A c-Myc inhibitor
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10058-F4

Item No. 15929

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5-[(4-ethylphenyl)methylene]-2-thioxo-4-thiazolidinone
CAS Number
403811-55-2
Molecular Formula
C12H11NOS2
Formula Weight
249.4
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMF:PBS (pH 7.2) (1:1): 0.5 mg/mlDMSO: 25 mg/mlEthanol: 0.3 mg/ml
λmax
233, 277, 379 nm
SMILES
CCC1=CC=C(/C=C2C(NC(S\2)=S)=O)C=C1
InChi Code
InChI=1S/C12H11NOS2/c1-2-8-3-5-9(6-4-8)7-10-11(14)13-12(15)16-10/h3-7H,2H2,1H3,(H,13,14,15)/b10-7+
InChi Key
SVXDHPADAXBMFB-JXMROGBWSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $69

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    10 mg

    $115

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    25 mg

    $198

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    50 mg

    $363

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    Cayman Chemical
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    Product Description

    The Myc proto-oncogenes interact with Max to form a dimer that regulates gene transcription. The protein c-Myc, in particular, promotes gene expression relevant to cell growth and thus drives cancer. 10058-F4 is a cell-permeable thiazolidinone that inhibits the dimerization of c-Myc and Max at 64 µM, preventing c-Myc-dependent gene expression and cell proliferation.1 It induces cell cycle arrest, apoptosis, and myeloid differentiation at 100 µM in human acute myeloid leukemia cells.2 10058-F4 is rapidly metabolized in mice when given intravenously, limiting its effects on tumors in vivo.3 In addition to c-Myc, 10058-F4 inhibits the nuclear Myc protein, N-Myc, at 50 µM, inducing arrest, apoptosis, and differentiation in neuroblastoma cells overexpressing the gene for N-Myc.4 This compound can be used to delineate novel actions of Myc proteins, especially those related to lipid and glucose metabolism.4,5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Yin, X., Giap, C., Lazo, J.S., et al. Low molecular weight inhibitors of Myc-Max interaction and function. Oncogene 22(40), 6151-6159 (2003).

    2. Huang, M.J., Cheng, Y.C., Liu, C.R., et al. A small-molecule c-Myc inhibitor, 10058-F4, induces cell-cycle arrest, apoptosis, and myeloid differentiation of human acute myeloid leukemia. Exp. Hematol. 34(11), 1480-1489 (2006).

    3. Guo, J., Parise, R.A., Joseph, E., et al. Efficacy, pharmacokinetics, tissue distribution, and metabolism of the Myc-Max disruptor, 10058-F4 [Z,E]-5-[4-ethylbenzylidine]-2-thioxothiazolidin-4-one, in mice. Cancer Chemother. Pharmacol. 63(4), 615-625 (2009).

    4. Zirath, H., Frenzel, A., Oliynyk, G., et al. MYC inhibition induces metabolic changes leading to accumulation of lipid droplets in tumor cells. Proc. Natl. Acad. Sci. USA 110(25), 10258-10263 (2013).

    5. Zhang, P., Metukuri, M.R., Bindom, S.M., et al. c-Myc is required for the ChREBP-dependent activation of glucose-responsive genes. Mol. Endocrinol. 24(6), 1274-1286 (2010).

    Product Citations

    Kumar, R., Bhat, T.A., Walsh, E.M., et al. Cytochrome c deficiency confers apoptosome and mitochondrial dysfunction in African-American men with prostate cancer. Cancer Res. 79(7), 1353-1368 (2019).