NIBR189Potent and selective EBI2 (GPR183) receptor antagonist CAS# 1599432-08-2 |
- Sulfo-NHS-Biotin
Catalog No.:BCC3576
CAS No.:119616-38-5
- Sulfo-NHS-LC-Biotin
Catalog No.:BCC3578
CAS No.:127062-22-0
- NHS-Biotin
Catalog No.:BCC3577
CAS No.:35013-72-0
- Biotin Hydrazide
Catalog No.:BCC3582
CAS No.:66640-86-6
- NHS-LC-Biotin
Catalog No.:BCC3579
CAS No.:72040-63-2
- Iodoacetyl-LC-Biotin
Catalog No.:BCC3584
CAS No.:93285-75-7
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
| Cas No. | 1599432-08-2 | SDF | Download SDF |
| PubChem ID | 36295259 | Appearance | Powder |
| Formula | C21H21BrN2O3 | M.Wt | 429.31 |
| Type of Compound | N/A | Storage | Desiccate at -20°C |
| Solubility | DMSO : ≥ 47 mg/mL (109.48 mM) *"≥" means soluble, but saturation unknown. | ||
| Chemical Name | (E)-3-(4-bromophenyl)-1-[4-(4-methoxybenzoyl)piperazin-1-yl]prop-2-en-1-one | ||
| SMILES | COC1=CC=C(C=C1)C(=O)N2CCN(CC2)C(=O)C=CC3=CC=C(C=C3)Br | ||
| Standard InChIKey | OFHXXBRBGWUOHR-NYYWCZLTSA-N | ||
| Standard InChI | 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+ | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
||
| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
||
| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | Potent and selective EBI2 (GPR183) receptor antagonist (IC50 values are 11 and 15 nM for human and mouse EBI2 receptors respectively). Exhibits selectivity for EBI2 over a panel of other receptors, enzymes and transporters. Blocks oxysterol-induced migration of U937 monocyte cells. Orally bioavailable. |
NIBR189 Dilution Calculator
NIBR189 Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.3293 mL | 11.6466 mL | 23.2932 mL | 46.5864 mL | 58.233 mL |
| 5 mM | 0.4659 mL | 2.3293 mL | 4.6586 mL | 9.3173 mL | 11.6466 mL |
| 10 mM | 0.2329 mL | 1.1647 mL | 2.3293 mL | 4.6586 mL | 5.8233 mL |
| 50 mM | 0.0466 mL | 0.2329 mL | 0.4659 mL | 0.9317 mL | 1.1647 mL |
| 100 mM | 0.0233 mL | 0.1165 mL | 0.2329 mL | 0.4659 mL | 0.5823 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
Calcutta University
University of Minnesota
University of Maryland School of Medicine
University of Illinois at Chicago
The Ohio State University
University of Zurich
Harvard University
Colorado State University
Auburn University
Yale University
Worcester Polytechnic Institute
Washington State University
Stanford University
University of Leipzig
Universidade da Beira Interior
The Institute of Cancer Research
Heidelberg University
University of Amsterdam
University of Auckland
TsingHua University
The University of Michigan
Miami University
DRURY University
Jilin University
Fudan University
Wuhan University
Sun Yat-sen University
Universite de Paris
Deemed University
Auckland University
The University of Tokyo
Korea University
NIBR189 is a small molecule antagonist of the Epstein-Barr virus-induced gene 2 (EBI2; GPR183) receptor with IC50 of 16 nM(Binding) and 11 nM (Functional).
