phosphate. Sphinganine levels increase significantly in response to certain mycotoxins, including fumonisins,[1,2] as well as in some cancers.[3] Sphinganine can block protein kinase C activation in some cases but not others.[4,5] Sphinganine-1-phosphate can emulate sphingosine-1-phosphate in cell signaling or have opposite intracellular effects.[6,7,8]

References:
1. Pruett, S.T., Bushnev, A., Hagedorn, K., et al. Biodiversity of sphingoid bases ("sphingosines") and related amino alcohols. J. Lipid Res. 49(8), 1621-1639 (2008).
2. Shephard, G.S., van der Westhuizen, L., and Sewram, V. Biomarkers of exposure to fumonisin mycotoxins: A review. Food Addit. Contam. 24(10), 1196-1201 (2007).
3. Yin, J., Miyazaki, K., Shaner, R.L., et al. Altered sphingolipid metabolism induced by tumor hypoxia - new vistas in glycolipid tumor markers. FEBS Lett. 584(9), 1872-1878 (2010).
4. Merrill, A.H., Jr., Sereni, A.M., Stevens, V.L., et al. Inhibition of phorbol ester-dependent differentiation of human promyelocytic leukemic (HL-60) cells by sphinganine and other long-chain bases. J. Biol. Chem. 261(27), 12610-12615 (1986).
5. Merrill, A.H., Jr., Nimkar, S., Menaldino, D., et al. Structural requirements for long-chain (shingoid) base inhibition of protein kinase C in vitro and for the cellular effects of these compounds. Biochemistry 28(8), 3138-3145 (1989).
6. Coste, O., Brenneis, C., Linke, B., et al. Sphingosine 1-phosphate modulates spinal nociceptive processing. J. Biol. Chem. 283(47), 32442-32451 (2008).
7. Bu, S., Yamanaka, M., Pei, H., et al. Dihydrosphingosine 1-phosphate stimulates MMP1 gene expression via activation of ERK1/2-Ets1 pathway in human fibroblasts. FASEB J. 20(1), 184-186 (2006).
8. Bu, S., Kapanadze, B., Hsu, T., et al. Opposite effects of dihydrosphingosine 1-phosphate and sphingosine 1-phosphate on transforming growth factor-β/Smad signaling are mediated through the PTEN/PPM1A-dependent pathway. J. Biol. Chem. 283(28), 19593-19602 (2008).

Chemical Properties

Cas No. 764-22-7 SDF
别名 D-赤式-C18-二氢-D-神经鞘氨醇
Canonical SMILES OC[C@H](N)[C@H](O)CCCCCCCCCCCCCCC
分子式 C18H39NO2 分子量 301.5
溶解度 DMF: 10 mg/ml,DMSO: 2 mg/ml,Ethanol: Miscible 储存条件 Store at -20°C
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1 mM 3.3167 mL 16.5837 mL 33.1675 mL
5 mM 0.6633 mL 3.3167 mL 6.6335 mL
10 mM 0.3317 mL 1.6584 mL 3.3167 mL
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Research Update

Palmitoyl-ceramide accumulation with necrotic cell death in A549 cells, followed by a steep increase in Sphinganine content

Biochim Open 2015 Jun 21;1:11-27.PMID:29632826DOI:10.1016/j.biopen.2015.06.001.

Ceramides (Cers) have recently been identified as key signaling molecules that mediate biological functions such as cell growth, differentiation, senescence, apoptosis, and autophagy. However, the functions of Cer accumulation in necrotic cell death remain unknown. The aim of this study was to clarify the relationship between Cer accumulation with inhibition of the conversion pathway of Cer and concomitant necrotic cell death. In order to minimize the effect of apoptosis against necrotic cell death, A549 cells having the inhibiting effect of caspase 9 by survivin were used in this study. Consequently, Cer accumulation in A549 cells would likely be associated with a pathway other than the mitochondrial caspase-dependent pathway of apoptosis. Here, we showed that the dual addition of a glucosyl-Cer synthase inhibitor and a ceramidase inhibitor to A549 cell culture induced palmitoyl-Cer accumulation with Cer synthase 5 expression and necrotic cell death with lysosomal rupture together with leakage of cathepsin B/alkalization after 2-3 h, although it is unknown in this study whether the necrotic cell death was caused by the lysosomal rupture. This Cer accumulation was followed by a steep increase in Sphinganine base levels via the activation of serine palmitoyltransferase activity brought about by the increase in palmitoyl-coenzyme A concentration as a substrate after 5-6 h. The increase in palmitoyl-coenzyme A concentration was achieved by activation of the fatty acid synthetic pathway from acetyl coenzyme A.