E7034
EX-527
≥98% (HPLC), SIRT1 and SIRT6 inhibitor, powder
Synonym(s):
6-Chloro-2,3,4,9-tetrahydro-1H-Carbazole-1-carboxamide
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About This Item
Empirical Formula (Hill Notation):
C13H13ClN2O
CAS Number:
Molecular Weight:
248.71
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
MDL number:
Product Name
EX-527, ≥98% (HPLC)
Quality Level
assay
≥98% (HPLC)
form
powder
color
white to beige
solubility
DMSO: >20 mg/mL
storage temp.
2-8°C
SMILES string
NC(=O)C1CCCc2c1[nH]c3ccc(Cl)cc23
InChI
1S/C13H13ClN2O/c14-7-4-5-11-10(6-7)8-2-1-3-9(13(15)17)12(8)16-11/h4-6,9,16H,1-3H2,(H2,15,17)
InChI key
FUZYTVDVLBBXDL-UHFFFAOYSA-N
Application
EX-527 has been used:
- in 1% dimethyl sulfoxide, 30%, polyethylene glycol-400 and 1% Tween 80 for treating C57BL/6 N mice to study its effect on intestinal morphological changes and crypt cell apoptosis
- as a an inhibitor of sirtuin 1, in treating human cancer lines MCF-7 (Michigan cancer foundation-7) and HCT116 (colon cancer cell line) incubated in Dulbecco′s modified Eagle′s medium, to study its effect on mitochondrial ATP (adenosine triphosphate) production
- Intracerebroventricularly infused in rat model of epileptogenesis, to access kainic acid–induced status epilepticus stimulated sirtuin 1 activity
Biochem/physiol Actions
EX-527 is a potent and selective sirtuin 1 (SIRT1) inhibitor (IC50 38 nM) identified from a high throughput screen. EX-527 is more selective (200-500-fold) for SIRT1 than for SIRT2 or SIRT3 and has been shown to be a potent SIRT6 inhibitor using H3K56 deacetylation site based substrate. EX-527 does not inhibit class I/II HDAC activity at concentrations up to 100uM. Enhances p53 acetylation in response to DNA damaging agents. EX-527 is racemic; the active isomer (EX-243) gives similar results and potency whereas the other isomer (designated EX-242) is inactive.
Potent SIRT1 and SIRT6 inhibitor.
Features and Benefits
This compound is a featured product for Gene Regulation research. Click here to discover more featured Gene Regulation products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
Storage Class
11 - Combustible Solids
wgk
WGK 3
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A Rise in ATP, ROS, and Mitochondrial Content upon Glucose Withdrawal Correlates with a Dysregulated Mitochondria Turnover Mediated by the Activation of the Protein Deacetylase SIRT1
Song S and Hwang E
Cells, 8(1), 11-11 (2019)
Hong-Xia Liu et al.
Experimental cell research, 357(2), 271-281 (2017-05-30)
Mitochondrial trifunctional protein α-subunit (MTPα) is involved in the fatty acid β-oxidation (FAO) pathway. Two MTPα activities, 3-hydroxyacyl-CoA dehydrogenase and long-chain hydratase, have been linked with the occurrence and development of obesity and obesity-related disorders. These activities catalyze two steps
Shuangdong Chen et al.
Biochemical and biophysical research communications, 516(4), 1196-1203 (2019-07-13)
Sirtuin1 (SIRT1), which is regulated by microRNA-34a (miR-34a), can modulate pathophysiology processes, including nonalcoholic fatty liver disease and intestinal ischemia/reperfusion injury. We previously reported that SIRT1, an NAD+-dependent deacetylase, plays a vital role in the development of neuropathic pain. However