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Safety Information

SML1798

Sigma-Aldrich

10-Cl-BBQ

≥98% (HPLC)

Synonym(s):

10-Chloro-7H-benzo[de]benzo[4,5]imidazo[2,1-a]isoquinolin-7-one

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About This Item

Empirical Formula (Hill Notation):
C18H9ClN2O
CAS Number:
23982-76-5
Molecular Weight:
304.73
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

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

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.).

Hazard Statements

H413

Precautionary Statements

P273 - P501

Hazard Classifications

Aquatic Chronic 4

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

SML1798-5MG:
SML1798-25MG:
SML1798-VAR:
SML1798-BULK:

Certificates of Analysis (COA)

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Allison K Ehrlich et al.
Journal of immunology (Baltimore, Md. : 1950), 196(1), 264-273 (2015-11-18)
Aryl hydrocarbon receptor (AhR) activation by high-affinity ligands mediates immunosuppression in association with increased regulatory T cells (Tregs), making this transcription factor an attractive therapeutic target for autoimmune diseases. We recently discovered 10-chloro-7H-benzimidazo[2,1-a]benzo[de]iso-quinolin-7-one (10-Cl-BBQ), a nanomolar affinity AhR ligand with
Sumit Punj et al.
PloS one, 9(2), e88726-e88726 (2014-03-04)
The aryl hydrocarbon receptor (AhR) is a ligand-activated transcription factor that plays multiple roles in regulation of immune and inflammatory responses. The ability of certain AhR ligands to induce regulatory T cells (Tregs) has generated interest in developing AhR ligands

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