A Rac1 and Rac3 inhibitor
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EHop-016

Item No. 21557

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N4-(9-ethyl-9H-carbazol-3-yl)-N2-[3-(4-morpholinyl)propyl]-2,4-pyrimidinediamine
CAS Number
1380432-32-5
Molecular Formula
C25H30N6O
Formula Weight
430.6
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMF:PBS (pH 7.2); (1:7): 0.125DMSO: 10 mg/ml
λmax
232, 305 nm
SMILES
CCN(C1=C2C=CC=C1)C(C2=C3)=CC=C3NC4=NC(NCCCN5CCOCC5)=NC=C4
InChi Code
InChI=1S/C25H30N6O/c1-2-31-22-7-4-3-6-20(22)21-18-19(8-9-23(21)31)28-24-10-12-27-25(29-24)26-11-5-13-30-14-16-32-17-15-30/h3-4,6-10,12,18H,2,5,11,13-17H2,1H3,(H2,26,27,28,29)
InChi Key
AFTZZRFCMOAFCR-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $54

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    10 mg

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    25 mg

    $209

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    50 mg

    $392

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    Cayman Chemical
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    Product Description

    EHop-016 is an inhibitor of the small Rho GTPases Rac1 and Rac3.1 It inhibits Rac1 activity in MDA-MB-435 breast cancer cells with an IC50 value of 1.1 μM in a Rac1 activation assay.2 At a concentration of 1 μM, EHop-016 inhibits 58% of Rac3 activity, and it inhibits Cdc42 activity but only at higher concentrations (5-10 μM). It also increases Rho GTPase RhoA activity ~1.3-fold at concentrations greater than 2 μM. EHop-016 (2-4 μM) inhibits Rac-regulated functions in MDA-MB-435 cells, including lamellipodia formation and serine/threonine p21-activated kinase 1 (PAK1)-mediated cell migration. In a nude mouse model of breast cancer metastasis, EHop-016 (25 mg/kg) significantly lowers mammary fat pad tumor growth, metastasis, and angiogenesis.3 It also inhibits mutant receptor tyrosine kinase (KIT)-induced growth in systemic mastocytosis and acute myeloid leukemia (AML) cells (≥2.5 μM).4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Dharmawardhane, S., Hernandez, E., and Vlaar, C. Development of EHop-016: A small molecule inhibitor of Rac. Enzymes 33 Pt A, 117-146 (2013).

    2. Montalvo-Ortiz, B.L., Castillo-Pichardo, L., Hernández, E., et al. Characterization of EHop-016, novel small molecule inhibitor of Rac GTPase. The Journal of Biological Chemisty 287(16), 13228-13238 (2012).

    3. Castillo-Pichardo, L., Humphries-Bickley, T., De La Parra, C., et al. The Rac inhibitor EHop-016 inhibits mammary tumor growth and metastasis in a nude mouse model. Transl. Oncol. 7(5), 546-555 (2014).

    4. Martin, H., Mali, R.S., Ma, P., et al. Pak and Rac GTPases promote oncogenic KIT-induced neoplasms. J. Clin. Invest. 123(10), 4449-4463 (2013).