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6-Formylindolo(3,2-b)carbazole

Ah receptor ligand
 
BML-GR206-0100 100 µg 94.00 USD
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A tryptophan-derived, high affinity aryl hydrocarbon receptor ligand (Kd=7x10-11 M). Proposed to be an endogenous AhR ligand. Induces rapid and transient expression of cytochrome P450-1A1 (CYP1A1) in human cells at 100 pM.

Product Specification

Alternative Name:FICZ
 
Formula:C19H12N2O
 
MW:284.3
 
CAS:172922-91-7
 
Purity:≥95% (HPLC)
 
Appearance:Yellow solid.
 
MeltingPoint:>300°C
 
Solubility:Soluble in DMSO (10mg/ml).
 
Shipping:Shipped on Blue Ice
 
Long Term Storage:-20°C
 
Use/Stability:Store solutions at -20°C for up to one month.
 
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Product Literature References

Aryl hydrocarbon receptor is required for optimal B-cell proliferation: M. Villa, et al.; EMBO J. 36, 116 (2017), Abstract;
T-bet overexpression regulates AHR-mediated Th-17 differentiation through an IFNγ-independent pathway: M. Yokosawa, et al.; Clin. Exp. Immunol. 188, 22 (2017), Abstract;
Balancing intestinal and systemic inflammation through cell type-specific expression of the aryl hydrocarbon receptor repressor: O. Brandstatter, et al.; Sci. Rep. 6, 26091 (2016), Application(s): In vitro T cell differentiation, Abstract; Full Text
The Aryl Hydrocarbon Receptor and Its Ligands Inhibit Myofibroblast Formation and Activation: Implications for Thyroid Eye Disease: C.F. Woeller, et al.; Am. J. Pathol. 186, 3189 (2016), Abstract;
L-Tryptophan as a Novel Potential Pharmacological Treatment for Wound Healing via Aryl Hydrocarbon Receptor Activation: N. Barouti, et al.; Dermatology 230, 332 (2015), Application(s): Cell Culture, Abstract; Full Text
Tryptophan derivatives regulate the transcription of Oct4 in stem-like cancer cells: J. Cheng, et al.; Nat. Commun. 6, 7209 (2015), Abstract; Full Text
Decreased expression of the aryl hydrocarbon receptor in ocular Behcet's disease: C. Wang, et al.; Mediators Inflamm. 2014, 195094 (2014), Abstract; Full Text
Differential consequences of two distinct AhR ligands on innate and adaptive immune responses to influenza A virus: J.L. Wheeler, et al.; Toxicol. Sci. 137, 324 (2014), Abstract; Full Text
Identification of amino acid residues in the ligand-binding domain of the aryl hydrocarbon receptor causing the species-specific response to omeprazole: possible determinants for binding putative endogenous ligands: K. Shiizaki, et al.; Mol. Pharmacol. 85, 279 (2014), Abstract; Full Text
The Ah receptor regulates growth factor expression in head and neck squamous cell carcinoma cell lines: K. John, et al.; Mol. Carcinog. 53, 765 (2014), Abstract;
The aryl hydrocarbon receptor promotes IL-10 production by NK cells: S. Wagage, et al.; J. Immunol. 192, 1661 (2014), Abstract;
The aryl hydrocarbon receptor: differential contribution to T helper 17 and T cytotoxic 17 cell development: M.D. Hayes, et al.; PLoS One 9, e106955 (2014), Abstract; Full Text
Non-dioxin-like AhR ligands in a mouse peanut allergy model: V.J. Schulz, et al.; Toxicol. Sci. 128, 92 (2012), Abstract; Full Text
Photo-oxidation products of skin surface squalene mediate metabolic and inflammatory responses to solar UV in human keratinocytes: V. Kostyuk, et al.; PLoS One 7, e44472 (2012), Abstract; Full Text
Tryptamine serves as a proligand of the AhR transcriptional pathway whose activation is dependent of monoamine oxidases: L. Vikström Bergander, et al.; Mol. Endocrinol. 26, 1542 (2012), Abstract;
IL-17RA is required for CCL2 expression, macrophage recruitment, and emphysema in response to cigarette smoke: K. Chen, et al.; PLoS One 6, e20333 (2011), Abstract; Full Text
Proinflammatory environment dictates the IL-17-producing capacity of human invariant NKT cells: L. Moreira-Teixeira, et al.; J. Immunol. 186, 5758 (2011), Abstract; Full Text
The aryl hydrocarbon receptor links TH17-cell-mediated autoimmunity to environmental toxins: M. Veldhoen, et al.; Nature 453, 106 (2008), Abstract;
Rapid and transient induction of CYP1A1 gene expression in human cells by the tryptophan photoproduct 6-formylindolo[3,2-b]carbazole: Y.D. Wei et al.; Chem. Biol. Interact. 110, 39 (1998), Abstract;
Structure elucidation of two tryptophan-derived, high affinity Ah receptor ligands: U. Rannug et al.; Chem. Biol. Drug. Des. 2, 841 (1995), Abstract;
Certain photooxidized derivatives of tryptophan bind with very high affinity to the Ah receptor and are likely to be endogenous signal substances: A. Rannug et al.; J. Biol. Chem. 262, 15422 (1987), Abstract;

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