An AhR activator
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6-Formylindolo[3,2-b]carbazole

Item No. 19529

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5,11-dihydro-indolo[3,2-b]carbazole-6-carboxaldehyde
CAS Number
172922-91-7
Synonyms
  • FICZ
Molecular Formula
C19H12N2O
Formula Weight
284.3
Purity
≥95%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 0.5 mg/mlDMSO: 0.3 mg/ml
λmax
214, 226, 249, 307, 334, 383, 454 nm
SMILES
[H]C(C1=C2C(C(C=CC=C3)=C3N2)=CC4=C1C(C=CC=C5)=C5N4)=O
InChi Code
InChI=1S/C19H12N2O/c22-10-14-18-12-6-2-4-8-16(12)20-17(18)9-13-11-5-1-3-7-15(11)21-19(13)14/h1-10,20-21H
InChi Key
ZUDXFBWDXVNRKF-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

    $69

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    1 mg

    $127

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    5 mg

    $493

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    10 mg

    $786

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    Product Description

    6-Formylindolo[3,2-b]carbazole (FICZ) is a degradation product of tryptophan upon exposure to visible light that activates the aryl hydrocarbon receptor (AhR; Kd = 70 pM).1 This endogenous AhR ligand is also a good substrate for cytochromes P450 (CYP) 1A1, 1A2, and 1B1 (Kis = 15.4, 3.9, and 13.3 µM, respectively).2 When activated by either environmental toxins or endogenous ligands, the AhR induces detoxifying enzymes and modulates immune cell differentiation. FICZ has been used to study the immunomodulatory and host defense mechanisms of AhR signaling pathways.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Rannug, U., Rannug, A., Sjöberg, U., et al. Structure elucidation of two tryptophan-derived, high affinity Ah receptor ligands. Chem. Biol. 2(12), 841-845 (1995).

    2. Wincent, E., Amini, N., Leuecke, S., et al. The suggested physiologic aryl hydrocarbon receptor activator and cytochrome P4501 substrate 6-formylindolo[3,2-b]carbazole is present in humans. The Journal of Biological Chemisty 284(5), 2690-2696 (2009).

    3. Moura-Alves, P., Faé, K., Houthuys, E., et al. AhR sensing of bacterial pigments regulates antibacterial defence. Nature 512(7515), 387-392 (2014).