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SML1981

Sigma-Aldrich

NIBR189

≥98% (HPLC)

Synonym(s):

(2E)-3-(4-Bromophenyl)-1-(4-(4-methoxybenzoyl)-1-piperazinyl)-2-propen-1-one, (E)-3-(4-Bromophenyl)-1-(4-(4-methoxybenzoyl)piperazin-1-yl)prop-2-en-1-one, NIBR 189

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About This Item

Empirical Formula (Hill Notation):
C21H21BrN2O3
CAS Number:
1599432-08-2
Molecular Weight:
429.31
UNSPSC Code:
12352200
NACRES:
NA.77

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 10 mg/mL, clear (warmed)

storage temp.

room temp

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

Biochem/physiol Actions

NBIR189 is a high-affinity, potent and selective EBI2 (GPR183) antagonist (IC50 = 16 nM against 10 nM 7α,25-OHC for binding human EBI2) that inhibits 7α,25-OHC-induced GTPγS binding (IC50 = 8.5 and 7.0 nM, respectively, against 0.33 and 0.1 nM OHC; human EBI2-expressing CHO membrane), calcium mobilization (IC50 = 11 and 15 nM using human or mouse EBI2-transfected cells, respectively), and chemotaxis (IC50 = 0.3 nM against 20 nM OHC-induced U937 migration). NBIR189 displays no inhibitory potency against 5HT2A, muscarinic acetylcholine receptor M2, adrenoreceptor α1A, nor significant affintiy toward 18 other GPCRs/transporters/enzymes, and exhibits good pharmacokinetic properties and oral availability in mice (AUC = 3608 nmol h/L, Cmax = 835 nM, tmax = 1 h, F = 49%; 3 mg/kg p.o.). A useful tool for probing EBI2-mediated physiological functions and autoimmune disorders.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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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Inga Preuss et al.
Biochemical and biophysical research communications, 446(3), 663-668 (2014-02-01)
Oxysterols such as 7 alpha, 25-dihydroxycholesterol (7α,25-OHC) are natural ligands for the Epstein-Barr virus (EBV)-induced gene 2 (EBI2, aka GPR183), a G protein-coupled receptor (GPCR) highly expressed in immune cells and required for adaptive immune responses. Activation of EBI2 by
Florian Wanke et al.
Cell reports, 18(5), 1270-1284 (2017-02-02)
Arrival of encephalitogenic T cells at inflammatory foci represents a critical step in development of experimental autoimmune encephalomyelitis (EAE), the animal model for multiple sclerosis. EBI2 and its ligand, 7α,25-OHC, direct immune cell localization in secondary lymphoid organs. CH25H and CYP7B1
Aurélie S Clottu et al.
Cell reports, 18(1), 213-224 (2017-01-05)
The interaction between oxysterols and the G protein-coupled receptor Epstein-Barr virus-induced gene 2 (EBI2) fine-tunes immune cell migration, a mechanism efficiently targeted by several disease-modifying treatments developed to treat multiple sclerosis (MS), such as natalizumab. We previously showed that memory
Aleksandra Rutkowska et al.
Scientific reports, 6, 25520-25520 (2016-05-12)
EBI2 is a G protein-coupled receptor activated by oxysterol 7α, 25-dihydroxycholesterol (7α25HC) and regulates T cell-dependant antibody response and B cell migration. We recently found EBI2 is expressed in human astrocytes, regulates intracellular signalling and modulates astrocyte migration. Here, we
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
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