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G5668

Sigma-Aldrich

GW1929 hydrate

>98% (HPLC), solid

Synonym(s):

N-(2-Benzoylphenyl)-O-[2-(methyl-2-pyridinylamino)ethyl]-L-tyrosine hydrate

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About This Item

Empirical Formula (Hill Notation):
C30H29N3O4 · xH2O
CAS Number:
1049740-86-4
Molecular Weight:
495.57 (anhydrous basis)
UNSPSC Code:
12352200
PubChem Substance ID:
24278789
NACRES:
NA.77

Quality Level

100

assay

>98% (HPLC)

form

solid

solubility

DMSO: 20 mg/mL

originator

GlaxoSmithKline

SMILES string

[H]O[H].CN(CCOc1ccc(C[C@H](Nc2ccccc2C(=O)c3ccccc3)C(O)=O)cc1)c4ccccn4

InChI

1S/C30H29N3O4.H2O/c1-33(28-13-7-8-18-31-28)19-20-37-24-16-14-22(15-17-24)21-27(30(35)36)32-26-12-6-5-11-25(26)29(34)23-9-3-2-4-10-23;/h2-18,27,32H,19-21H2,1H3,(H,35,36);1H2/t27-;/m0./s1

InChI key

XSITZVFUXCLFMK-YCBFMBTMSA-N

Gene Information

human ... PPARG(5468)

Application

GW1929 has been used as a peroxisome proliferator-activated receptor γ (PPARγ) ligand:
  • to study its effects on plant homeodomain finger protein 16 (Phf16) and patatin-like phospholipase domain containing 3 (Pnpla3) expression involved in adipogenesis
  • to study its effects on complement component 3 (C3) gene expression in human hepatoma cells
  • to activate PPARγ in human breast cancer cells

Biochem/physiol Actions

GW1929 is a non-thiazolidinedione and is involved in cell growth inhibition and regulating gene expression. It exhibits neuroprotective effects against global cerebral ischemic-reperfusion injury by DNA fragmentation and minimizing the inflammation. GW1929 participates in the inhibition of α7 N-acetylcholine receptor expression and promoter activity. It also influences the early growth response-1 (Egr-1) protein expression.
GW1929 is a high affinity agonist of PPAR-γ.

Features and Benefits

This compound is featured on the Nuclear Receptors (PPARs) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound was developed by GlaxoSmithKline. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Legal Information

Sold for research purposes only, pursuant to an agreement with Glaxo­Smith­Kline

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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Miaozhen Pan et al.
Experimental eye research, 202, 108332-108332 (2020-11-06)
Form deprivation myopia (FDM) is characterized by loss of choroidal thickness (ChT), reduced choroidal blood perfusion (ChBP), and consequently scleral hypoxia. In some tissues, changes in levels of peroxisome proliferator-activated receptor γ (PPARγ) expression modulate hypoxia-induced pathological responses. We determined
Swei Sunny Hahn et al.
Cellular signalling, 26(4), 730-739 (2014-01-15)
Studies demonstrated that peroxisome proliferator-activated receptor gamma (PPARγ) ligands reduce nicotine-induced non small cell lung carcinoma (NSCLC) cell growth through inhibition of nicotinic acetylcholine receptor (nAChR) mediated signaling pathways. However, the mechanisms by which PPARγ ligands inhibited nAChR expression remain
Seo-Hyuk Chang et al.
Journal of cellular biochemistry, 120(3), 3599-3610 (2018-10-03)
Adipocyte differentiation is controlled by multiple signaling pathways. To identify new adipogenic factors, C3H10T1/2 adipocytes were treated with previously known antiadipogenic phytochemicals (resveratrol, butein, sulfuretin, and fisetin) for 24 hours. Commonly regulated genes were then identified by transcriptional profiling analysis. Three

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