Sphingosine-1-phosphate, D-erythro__Signaling molecule Nemorubicin
Product Name
Sphingosine-1-phosphate, D-erythro
Description
Signaling molecule
Purity
>98%
CAS No.
26993-30-6
Molecular Formula
C18H38NO5P
Molecular Weight
379.5
Storage Temperature
-20ºC
Shipping Temperature
Shipped Ambient
Product Type
Second Messenger
Solubility
Sparingly soluble in 1:1 ethanol:water. Addition of small amounts of acetic acid may help dissolve this product. Soluble in warm methanol.
Source
Synthetic
Appearance
White solid
SMILES
C@@H(N)(email protected(O)C=CCCCCCCCCCCCCC)COP(=O)(O)O
InChI
InChI=1S/C18H38NO5P/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/h14-15,17-18,20H,2-13,16,19H2,1H3,(H2,21,22,23)/b15-14+/t17-,18+/m0/s1
InChIKey
DUYSYHSSBDVJSM-KRWOKUGFSA-N
Safety Phrases
Classification: Caution. Substance not yet fully tested.
Safety Phrases:
S22 – Do not breathe dust
S36/37/39 – Wear suitable protective clothing, gloves and eye/face protection
S24/25 – Avoid contact with skin and eyes
Hazard Phrases:
H315 – Causes skin irritation.
H319 – Causes serious eye irritation.
H335 – May cause respiratory irritation.
Precautionary Phrases:
P261 Avoid breathing dust/fume/gas/mist/vapours/spray.
P280 Wear protective gloves/protective clothing/eye protection/face protection.
P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing
P321 Specific treatment (see on this label).
P405 Store locked up.
P501 Dispose of contents/container in accordance with local/regional/national/international regulations
Cite This Product
Sphingosine-1-phosphate, D-erythro (StressMarq Biosciences Inc., Victoria BC CANADA, Catalog # SIH-386)
Alternative Names
(E,2S,3R)-2-Amino-3-hydroxyoctadec-4-enyl dihydrogen phosphate
Research Areas
Cell Signaling
PubChem ID
5283560
Scientific Background
D-erythro-Sphingosine-1-phosphate (S1P) is a polar sphingolipid metabolite which regulates diverse cellular responses including cell growth, survival and migration. S1P was reported to stimulate DNA synthesis and cell division in quiescent cultures of Swiss 3T3 fibroblasts and to trigger the dual signal transduction pathways of calcium mobilization and PC-PLD (phospholipase D) activation. S1P serves as a second messenger for intracellular calcium mobilization in U-937 cells (sc-2239) and decreases cellular cAMP. Recent studies show that S1P is a G-protein-coupled receptor (GPCR) ligand for the EDG-1 family, including EDG-1, -3, -5, -6 and -8. This bioactive lipid mediator has been shown to stimulate the ERK pathway and to also counteract the ceramide-induced activation of stress-activated protein kinase (SAPK/JNK). Researchers have also found that S1P is a strong inhibitor of cell motility and phagokinesis in B16 melanoma cells. Additionally, it induces rapid and transient tyrosine phosphorylation of epidermal growth factor receptor (EGFR) and c-Met in gastric cancer cells. S1P has also been known as a tumor-promoting lipid. Suggested to be an activator of GPR3, GPR6, and GPR12. D-erythro-Sphingosine-1-phosphate is an activator of EDG-1, EDG-3, EDG-2, EDG-4 and EDG-5.¬
References
1. Van Veldhoven P.P., et al. (1989). J. Lipid Res. 30(4): 611-6.
2. Desai N.N., et al. (1992). J. Biol. Chem. 267(32): 23122-8.
3. Sadahira Y., et al. (1992). Proc. Natl. Acad. Sci. U.S.A. 89(20): 9686-90.
4. Olivera A. and Spiegel, S. (1993). Nature. 365(6446): 557-60.
5. Mattie M., et al. (1994). J. Biol. Chem. 269(5): 3181-8.
6. Wu J., et al. (1995). J. Biol. Chem. 270(19): 11484-8.
7. Choi O.H., et al. (1996). Nature. 380(6575): 634-6.
8. Cuvillier O., et al. (1996). Nature. 381(6585): 800-3.
9. Spiegel S., et al. (2000). Biochim. Biophys. Acta. 1484(2-3): 107-16.
10. Spiegel S. and Milstien, S. (2000). FEBS Lett. 476(1-2): 55-57.
11. Shida, D., et al. (2004). FEBS Lett. 577(3): 333-8.
12. Watterson, K.R., et al. (2005). Cell. Signal. 17(3): 289-98.
Signaling molecule
Safety Phrases:
S22 – Do not breathe dust
S36/37/39 – Wear suitable protective clothing, gloves and eye/face protection
S24/25 – Avoid contact with skin and eyes
Hazard Phrases:
H315 – Causes skin irritation.
H319 – Causes serious eye irritation.
H335 – May cause respiratory irritation.
Precautionary Phrases:
P261 Avoid breathing dust/fume/gas/mist/vapours/spray.
P280 Wear protective gloves/protective clothing/eye protection/face protection.
P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing
P321 Specific treatment (see on this label).
P405 Store locked up.
P501 Dispose of contents/container in accordance with local/regional/national/international regulations
2. Desai N.N., et al. (1992). J. Biol. Chem. 267(32): 23122-8.
3. Sadahira Y., et al. (1992). Proc. Natl. Acad. Sci. U.S.A. 89(20): 9686-90.
4. Olivera A. and Spiegel, S. (1993). Nature. 365(6446): 557-60.
5. Mattie M., et al. (1994). J. Biol. Chem. 269(5): 3181-8.
6. Wu J., et al. (1995). J. Biol. Chem. 270(19): 11484-8.
7. Choi O.H., et al. (1996). Nature. 380(6575): 634-6.
8. Cuvillier O., et al. (1996). Nature. 381(6585): 800-3.
9. Spiegel S., et al. (2000). Biochim. Biophys. Acta. 1484(2-3): 107-16.
10. Spiegel S. and Milstien, S. (2000). FEBS Lett. 476(1-2): 55-57.
11. Shida, D., et al. (2004). FEBS Lett. 577(3): 333-8.
12. Watterson, K.R., et al. (2005). Cell. Signal. 17(3): 289-98.