ChemicalBook--->CAS DataBase List--->23982-76-5

23982-76-5

23982-76-5 Structure

23982-76-5 Structure
IdentificationBack 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 PropertiesBack Directory
[storage temp. ]

Store at -20°C
[solubility ]

Soluble in DMSO
[form ]

Solid
[color ]

Light yellow to yellow
Hazard InformationBack 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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