SML1798

10-Cl-BBQ

≥98% (HPLC)

• Synonym(s): 10-Chloro-7H-benzo[de]benzo[4,5]imidazo[2,1-a]isoquinolin-7-one
• Empirical Formula (Hill Notation): C₁₈H₉ClN₂O
• CAS Number: 23982-76-5
• Molecular Weight: 304.73
• UNSPSC Code: 12352200
• NACRES: NA.77
• Assay: ≥98% (HPLC)
• Form: powder

Properties

• Quality Segment: 100
• assay: ≥98% (HPLC)
• form: powder
• color: white to beige
• solubility: DMSO: 0.5 mg/mL, clear (warmed)
• storage temp.: room temp
• SMILES string: O=C(C1=C2C(C=CC=C23)=CC=C1)N4C3=NC5=C4C=C(Cl)C=C5
• 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
• InChI key: ZJESJVGSDQOZAT-UHFFFAOYSA-N

Description

Biochem/physiol Actions

10-Cl-BBQ is an orally bioavailable, non-toxic benzimidazoisoquinoline derivative that 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 that 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.).

10-Cl-BBQ is an orally bioavailable, non-toxic benzimidazoisoquinoline derivative.

Safety Information

• Hazard Codes: H413
• Precautionary Statements: P273 - P501
• Hazard Classifications: Aquatic Chronic 4
• Storage Class: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point (°F): Not applicable
• Flash Point (°C): Not applicable