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E7034

Sigma-Aldrich

EX-527

≥98% (HPLC)

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:
49843-98-3
Molecular Weight:
248.71
MDL number:
MFCD03009471
UNSPSC Code:
12352200
PubChem Substance ID:
329799003
NACRES:
NA.77

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.

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.

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Product No.
Description
Pricing

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Certificates of Analysis (COA)

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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
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)
Takahito Abe et al.
The Journal of reproduction and development, 63(5), 455-461 (2017-06-13)
Resveratrol is a potent activator of NAD-dependent deacetyltransferase sirtuin-1 (SIRT1) and affects lipid metabolism and ATP generation in somatic cells. In the present study, the effects of supplementing culture medium with resveratrol on lipid metabolism, ATP generation, and cryosensitivity of
The Role of Sirt1 in Epileptogenesis
Hall Alicia M, et al.
eNeuro, 4(1) (2017)
The protective effects of Resveratrol against radiation-induced intestinal injury
Zhang H, et al.
BMC Complementary and Alternative Medicine, 17(1), 410-410 (2017)
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