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MedKoo Cat#: 407250 | Name: VPC-23019
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

VPC-23019 is a sphingosine-1-phosphate receptor antagonist. VPC-23019 acts as a competitive antagonist at both S1P1 and S1P3 receptors (pKis = 7.86 and 5.93, respectively). VPC-23019 can inhibit S1P-induced migration of thyroid cancer cells, ovarian cancer cells, and neural stem cells.

Chemical Structure

VPC-23019
VPC-23019
CAS#449173-19-7

Theoretical Analysis

MedKoo Cat#: 407250

Name: VPC-23019

CAS#: 449173-19-7

Chemical Formula: C17H29N2O5P

Exact Mass: 372.1814

Molecular Weight: 372.40

Elemental Analysis: C, 54.83; H, 7.85; N, 7.52; O, 21.48; P, 8.32

Price and Availability

Size Price Availability Quantity
5mg USD 350.00 2 Weeks
50mg USD 750.00 2 Weeks
100mg USD 1,250.00 2 Weeks
1g USD 4,250.00 2 Weeks
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Related CAS #
No Data
Synonym
VPC-23019, VPC23019, VPC 23019
IUPAC/Chemical Name
(R)-2-amino-3-((3-octylphenyl)amino)-3-oxopropyl dihydrogen phosphate
InChi Key
MRUSUGVVWGNKFE-MRXNPFEDSA-N
InChi Code
InChI=1S/C17H29N2O5P/c1-2-3-4-5-6-7-9-14-10-8-11-15(12-14)19-17(20)16(18)13-24-25(21,22)23/h8,10-12,16H,2-7,9,13,18H2,1H3,(H,19,20)(H2,21,22,23)/t16-/m1/s1
SMILES Code
O=P(O)(OC[C@@H](N)C(NC1=CC=CC(CCCCCCCC)=C1)=O)O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 372.40 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Omi M, Yamada H, Takahashi H, Mori H, Oba S, Hattori Y, Yokota K, Toyama K, Takahashi K. Differences in collateral vessel formation after experimental retinal vein occlusion in spontaneously hypertensive rats and wild-type rats. Heliyon. 2024 Mar 1;10(6):e27160. doi: 10.1016/j.heliyon.2024.e27160. PMID: 38509953; PMCID: PMC10950832. 2: Wang RH, Dai XJ, Wu H, Wang MD, Deng R, Wang Y, Bu YH, Sun MH, Zhang H. Anti- Inflammatory Effect of Geniposide on Regulating the Functions of Rheumatoid Arthritis Synovial Fibroblasts via Inhibiting Sphingosine-1-Phosphate Receptors1/3 Coupling Gαi/Gαs Conversion. Front Pharmacol. 2020 Dec 8;11:584176. doi: 10.3389/fphar.2020.584176. PMID: 33363467; PMCID: PMC7753157. 3: Kawa Y, Nagano T, Yoshizaki A, Dokuni R, Katsurada M, Terashita T, Yasuda Y, Umezawa K, Yamamoto M, Kamiryo H, Kobayashi K, Nishimura Y. Role of S1P/S1PR3 axis in release of CCL20 from human bronchial epithelial cells. PLoS One. 2018 Sep 7;13(9):e0203211. doi: 10.1371/journal.pone.0203211. PMID: 30192865; PMCID: PMC6128515. 4: Perségol L, Darabi M, Dauteuille C, Lhomme M, Chantepie S, Rye KA, Therond P, Chapman MJ, Salvayre R, Nègre-Salvayre A, Lesnik P, Monier S, Kontush A. Small dense HDLs display potent vasorelaxing activity, reflecting their elevated content of sphingosine-1-phosphate. J Lipid Res. 2018 Jan;59(1):25-34. doi: 10.1194/jlr.M076927. Epub 2017 Nov 17. PMID: 29150495; PMCID: PMC5748494. 5: Kitada Y, Kajita K, Taguchi K, Mori I, Yamauchi M, Ikeda T, Kawashima M, Asano M, Kajita T, Ishizuka T, Banno Y, Kojima I, Chun J, Kamata S, Ishii I, Morita H. Blockade of Sphingosine 1-Phosphate Receptor 2 Signaling Attenuates High-Fat Diet-Induced Adipocyte Hypertrophy and Systemic Glucose Intolerance in Mice. Endocrinology. 2016 May;157(5):1839-51. doi: 10.1210/en.2015-1768. Epub 2016 Mar 4. PMID: 26943364; PMCID: PMC4870879. 6: Malik FA, Meissner A, Semenkov I, Molinski S, Pasyk S, Ahmadi S, Bui HH, Bear CE, Lidington D, Bolz SS. Sphingosine-1-Phosphate Is a Novel Regulator of Cystic Fibrosis Transmembrane Conductance Regulator (CFTR) Activity. PLoS One. 2015 Jun 16;10(6):e0130313. doi: 10.1371/journal.pone.0130313. PMID: 26079370; PMCID: PMC4469317. 7: Li C, Li JN, Kays J, Guerrero M, Nicol GD. Sphingosine 1-phosphate enhances the excitability of rat sensory neurons through activation of sphingosine 1-phosphate receptors 1 and/or 3. J Neuroinflammation. 2015 Apr 12;12:70. doi: 10.1186/s12974-015-0286-8. PMID: 25880547; PMCID: PMC4397880. 