172922-91-7

Basic information

• Product Name: 6-FORMYLINDOLO [3,2-B] CARBAZOLE
• Synonyms: 6-FORMYLINDOLO [3,2-B] CARBAZOLE;Indolo[3,2-b]carbazole-6-carbaldehyde;5,11-dihydroindolo[3,2-b]carbazole-6-carbaldehyde;FICZ
• CAS NO: 172922-91-7
• Molecular Formula: C19H10N2O
• Molecular Weight: 282.3
• Mol File: 172922-91-7.mol

Chemical Properties

• Boiling Point: 630.3±35.0 °C(Predicted)
• Appearance: /
• Density: 1.463±0.06 g/cm3(Predicted)
• Storage Temp.: -20°C
• Solubility: Soluble in DMSO (up to 10 mg/ml).
• PKA: 15.66±0.30(Predicted)
• Stability: Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 1 month.
• CAS DataBase Reference: 6-FORMYLINDOLO [3,2-B] CARBAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-FORMYLINDOLO [3,2-B] CARBAZOLE(172922-91-7)
• EPA Substance Registry System: 6-FORMYLINDOLO [3,2-B] CARBAZOLE(172922-91-7)

Safety Data

• WGK Germany: 1
• Hazardous Substances Data: 172922-91-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
6-Formylindolo[3,2-b]carbazole is used as a therapeutic agent for suppressing pulmonary eosinophilia and Th2-type cytokine production. This application is particularly relevant in the treatment of allergic asthma, as it has been demonstrated to exhibit these effects in a mouse model of ovalbumin-induced allergic asthma.
Used in Research and Development:
FICZ is utilized as a research tool in the study of the aryl hydrocarbon receptor (AhR) and its role in various biological processes. As a potent ligand for AhR, FICZ can help researchers understand the receptor's function, signaling pathways, and potential therapeutic applications in different diseases.
Used in Drug Discovery:
6-Formylindolo[3,2-b]carbazole may be employed in the development of new drugs targeting the aryl hydrocarbon receptor (AhR). Given its high affinity for AhR, FICZ can serve as a lead compound or a starting point for the design and synthesis of novel AhR modulators with potential applications in various diseases, including asthma and other immune-related disorders.

Biochem/physiol Actions

FICZ is a potent high affinity ligand of the aryl hydrocarbon receptor (AhR), which is a ligand-activated transcription factor that activates the expression of aromatic hydrocarbon metabolizing enzyme genes such as the CYP1A1 gene and has also been shown to have multiple additional roles in cell-cycle regulation, development and maturation of many tissues, control of inflammation, and immune response. FICZ is a photoproduct of tryptophan and is believed to be an endogenous AhR ligand. It is extremely potent, with a Kd value of 0.07 nM.

References

1) Rannung?et al. (1987)?Certain photooxidized derivatives of tryptophan bind with very high affinity to the Ah receptor and are likely to be endogenous signal substances; J. Biol. Chem.,?262?15422 .2) Wincent?et al. (2009)?The Suggested Physiologic Aryl Hydrocarbon Receptor Activator and Cytochrome P4501 Substrate 6-Formylindolo[3,2-b}carbazole is Present in Humans; J. Biol. Chem.,?284?2690

Upstream product

• 229020-86-4 ethyl 5,11-dihydroindolo[3,2-b]carbazole-6-carboxylate 
• 1432053-78-5 (5,11-Dihydroindolo[3,2-b]carbazol-6-yl)methanol 
• 229020-82-0 N,N'-di-tert-butoxycarbonyl-6-formylindolo[3,2-b]carbazole 
• 204455-46-9 2,2-dichloro-1-[2-(1H-indol-3-ylmethyl)-1H-indol-3-yl]-ethanone 

Relevant articles and documents

Engineered Th17 Cell Differentiation Using a Photoactivatable Immune Modulator

T helper 17 (Th17) cells, an important subset of CD4+ T cells, help to eliminate extracellular infectious pathogens that have invaded our tissues. Despite the critical roles of Th17 cells in immunity, how the immune system regulates the production and maintenance of this cell type remains poorly understood. In particular, the plasticity of these cells or their dynamic ability to trans-differentiate into other CD4+ T cell subsets remains mostly uncharacterized. Here, we report a synthetic immunology approach using a photoactivatable immune modulator (PIM) to increase Th17 cell differentiation on demand with spatial and temporal precision to help elucidate this important and dynamic process. In this chemical strategy, we developed a latent agonist that upon photochemical activation releases a small-molecule ligand that targets the aryl hydrocarbon receptor (AhR) and ultimately induces Th17 cell differentiation. We used this chemical tool to control AhR activation with spatiotemporal precision within cells and to modulate Th17 cell differentiation on demand using UV light illumination. We envision that this approach will enable an understanding of the dynamic functions and behaviors of Th17 cells in vivo during immune responses and in mouse models of inflammatory disease.

Concise synthesis of 6-formylindolo[3,2-b]carbazole (FICZ)

A concise synthesis of 6-formylindolo[3,2-b]carbazole (FICZ), a potent ligand of the aryl hydrocarbon receptor (AhR), has been established. The conjugate addition of the enolate derived from indolylacetate 2 to 2-chloro-3-formylindole 3 was accomplished. The following cyclization reaction under the acidic conditions gave the indolo[3,2-b]carbazole skeleton.

Synthesis of metabolites of the Ah receptor ligand 6-formylindolo[3,2-b] carbazole

Synthesis of the five mono- and di-hydroxylated metabolites of the aryl hydrocarbon receptor high affinity ligand 6-formylindolo[3,2-b]carbazole is described. The structures of the metabolites were unequivocally established as 2-hydroxy-, 8-hydroxy-, 2,10-dihydroxy-, 4,8-dihydroxy- and 2,8- dihydroxyindolo[3,2-b]carbazole-6-carboxaldehyde. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

Syntheses of 6-substituted indolo[3,2-b]carbazoles, including 6- formylindolo[3,2-b]carbazole, an extremely efficient ligand for the TCDD (Ah) receptor

A number of 6-substituted indolo[3,2-b]carbazoles have been synthesized using 2,3-diindolylmethane 5 as a crucial precursor. Most notably, 6- formylindolo[3,2-b]carbazole 3 has been synthesized, and thereby a previously assigned structure has been confirmed. 6-Formylindolo[3,2-b]carbazole 3 is an extremely efficient ligand for the TCDD (Ah) receptor. A much improved synthesis of 2,3-diindolylmethane 5 has also been developed.

Synthesis of 6-formylindolo[3,2-b]carbazole, an extremely potent ligand for the aryl hydrogen (Ah) receptor

Dichloroacetylation of 2,3-diindolylmethane followed by a tandem cyclization-hydrolysis reaction under acidic conditions gave the title compound.