Skip to Content
MilliporeSigma
All Photos(2)

Key Documents

View All Documentation

857346P

Avanti

VPC 44116

Avanti Research™ - A Croda Brand 857346P, powder

Synonym(s):

(R)-(3-amino-4-((3-octylphenyl)amino)-4-oxobutyl)phosphonic acid

Sign Into View Organizational & Contract Pricing

Select a Size

All Photos(2)

Select a Size

Change View

About This Item

Empirical Formula (Hill Notation):
C18H31N2O4P
CAS Number:
925978-30-9
Molecular Weight:
370.42
UNSPSC Code:
12352211
NACRES:
NA.25

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

SMILES string

CCCCCCCCC1=CC(NC([C@H](N)CCP(O)(O)=O)=O)=CC=C1

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.[1][2][3] 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_germany

WGK 3

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

It looks like we've run into a problem, but you can still download Certificates of Analysis from our Documents section.

If you need assistance, please contact Customer Support.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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
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.
Enhancement of capillary leakage and restoration of lymphocyte egress by a chiral S1P1 antagonist in vivo.
Sanna MG, et al.
Nature Chemical Biology, 2, 434-441 (2006)
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
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)
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service