Benzanthrone
Based on 1 Customer Validation
Benzanthrone is an immunotoxic, pro-inflammatory Photosensitizer. Benzanthrone upregulates iNOS, COX-2 and inflammatory cytokines; activates ERK1/2, p38, JNK, AP-1 and NF-κB; inhibits Nrf2; and induces oxidative stress and DNA damage. Upon radiation exposure, Benzanthrone generates singlet oxygen and superoxide anion radicals, induces photohemolysis and lipid peroxidation, and alters the levels of skin xenobiotic enzymes. Benzanthrone exhibits differential genotoxicity in different cell lines. Benzanthrone possesses skin tumor-initiating and promoting activities. Benzanthrone can be used in skin tumor-related studies.
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- Pureza: 99.69%
- No. CAS: 82-05-3
- Fòrmula: C17H10O
- Peso molecular:230.26
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Almacenamiento:
Store at room temperature 3 years.
In solvent -80°C, 2 years , -20°C, 1 year
To place orders, for customer services and technical support, please contact: MedChemExpress USA
Tel: 609-228-6898 E-mail: [email protected] [email protected]
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Chemical Information
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Solvente y solubilidad
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Ver todos los productos específicos de isoformas AP-1
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Actividad biológica
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iNOS |
COX-2 |
ERK1 |
ERK2 |
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Cell Line
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Type | Value | Description | References |
|---|---|---|---|---|
| CHO | Inhibition |
127.309 %
Compound: BENZANTHRONE
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Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM
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[PMID: 23571415] |
| CHO | Inhibition |
69.7396 %
Compound: BENZANTHRONE
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Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM
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[PMID: 23571415] |
Benzanthrone (10 μM; 18 h) does not induce detectable DNA adduct formation in human A549 or HepG2 cells[2].
Benzanthrone (10 μM; 18 h) induces significant genotoxic lesions (DNA strand breaks/alkali-labile sites) in human A549 cells, but not in human HepG2 cells[2].
Benzanthrone (10 μM; 18 h) induces significant oxidative DNA damage in human A549 and HepG2 cells, with greater damage observed in A549 cells[2].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
Benzanthrone (0.3%; topical administration; once daily for 3 consecutive days, sensitization; 0.15%; topical administration; single dose, challenge) induces significant delayed-type hypersensitivity in female Balb/c mice, characterized by ear swelling, increased MPO activity, and inflammatory cell infiltration[1].
Benzanthrone (0.5-2.0 × 10-7 mol/cm2; percutaneous administration; single dose) acts as a potent skin photosensitizer in guinea pigs. After exposure to natural sunlight or simulated UVA radiation, the duration of its induced erythema, edema, pigmentation and skin toxicity increases in a dose-dependent manner[4].
Topical administration of commercial Benzanthrone (150 nmol; twice weekly for 30 weeks) induces abnormal changes in xenobiotic-metabolizing enzymes in mouse skin[5].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Animal Model:Balb/c (female, 6-8 weeks old, 18-20 g)[1]
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Dosage:3.25 mg/kg; 7.5 mg/kg; 15 mg/kg
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Administration:i.p.; daily; 1 week
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Result:Caused dose-dependent inflammation at 7.5 mg/kg and 15 mg/kg.
Induced splenic hyperplasia with megakaryocyte infiltration, and lung alveolar septal thickening, edema, and focal hemorrhages at 15 mg/kg.
Showed no notable changes at 3.25 mg/kg.
Increased splenic MPO activity by 157% and lung MPO activity by 193% at 7.5 mg/kg.
Increased splenic MPO activity by 571% and lung MPO activity by 666% at 15 mg/kg.
Increased ROS generation (2-fold), lipid peroxidation (106%), and protein carbonyl content (25%); decreased GSH content (55%), SOD activity (24%), GST activity (37%), GR activity (34%), catalase activity (12%), and GPx activity (74%); reduced Nrf2 protein levels; and increased γ-H2AX protein levels (1.9-fold) in spleen at 7.5 mg/kg.
Increased ROS generation (2.9-fold), lipid peroxidation (450%), and protein carbonyl content (173%); decreased GSH content (73%), SOD activity (66%), GST activity (75%), GR activity (55%), catalase activity (29%), and GPx activity (85%); further reduced Nrf2 protein levels; and increased γ-H2AX protein levels (2.2-fold) in spleen at 15 mg/kg.
Increased TNF-α (1.2-fold), IL-4 (1.5-fold), and IL-1 (81-fold) in serum at 7.5 mg/kg.
