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About This Item
Empirical Formula (Hill Notation):
C18H31N2O4P
CAS Number:
Molecular Weight:
370.42
UNSPSC Code:
12352211
NACRES:
NA.25
Product Name
VPC 44116, Avanti Research™ - A Croda Brand 857346P, powder
SMILES string
CCCCCCCCC1=CC(NC([C@H](N)CCP(O)(O)=O)=O)=CC=C1
assay
>99% (TLC)
form
powder
packaging
pkg of 1 × 1 mg (857346P-1mg)
manufacturer/tradename
Avanti Research™ - A Croda Brand 857346P
lipid type
cardiolipins
sphingolipids
shipped in
dry ice
storage temp.
−20°C
General description
In addition to receptor-selective agonists such as SEW2871, competitive S1P receptor antagonists have provided insight into the physiological effects of S1P signaling, particularly involving S1P1. (R)-3-amino-(3-octylphenylamino)-4-oxobutylphosphonic acid (VPC44116) (S1P1/3 antagonist) and an analog, (R)-3-amino-(3-hexylphenylamino)-4-oxobutylphosphonic acid (W146) (S1P1 antagonist), both were found to increase capillary permeability as measured by Evans blue dye leakage in mouse lung tissue. This product is covered by Patent Number US 7,888,527 B2. Avanti manufactures this under license from University of Virginia
Packaging
5 mL Amber Glass Screw Cap Vial (857346P-1mg)
Legal Information
Avanti Research is a trademark of Avanti Polar Lipids, LLC
Storage Class
13 - Non Combustible Solids
wgk
WGK 3
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Vijay Avin Balaji Ragunathrao et al.
Cell reports, 29(11), 3472-3487 (2019-12-12)
The vascular endothelial growth factor-A (VEGF-A)-VEGFR2 pathway drives tumor vascularization by activating proangiogenic signaling in endothelial cells (ECs). Here, we show that EC-sphingosine-1-phosphate receptor 1 (S1PR1) amplifies VEGFR2-mediated angiogenic signaling to enhance tumor growth. We show that cancer cells induce
Characterization of a sphingosine 1-phosphate receptor antagonist prodrug.
Kennedy PC, et al.
Journal of Pharmacology and Experimental Therapeutics, 338, 879-889 (2011)
Perry C Kennedy et al.
The Journal of pharmacology and experimental therapeutics, 338(3), 879-889 (2011-06-03)
Sphingosine 1-phosphate (S1P) is a phospholipid that binds to a set of G protein-coupled receptors (S1P(1)-S1P(5)) to initiate an array of signaling cascades that affect cell survival, differentiation, proliferation, and migration. On a larger physiological scale, the effects of S1P
Frank W Foss et al.
Bioorganic & medicinal chemistry, 15(2), 663-677 (2006-11-23)
The synthesis of N-arylamide phosphonates and related arylether and arylamine analogues provided potent, subtype-selective agonists and antagonists of the five known sphingosine 1-phosphate (S1P) receptors (S1P(1-5)). To this end, the syntheses of phosphoserine mimetics-selectively protected and optically active phosphonoserines-are described.
Synthesis and biological evaluation of gamma-aminophosphonates as potent, subtype-selective sphingosine 1-phosphate receptor agonists and antagonists.
Foss FW Jr, et al.
Bioorganic & Medicinal Chemistry, 15, 663-677 (2007)
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