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EHT 1864

Catalog #: 3872
32 Citations Datasheet
Catalog # Availability Size / Price Qty
3872/10
3872/50
EHT 1864 | CAS No. 754240-09-0 | Rho GTPase Inhibitors
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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%

Product Details
Citations (32)
Reviews
Biological Activity Technical Data Additional Information Background Product Datasheets Calculators

Biological Activity

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.

Technical Data

M.Wt:
581.47
Formula:
C25H27F3N2O4S.2HCl
Solubility:
Soluble to 20 mM in water and to 75 mM in DMSO
Purity:
≥98%
Storage:
Store at +4°C
CAS No:
754240-09-0

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.

Additional Information

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

Background References

  1. Endophilin marks and controls a clathrin-independent endocytic pathway.
    Boucrot E, Ferreira A, Almeida-Souza L, Debard S, Vallis Y, Howard G, Bertot L, Sauvonnet N, McMahon H
    Nature, 2015;517(7535):460-5.
  2. Role of focal adhesion tyrosine kinases in GPVI-dependent platelet activation and reactive oxygen species formation.
    Carrim N, Walsh T, Consonni A, Torti M, Berndt M, Metharom P
    PLoS ONE, 2014;9(11):e113679.
  3. Phosphatidylinositol-3,4,5-triphosphate-dependent Rac exchange factor 1 regulates epinephrine-induced exocytosis of Weibel-Palade bodies.
    van Hooren K, van Breevoort D, Fernandez-Borja M, Meijer A, Eikenboom J, Bierings R, Voorberg J
    J Thromb Haemost, 2014;12(2):273-81.
  4. HIF-1alpha activation results in actin cytoskeleton reorganization and modulation of Rac-1 signaling in endothelial cells.
    Weidemann A, Breyer J, Rehm M, Eckardt K, Daniel C, Cicha I, Giehl K, Goppelt-Struebe M
    Cell Commun Signal, 2013;11(0):80.
  5. Lysophosphatidic acid regulates the motility of MCF10CA1a breast cancer cell sheets via two opposing signaling pathways
    CH Stuelten, RM Lee, W Losert, CA Parent
    Cell. Signal., 2018;0(0):.
  6. EHT 1864, a small molecule inhibitor of Ras-related C3 botulinum toxin substrate 1 (Rac1), attenuates glucose-stimulated insulin secretion in pancreatic beta-cells.
    Sidarala V, Veluthakal R, Syeda K, Kowluru A
    Cell Signal, 2015;27(6):1159-67.
  7. The effect of statin on epithelial-mesenchymal transition in peritoneal mesothelial cells.
    Chang T, Kang H, Kim K, Lee S, Nam B, Paeng J, Kim S, Park J, Yoo T, Kang S, Han S
    PLoS ONE, 2014;9(10):e109628.
  8. Nuclear factor of activated T cells c1 mediates p21-activated kinase 1 activation in the modulation of chemokine-induced human aortic smooth muscle cell F-actin stress fiber formation, migration, and proliferation and injury-induced vascular wall remodeling.
    Kundumani-Sridharan, Venkates, Singh, Nikhlesh, Kumar, Sanjay, Gadepalli, Ravisekh, Rao, Gadipart
    J Biol Chem, 2013;288(30):22150-62.
  9. In PC3 prostate cancer cells ephrin receptors crosstalk to beta1-integrins to strengthen adhesion to collagen type I.
    Yu M, Wang J, Muller D, Helenius J
    Sci Rep, 2015;5(0):8206.
  10. RAC1 inhibition targets amyloid precursor protein processing by γ-secretase and decreases Aβ production in vitro and in vivo.
    Desire et al.
    J.Biol.Chem., 2005;280:37516
  11. Specificity and mechanism of action of EHT 1864, a novel small molecule inhibitor of rac family small GTPases.
    Shutes et al.
    J.Biol.Chem., 2007;282:35666
  12. Characterization of EHT1864, a novel small molecule inhibitor of Rac family small GTPases.
    Onesto et al.
    Methods Enzymol., 2008;439:111

Product Datasheets

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Citations for EHT 1864

The citations listed below are publications that use Tocris products. Selected citations for EHT 1864 include:

