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Merck
CN

857346P

Avanti

VPC 44116

Avanti Research™ - A Croda Brand

Synonym(s):

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

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About This Item

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

Key Documents

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Product Name

VPC 44116, Avanti Research™ - A Croda Brand 857346P, powder

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. 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 Code

13 - Non Combustible Solids

WGK

WGK 3

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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)
Characterization of a sphingosine 1-phosphate receptor antagonist prodrug.
Kennedy PC, et al.
Journal of Pharmacology and Experimental Therapeutics, 338, 879-889 (2011)
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)
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.
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