S32826 disodium
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 562163

CAS#: 1103672-43-0

Description: S32826 is an inhibitor of autotaxin.


Chemical Structure

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S32826 disodium
CAS# 1103672-43-0

Theoretical Analysis

MedKoo Cat#: 562163
Name: S32826 disodium
CAS#: 1103672-43-0
Chemical Formula: C21H34NNa2O4P
Exact Mass: 0.00
Molecular Weight: 441.450
Elemental Analysis: C, 57.14; H, 7.76; N, 3.17; Na, 10.42; O, 14.50; P, 7.02

Price and Availability

Size Price Availability Quantity
5mg USD 550 2 Weeks
25mg USD 1150 2 Weeks
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Synonym: S32826; S-32826; S 32826;

IUPAC/Chemical Name: Disodium N-[4-(phosphonatomethyl)phenyl]tetradecanamide

InChi Key: DGRFALMFDGBLCP-UHFFFAOYSA-L

InChi Code: InChI=1S/C21H36NO4P.2Na/c1-2-3-4-5-6-7-8-9-10-11-12-13-21(23)22-20-16-14-19(15-17-20)18-27(24,25)26;;/h14-17H,2-13,18H2,1H3,(H,22,23)(H2,24,25,26);;/q;2*+1/p-2

SMILES Code: CCCCCCCCCCCCCC(NC1=CC=C(CP([O-])([O-])=O)C=C1)=O.[Na+].[Na+]

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 ethanol

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:

Product Data:
Biological target: S32826 is a potent autotaxin inhibitor, with an IC50 of 8.8 nM. S32826 inhibits LPA release from adipocytes.
In vitro activity: S32826 effectively decreased the concentration of LPA in cellular supernatant in a dose- and time-dependent manner. S32826 reduced the expression and altered the sublocalization of total focal adhesion kinase (FAK) and phosphorylated FAK (pY397 FAK) along the cell membrane, which significantly reduced cell viability and migration while increasing the proportion of apoptotic cells. Reference: In Vitro Cell Dev Biol Anim. 2022 Apr;58(4):307-315. https://pubmed.ncbi.nlm.nih.gov/35426066/
In vivo activity: S32826 significantly decreased intraocular pressure (IOP) in Dutch-Belted rabbits. This reduction in IOP was observed when S32826 was topically applied and intracamerally injected into the rabbits. S32826 has the potential to serve as a therapeutic agent for lowering IOP in glaucoma patients, based on its positive effects in this rabbit model. Reference: PLoS One. 2012;7(8):e42627. https://pubmed.ncbi.nlm.nih.gov/22916143/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
Ethanol 2.4 5.44

Preparing Stock Solutions

The following data is based on the product molecular weight 441.45 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
Formulation protocol: 1. Liao Y, Liu L, Yang J, Shi Z. ATX/LPA axis regulates FAK activation, cell proliferation, apoptosis, and motility in human pancreatic cancer cells. In Vitro Cell Dev Biol Anim. 2022 Apr;58(4):307-315. doi: 10.1007/s11626-022-00660-3. Epub 2022 Apr 14. PMID: 35426066. 2. Ferry G, Moulharat N, Pradère JP, Desos P, Try A, Genton A, Giganti A, Beucher-Gaudin M, Lonchampt M, Bertrand M, Saulnier-Blache JS, Tucker GC, Cordi A, Boutin JA. S32826, a nanomolar inhibitor of autotaxin: discovery, synthesis and applications as a pharmacological tool. J Pharmacol Exp Ther. 2008 Dec;327(3):809-19. doi: 10.1124/jpet.108.141911. Epub 2008 Aug 28. PMID: 18755937. 3. Iyer P, Lalane R 3rd, Morris C, Challa P, Vann R, Rao PV. Autotaxin-lysophosphatidic acid axis is a novel molecular target for lowering intraocular pressure. PLoS One. 2012;7(8):e42627. doi: 10.1371/journal.pone.0042627. Epub 2012 Aug 20. PMID: 22916143; PMCID: PMC3423407.
In vitro protocol: 1. Liao Y, Liu L, Yang J, Shi Z. ATX/LPA axis regulates FAK activation, cell proliferation, apoptosis, and motility in human pancreatic cancer cells. In Vitro Cell Dev Biol Anim. 2022 Apr;58(4):307-315. doi: 10.1007/s11626-022-00660-3. Epub 2022 Apr 14. PMID: 35426066. 2. Ferry G, Moulharat N, Pradère JP, Desos P, Try A, Genton A, Giganti A, Beucher-Gaudin M, Lonchampt M, Bertrand M, Saulnier-Blache JS, Tucker GC, Cordi A, Boutin JA. S32826, a nanomolar inhibitor of autotaxin: discovery, synthesis and applications as a pharmacological tool. J Pharmacol Exp Ther. 2008 Dec;327(3):809-19. doi: 10.1124/jpet.108.141911. Epub 2008 Aug 28. PMID: 18755937.
In vivo protocol: 1. Iyer P, Lalane R 3rd, Morris C, Challa P, Vann R, Rao PV. Autotaxin-lysophosphatidic acid axis is a novel molecular target for lowering intraocular pressure. PLoS One. 2012;7(8):e42627. doi: 10.1371/journal.pone.0042627. Epub 2012 Aug 20. PMID: 22916143; PMCID: PMC3423407.

