S32826 disodium | CAS#1103672-43-0 | autotaxin inhibitor

MedKoo Cat#: 562163 | Name: S32826 disodium

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Description:

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

S32826 is an inhibitor of autotaxin.

Chemical Structure

S32826 disodium

CAS#1103672-43-0 (sodium)

Theoretical Analysis

MedKoo Cat#: 562163

Name: S32826 disodium

CAS#: 1103672-43-0 (sodium)

Chemical Formula: C21H34NNa2O4P

Exact Mass: 0.0000

Molecular Weight: 441.45

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 550.00	2 Weeks

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Related CAS #

1103672-43-0 (sodium)

Synonym

S32826; S-32826; S 32826; S32826 disodium;

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

Product Data

Instruction

View handling instruction

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/

	Solvent	mg/mL	mM
Solubility
	Ethanol	2.4	5.44

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

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.

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:

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.

1: Tsutsumi T, Kawabata K, Yamazaki N, Tsukigawa K, Nishi H, Tokumura A. Extracellular and intracellular productions of lysophosphatidic acids and cyclic phosphatidic acids by lysophospholipase D from exogenously added lysophosphatidylcholines to cultured NRK52E cells. Biochim Biophys Acta Mol Cell Biol Lipids. 2023 Sep;1868(9):159349. doi: 10.1016/j.bbalip.2023.159349. Epub 2023 Jun 7. PMID: 37295607. 2: 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. 3: Kitakaze K, Tsuboi K, Tsuda M, Takenouchi Y, Ishimaru H, Okamoto Y. Development of a selective fluorescence-based enzyme assay for glycerophosphodiesterase family members GDE4 and GDE7. J Lipid Res. 2021;62:100141. doi: 10.1016/j.jlr.2021.100141. Epub 2021 Oct 18. PMID: 34673020; PMCID: PMC8591415. 4: 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. PMID: 26377854. 5: 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. PMID: 26116018. 6: 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. PMID: 24900771; PMCID: PMC4027627. 7: 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. 8: 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. PMID: 21489790; PMCID: PMC3140587. 9: 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. PMID: 21314984; PMCID: PMC3055229. 10: 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.