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S1825

Sigma-Aldrich

S32826 disodium salt hydrate

≥98% (HPLC)

Synonym(s):

[4-(Tetradecanoylamino)benzyl]phosphonic acid disodium salt hydrate

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About This Item

Empirical Formula (Hill Notation):
C21H34NNa2O4P · xH2O
CAS Number:
1096770-84-1
Molecular Weight:
441.45 (anhydrous basis)
MDL number:
MFCD12912442
UNSPSC Code:
12352200
PubChem Substance ID:
329824492
NACRES:
NA.25

Quality Level

100

assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white

solubility

H2O: ≥10 mg/mL

storage temp.

−20°C

SMILES string

[Na+].[Na+].CCCCCCCCCCCCCC(=O)Nc1ccc(CP([O-])([O-])=O)cc1

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

InChI key

DGRFALMFDGBLCP-UHFFFAOYSA-L

Application

S32826, a potent inhibitor of autotaxin (ATX), may be used to identify and characterize the lyso-phospholipase D (lysoPLD, ATX) involved in bioactive lyso-phosphatidic acid (LPA) formation. S32826 may be used to help determine the role of ATX in malignant cell processes such as tumorigenesis, invasion, and metastases; cardia bifida and atherosclerosis.

Biochem/physiol Actions

S32826 is a potent inhibitor of autotaxin. Autotaxin is a newly discovered lyso-phospholipase D (lysoPLD). Autotaxin and lyso-phosphatidic acid (LPA) have been associated with early cancer progression and motility of cancer cells as well as with metastasis. Because of localization (adipose tissue), the enzyme might play an important role in diabetes and obesity. Autotaxin might be the only source of LPA. S32826 is the strongest inhibitor of autotaxin reported. The compound shows activity in cellular or ex vivo models.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Guowei Jiang et al.
Bioorganic & medicinal chemistry letters, 21(17), 5098-5101 (2011-04-15)
Autotaxin (ATX) is an attractive target for the anticancer therapeutics that inhibits angiogenesis, invasion and migration. ATX is an extracellular lysophospholipase D that hydrolyzes lysophosphatidylcholine to form the bioactive lipid lysophosphatidic acid. The aromatic phosphonate S32826 was the first described
Padma Iyer et al.
PloS one, 7(8), e42627-e42627 (2012-08-24)
Primary open-angle glaucoma is the second leading cause of blindness in the United States and is commonly associated with elevated intraocular pressure (IOP) resulting from diminished aqueous humor (AH) drainage through the trabecular pathway. Developing effective therapies for increased IOP
Yoshinori Okamoto et al.
Toxicology letters, 288, 65-70 (2018-02-20)
Estrogen is reported to be involved in mammary tumorigenesis. To unveil metabolic signatures for estrogen-induced mammary tumorigenesis, we carried out serum metabolomic analysis in an estrogen-induced mammary tumor model, female August Copenhagen-Irish/Segaloff (ACI/Seg) rats, using liquid chromatography-mass spectrometry. In contrast
Anja Pucer et al.
Molecular cancer, 12(1), 111-111 (2013-09-28)
Alterations in lipid metabolism are inherent to the metabolic transformations that support tumorigenesis. The relationship between the synthesis, storage and use of lipids and their importance in cancer is poorly understood. The human group X secreted phospholipase A2 (hGX sPLA2)

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