8: Kurano M, Hara M, Tsuneyama K, Sakoda H, Shimizu T, Tsukamoto K, Ikeda H, Yatomi Y. Induction of insulin secretion by apolipoprotein M, a carrier for sphingosine 1-phosphate. Biochim Biophys Acta. 2014 Sep;1841(9):1217-26. doi: 10.1016/j.bbalip.2014.05.002. Epub 2014 May 9. PMID: 24814049. 9: Oizumi A, Nakayama H, Okino N, Iwahara C, Kina K, Matsumoto R, Ogawa H, Takamori K, Ito M, Suga Y, Iwabuchi K. Pseudomonas-derived ceramidase induces production of inflammatory mediators from human keratinocytes via sphingosine-1-phosphate. PLoS One. 2014 Feb 25;9(2):e89402. doi: 10.1371/journal.pone.0089402. PMID: 24586752; PMCID: PMC3934885. 10: Koch A, Völzke A, Puff B, Blankenbach K, Meyer Zu Heringdorf D, Huwiler A, Pfeilschifter J. PPARγ agonists upregulate sphingosine 1-phosphate (S1P) receptor 1 expression, which in turn reduces S1P-induced [Ca(2+)]i increases in renal mesangial cells. Biochim Biophys Acta. 2013 Nov;1831(11):1634-43. doi: 10.1016/j.bbalip.2013.07.011. Epub 2013 Jul 30. PMID: 23906789. 11: Tong X, Peng H, Liu D, Ji L, Niu C, Ren J, Pan B, Hu J, Zheng L, Huang Y. High-density lipoprotein of patients with type 2 diabetes mellitus upregulates cyclooxgenase-2 expression and prostacyclin I-2 release in endothelial cells: relationship with HDL-associated sphingosine-1-phosphate. Cardiovasc Diabetol. 2013 Jan 30;12:27. doi: 10.1186/1475-2840-12-27. PMID: 23360427; PMCID: PMC3599898. 12: Asghar MY, Viitanen T, Kemppainen K, Törnquist K. Sphingosine 1-phosphate and human ether-a'-go-go-related gene potassium channels modulate migration in human anaplastic thyroid cancer cells. Endocr Relat Cancer. 2012 Sep 21;19(5):667-80. doi: 10.1530/ERC-12-0092. PMID: 22889737. 13: Mousseau Y, Mollard S, Faucher-Durand K, Richard L, Nizou A, Cook-Moreau J, Baaj Y, Qiu H, Plainard X, Fourcade L, Funalot B, Sturtz FG. Fingolimod potentiates the effects of sunitinib malate in a rat breast cancer model. Breast Cancer Res Treat. 2012 Jul;134(1):31-40. doi: 10.1007/s10549-011-1903-6. Epub 2011 Dec 9. PMID: 22160641. 14: Lee SY, Kim DH, Sung SA, Kim MG, Cho WY, Kim HK, Jo SK. Sphingosine-1-phosphate reduces hepatic ischaemia/reperfusion-induced acute kidney injury through attenuation of endothelial injury in mice. Nephrology (Carlton). 2011 Feb;16(2):163-73. doi: 10.1111/j.1440-1797.2010.01386.x. PMID: 21272128. 15: Tao R, Hoover HE, Honbo N, Kalinowski M, Alano CC, Karliner JS, Raffai R. High-density lipoprotein determines adult mouse cardiomyocyte fate after hypoxia-reoxygenation through lipoprotein-associated sphingosine 1-phosphate. Am J Physiol Heart Circ Physiol. 2010 Mar;298(3):H1022-8. doi: 10.1152/ajpheart.00902.2009. Epub 2010 Jan 8. PMID: 20061542; PMCID: PMC2838562. 16: Lee JF, Gordon S, Estrada R, Wang L, Siow DL, Wattenberg BW, Lominadze D, Lee MJ. Balance of S1P1 and S1P2 signaling regulates peripheral microvascular permeability in rat cremaster muscle vasculature. Am J Physiol Heart Circ Physiol. 2009 Jan;296(1):H33-42. doi: 10.1152/ajpheart.00097.2008. Epub 2008 Nov 14. PMID: 19011048; PMCID: PMC2637780. 17: Vessey DA, Li L, Kelley M, Zhang J, Karliner JS. Sphingosine can pre- and post-condition heart and utilizes a different mechanism from sphingosine 1-phosphate. J Biochem Mol Toxicol. 2008 Mar-Apr;22(2):113-8. doi: 10.1002/jbt.20227. PMID: 18418901. 18: Brizuela L, Rábano M, Gangoiti P, Narbona N, Macarulla JM, Trueba M, Gómez- Muñoz A. Sphingosine-1-phosphate stimulates aldosterone secretion through a mechanism involving the PI3K/PKB and MEK/ERK 1/2 pathways. J Lipid Res. 2007 Oct;48(10):2264-74. doi: 10.1194/jlr.M700291-JLR200. Epub 2007 Jul 3. PMID: 17609523. 19: Kim MK, Park KS, Lee H, Kim YD, Yun J, Bae YS. Phytosphingosine-1-phosphate stimulates chemotactic migration of L2071 mouse fibroblasts via pertussis toxin- sensitive G-proteins. Exp Mol Med. 2007 Apr 30;39(2):185-94. doi: 10.1038/emm.2007.21. PMID: 17464180. 20: Park KS, Kim MK, Lee HY, Kim SD, Lee SY, Kim JM, Ryu SH, Bae YS. S1P stimulates chemotactic migration and invasion in OVCAR3 ovarian cancer cells. Biochem Biophys Res Commun. 2007 Apr 27;356(1):239-44. doi: 10.1016/j.bbrc.2007.02.112. Epub 2007 Feb 28. PMID: 17349972.

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