EHT 1864

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Cat.No. 3872 - EHT 1864 | C25H27F3N2O4S.2HCl | CAS No. 754240-09-0
Description: Potent inhibitor of Rac family GTPases
Chemical Name: 5-(5-(7-(Trifluoromethyl)quinolin-4-ylthio)pentyloxy)-2-(morpholinomethyl)-4H-pyran-4-one dihydrochloride
Purity: ≥98% (HPLC)
Datasheet
Citations (10)
Literature

Biological Activity

Inhibitor of Rac family GTPases. Blocks activation by direct binding to Rac1, Rac1b, Rac2 and Rac3 (KD values are 40, 50, 60 and 250 nM respectively). Inhibits Rac, Ras and Tiam-induced growth transformation of NIH-3T3 fibroblasts. Reduces β-amyloid peptide production in vivo.

Licensing Information

Sold for research use only under license from ExonHit Therapeutics S.A.

Technical Data

M. Wt 581.47
Formula C25H27F3N2O4S.2HCl
Storage Store at +4°C
Purity ≥98% (HPLC)
CAS Number 754240-09-0
PubChem ID 9938202
InChI Key LSECOAJFCKFQJG-UHFFFAOYSA-N
Smiles O=C1C=C(CN4CCOCC4)OC=C1OCCCCCSC3=CC=NC2=CC(C(F)(F)F)=CC=C23.Cl.Cl

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.

All Tocris products are intended for laboratory research use only.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 43.61 75
water 58.15 100

Preparing Stock Solutions

The following data is based on the product molecular weight 581.47. Batch specific molecular weights may vary from batch to batch due to solvent of hydration, which will affect the solvent volumes required to prepare stock solutions.

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.72 mL 8.6 mL 17.2 mL
5 mM 0.34 mL 1.72 mL 3.44 mL
10 mM 0.17 mL 0.86 mL 1.72 mL
50 mM 0.03 mL 0.17 mL 0.34 mL

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Product Datasheets

Safety Datasheet

References

References are publications that support the products' biological activity.

Desire et al (2005) RAC1 inhibition targets amyloid precursor protein processing by γ-secretase and decreases Aβ production in vitro and in vivo. J.Biol.Chem. 280 37516 PMID: 16150730

Shutes et al (2007) Specificity and mechanism of action of EHT 1864, a novel small molecule inhibitor of rac family small GTPases. J.Biol.Chem. 282 35666 PMID: 17932039

Onesto et al (2008) Characterization of EHT1864, a novel small molecule inhibitor of Rac family small GTPases. Methods Enzymol. 439 111 PMID: 18374160


If you know of a relevant reference for EHT 1864, please let us know.

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View all G Protein (Small) Inhibitors

Keywords: Rac-GEF interaction antioncogenic G Proteins Small transformation Rac1 Rac1b Rac2 Rac3 Ras Tiam inhibits inhibitors GTPases EHT1864 G Proteins (Small)

10 Citations for EHT 1864

Citations are publications that use Tocris products. Selected citations for EHT 1864 include:

Goodnough et al (2012) Inhibition of hepcidin transcription by growth factors. Hepatology 56 291 PMID: 22278715

Katz et al (2012) Targeting of Rac GTPases blocks the spread of intact human breast cancer. Oncotarget 3 608 PMID: 22689141

Mishima and Sharma (2011) Tannerella forsythia invasion in oral epithelial cells requires phosphoinositide 3-kinase activation and clathrin-mediated endocytosis. Arthritis Rheum 157 2382 PMID: 21622527

Li et al (2016) Unravelling the Mechanism of TrkA-Induced Cell Death by Macropinocytosis in Medulloblastoma Daoy Cells. Mol.Cell Biol. 36 2596 PMID: 27503856

Chung et al (2015) Albumin-associated free fatty acids induce macropinocytosis in podocytes. J Clin Invest 125 2307 PMID: 25915582

Goka and Lippman (2015) Loss of the E3 ubiquitin ligase HACE1 results in enhanced Rac1 signaling contributing to breast cancer progression. Am J Physiol Lung Cell Mol Physiol 34 5395 PMID: 25659579

Zhang et al (2013) The slow afterhyperpolarization: a target of β1-adrenergic signaling in hippocampus-dependent memory retrieval. J Neurosci 33 5006 PMID: 23486971

Gadepalli et al (2013) Novel role for p21-activated kinase 2 in thrombin-induced monocyte migration. Oncogene 288 30815 PMID: 24025335

Dipaolo et al (2013) Rac1 pathway mediates stretch response in pulmonary alveolar epithelial cells. Microbiology 305 L141 PMID: 23686855

Long et al (2013) Rac1 is required for matrix metalloproteinase 13 production by chondrocytes in response to fibronectin fragments. Cell Cycle 65 1561 PMID: 23460186


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Cancer

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