An inhibitor of Rac GTPases
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EHT 1864

Item No. 17258

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-(4-morpholinylmethyl)-5-[[5-[[7-(trifluoromethyl)-4-quinolinyl]thio]pentyl]oxy]-4H-pyran-4-one, dihydrochloride
CAS Number
754240-09-0
Molecular Formula
C25H27F3N2O4S • 2HCl
Formula Weight
581.5
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 50 mg/mlDMSO: 30 mg/mlEthanol: 30 mg/mlPBS (pH 7.2): 10 mg/ml
λmax
221, 317, 329 nm
SMILES
O=C1C(OCCCCCSC2=CC=NC3=C2C=CC(C(F)(F)F)=C3)=COC(CN4CCOCC4)=C1.Cl.Cl
InChi Code
InChI=1S/C25H27F3N2O4S.2ClH/c26-25(27,28)18-4-5-20-21(14-18)29-7-6-24(20)35-13-3-1-2-10-33-23-17-34-19(15-22(23)31)16-30-8-11-32-12-9-30;;/h4-7,14-15,17H,1-3,8-13,16H2;2*1H
InChi Key
LSECOAJFCKFQJG-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    50 mg

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    Cayman Chemical
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    Product Description

    EHT 1864 is an inhibitor of the Rac subfamily of Rho GTPases, that binds to Rac1, Rac1b, Rac2, and Rac3 with Kd values of 40, 50, 50, and 250 nM, respectively.1 It can reverse transformation of NIH 3T3 fibroblasts caused by constitutively activated Rac1, as well as Rac-dependent transformation caused by Tiam1 or Ras.1 EHT 1864 inhibits APP processing by γ-secretase, reducing Αβ40 and Αβ42 accumulation.2 It blocks breast cancer cell invasion in a collagen matrix assay and, at 10 µM, increases the size but decreases the density of dendritic spines of hippocampal neurons in culture.3,4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Shutes, A., Onesto, C., Picard, V., et al. Specificity and mechanism of action of EHT 1864, a novel small molecule inhibitor of Rac family small GTPases. The Journal of Biological Chemisty 282(9), 35666-35678 (2007).

    2. Désiré, L., Bourdin, J., Loiseau, N., et al. RAC1 inhibition targets amyloid precursor protein processing by γ-secretase and decreases Αβ production in vitro and in vivo. The Journal of Biological Chemisty 280(45), 37516-37525 (2005).

    3. Katz, E., Sims, A.H., Sproul, D., et al. Targeting of Rac GTPases blocks the spread of intact human breast cancer. Oncotarget 3(6), 608-619 (2012).

    4. Raynaud, F., Moutin, E., Schmidt, S., et al. Rho-GTPase-activating protein interacting with Cdc-42-interacting protein 4 homolog 2 (Rich2): A new Ras-related C3 botulinum toxin substrate 1 (Rac1) GTPase-activating protein that controls dendritic spine morphogenesis. The Journal of Biological Chemisty 289(5), 2600-2609 (2014).