| Identification | Back Directory | [Name]
VPC 23019 | [CAS]
449173-19-7 | [Synonyms]
VPC 23019
2-Amino-N-(3-octylphenyl)-3-(phosphonooxy)-propanamaide
(2R)-2-Amino-N-(3-octylphenyl)-3-(phosphonooxy)-propanamide
Propanamide, 2-amino-N-(3-octylphenyl)-3-(phosphonooxy)-, (2R)-
(R)-phosphoric acid Mono-[2-aMino-2-(3-octyl-phenylcarbaMoyl)-ethyl] ester
(R)-PHOSPHORIC ACID MONO-[2-AMINO-2-(3-OCTYL-PHENYLCARBAMOYL)-ETHYL] ESTER;VPC 23019 | [Molecular Formula]
C17H29N2O5P | [MDL Number]
MFCD19690948 | [MOL File]
449173-19-7.mol | [Molecular Weight]
372.4 |
| Chemical Properties | Back Directory | [density ]
1.239±0.06 g/cm3(Predicted) | [storage temp. ]
Store at -20°C | [solubility ]
Soluble in DMSO | [form ]
crystalline solid | [pka]
1.72±0.10(Predicted) | [color ]
Light yellow to yellow |
| Hazard Information | Back Directory | [Uses]
VPC 23019 is a sphinosine-1 phosphate antagonist. | [Definition]
ChEBI: VPC 23019 is a secondary carboxamide resulting from the formal condensation of the carboxy group of O-phospho-D-serine with the amino group of m-octylaniline. An analogue of sphingosine-1-phosphate (S1P), it is a potent antagonist for both S1P1 and S1P3 receptors. It can inhibit S1P-induced migration of thyroid cancer cells, ovarian cancer cells, and neural stem cells. It has a role as a sphingosine-1-phosphate receptor 3 antagonist and a sphingosine-1-phosphate receptor 1 antagonist. It is a D-serine derivative, a secondary carboxamide, an organic phosphate, a phosphoric ester and an aromatic amide. It is functionally related to an O-phospho-D-serine. | [Biological Activity]
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]. | [storage]
Store at -20°C | [References]
[1]. arthur c.m. mulders, mari?lle 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. |
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