C 646 Chemical Properties

Melting point:

224-226℃

Boiling point:

662.6±65.0 °C(Predicted)

Density 

1.38±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

DMSO: >25mg/mL

pka

4.20±0.10(Predicted)

form 

powder

color 

red to brown

Stability:

Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 2 months.

InChIKey

HEKJYZZSCQBJGB-XDHOZWIPSA-N

Safety Information

Hazard Codes 

N

Risk Statements 

50

Safety Statements 

61

RIDADR 

UN 3077 9 / PGIII

WGK Germany 

3

C 646 Usage And Synthesis

Description

C-646 (328968-36-1) is a potent and selective inhibitor of the histone acetyl transferase p300/CBP (Ki=400 nM ). Induces apoptosis in prostate cancer cells. C-646 enhances fear extinction memory and synaptic plasticity in mice. Promotes tau deacetylation reducing levels of pathogenic p-tau. Cell permeable.

Uses

C646 is an inhibitor for histone acetyltransferase p300 and may be a potential candidate for treating AML1-ETO (AE) positive acute myeloid leukemia (AML). It is shown that C646 inhibited cellular proliferation, reduced colony formation, evoked partial cell cycle arrest in the G1 phase, and induced apoptosis in AE-positive AML cell lines and primary blasts isolated from leukemic mice and AML patients.

Uses

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

Definition

ChEBI: A pyrazolone that is 5-methyl-4-methylene-2-(p-carboxyphenyl)-2,4-dihydro-3H-pyrazol-3-one in which the exocyclic carbon of the methylene group is attached to a 5-(4,5-dimethyl-2-nitrophenyl)furan-2-yl group by a single bond C646 is a potent, cell permeable and selective competitive inhibitor of p300 and CBP (p300/CBP) histone acetyltransferases.

Biochem/physiol Actions

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.

storage

Store at +4°C

References

1) Bowers et al. (2010), Virtual ligand screening of the p300/CBP histone acetyltransferase: identification of a selective small molecule inhibitor; Chem. Biol., 17 471 2) Santer et al. (2011), Inhibition of the acetyltransferases p300 and CBP reveals a targetable function for p300 in the survival and invasion pathways of prostate cancer cell lines; Mol. Cancer Ther., 10 1644 3) Marek et al. (2011), Paradoxical enhancement of fear extinction memory and synaptic plasticity by inhibition of the histone acetyltransferase p300; J. Neurosci.., 31 7486 4) Min et al. (2010), Acetylation of tau inhibits its degradation and contributes to tauopathy; Neuron, 67 953

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