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857397P

Avanti

NIBR189

Avanti Research™ - A Croda Brand 857397P, powder

Synonym(s):

(E)-3-(4-bromophenyl)-1-(4-(4-methoxybenzoyl)piperazin-1-yl)prop-2-en-1-one

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About This Item

Empirical Formula (Hill Notation):
C21H21BrN2O3
CAS Number:
1599432-08-2
Molecular Weight:
429.31
UNSPSC Code:
12352211
NACRES:
NA.25

Assay

>99% (TLC)

form

powder

packaging

pkg of 1 × 10 mg (857397P-10mg)

manufacturer/tradename

Avanti Research™ - A Croda Brand 857397P

shipped in

dry ice

storage temp.

−20°C

SMILES string

BrC(C=C1)=CC=C1/C=C/C(N2CCN(C(C3=CC=C(OC)C=C3)=O)CC2)=O

InChI

1S/C21H21BrN2O3/c1-27-19-9-5-17(6-10-19)21(26)24-14-12-23(13-15-24)20(25)11-4-16-2-7-18(22)8-3-16/h2-11H,12-15H2,1H3/b11-4+

InChI key

OFHXXBRBGWUOHR-NYYWCZLTSA-N

General description

Potent and selective antagonist of the G protein-coupled receptor identified as EBI2 (GPR183) (IC50 values are 11 and 15 nM for human and mouse EBI2 receptors, respectively). This compound exhibits selectivity for EBI2 over other receptors, enzymes and transporters. In addition, NIBR189 blocks oxysterol-induced migration of U937 monocyte cells.

Application

NIBR189 has been used to test the effects of chronic Epstein-Barr virus-induced gene 2 (EBI2) deficiency on dendritic cells (DC) numbers. It has also been used in chemotaxis assay of RAW264.7 macrophages directed towards 7β,25-dihydroxycholesterol (7β25OHC).

Biochem/physiol Actions

NIBR189 is a potent and selective antagonist of the G protein-coupled receptor (GPR183). This compound exhibits selectivity for Epstein-Barr virus-induced gene 2 (EBI2) receptor over other receptors, enzymes and transporters. NIBR189 has an IC50 value of 11 and 15 nM for human and mouse EBI2 receptors, respectively.It is known to block oxysterol.

Packaging

5 mL Amber Glass Screw Cap Vial (857397P-10mg)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Distinct oxysterol requirements for positioning naive and activated dendritic cells in the spleen
Lu E, et al.
Science immunology, 2(10) (2017)
Identification and characterization of small molecule modulators of the Epstein-Barr virus-induced gene 2 (EBI2) receptor
Gessier F, et al.
Journal of Medicinal Chemistry, 57(8), 3358-3368 (2014)
Francois Gessier et al.
Journal of medicinal chemistry, 57(8), 3358-3368 (2014-04-01)
Oxysterols have recently been identified as natural ligands for a G protein-coupled receptor called EBI2 (aka GPR183) ( Nature 2011 , 475 , 524 ; 519 ). EBI2 is highly expressed in immune cells ( J. Biol. Chem. 2006
Katharina R Beck et al.
The Journal of steroid biochemistry and molecular biology, 190, 19-28 (2019-03-25)
Oxysterols are cholesterol metabolites derived through either autoxidation or enzymatic processes. They consist of a large family of bioactive lipids that have been associated with the progression of multiple pathologies. In order to unravel (patho-)physiological mechanisms involving oxysterols, it is

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