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Merck
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Documentos

E1657

Sigma-Aldrich

EHT 1864

≥98% (HPLC)

Sinónimos:

5-(5-(7-(Trifluoromethyl)quinolin-4-ylthio)pentyloxy)-2-(morpholinomethyl)-4H-pyran-4-one dihydrochloride

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About This Item

Fórmula empírica (notación de Hill):
C25H27F3N2O4S · 2HCl
Número de CAS:
754240-09-0
Peso molecular:
581.47
MDL number:
MFCD11114384
UNSPSC Code:
12352200
PubChem Substance ID:
329799014
NACRES:
NA.77

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

H2O: 10 mg/mL, clear

storage temp.

2-8°C

SMILES string

Cl.Cl.FC(F)(F)c1ccc2c(SCCCCCOC3=COC(CN4CCOCC4)=CC3=O)ccnc2c1

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

Application

EHT 1864 has been used to study the regulation of the adapter protein dishevelled-1 ubiquitylation by Rac1 activity.

Biochem/physiol Actions

EHT 1864 induces dissociation of bound nucleotides. EHT 1864 induced inhibition of Rac prevents its association with downstream effectors. It is known to prevent estrogen-induced tumor cell proliferation in breast cancer.
EHT 1864 inhibits Rac function. It prevents Aβ40 and Aβ42 production in vitro without direct inhibition of g-secretase.

Features and Benefits

This compound is a featured product for Cyclic Nucleotide research. Click here to discover more featured Cyclic Nucleotide products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the GTP Binding Proteins (Low Molecular Weight) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Legal Information

EHT 1864 compound sold under license from ExonHit Therapeutics S.A. (www.exonhit.com)

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Visite la Librería de documentos

Wan-Yun Cheng et al.
Environmental health perspectives, 118(7), 902-908 (2010-04-24)
The mechanisms of action of many environmental agents commonly involve oxidative stress resulting from mitochondrial dysfunction. Zinc is a common environmental metallic contaminant that has been implicated in a variety of oxidant-dependent toxicological responses. Unlike ions of other transition metals
Rac1 acts in conjunction with Nedd4 and dishevelled-1 to promote maturation of cell-cell contacts
Nethe M, et al.
Journal of Cell Science, jcs-100925 (2012)
Handbook of Cell Signaling, 2851-2851 (2009)
Advances in Cancer Research, 134-134 (2011)
Charlotte Ford et al.
PLoS pathogens, 14(5), e1007051-e1007051 (2018-05-05)
Pathogens hijack host endocytic pathways to force their own entry into eukaryotic target cells. Many bacteria either exploit receptor-mediated zippering or inject virulence proteins directly to trigger membrane reorganisation and cytoskeletal rearrangements. By contrast, extracellular C. trachomatis elementary bodies (EBs)
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Discover Bioactive Small Molecules for Cyclic Nucleotides

Cyclic nucleotides, including cyclic AMP (cAMP), cyclic GMP (cGMP) and cyclic ADP-ribose, have been extensively studied as second messengers of intracellular events initiated by activation of GPCRs. cAMP modifies cell function in all eukaryotic cells, principally through the activation of cAMP-dependent protein kinase (PKA), but also through cAMP-gated ion channels and guanine nucleotide exchange factors directly activated by cAMP.

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