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Purity: ≥98%
FICZ is a novel and potent aryl hydrogen receptor (AhR) agonist (Kd = 70 pM), acting by inducing transient expression of CYP1A1 (cytochrome P450-1A1) in vitro.
| Targets |
Aryl hydrocarbon receptor (AHR) [1,2,4]
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|---|---|
| ln Vitro |
FICZ (0.01 nM-1 µM) either by itself or in conjunction with 50 nM MNF stimulates long-term CYP1A1 activity, which in turn causes oxidative stress and initiates apoptosis via pathways that are dependent on the mitochondria. FICZ inhibits cell proliferation at high concentrations but increases it at low quantities in HepG2 cells [1]. A substantial reduction in CEH activity was seen with FICZ (10,000-30,000 nM), with an estimated LC50 (95% confidence interval) of 14,000 nM. In CEH cultures, FICZ had a concentration-dependent influence on EROD activity; at 3, 8, and 24 hours, the average EC50 values were 0.016 nM, 0.80 nM, and 11 nM, respectively [2]. In parental iPSC lines and CYP1A1-targeted clones, FICZ treatment boosts CYP1A1 transcriptional expression in a dose-dependent manner [3]. Increased AHR activation is the outcome of CYP1 inhibition in the presence of FICZ, indicating that FICZ builds up in cells when cellular metabolism is inhibited. One enzyme that helps control the physiological effects of FICZ is CYP1 [4]. There are two more phases in the AHR-mediated signal transduction pathway: nuclear export and AHR protein degradation [5]. AhR-expressing cells downregulate the receptor via the ubiquitin/proteasome degradation pathway in response to exposure to AhR agonists [6].
- FICZ exhibits bi-functional roles in cell growth and apoptosis. At lower concentrations, it promotes cell proliferation, while at higher concentrations, it induces apoptosis in various cell lines. This effect is mediated through AHR activation, as shown by changes in AHR target gene expression and the involvement of downstream signaling pathways [1] - FICZ activates AHR, leading to time-dependent transcriptomic and biochemical responses. It induces the expression of AHR target genes such as CYP1A1, CYP1A2, and CYP1B1, with peak expression occurring earlier compared to TCDD. The activation of AHR by FICZ is transient, and the receptor undergoes rapid degradation after activation [2] |
| ln Vivo |
In animals with loss of CYP1A function, the biological effects of FICZ are enhanced in an Ahr2-dependent manner. This includes increased induction of AHR target genes in various tissues and amplified physiological responses related to AHR activation. The effects are attenuated in Ahr2-deficient animals, confirming the role of Ahr2 in mediating FICZ's actions [4]
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| Enzyme Assay |
To measure AHR activation by FICZ, a reporter gene assay is used. Cells transfected with an AHR-responsive luciferase reporter plasmid are treated with FICZ at different concentrations. After incubation, luciferase activity is measured, which reflects the activation level of AHR. Additionally, the activity of CYP1A1, a downstream target enzyme of AHR, is assessed using a specific substrate; the rate of substrate metabolism is quantified to determine enzyme activity [2,4]
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| Cell Assay |
- For cell growth and apoptosis studies: Cells are seeded in culture plates and treated with FICZ at concentrations ranging from low to high. Cell proliferation is measured using a cell counting assay or MTT assay at various time points. Apoptosis is evaluated by annexin V-FITC/PI staining followed by flow cytometry, and the expression of apoptotic markers (e.g., cleaved caspase-3) is detected by western blot. AHR and its target gene expression (e.g., CYP1A1) are analyzed by RT-PCR and western blot [1]
- For transcriptomic and biochemical response studies: Cells are treated with FICZ for different durations. Total RNA is extracted, and gene expression profiles are analyzed using microarrays or qPCR to assess changes in AHR target genes. Protein levels of AHR and CYP1A1 are measured by western blot to monitor AHR activation and degradation [2] |
| Animal Protocol |
- Wild-type, CYP1A-deficient, and Ahr2-deficient animals are used. FICZ is administered via intraperitoneal injection at a specific dose. After a certain period, tissues (e.g., liver, intestine) are collected. The expression of AHR target genes in these tissues is analyzed by RT-PCR and western blot. Physiological responses related to AHR activation are assessed through histological examination and biochemical assays. The dose and frequency of FICZ administration are adjusted based on the experimental design [4]
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| References |
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| Additional Infomation |
- FICZ is a naturally occurring AHR ligand and a highly bioactive signal substance. It is metabolized by CYP1A enzymes, and the loss of CYP1A function prolongs its biological activity in vivo [4]
- The transient activation of AHR by FICZ contrasts with the persistent activation induced by TCDD, leading to distinct time-dependent transcriptomic and biochemical responses [2] - The bi-functional role of FICZ in cell growth and apoptosis suggests it may have context-dependent effects, potentially influencing processes such as tissue homeostasis and carcinogenesis [1] 5,11-dihydroindolo[3,2-b]carbazole-12-carboxaldehyde is an indolocarbazole. |
| Molecular Formula |
C19H12N2O
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|---|---|
| Molecular Weight |
284.31138420105
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| Exact Mass |
282.079
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| Elemental Analysis |
C, 80.84; H, 3.57; N, 9.92; O, 5.67
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| CAS # |
172922-91-7
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| PubChem CID |
1863
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| Appearance |
Light yellow to khaki solid powder
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| Density |
1.4±0.1 g/cm3
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| Boiling Point |
463.8±45.0 °C at 760 mmHg
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| Flash Point |
191.1±34.1 °C
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| Vapour Pressure |
0.0±1.1 mmHg at 25°C
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| Index of Refraction |
1.772
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| LogP |
3.31
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
1
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
22
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| Complexity |
453
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| Defined Atom Stereocenter Count |
0
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| SMILES |
O=CC1C2=C(C=C3C=1C1C=CC=CC=1N3)C1C=CC=CC=1N2
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| InChi Key |
ZUDXFBWDXVNRKF-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C19H12N2O/c22-10-14-18-12-6-2-4-8-16(12)20-17(18)9-13-11-5-1-3-7-15(11)21-19(13)14/h1-10,20-21H
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| Chemical Name |
5,11-dihydroindolo[3,2-b]carbazole-12-carbaldehyde
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| Synonyms |
6-Formylindolo[3,2-b]carbazole; 172922-91-7; 6-formylindolo[3,2-b]carbazole; 5,11-dihydroindolo[3,2-b]carbazole-6-carbaldehyde; 5,11-dihydroindolo[3,2-b]carbazole-12-carbaldehyde; 6-formylindolo(3,2-b)carbazole; DTXSID30274338; 5,11-Dihydroindolo(3,2-b)carbazole-6-carbaldehyde; FICZ
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~10 mg/mL (~35.17 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: 1.11 mg/mL (3.90 mM) in 5% DMSO + 40% PEG300 + 5% Tween80 + 50% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with sonication.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 0.83 mg/mL (2.92 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 8.3 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. View More
Solubility in Formulation 3: 3.33 mg/mL (11.71 mM) in 15% Solutol HS 15 10% Cremophor EL 35% PEG 400 40% water (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.5173 mL | 17.5864 mL | 35.1729 mL | |
| 5 mM | 0.7035 mL | 3.5173 mL | 7.0346 mL | |
| 10 mM | 0.3517 mL | 1.7586 mL | 3.5173 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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