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AdipoGen Life Sciences
D-erythro-Dihydrosphingosine [Sphinganine]
50
CHF
CHF 50.00
In stock
AG-CR1-3556-M0055 mgCHF 50.00
| Product Details | |
|---|---|
| Synonyms | Sphinganine (d18:0); Dihydrosphingosine; (2S,3R)-2-Aminooctadecane-1,3-diol |
| Product Type | Chemical |
| Properties | |
| Formula |
C18H39NO2 |
| MW | 301.5 |
| CAS | 764-22-7 |
| Purity Chemicals | ≥95% |
| Appearance | White to off-white solid. |
| Solubility | Soluble in DMSO (20mg/ml) or ethanol (20mg/ml). |
| InChi Key | OTKJDMGTUTTYMP-ZWKOTPCHSA-N |
| Smiles | OC[C@H](N)[C@H](O)CCCCCCCCCCCCCCC |
| Shipping and Handling | |
| Shipping | AMBIENT |
| Short Term Storage | +4°C |
| Long Term Storage | -20°C |
| Use/Stability | Stable for at least 2 years after receipt when stored at -20°C. |
| Documents | |
| MSDS |
 Download PDF |
| Product Specification Sheet | |
| Datasheet |
Download PDF |
Description
- The metabolite sphinganine activates the CD4+ regulatory T (Treg) cells, which accumulate in the tumor microenvironment (TME) and suppress the immune system. Sphinganine activates the Treg cells by physically interacting with the transcription factor c-Fos, and consequently increasing Treg cell proliferation.
- Sphinganine is a precursor of ceramide and sphingosine as well as a substrate of sphingosine kinases, which generate sphinganine-1-phosphate.
- Sphinganine is an inhibitor of protein kinase C and phospholipases A2 and D.
- Sphinganine levels increase significantly in response to certain mycotoxins, including fumonisins, as well as in some cancers.
- Sphinganine has been proposed to function as a c-Src kinase inhibitor in a drug-induced cancer cell model.
Product References
- Inhibition of phorbol ester-dependent differentiation of human promyelocytic leukemic (HL-60) cells by sphinganine and other long-chain bases: A.H. Merrill, et al.; J. Biol. Chem. 261, 12610 (1986)
- Structural requirements for long-chain (shingoid) base inhibition of protein kinase C in vitro and for the cellular effects of these compounds: A.H. Merrill, et al.; Biochemistry 28, 3138 (1989)
- Sphingolipid metabolism and signal transduction: inhibition of in vitro phospholipase activity by sphingosine: R.C. Franson, et al.; Biochim. Biophys. Acta 1136, 169 (1992)
- Biomarkers of exposure to fumonisin mycotoxins: A review: G.S. Shephard, et al.; Food Addit. Contam. 24, 1196 (2007)
- Biodiversity of sphingoid bases ("sphingosines") and related amino alcohols: S.T. Pruett, et al.; J. Lipid Res. 49, 1621 (2008)
- Altered sphingolipid metabolism induced by tumor hypoxia - new vistas in glycolipid tumor markers: J. Yin, et al.; FEBS Lett. 584, 1872 (2010)
- Secretion of Sphinganine by Drug-Induced Cancer Cells and Modified Mimetic Sphinganine (MMS) as c-Src Kinase Inhibitor: R. Nandangiri, et al.; Asian Pac. J. Cancer Prev. 25, 433 (2024)
- Serine enrichment in tumors promotes regulatory T cell accumulation through sphinganine-mediated regulation of c-Fos: S. Ma, et al.; Sci. Immunol. 9, eadg8817 (2024)
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