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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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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

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.

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.

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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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
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
Zhuofeng Ding et al.
Frontiers in neuroscience, 12, 341-341 (2018-06-08)
Peripheral nerve injuries are generally associated with incomplete restoration of motor function. The slow rate of nerve regeneration after injury may account for this. Although many benefits of resveratrol have been shown in the nervous system, it is not clear
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