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SML0002

C646

Name: C646
Brand: SIGMA

≥98% (HPLC), p300/CBP histone acetyltransferase inhibitor, powder

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

UNSPSC Code:

12352200

PubChem Substance ID:

329825079

NACRES:

NA.77

MDL number:

MFCD01784780

Assay:

≥98% (HPLC)

Form:

powder

Quality level:

100

Storage condition:

desiccated

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Product Name

C646, ≥98% (HPLC)

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

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Bioactive Small Molecule Inhibitors

Bioactive Small Molecules

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.

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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Endotoxemia-mediated activation of acetyltransferase P300 impairs insulin signaling in obesity.

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

Acetylation as a major determinant to microtubule-dependent autophagy: Relevance to Alzheimer's and Parkinson disease pathology.

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

Virtual ligand screening of the p300/CBP histone acetyltransferase: identification of a selective small molecule inhibitor.

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

miRNA-584-3p inhibits gastric cancer progression by repressing Yin Yang 1- facilitated MMP-14 expression.

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

CX Chemokine Receptor 7 Contributes to Survival of KRAS-Mutant Non-Small Cell Lung Cancer upon Loss of Epidermal Growth Factor Receptor.

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

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Discover Bioactive Small Molecules for Gene Regulation

We offer a variety of small molecule research tools, such as transcription factor modulators, inhibitors of chromatin modifying enzymes, and agonists/antagonists for target identification and validation in gene regulation research; a selection of these research tools is shown below.

Global Trade Item Number

SKU	GTIN
SML0002-25MG	04061832632803
SML0002-5MG	04061837076534

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