32 Citations: Showing 1 - 10

  1. Cell surface protein aggregation triggers endocytosis to maintain plasma membrane proteostasis.
    Authors: Yvonne Et al.
    Nat Commun  2023;14:947
  2. Statin-mediated disruption of Rho GTPase prenylation and activity inhibits respiratory syncytial virus infection.
    Authors: Wenming Et al.
    Commun Biol  2021;4:1239
  3. Attenuation of apoptotic cell detection triggers thymic regeneration after damage.
    Authors: Shahin Et al.
    Cell Rep  2021;37:109789
  4. Mechanosensitive smooth muscle cell phenotypic plasticity emerging from a null state and the balance between Rac and Rho.
    Authors: Richard K Et al.
    Cell Rep  2021;35:109019
  5. Endothelial junctional membrane protrusions serve as hotspots for neutrophil transmigration.
    Authors: John M Et al.
    Elife  2021;10
  6. Epac1 Is Crucial for Maintenance of Endothelial Barrier Function through A Mechanism Partly Independent of Rac1.
    Authors: Rolf K Et al.
    Cells  2020;9
  7. Podocyte-Released Migrasomes in Urine Serve as an Indicator for Early Podocyte Injury.
    Authors: Ying Et al.
    Kidney Dis (Basel)  2020;6:422-433
  8. Modular and Distinct Plexin-A4/FARP2/Rac1 Signaling Controls Dendrite Morphogenesis.
    Authors: Avraham Et al.
    J Neurosci  2020;40:5413-5430
  9. Actin Assembly around the Shigella-Containing Vacuole Promotes Successful Infection.
    Authors: Jost Et al.
    Cell Rep  2020;31:107638
  10. Polypharmacological Perturbation of the 14-3-3 Adaptor Protein Interactome Stimulates Neurite Outgrowth.
    Authors: Alyson E Et al.
    Cell Chem Biol  2020;27:657-667.e6
  11. Blockade of the renin-angiotensin system suppresses hydroxyl radical production in the rat striatum during carbon monoxide poisoning.
    Authors: Hajime Et al.
    Sci Rep  2020;10:2602
  12. RAC1P29S Induces a Mesenchymal Phenotypic Switch via Serum Response Factor to Promote Melanoma Development and Therapy Resistance.
    Authors: Lionarons Et al.
    Cancer Cell  2019;36:68
  13. WASP Restricts Active Rac to Maintain Cells' Front-Rear Polarization.
    Authors: Laura M Et al.
    Curr Biol  2019;29:4169-4182.e4
  14. Reciprocal Activation within a Kinase-Effector Complex Underlying Persistence of Structural LTP.
    Authors: Akio Et al.
    Neuron  2019;102:1199-1210.e6
  15. Myosin VI-Dependent Actin Cages Encapsulate Parkin-Positive Damaged Mitochondria.
    Authors: Kruppa Et al.
    Dev Cell  2018;44:484
  16. Induction of non-apoptotic programmed cell death by oncogenic RAS in human epithelial cells and its suppression by MYC overexpression.
    Authors: Dendo Et al.
    Carcinogenesis  2018;39:202
  17. Chlamydia exploits filopodial capture and a macropinocytosis-like pathway for host cell entry.
    Authors: Ford Et al.
    PLoS Pathog  2018;14:e1007051
  18. Extracellular matrix promotes clathrin-dependent endocytosis of prolactin and STAT5 activation in differentiating mammary epithelial cells.
    Authors: Bridgewater Et al.
    Sci Rep  2017;7:4572
  19. Unravelling the Mechanism of TrkA-Induced Cell Death by Macropinocytosis in Medulloblastoma Daoy Cells.
    Authors: Li Et al.
    Mol.Cell Biol.  2016;36:2596
  20. 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.
    Authors: Xiang Et al.
    J Biol Chem  2016;291:6912
  21. Deletion of Rac1GTPase in the Myeloid Lineage Protects against Inflammation-Mediated Kidney Injury in Mice.
    Authors: Nagase Et al.
    PLoS One  2016;11:e0150886
  22. Loss of the E3 ubiquitin ligase HACE1 results in enhanced Rac1 signaling contributing to breast cancer progression.
    Authors: Goka and Lippman
    Am J Physiol Lung Cell Mol Physiol  2015;34:5395
  23. P-REX1 creates a positive feedback loop to activate growth factor receptor, PI3K/AKT and MEK/ERK signaling in breast cancer.
    Authors: Dillon Et al.
    Oncogene  2015;34:3968
  24. Inhibition of prostate smooth muscle contraction and prostate stromal cell growth by the inhibitors of Rac, NSC23766 and EHT1864.
    Authors: Wang Et al.
    Br J Pharmacol  2015;172:2905
  25. Albumin-associated free fatty acids induce macropinocytosis in podocytes.
    Authors: Chung Et al.
    J Clin Invest  2015;125:2307
  26. Rac1 is required for matrix metalloproteinase 13 production by chondrocytes in response to fibronectin fragments.
    Authors: Long Et al.
    Cell Cycle  2013;65:1561
  27. The slow afterhyperpolarization: a target of β1-adrenergic signaling in hippocampus-dependent memory retrieval.
    Authors: Zhang Et al.
    J Neurosci  2013;33:5006
  28. Rac1 pathway mediates stretch response in pulmonary alveolar epithelial cells.
    Authors: Dipaolo Et al.
    Microbiology  2013;305:L141
  29. Novel role for p21-activated kinase 2 in thrombin-induced monocyte migration.
    Authors: Gadepalli Et al.
    Oncogene  2013;288:30815
  30. Inhibition of hepcidin transcription by growth factors.
    Authors: Goodnough Et al.
    Hepatology  2012;56:291
  31. Targeting of Rac GTPases blocks the spread of intact human breast cancer.
    Authors: Katz Et al.
    Oncotarget  2012;3:608
  32. Tannerella forsythia invasion in oral epithelial cells requires phosphoinositide 3-kinase activation and clathrin-mediated endocytosis.
    Authors: Mishima and Sharma
    Arthritis Rheum  2011;157:2382

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