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Key Documents

SML1489

Sigma-Aldrich

FICZ

≥95% (HPLC), lyophilized powder, AhR agonist

Synonyme(s) :

5,11-Dihydro-indolo[3,2-b]carbazole-6-carboxaldehyde, 6-Formylindolo[3,2-b]carbazole

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About This Item

Formule empirique (notation de Hill):
C19H12N2O
Numéro CAS:
172922-91-7
Poids moléculaire :
284.31
Code UNSPSC :
12352200
Nomenclature NACRES :
NA.77

product name

FICZ, ≥95% (HPLC)

Niveau de qualité

100

Pureté

≥95% (HPLC)

Forme

lyophilized powder

Couleur

yellow

Solubilité

DMSO: 0.5 mg/mL, clear (warmed)

Température de stockage

−20°C

Actions biochimiques/physiologiques

FICZ (6-formylindolo(3,2b)carbazole) being a photooxidation product of tryptophan, might serve as a chemical messenger of light.
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.

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H302

Classification des risques

Acute Tox. 4 Oral

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 1

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

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Sibei Tao et al.
Journal of cellular and molecular medicine, 25(2), 1035-1047 (2020-12-07)
Acute kidney injury (AKI) is a multifactorial disease of various aetiologies. Aryl hydrocarbon receptor (AhR) is a ligand-activated transcription factor that responds to ligands to induce or repress gene expressions, thereby regulating a diverse spectrum of biological or pathophysiologic effects.
Yann Malaisé et al.
Toxicology in vitro : an international journal published in association with BIBRA, 69, 104993-104993 (2020-09-11)
The endocrine disruptor and food contaminant bisphenol A (BPA) is frequently present in consumer plastics and can produce several adverse health effects participating in the development of inflammatory and autoimmune diseases. Regulatory restrictions have been established to prevent risks for
Activation of the aryl hydrocarbon receptor by structurally diverse exogenous and endogenous chemicals.
Denison M S and Nagy S R
Annual Review of Pharmacology, 43(1), 309-334 (2003)
Aayushi Uberoi et al.
Cell host & microbe, 29(8), 1235-1248 (2021-07-03)
The epidermis forms a barrier that defends the body from desiccation and entry of harmful substances, while also sensing and integrating environmental signals. The tightly orchestrated cellular changes needed for the formation and maintenance of this epidermal barrier occur in
Rebecca Justiniano et al.
Photochemistry and photobiology, 97(1), 180-191 (2020-08-09)
UV-chromophores contained in human skin may act as endogenous sensitizers of photooxidative stress and can be employed therapeutically for the photodynamic elimination of malignant cells. Here, we report that 6-formylindolo[3,2-b]carbazole (FICZ), a tryptophan-derived photoproduct and endogenous aryl hydrocarbon receptor agonist
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