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E1657

Sigma-Aldrich

EHT 1864

≥98% (HPLC)

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
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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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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