D-erythro-Dihydrosphingosine 1-phosphate
| Code | Size | Price |
|---|
| AG-CR1-0005-M001 | 1 mg | £95.00 |
Quantity:
| AG-CR1-0005-M005 | 5 mg | £350.00 |
Quantity:
Prices exclude any Taxes / VAT
Overview
Regulatory Status: RUO
Shipping:
Ambient
Storage:
-20°C
Documents
Further Information
Alternate Names/Synonyms:
(2S,3R)-Dihydro-sphingosine 1-phosphate; Dihydro-S1P; dhS1P; HSPP
Appearance:
White to off-white solid.
CAS:
19794-97-9
EClass:
32160000
Form (Short):
liquid
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
Long Description:
Chemical. CAS: 19794-97-9. Formula: C18H40NO5P. MW: 381.5. Saturated analog of sphingosine 1-phosphate (1-SP1). Ligand for sphingosine 1-phosphate (S1P/EDG) receptors. Negative control for intracellular effects of sphingosine 1-phosphate. Induces chemotaxis. Antifibrotic.
MDL:
MFCD00871363
Molecular Formula:
C18H40NO5P
Molecular Weight:
381.5
Other data:
For delivery of dihydrosphingosine 1-phosphate (HSPP) to cells, prepare a 125µM stock in 4mg/ml BSA as follows: Dissolve HSPP in methanol/THF/water (60/30/10) (0.5mg/ml). This may require boiling (75°C), with occasional replacement of evaporated methanol. Crushing of solid prior to addition of solvent and crushing and stirring during heating is helpful. Aliquot desired amounts of stock solution to tubes. Evaporate the solvent with a stream of nitrogen, swirling to deposit a thin film of HSPP on the inside of the tube. Aliquots may be stored at -20 °C at this point or dissolved with enough 4mg/ml BSA (fatty acid free bovine serum albumin in water; 37°C, 30 min. with repeated vortexing) to make 125µM stock solution. Stock solutions are stable for up to 3 months when stored at -20°C.
Package Type:
Vial
Product Description:
Saturated analog of sphingosine 1-phosphate (1-SP1). Ligand for sphingosine 1-phosphate (S1P/EDG) receptors [1,3]. Negative control for intracellular effects of sphingosine 1-phosphate [1]. Induces chemotaxis [2]. Antifibrotic [4].
Purity:
>98% (NMR)
SMILES:
CCCCCCCCCCCCCCC[C@@H](O)[C@@H](N)COP(O)(O)=O
Solubility Chemicals:
Soluble in methanol/THF/water (60/30/10) (0.5 mg/ml). Slightly soluble in DMSO, methanol or acetic acid.
Transportation:
Non-hazardous
UNSPSC Category:
Biochemical Reagents
UNSPSC Number:
12352200
Use & Stability:
Stable for at least 2 years after receipt when stored at -20°C.
References
Dual actions of sphingosine-1-phosphate: extracellular through the Gi-coupled receptor Edg-1 and intracellular to regulate proliferation and survival: J.R. van Brocklyn, et al.; J. Cell Biol. 142, 229 (1998) | Sphingosine 1-phosphate stimulates cell migration through a G(i)-coupled cell surface receptor. Potential involvement in angiogenesis: F. Wang, et al.; JBC 274, 35343 (1999) | Sphingosine 1-phosphate-induced cell rounding and neurite retraction are mediated by the G protein-coupled receptor H218: J.R. van Brocklyn, et al. JBC 274, 4626 (1999) | Dihydrosphingosine 1-phosphate has a potent antifibrotic effect in scleroderma fibroblasts via normalization of phosphatase and tensin homolog levels: Arthritis Rheum. 62, 2117 (2010) | Sphingosine-1-phosphate (S1P) induces potent anti-inflammatory effects in vitro and in vivo by S1P receptor 4?mediated suppression of 5-lipoxygenase activity: J. Fettel, et al.; FASEB J. ahead of print (2018)