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| | 10-chloro-7H-benzimidazo[2,1-a]benzo[de]isoquinolin-7-one Basic information |
| | 10-chloro-7H-benzimidazo[2,1-a]benzo[de]isoquinolin-7-one Chemical Properties |
| 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 |
| WGK Germany | WGK 3 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Aquatic Chronic 4 |
| | 10-chloro-7H-benzimidazo[2,1-a]benzo[de]isoquinolin-7-one Usage And Synthesis |
| 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 bioavailable, non-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 CD25, CTLA-4 and ICOS, as well as several other genes associated with regulatory T cell (Treg) function in a graft versus host response model (GVH, C57BI/6 T cells injected into B6D2F1 host mice). 10-Cl-BBQ displays good pharmacokinetic profile in mice (t1/2 = 2 h, Cmax = 21.5 μg/L, 10 mg/kg, i.p.). Also shown to prevent insulitis in a NOD T1D mouse model which is independent of Fox3 + Tregs (60 mg/kg, p.o, q.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 |
| | 10-chloro-7H-benzimidazo[2,1-a]benzo[de]isoquinolin-7-one Preparation Products And Raw materials |
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