Increased IL-17 (4.8-fold), TNF-α (1.52-fold), IFN-γ (4.2-fold), IL-4 (4.25-fold), IL-10 (12.3-fold), and IL-1 (427-fold) in serum at 15 mg/kg.
Dose-dependently increased mRNA levels of IL-4, IL-1, IL-10, IFN-γ, and TNF-α in splenic cytokine at 7.5 mg/kg and 15 mg/kg.
Increased p-JNK (2.5-fold), p-ERK (1.6-fold), and p-p38 (2-fold) at 7.5 mg/kg.
Increased p-JNK (2.9-fold), p-ERK (2.2-fold), and p-p38 (2.3-fold) at 15 mg/kg.
Increased p-NF-κB (1.8-fold), c-fos (1.9-fold), c-jun (2-fold), COX-2 (2.2-fold), and iNOS (2-fold) at 7.5 mg/kg.
Increased p-NF-κB (2.3-fold), c-fos (2.9-fold), c-jun (3-fold), COX-2 (2.9-fold), and iNOS (3-fold) at 15 mg/kg.
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Animal Model:Balb/c (female)[1]
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Dosage:0.3% (sensitization); 0.15% (challenge)
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Administration:topical; once daily for 3 consecutive days (sensitization); single dose (challenge)
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Result:Increased ear swelling by 69% compared to vehicle control.
Significantly elevated ear pinna MPO activity.
Induced epidermal hyperplasia protruding into the dermis and infiltration of mixed inflammatory cells.
Chemical Information
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No. CAS 82-05-3
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Appearance Solid
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Peso molecular 230.26
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Fòrmula C17H10O
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Color Light yellow to yellow
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SMILES
O=C1C2=C(C3=C4C1=CC=CC4=CC=C3)C=CC=C2
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Envío
Room temperature in continental US; may vary elsewhere.
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Almacenamiento
Store at room temperature 3 years
In solvent -80°C 2 years -20°C 1 year
Solvente y solubilidad
DMSO : 4 mg/mL (17.37 mM; ultrasonic and warming and heat to 60°C; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 2 years; -20°C, 1 year. When stored at -80°C, please use it within 2 years. When stored at -20°C, please use it within 1 year.
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 2 years; -20°C, 1 year. When stored at -80°C, please use it within 2 years. When stored at -20°C, please use it within 1 year.
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
Pureza y Documentación
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Ficha de datos (284 KB)
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SDS (393 KB)
- English - EN (393 KB)
- Français - FR (393 KB)
- Deutsch - DE (393 KB)
- Norwegian - NO (393 KB)
- Español - ES (393 KB)
- Swedish - SV (393 KB)
- Italian - IT (393 KB)
- Korean - KR (393 KB)
- Portuguese - PT (393 KB)
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Instrucciones de manejo (2659 KB)
Referencias
[1]. Tewari P, et al. Benzanthrone induced immunotoxicity via oxidative stress and inflammatory mediators in Balb/c mice. Immunobiology. 2015;220(3):369-381. [Content Brief]
[2]. Nagy E, et al. DNA adduct formation and oxidative stress from the carcinogenic urban air pollutant 3-nitrobenzanthrone and its isomer 2-nitrobenzanthrone, in vitro and in vivo. Mutagenesis. 2007;22(2):135-145. [Content Brief]
[3]. Ramdahl T. Polycyclic aromatic ketones in environmental samples. Environ Sci Technol. 1983 Nov 1;17(11):666-70. [Content Brief]
[4]. Srivastava LP, et al. Photosensitizing potential of benzanthrone. Food Chem Toxicol. 1990;28(9):653-658. [Content Brief]
[5]. Dwivedi N, et al. Skin tumorigenic potential of benzanthrone: prevention by ascorbic acid. Food Chem Toxicol. 2013;59:687-695. [Content Brief]
Complete Stock Solution Preparation Table
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 2 years; -20°C, 1 year. When stored at -80°C, please use it within 2 years. When stored at -20°C, please use it within 1 year.
| Optional Solvent | Concentration Solvent Mass | 1 mg | 5 mg | 10 mg | 25 mg |
|---|---|---|---|---|---|
| DMSO | 1 mM | 4.3429 mL | 21.7146 mL | 43.4292 mL | 108.5729 mL |
| 5 mM | 0.8686 mL | 4.3429 mL | 8.6858 mL | 21.7146 mL | |
| 10 mM | 0.4343 mL | 2.1715 mL | 4.3429 mL | 10.8573 mL | |
| 15 mM | 0.2895 mL | 1.4476 mL | 2.8953 mL | 7.2382 mL |
Benzanthrone Related Classifications
HY-W026930 Related Classifications
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