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VPC 23019

Catalog No.
S1P1/S1P3 receptor antagonist
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Ship with 5-10 days
Ship with 5-10 days

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VPC 23019, phosphoric acid mono-[2-amino-2-(3-octyl-phenylcarbamoyl)-ethyl] ester, is an S1P1/S1P3 receptor antagonist. S1P is short for sphingosine-1-phosphate [1]. VPC 23019 abolished S1P-induced, cell migration, Gi-dependent Rac stimulation and tube formation [2]. VPC 23019 inhibited SIP1 activity with an IC50 value of 8 nM [3].

S1P can act on specific G protein-coupled receptors. 5 subtypes of these receptors have been found and termed S1P1–5. These receptors couple to intracellular second messenger systems including intracellular Ca2+, phospholipase C, adenylyl cyclase, phosphatidylinositol 3 (PI3)-kinase, mitogen-activated protein kinases, protein kinase Akt, and Ras- and Rho-dependent pathways [1].

In the bEnd.3 cell line, VPC 23019 did not affect basal NO production. Preincubation with 10 µmol/L VPC 23019 made Ang II–induced NO production decrease to approximately basal level [1]. S1P, in a dose-dependent manner, stimulated trans-well migration of mouse vascular endothelial cells with a peak response at 10-7M. VPC 23019 was able to abolish this stimulatory effect of S1P [2]. Preincubation with 10 µM of VPC 23019 partially inhibited S1P-induced calcium increase in L2071 cells [4].

In rat, VPC 23019 significantly increased the S1P-induced vasoconstriction in preparation with intact endothelium (P< 0.01), but did not change it in preparation without endothelium. In intact mouse basilar artery (relaxation to ACh, 45.6±7.2%, n= 16), VPC 23019 left-shifted the concentration-contraction curve to S1P by a half log. VPC 23019 did not modify contractile responses to 5-HT, KCl or U46619 [5].

[1].  Arthur C.M. Mulders, Mariëlle C. Hendriks-Balk, Marie-Jeanne Mathy, et al. Sphingosine Kinase-dependent Activation of Endothelial Nitric Oxide Synthase by Angiotensin II. Arterioscler Thromb Vasc Biol., 2006, 26:2043-2048.
[2].  Isao Inoki, Noriko Takuwa, Naotoshi Sugimoto, et al. Negative regulation of endothelial morphogenesis and angiogenesis by S1P2 receptor. Biochemical and Biophysical Research Communications, 2006, 346: 293-300.
[3].  Ju Wang, Zi-Qi Shi, Xiaojun Xu, et al. Triptolide Inhibits Amyloid-β Production and Protects Neural Cells by Inhibiting CXCR2 Activity. Journal of Alzheimer’s Disease, 2013, 33:1-2.
[4].  Mi-Kyoung Kim, Kyoung Sun Park, Hyuck Lee, et al. Phytosphingosine-1-phosphate stimulates chemotactic migration of L2071 mouse fibroblasts via pertussis toxin-sensitive G-proteins. Exp. Mol. Med., 2007, 39(2):185-194.
[5].  S Salomone, EM Potts, S Tyndall, et al. Analysis of sphingosine 1-phosphate receptors involved in constriction of isolated cerebral arteries with receptor null mice and pharmacological tools. British Journal of Pharmacology, 2008, 153:140-147.

Product Citation

Chemical Properties

Physical AppearanceA crystalline solid
StorageStore at -20°C
Cas No.449173-19-7
SolubilitySoluble in DMSO
Chemical Name(R)-2-amino-3-((3-octylphenyl)amino)-3-oxopropyl dihydrogen phosphate
SDFDownload SDF
Canonical SMILESO=C([[email protected]@H](COP(O)(O)=O)N)NC1=CC(CCCCCCCC)=CC=C1
Shipping ConditionEvaluation sample solution: ship with blue ice. All other available sizes: ship with RT, or blue ice upon request.
General tipsFor obtaining a higher solubility, please warm the tube at 37°C and shake it in the ultrasonic bath for a while. Stock solution can be stored below -20°C for several months.

Quality Control

Quality Control & MSDS

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Chemical structure

VPC 23019

Related Biological Data

VPC 23019