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Merck

E1657

EHT 1864

≥98% (HPLC), Rac function inhibitor, powder

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C25H27F3N2O4S · 2HCl
CAS Number:
754240-09-0
Molecular Weight:
581.47
UNSPSC Code:
12352200
PubChem Substance ID:
329799014
NACRES:
NA.77
MDL number:
MFCD11114384

Product Name

EHT 1864, ≥98% (HPLC)

SMILES string

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

InChI key

LSECOAJFCKFQJG-UHFFFAOYSA-N

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

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

H2O: 10 mg/mL, clear

storage temp.

2-8°C

Quality Level

100

Related Categories

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.
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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000503176
0000503176
0000230619
0000230619
089K4604V

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Advances in Cancer Research, 134-134 (2011)
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)
Jinkun Liu et al.
Evidence-based complementary and alternative medicine : eCAM, 2020, 2760979-2760979 (2020-05-19)
The infructescence of Platycarya strobilacea Sieb. et Zucc. (PS) has been used in the treatment of rhinitis and sinusitis in clinical practice. Our preliminary study showed that an ethanol extract of the infructescence of PS (EPS) had significant antinasopharyngeal carcinoma
Kara R Eichelberger et al.
mBio, 10(6) (2019-12-12)
Inhalation of Yersinia pestis causes primary pneumonic plague, the most severe manifestation of plague that is characterized by a dramatic neutrophil influx to the lungs. Neutrophils are ineffective during primary pneumonic plague, failing to control Y. pestis growth in the
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
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