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Merck

SML1981

NIBR189

≥98% (HPLC), GPR183 antagonist, powder

Sinonimo/i:

(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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Informazioni su questo articolo

Formula empirica (notazione di Hill):
C21H21BrN2O3
Numero CAS:
1599432-08-2
Peso molecolare:
429.31
UNSPSC Code:
12352200
NACRES:
NA.77
Assay:
≥98% (HPLC)
Form:
powder

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Nome del prodotto

NIBR189, ≥98% (HPLC)

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 10 mg/mL, clear (warmed)

storage temp.

room temp

SMILES string

Brc1ccc(cc1)\C=C\C(=O)N2CCN(CC2)C(=O)c3ccc(cc3)OC

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

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Questo articolo
SML1601SML2256SML1405
NIBR189 ≥98% (HPLC)

Sigma-Aldrich

SML1981

NIBR189

NSC59984 ≥98% (HPLC)

Sigma-Aldrich

SML1601

NSC59984

D3-βArr ≥98% (HPLC)

Sigma-Aldrich

SML2256

D3-βArr

MS37452 ≥98% (HPLC)

Sigma-Aldrich

SML1405

MS37452

form

powder

form

powder

form

powder

form

powder

assay

≥98% (HPLC)

assay

≥98% (HPLC)

assay

≥98% (HPLC)

assay

≥98% (HPLC)

storage temp.

room temp

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

−20°C

solubility

DMSO: 10 mg/mL, clear (warmed)

solubility

DMSO: 5 mg/mL, clear (warmed)

solubility

DMSO: 2 mg/mL, clear

solubility

DMSO: 20 mg/mL, clear

color

white to beige

color

yellow to brown

color

white to beige

color

white to beige

Biochem/physiol Actions

High-affinity, potent and selective EBI2 (GPR183) antagonist with good pharmacokinetic properties and oral availability in mice in vivo.
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.

Classe di stoccaggio

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificati d'analisi (COA)

Lot/Batch Number
0000535168
0000535168
0000229832
0000229832
0000203755

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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
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
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
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
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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Numero articolo commerciale globale

SKUGTIN
SML1981-25MG04061835302741
SML1981-5MG04061835302758

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