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1: Hirane M, Ishii S, Tomimatsu A, Fukushima K, Takahashi K, Fukushima N, Honoki K, Tsujiuchi T. Different induction of LPA receptors by chemical liver carcinogens regulates cellular functions of liver epithelial WB-F344 cells. Mol Carcinog. 2016 Nov;55(11):1573-1583. doi: 10.1002/mc.22410. Epub 2015 Sep 17. PubMed PMID: 26377854.

2: Mori S, Araki M, Ishii S, Hirane M, Fukushima K, Tomimatsu A, Takahashi K, Fukushima N, Tsujiuchi T. LPA signaling through LPA receptors regulates cellular functions of endothelial cells treated with anticancer drugs. Mol Cell Biochem. 2015 Oct;408(1-2):147-54. doi: 10.1007/s11010-015-2490-3. Epub 2015 Jun 27. PubMed PMID: 26116018.

3: Katakai T, Kondo N, Ueda Y, Kinashi T. Autotaxin produced by stromal cells promotes LFA-1-independent and Rho-dependent interstitial T cell motility in the lymph node paracortex. J Immunol. 2014 Jul 15;193(2):617-26. doi: 10.4049/jimmunol.1400565. Epub 2014 Jun 16. PubMed PMID: 24935929.

4: Fisher N, Hilton-Bolt T, Edwards MG, Haxton KJ, McKenzie M, Allin SM, Richardson A. Dendrimer Conjugate of [4-(Tetradecanoylamino)benzyl]phosphonic Acid (S32826) as an Autotaxin Inhibitor. ACS Med Chem Lett. 2013 Nov 18;5(1):34-9. doi: 10.1021/ml4003106. eCollection 2014 Jan 9. PubMed PMID: 24900771; PubMed Central PMCID: PMC4027627.

5: Iyer P, Lalane R 3rd, Morris C, Challa P, Vann R, Rao PV. Autotaxin-lysophosphatidic acid axis is a novel molecular target for lowering intraocular pressure. PLoS One. 2012;7(8):e42627. doi: 10.1371/journal.pone.0042627. Epub 2012 Aug 20. PubMed PMID: 22916143; PubMed Central PMCID: PMC3423407.

6: Jiang G, Madan D, Prestwich GD. Aromatic phosphonates inhibit the lysophospholipase D activity of autotaxin. Bioorg Med Chem Lett. 2011 Sep 1;21(17):5098-101. doi: 10.1016/j.bmcl.2011.03.068. Epub 2011 Mar 23. PubMed PMID: 21489790; PubMed Central PMCID: PMC3140587.

7: Li S, Wang B, Xu Y, Zhang J. Autotaxin is induced by TSA through HDAC3 and HDAC7 inhibition and antagonizes the TSA-induced cell apoptosis. Mol Cancer. 2011 Feb 12;10:18. doi: 10.1186/1476-4598-10-18. PubMed PMID: 21314984; PubMed Central PMCID: PMC3055229.

8: Gaetano CG, Samadi N, Tomsig JL, Macdonald TL, Lynch KR, Brindley DN. Inhibition of autotaxin production or activity blocks lysophosphatidylcholine-induced migration of human breast cancer and melanoma cells. Mol Carcinog. 2009 Sep;48(9):801-9. doi: 10.1002/mc.20524. PubMed PMID: 19204929; PubMed Central PMCID: PMC2736327.

9: Ferry G, Moulharat N, Pradère JP, Desos P, Try A, Genton A, Giganti A, Beucher-Gaudin M, Lonchampt M, Bertrand M, Saulnier-Blache JS, Tucker GC, Cordi A, Boutin JA. S32826, a nanomolar inhibitor of autotaxin: discovery, synthesis and applications as a pharmacological tool. J Pharmacol Exp Ther. 2008 Dec;327(3):809-19. doi: 10.1124/jpet.108.141911. Epub 2008 Aug 28. PubMed PMID: 18755937.