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 Details
| 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: | Blue Ice |
| |
| Long Term Storage: | -20°C |
| |
| Use/Stability: | Store solutions at -20°C for up to one month. |
| |
| Regulatory Status: | RUO - Research Use Only |
| |
Please mouse over
Product Literature References
Total parenteral nutrition impairs glucose metabolism by modifying the gut microbiome: P. Wang, et al.; Nat. Metab.
5, 331 (2023),
Abstract;
AhR Mediated Activation of Pro-Inflammatory Response of RAW 264.7 Cells Modulate the Epithelial-Mesenchymal Transition: P. Selvam, et al.; Toxics
10, 642 (2022),
Abstract;
Extensive Phenotype of Human Inflammatory Monocyte-Derived Dendritic Cells: F. Coutant, et al.; Cells
10, 1663 (2021),
Abstract;
Non-Genomic AhR-Signaling Modulates the Immune Response in Endotoxin-Activated Macrophages After Activation by the Environmental Stressor BaP: H. Großkop, et al.; Front. Immunol.
12, 620270 (2021),
Abstract;
Full Text
A genome-wide CRISPR screen identifies regulation factors of the TLR3 signalling pathway: L. Zablocki-Thomas, et al.; Innate Immun.
26, 459 (2020),
Abstract;
Full Text
An immunoregulatory and tissue-residency program modulated by c-MAF in human TH17 cells: D. Aschenbrenner, et al.; Nat. Immunol.
19, 1126 (2018),
Abstract;
Full Text
Aryl hydrocarbon receptor/IL-22/Stat3 signaling pathway is involved in the modulation of intestinal mucosa antimicrobial molecules by commensal microbiota in mice: J. Wang, et al.; Innate Immun.
24, 297 (2018),
Abstract;
TGFβ1 signaling sustains aryl hydrocarbon receptor (AHR) expression and restrains the pathogenic potential of TH17 cells by an AHR-independent mechanism: K.A. de Lima, et al.; Cell Death Dis.
9, 1130 (2018),
Abstract;
Full Text
Tryptophan photo-product FICZ upregulates AHR/MEK/ERK-mediated MMP1 expression: Implications in anti-fibrotic phototherapy: M. Murai, et al.; J. Dermatol. Sci.
91, 97 (2018),
Abstract;
Full Text
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;
The impact of age and gut microbiota on Th17 and Tfh cells in K/BxN autoimmune arthritis: F. Teng, et al.; Arthritis Res. Ther.
19, 188 (2017),
Application(s): Mouse T Cells,
Abstract;
Full Text
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;
