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Ah receptor ligand
A tryptophan-derived, high affinity aryl hydrocarbon receptor ligand (Kd=7×10-11 M). Proposed to be an endogenous AhR ligand. Induces rapid and transient expression of cytochrome P450-1A1 (CYP1A1) in human cells at 100 pM.
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Product Details
| Alternative Name |
FICZ |
|---|---|
| Appearance |
Yellow solid. |
| CAS |
172922-91-7 |
| Couple Target |
Ah receptor |
| Couple Type |
Ligand |
| Formula |
C19H12N2O |
| MW |
284.3 |
| MeltingPoint |
>300°C |
| Purity |
≥95% (HPLC) |
| Solubility |
Soluble in DMSO (10mg/ml). |
Handling & Storage
| Use/Stability |
As indicated on product label or CoA when stored as recommended. Store solutions at -20°C for up to one month. |
|---|---|
| Long Term Storage |
-20°C |
| Shipping |
Blue Ice |
| Regulatory Status |
RUO – Research Use Only |
|---|
- Regulation of the STAT3 pathway by lupus susceptibility gene Pbx1 in T cells: T. Roach, et al.; Mol. Immunol. 165, 1 (2024), Abstract
- Bioluminescence imaging of Cyp1a1-luciferase reporter mice demonstrates prolonged activation of the aryl hydrocarbon receptor in the lung: Veland, N., Gleneadie, H. J., et al.; Commun. Biol. 7, 442 (2024), Abstract
- Bioluminescence imaging ofCyp1a1-luciferase reporter mice demonstrates prolonged activation of the aryl hydrocarbon receptor in the lung: Veland, N., Gleneadie, H. J., et al.; bioRxiv , (2023)
- 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
- Intestinal Stem Cells Damaged by Deoxycholic Acid via AHR Pathway Contributes to Mucosal Barrier Dysfunction in High-Fat Feeding Mice: Liu, L., Xu, J., et al.; Int. J. Mol. Sci. 23, (2022), Abstract
- Induction of the hepatic aryl hydrocarbon receptor by alcohol dysregulates autophagy and phospholipid metabolism via PPP2R2D: Kim, Y. S., Ko, B., et al.; Nat. Commun. 13, 6080 (2022), Abstract
- Extensive Phenotype of Human Inflammatory Monocyte-Derived Dendritic Cells: F. Coutant, et al.; Cells 10, 1663 (2021), Abstract
- AHR Regulates NK Cell Migration via ASB2-Mediated Ubiquitination of Filamin A: Shin, J. H., Moreno-Nieves, U. Y., et al.; Front. Immunol. 12, 624284 (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
- 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
- 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
- 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
- Visualization of RNA at the Single Cell Level by Fluorescent in situ Hybridization Coupled to Flow Cytometry: Coillard, A., Segura, E., et al.; Bio Protoc. 8, e2892 (2018), Abstract
- Aryl hydrocarbon receptor is required for optimal B-cell proliferation: M. Villa, et al.; EMBO J. 36, 116 (2017), Abstract
- In vitro Treatment of Mouse and Human Cells with Endogenous Ligands for Activation of the Aryl Hydrocarbon Receptor: Yamada, T., Takaoka, A., et al.; Bio Protoc. 7, e2097 (2017), Abstract
- HELZ2 Is an IFN Effector Mediating Suppression of Dengue Virus: Fusco, D. N., Pratt, H., et al.; Front. Microbiol. 8, 240 (2017), Abstract
- FICZ Exposure and Viral Infection in Mice: Yamada, T., Takaoka, A., et al.; Bio Protoc. 7, e2096 (2017), Abstract
- Aryl Hydrocarbon Receptor Controls Monocyte Differentiation into Dendritic Cells versus Macrophages: Goudot, C., Coillard, A., et al.; Immunity 47, 582 (2017), Abstract
- Aryl hydrocarbon receptor (AhR)-dependent regulation of pulmonary miRNA by chronic cigarette smoke exposure: Rogers, S., de Souza, A. R., et al.; Sci. Rep. 7, 40539 (2017), Abstract
- Segmented Filamentous Bacteria Provoke Lung Autoimmunity by Inducing Gut-Lung Axis Th17 Cells Expressing Dual TCRs: Bradley, C. P., Teng, F., et al.; Cell Host Microbe 22, 697 (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
- CARD9 impacts colitis by altering gut microbiota metabolism of tryptophan into aryl hydrocarbon receptor ligands: Lamas, B., Richard, M. L., et al.; Nat. Med. 22, 598 (2016), Abstract
- Ultraviolet light converts propranolol, a nonselective β-blocker and potential lupus-inducing drug, into a proinflammatory AhR ligand: Dorgham, K., Amoura, Z., et al.; Eur. J. Immunol. 45, 3174 (2015), Abstract
- The Tryptophan-Derived Endogenous Aryl Hydrocarbon Receptor Ligand 6-Formylindolo[3,2-b]Carbazole Is a Nanomolar UVA Photosensitizer in Epidermal Keratinocytes: Park, S. L., Justiniano, R., et al.; J. Invest. Dermatol. 135, 1649 (2015), Abstract
- Tryptophan derivatives regulate the transcription of Oct4 in stem-like cancer cells: J. Cheng, et al.; Nat. Commun. 6, 7209 (2015), Abstract — Full Text
- 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
- 6-Formylindolo(3,2-b)Carbazole (FICZ) Modulates the Signalsome Responsible for RA-Induced Differentiation of HL-60 Myeloblastic Leukemia Cells: Bunaciu, R. P., Jensen, H. A., et al.; PLoS One 10, e0135668 (2015), Abstract
- An Aryl Hydrocarbon Receptor from the Salamander Ambystoma mexicanum Exhibits Low Sensitivity to 2,3,7,8-Tetrachlorodibenzo-p-dioxin: Shoots, J., Fraccalvieri, D., et al.; Environ. Sci. Technol. 49, 6993 (2015), Abstract
- 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 transcription Factor AHR prevents the differentiation of a stage 3 innate lymphoid cell subset to natural killer cells: Hughes, T., Briercheck, E. L., et al.; Cell Rep. 8, 150 (2014), Abstract
- Decreased expression of the aryl hydrocarbon receptor in ocular Behcet’s disease: C. Wang, et al.; Mediators Inflamm. 2014, 195094 (2014), Abstract — Full Text
- The aryl hydrocarbon receptor promotes IL-10 production by NK cells: S. Wagage, et al.; J. Immunol. 192, 1661 (2014), Abstract
- 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
- 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
- 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
- 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
- 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
- FICZ, a Tryptophan photoproduct, suppresses pulmonary eosinophilia and Th2-type cytokine production in a mouse model of ovalbumin-induced allergic asthma: K.T. Jeong, et al.; Int. Immunopharmacol. 13, 377 (2012), Abstract
- Non-dioxin-like AhR ligands in a mouse peanut allergy model: V.J. Schulz, et al.; Toxicol. Sci. 128, 92 (2012), Abstract — Full Text
- 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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