An inhibitor of the HAT p300
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C646

Item No. 10549

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4-[4-[[5-(4,5-dimethyl-2-nitrophenyl)-2-furanyl]methylene]-4,5-dihydro-3-methyl-5-oxo-1H-pyra-zol-1-yl]-benzoic acid
CAS Number
328968-36-1
Molecular Formula
C24H19N3O6
Formula Weight
445.4
Purity
≥98% (mixture of isomers)
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 1.5 mg/mlDMSO: 11 mg/mlDMSO:PBS (pH 7.2) (1:1): 0.5 mg/ml
λmax
275, 283, 405 nm
SMILES
CC(C=C1[N+]([O-])=O)=C(C)C=C1C2=CC=C(/C=C3C(C)=NN(C4=CC=C(C(O)=O)C=C4)C/3=O)O2
InChi Code
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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $41

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    5 mg

    $116

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    10 mg

    $189

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    Cayman Chemical
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    Product Description

    C646 is an inhibitor of the histone acetyltransferase p300 (IC50 = 1.6 μM).1 It competitively (versus acetyl-CoA) binds p300 (Ki = 400 nM) and does not inhibit several other acetyltransferases.1 The action of C646 appears to be irreversible through covalent modification of the enzyme target.1 It blocks the growth of human melanoma, leukemia, lung, and prostate cancer cells in vitro.1,2,3 C646 has been used to study the role of p300-mediated acetylation in such models as fear extinction memory and the regulation of immediate-early genes.4,5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Bowers, E.M., Yan, G., Mukherjee, C., et al. Virtual ligand screening of the p300/CBP histone acetyltransferase: Identification of a selective small molecule inhibitor. Chem. Biol. 17(5), 471-482 (2010).

    2. Gao, X.n., Lin, J., Ning, Q.y., et al. A histone acetyltransferase p300 inhibitor C646 induces cell cycle arrest and apoptosis selectively in AML1-ETO-positive AML cells. PLoS One 8(2), (2013).

    3. Santer, F.R., Höschele, P.P.S., Oh, S.J., et al. 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(9), 1644-1655 (2011).

    4. Marek, R., Coelho, C.M., Sullivan, R.K.P., et al. Paradoxical enhancement of fear extinction memory and synaptic plasticity by inhibition of the histone acetyltransferase p300. J. Neurosci. 31(20), 7486-7491 (2011).

    5. Crump, N.T., Hazzalin, C.A., Bowers, E.M., et al. Dynamic acetylation of all lysine-4 trimethylated histone H3 is evolutionarily conserved and mediated by p300/CBP. Proc. Natl. Acad. Sci. USA 108(19), 7814-7819 (2011).