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Description: Potent Rac family inhibitor
Chemical Name: 5-(5-(7-(Trifluoromethyl)quinolin-4-ylthio)pentyloxy)-2-(morpholinomethyl)-4H-pyran-4-one dihydrochloride
Purity: ≥98% (HPLC)
Biological Activity for EHT 1864
EHT 1864 is an 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.
Compound Libraries for EHT 1864
EHT 1864 is also offered as part of the Tocriscreen 2.0 Max. Find out more about compound libraries available from Tocris.
Technical Data for EHT 1864
| 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.
Tocris products are intended for laboratory research use only, unless stated otherwise.
Solubility Data for EHT 1864
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| water | 11.63 | 20 | |
| DMSO | 43.61 | 75 |
Preparing Stock Solutions for EHT 1864
The following data is based on the product molecular weight 581.47. Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 0.75 mM | 2.29 mL | 11.47 mL | 22.93 mL |
| 3.75 mM | 0.46 mL | 2.29 mL | 4.59 mL |
| 7.5 mM | 0.23 mL | 1.15 mL | 2.29 mL |
| 37.5 mM | 0.05 mL | 0.23 mL | 0.46 mL |
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Product Datasheets for EHT 1864
References for EHT 1864
References are publications that support the biological activity of the product.
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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Keywords: EHT 1864, EHT 1864 supplier, Rac-GEF, interaction, antioncogenic, G, Proteins, Small, transformation, Rac1, Rac1b, Rac2, Rac3, Ras, Tiam, inhibits, inhibitors, GTPases, EHT1864, Rho, 3872, Tocris Bioscience
32 Citations for EHT 1864
Citations are publications that use Tocris products. Selected citations for EHT 1864 include:
Akio et al (2019) Reciprocal Activation within a Kinase-Effector Complex Underlying Persistence of Structural LTP. Neuron 102 1199-1210.e6 PMID: 31078368
Laura M et al (2019) WASP Restricts Active Rac to Maintain Cells' Front-Rear Polarization. Curr Biol 29 4169-4182.e4 PMID: 31786060
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
Nagase et al (2016) Deletion of Rac1GTPase in the Myeloid Lineage Protects against Inflammation-Mediated Kidney Injury in Mice. PLoS One 11 e0150886 PMID: 26939003
Zhang et al (2013) The slow afterhyperpolarization: a target of β1-adrenergic signaling in hippocampus-dependent memory retrieval. J Neurosci 33 5006 PMID: 23486971
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
Yvonne et al (2023) Cell surface protein aggregation triggers endocytosis to maintain plasma membrane proteostasis. Nat Commun 14 947 PMID: 36854675
Ying et al (2020) Podocyte-Released Migrasomes in Urine Serve as an Indicator for Early Podocyte Injury. Kidney Dis (Basel) 6 422-433 PMID: 33313063
Jost et al (2020) Actin Assembly around the Shigella-Containing Vacuole Promotes Successful Infection. Cell Rep 31 107638 PMID: 32402280
Rolf K et al (2020) Epac1 Is Crucial for Maintenance of Endothelial Barrier Function through A Mechanism Partly Independent of Rac1. Cells 9 PMID: 32992982
Avraham et al (2020) Modular and Distinct Plexin-A4/FARP2/Rac1 Signaling Controls Dendrite Morphogenesis. J Neurosci 40 5413-5430 PMID: 32499377
Hajime et al (2020) Blockade of the renin-angiotensin system suppresses hydroxyl radical production in the rat striatum during carbon monoxide poisoning. Sci Rep 10 2602 PMID: 32054947
Alyson E et al (2020) Polypharmacological Perturbation of the 14-3-3 Adaptor Protein Interactome Stimulates Neurite Outgrowth. Cell Chem Biol 27 657-667.e6 PMID: 32220335
Kruppa et al (2018) Myosin VI-Dependent Actin Cages Encapsulate Parkin-Positive Damaged Mitochondria. Dev Cell 44 484 PMID: 29398621
Dendo et al (2018) Induction of non-apoptotic programmed cell death by oncogenic RAS in human epithelial cells and its suppression by MYC overexpression. Carcinogenesis 39 202 PMID: 29106503
Ford et al (2018) Chlamydia exploits filopodial capture and a macropinocytosis-like pathway for host cell entry. PLoS Pathog 14 e1007051 PMID: 29727463
Dillon et al (2015) P-REX1 creates a positive feedback loop to activate growth factor receptor, PI3K/AKT and MEK/ERK signaling in breast cancer. Oncogene 34 3968 PMID: 25284585
Wang et al (2015) Inhibition of prostate smooth muscle contraction and prostate stromal cell growth by the inhibitors of Rac, NSC23766 and EHT1864. Br J Pharmacol 172 2905 PMID: 25631101
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
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
Richard K et al (2021) Mechanosensitive smooth muscle cell phenotypic plasticity emerging from a null state and the balance between Rac and Rho. Cell Rep 35 109019 PMID: 33882318
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
John M et al (2021) Endothelial junctional membrane protrusions serve as hotspots for neutrophil transmigration. Elife 10 PMID: 34431475
Wenming et al (2021) Statin-mediated disruption of Rho GTPase prenylation and activity inhibits respiratory syncytial virus infection. Commun Biol 4 1239 PMID: 34716403
Shahin et al (2021) Attenuation of apoptotic cell detection triggers thymic regeneration after damage. Cell Rep 37 109789 PMID: 34610317
Lionarons et al (2019) RAC1P29S Induces a Mesenchymal Phenotypic Switch via Serum Response Factor to Promote Melanoma Development and Therapy Resistance. Cancer Cell 36 68 PMID: 31257073
Chung et al (2015) Albumin-associated free fatty acids induce macropinocytosis in podocytes. J Clin Invest 125 2307 PMID: 25915582
Bridgewater et al (2017) Extracellular matrix promotes clathrin-dependent endocytosis of prolactin and STAT5 activation in differentiating mammary epithelial cells. Sci Rep 7 4572 PMID: 28676702
Xiang et al (2016) Ras-related C3 botulinum. Substrate (Rac) and Src Family Kinases (SFK) Are Proximal and Essential for Phosphatidylinositol 3-Kinase (PI3K) Activation in Natural Killer (NK) Cell-mediated Direct Cytotoxicity against Cryptococcus neoformans. J Biol Chem 291 6912 PMID: 26867574
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Reviews for EHT 1864
Average Rating: 3 (Based on 1 Review.)
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Rac inhibitor.
By
Anonymous on 01/31/2018
Assay Type: Ex Vivo
Species: Mouse
Cell Line/Tissue: Brain slice
Used to block Rac but no effect seen. Can't say if the compound actually works or not.