- 3,5-Di-O-caffeoylquinic acid methyl ester
Catalog No.:BCN6491
CAS No.:159934-13-1
- Mc-Val-Cit-PABC-PNP
Catalog No.:BCC4028
CAS No.:159857-81-5
- 4'-O-Methylirenolone
Catalog No.:BCN7174
CAS No.:159853-36-8
- Sikokianin C
Catalog No.:BCN6827
CAS No.:159813-69-1
- Ulipristal
Catalog No.:BCC4944
CAS No.:159811-51-5
- Fmoc-Lys(Ac)-OH
Catalog No.:BCC3514
CAS No.:159766-56-0
- Ibutamoren Mesylate
Catalog No.:BCC1638
CAS No.:159752-10-0
- ISRIB (trans-isomer)
Catalog No.:BCC5340
CAS No.:1597403-47-8
- Wikstrol A
Catalog No.:BCN7938
CAS No.:159736-35-3
- Saropyrone
Catalog No.:BCN7692
CAS No.:159650-12-1
- 3,4-Secotirucalla-4(28,7,24-triene-3),26-dioic acid
Catalog No.:BCN1549
CAS No.:159623-48-0
- Daminozide
Catalog No.:BCC1514
CAS No.:1596-84-5
- Nelfinavir
Catalog No.:BCC4138
CAS No.:159989-64-7
- Nelfinavir Mesylate
Catalog No.:BCC1794
CAS No.:159989-65-8
- Iniparib (BSI-201)
Catalog No.:BCC2208
CAS No.:160003-66-7
- Antibiotic AB 4063B
Catalog No.:BCN1827
CAS No.:160041-33-8
- Sambutoxin
Catalog No.:BCN1709
CAS No.:160047-56-3
- Huwentoxin XVI
Catalog No.:BCC8041
CAS No.:1600543-88-1
- Cryptofolione
Catalog No.:BCN7197
CAS No.:160098-78-2
- SCH 58261
Catalog No.:BCC7306
CAS No.:160098-96-4
- 2-Iminopiperidine hydrochloride
Catalog No.:BCC6862
CAS No.:16011-96-4
- L-BMAA hydrochloride
Catalog No.:BCC7400
CAS No.:16012-55-8
- 7-Chloro-1,2,3,4-tetrahydrobenzo[b]azepin-5-one
Catalog No.:BCC8779
CAS No.:160129-45-3
- BIM 23127
Catalog No.:BCC5822
CAS No.:160161-61-5
EBI2 regulates pro-inflammatory signalling and cytokine release in astrocytes.[Pubmed:29374507]
Neuropharmacology. 2018 May 1;133:121-128.
The endogenous oxysterol 7alpha, 25-dihydroxycholesterol (7alpha25HC) ligand activates the G protein-coupled receptor EBI2 to regulate T cell-dependant antibody response and B cell migration. We have demonstrated that EBI2 is expressed in human and mouse astrocytes, that 7alpha25HC induces intracellular signalling and astrocyte migration, and that EBI2 plays a role in the crosstalk between astrocytes and macrophages. Recently, we demonstrate that EBI2 regulates myelin development and inhibits LPC-induced demyelination. Here, we show that 7alpha25HC inhibits LPS- and IL17/TNF-induced pro-inflammatory cytokine release in astrocytes. We observe the following: 1. Human astrocytes treated with IL17/TNF increases the nuclear translocation of NFkappaB, which is attenuated by pre-treatment with 7alpha25HC; 2. IL17/TNF increases cell impedance in human astrocytes, which is also attenuated by pre-treatment with 7alpha25HC; 3. The EBI2 antagonist NIBR189 inhibits these effects of 7alpha25HC, supporting the role of EBI2; 4. in vivo data corroborate these in vitro findings, showing that EBI2 knock-out (KO) animals display enhanced pro-inflammatory cytokine in response to LPS challenge, in the brain. These results demonstrate a role for oxysterol/EBI2 signalling in attenuating the response of astrocytes to pro-inflammatory signals as well as limiting the levels of pro-inflammatory cytokines in the brain.
The EBI2 signalling pathway plays a role in cellular crosstalk between astrocytes and macrophages.[Pubmed:27166278]
Sci Rep. 2016 May 11;6:25520.
EBI2 is a G protein-coupled receptor activated by oxysterol 7alpha, 25-dihydroxycholesterol (7alpha25HC) 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 report that LPS treatment of mouse astrocytes alters mRNA levels of EBI2 and oxysterols suggesting that the EBI2 signalling pathway is sensitive to LPS-mediated immune challenge. We also find that conditioned media obtained from LPS-stimulated mouse astrocytes induces macrophage migration, which is inhibited by the EBI2 antagonist NIBR189. These results demonstrate a role for the EBI2 signalling pathway in astrocytes as a sensor for immune challenge and for communication with innate immune cells such as macrophages.
Identification and characterization of small molecule modulators of the Epstein-Barr virus-induced gene 2 (EBI2) receptor.[Pubmed:24678947]
J Med Chem. 2014 Apr 24;57(8):3358-68.
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 , 281 , 13199 ), and its activation has been shown to be critical for the adaptive immune response and has been genetically linked to autoimmune diseases such as type I diabetes ( Nature 2010 , 467 , 460 ). Here we describe the isolation of a potent small molecule antagonist for the EBI2 receptor. First, we identified a small molecule agonist NIBR51 (1), which enabled identification of inhibitors of receptor activation. One antagonist called NIBR127 (2) was used as a starting point for a medicinal chemistry campaign, which yielded NIBR189 (4m). This compound was extensively characterized in binding and various functional signaling assays. Furthermore, we have used 4m to block migration of a monocyte cell line called U937, suggesting a functional role of the oxysterol/EBI2 pathway in these immune cells.
