857346 | VPC 44116

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


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VPC 44116

VPC 44116

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

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.
Kennedy, P.C., et al. (2011).
Also refer Sanna et al., 2006 and Foss et al., 2007.

This product is covered by Patent Number US 7,888,527 B2. Avanti manufactures this under license from University of Virginia

Hygroscopic
Yes
Light Sensitive
No
Molecular Formula
C18H31N2O4P
Percent Composition
C 58.36%, H 8.44%, N 7.56%, O 17.28%, P 8.36%
Purity
>99%
Stability
1 year
Storage Temperature
-20°C
CAS Number
925978-30-9
CAS Registry Number is a Registered Trademark of the American Chemical Society
Formula Weight
370.424
Exact Mass
370.202

Balaji Ragunathrao VA, Anwar M, Akhter MZ, Chavez A, Mao Y, Natarajan V, Lakshmikanthan S, Chrzanowska-Wodnicka M, Dudek AZ, Claesson-Welsh L, Kitajewski JK, Wary KK, Malik AB, Mehta D. Sphingosine-1-Phosphate Receptor 1 Activity Promotes Tumor Growth by Amplifying VEGF-VEGFR2 Angiogenic Signaling. Cell Rep. 2019 Dec 10;29(11):3472-3487.e4. doi: 10.1016/j.celrep.2019.11.036. PMID: 31825830; PMCID: PMC6927555.

PubMed ID: 31825830

Kennedy PC, Zhu R, Huang T, et al. Characterization of a sphingosine 1-phosphate receptor antagonist prodrug. J Pharmacol Exp Ther. 2011;338(3):879–889. doi:10.1124/jpet.111.181552

PubMed ID: 21632869

Sanna MG, Wang SK, Gonzalez-Cabrera PJ, Don A, Marsolais D, Matheu MP, Wei SH, Parker I, Jo E, Cheng WC, Cahalan MD, Wong CH, Rosen H. Enhancement of capillary leakage and restoration of lymphocyte egress by a chiral S1P1 antagonist in vivo. Nat Chem Biol. 2006 Aug;2(8):434-41. doi: 10.1038/nchembio804. Epub 2006 Jul 9. PMID: 16829954.

PubMed ID: 16829954

Foss FW Jr, Snyder AH, Davis MD, Rouse M, Okusa MD, Lynch KR, Macdonald TL. Synthesis and biological evaluation of gamma-aminophosphonates as potent, subtype-selective sphingosine 1-phosphate receptor agonists and antagonists. Bioorg Med Chem. 2007 Jan 15;15(2):663-77. doi: 10.1016/j.bmc.2006.10.060. Epub 2006 Nov 1. PMID: 17113298; PMCID: PMC1963459.

PubMed ID: 17113298