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SML0002

Sigma-Aldrich

C646

≥98% (HPLC)

Synonym(s):

4-[4-[[5-(4,5-Dimethyl-2-nitrophenyl)-2-furanyl]methylene]-4,5-dihydro-3-methyl-5-oxo-1H-pyrazol-1-yl]benzoic acid

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$141.30
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$441.70

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5 MG
$141.30
25 MG
$441.70

About This Item

Empirical Formula (Hill Notation):
C24H19N3O6
CAS Number:
328968-36-1
Molecular Weight:
445.42
MDL number:
MFCD01784780
UNSPSC Code:
12352200
PubChem Substance ID:
329825079
NACRES:
NA.77

$141.30

List price$157.00Save 10%
Web-Only Promotion

Available to ship onApril 08, 2025Details

Request a Bulk Order

Quality Level

100

assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

red to brown

solubility

DMSO: >25 mg/mL

storage temp.

2-8°C

SMILES string

Cc1cc(-c2ccc(\C=C3\C(C)=NN(c4ccc(cc4)C(O)=O)C3=O)o2)c(cc1C)[N+]([O-])=O

InChI

1S/C24H19N3O6/c1-13-10-20(21(27(31)32)11-14(13)2)22-9-8-18(33-22)12-19-15(3)25-26(23(19)28)17-6-4-16(5-7-17)24(29)30/h4-12H,1-3H3,(H,29,30)/b19-12-

InChI key

HEKJYZZSCQBJGB-UNOMPAQXSA-N

Application

C646 was used to study the role of p300 in chronic neuropathic pain in rats with chronic constriction injury.[1]

Biochem/physiol Actions

C646 is a competitive histone acetyltransferase (HAT) p300/CBP inhibitor with a Ki of 400 nM and is selective versus other acetyltransferases.
C646 is a potent, cell permeable and selective inhibitor of p300 and CBP (p300/CBP) histone acetyltransferases. Inhibition of p300/CBP by C646 affects the activity of a variety of transcriptional factors such as NF-κB, p53 and MyoD that are associated with physiology, disease processes, hippocampal synaptic plasticity, spatial memory and contextual fear.[2][3]
C646 is a potent, competitive, and selective histone acetyltransferase (HAT) p300/CBP 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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000235500
106M4611V
104M4614V
073M4602V
102M4614V

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Jia Cao et al.
Nature communications, 8(1), 131-131 (2017-07-27)
Diabetes and obesity are characterized by insulin resistance and chronic low-grade inflammation. An elevated plasma concentration of lipopolysaccharide (LPS) caused by increased intestinal permeability during diet-induced obesity promotes insulin resistance in mice. Here, we show that LPS induces endoplasmic reticulum
Erin M Bowers et al.
Chemistry & biology, 17(5), 471-482 (2010-06-11)
The histone acetyltransferase (HAT) p300/CBP is a transcriptional coactivator implicated in many gene regulatory pathways and protein acetylation events. Although p300 inhibitors have been reported, a potent, selective, and readily available active-site-directed small molecule inhibitor is not yet known. Here
Liduan Zheng et al.
Scientific reports, 7(1), 8967-8967 (2017-08-23)
Recent evidence shows the emerging roles of promoter-targeting endogenous microRNAs (miRNAs) in regulating gene transcription. However, miRNAs affecting the transcription of matrix metalloproteinase 14 (MMP-14) in gastric cancer remain unknown. Herein, through integrative mining of public datasets, we identified the
A R Esteves et al.
Biochimica et biophysica acta. Molecular basis of disease, 1865(8), 2008-2023 (2018-12-21)
Protein post-translational modifications (PTMs) that potentiate protein aggregation have been implicated in several neurological disorders, including Alzheimer's (AD) and Parkinson's disease (PD). In fact, Tau and alpha-synuclein (ASYN) undergo several PTMs potentiating their aggregation and neurotoxicity. Recent data posits a
Bin Liu et al.
Cancers, 11(4) (2019-04-03)
KRAS-driven non-small cell lung cancer (NSCLC) patients have no effective targeted treatment. In this study, we aimed to investigate targeting epidermal growth factor receptor (EGFR) as a therapeutic approach in KRAS-driven lung cancer cells. We show that ablation of EGFR
View All Related Papers

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