2. Apoptosis Immunology/Inflammation Stem Cell/Wnt MAPK/ERK Pathway NF-κB Cell Cycle/DNA Damage
  3. Photosensitizer NO Synthase COX ERK p38 MAPK JNK AP-1 NF-κB Keap1-Nrf2 DNA/RNA Synthesis
  4. Benzanthrone

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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Benzanthrone

Benzanthrone Chemical Structure

CAS No. : 82-05-3

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Benzanthrone Related Antibodies

Top Publications Citing Use of Products

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nNOS iNOS eNOS

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COX COX-1 COX-2 COX-3

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ERK ERK1 ERK2 ERK5 ERK8

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p38 MAPK Akt1 p38α p38β MAPK13 p38δ p38γ

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JNK1 JNK2 JNK3 JNK

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c-Fos FosB Fra1/FOSL1 Fra2/FOSL2 c-Jun

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NF-κB NF-κB1/p50 RelA/p65 RelB c-Rel

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RNASE L DNA Polymerases RNA Polymerases Helicases DNA Ligase

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Description

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[1][2][3][4][5].

IC50 & Target[1]

iNOS

 

COX-2

 

ERK1

 

ERK2

 

Cellular Effect
Cell Line Type Value Description References
CHO Inhibition
127.309 %
Compound: BENZANTHRONE
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
[PMID: 23571415]
CHO Inhibition
69.7396 %
Compound: BENZANTHRONE
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
[PMID: 23571415]
In Vitro

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 Related Antibodies
In Vivo

Benzanthrone (i.p.; daily; for 1 week, at doses of 3.25-15 mg/kg) induces dose-dependent immunotoxicity and inflammatory responses in female Balb/c mice via oxidative stress, DNA damage, activation of the MAPK pathway, and upregulation of inflammatory cytokines and markers, with the most significant effects observed at the 15 mg/kg dose[1].
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.

Animal Model: Balb/c (female, 6-8 weeks old, 18-20 g)[1]
Dosage: 3.25 mg/kg; 7.5 mg/kg; 15 mg/kg
Administration: i.p.; daily; 1 week
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.
Animal Model: Balb/c (female)[1]
Dosage: 0.3% (sensitization); 0.15% (challenge)
Administration: topical; once daily for 3 consecutive days (sensitization); single dose (challenge)
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.
Molecular Weight

230.26

Formula

C17H10O
CAS No.
Appearance

Solid

Color

Light yellow to yellow

SMILES

O=C1C2=C(C3=C4C1=CC=CC4=CC=C3)C=CC=C2
Shipping

Room temperature in continental US; may vary elsewhere.
Storage

Store at room temperature 3 years

In solvent -80°C 2 years
-20°C 1 year
Solvent & Solubility
In Vitro: 

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)

Preparing
Stock Solutions
Concentration Solvent Mass 1 mg 5 mg 10 mg
1 mM 4.3429 mL 21.7146 mL 43.4292 mL
5 mM 0.8686 mL 4.3429 mL 8.6858 mL
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* 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, 1 year; -20°C, 6 months. When stored at -80°C, please use it within 1 year. When stored at -20°C, please use it within 6 months.

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Purity & Documentation
References

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, 1 year; -20°C, 6 months. When stored at -80°C, please use it within 1 year. When stored at -20°C, please use it within 6 months.

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
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Benzanthrone Related Classifications

Help & FAQs
  • Do most proteins show cross-species activity?

    Species cross-reactivity must be investigated individually for each product. Many human cytokines will produce a nice response in mouse cell lines, and many mouse proteins will show activity on human cells. Other proteins may have a lower specific activity when used in the opposite species.

Keywords:

Benzanthrone82-05-3PhotosensitizerNO SynthaseCOXERKp38 MAPKJNKAP-1NF-κBKeap1-Nrf2DNA/RNA SynthesisNitric oxide synthasesNOSCyclooxygenaseExtracellular signal regulated kinasesc-Jun N-terminal kinaseActivator Protein 1Nuclear factor-κBNuclear factor-kappaBhuman HepG2 cellsiNOSNrf2human A549 cellsCOX-2p38ERK1/2Inhibitorinhibitorinhibit

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