| Identification | Back Directory | [Name]
10-chloro-7H-benzimidazo[2,1-a]benzo[de]isoquinolin-7-one | [CAS]
23982-76-5 | [Synonyms]
10-Cl-BBQ
10-Cl-BBQ >=98% (HPLC)
10-Chloro-7H-benzimidazo[2
1-a]benzo[de]Iso-quinolin-7-one
10-chloro-7H-benzimidazo[2,1-a]benzo[de]isoquinolin-7-one | [Molecular Formula]
C18H9ClN2O | [MDL Number]
MFCD03863624 | [MOL File]
23982-76-5.mol | [Molecular Weight]
304.73 |
| Chemical Properties | Back Directory | [storage temp. ]
Store at -20°C | [solubility ]
Soluble in DMSO | [form ]
Solid | [color ]
Light yellow to yellow | [InChI]
1S/C18H9ClN2O/c19-11-7-8-14-15(9-11)21-17(20-14)12-5-1-3-10-4-2-6-13(16(10)12)18(21)22/h1-9H | [InChIKey]
ZJESJVGSDQOZAT-UHFFFAOYSA-N | [SMILES]
O=C(C1=C2C(C=CC=C23)=CC=C1)N4C3=NC5=C4C=C(Cl)C=C5 |
| Hazard Information | Back Directory | [Uses]
10-Cl-BBQ is a high affinity AhR ligand with immunosuppressive activity. 10-Cl-BBQ promotes cytosol to nuclear translocation of AhR and activates the AhR-regulated reporter gene at nanomolar concentrations[1][2]. | [Biological Activity]
10-Cl-BBQ is an orally bioavailablenon-toxic benzimidazoisoquinoline derivative th at acts as an aryl hydrocarbon receptor (AhR) agonist via directly binding to AhR (IC50 = 2.6 nM in a competitive binding assay) and induces its nuclear translocation. 10-Cl-BBQ is shown to increase CD4+ T-cells th at co-express CD25CTLA-4 and ICOSas well as several other genes associated with regulatory T cell (Treg) function in a graft versus host response model (GVHC57BI/6 T cells injected into B6D2F1 host mice). 10-Cl-BBQ displays good pharmacokinetic profile in mice (t1/2 = 2 hCmax = 21.5 μg/L10 mg/kgi.p.). Also shown to prevent insulitis in a NOD T1D mouse model which is independent of Fox3 + Tregs (60 mg/kgp.oq.o.d.). | [storage]
Store at +4°C | [References]
[1] Sumit Punj, et al. Benzimidazoisoquinolines: a new class of rapidly metabolized aryl hydrocarbon receptor (AhR) ligands that induce AhR-dependent Tregs and prevent murine graft-versus-host disease. PLoS One. 2014 Feb 19;9(2):e88726. DOI:10.1371/journal.pone.0088726
[2] Allison K Ehrlich, et al. Activation of the Aryl Hydrocarbon Receptor by 10-Cl-BBQ Prevents Insulitis and Effector T Cell Development Independently of Foxp3+ Regulatory T Cells in Nonobese Diabetic Mice. J Immunol. 2016 Jan 1;196(1):264-73. DOI:10.4049/jimmunol.1501789 |
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| Company Name: |
Energy Chemical
|
| Tel: |
021-58432009 400-005-6266 |
| Website: |
http://www.energy-chemical.com |
| Company Name: |
Wuhan Topule
|
| Tel: |
+86-02787215551 19945035818 |
| Website: |
http://www.topule.com/ |
|