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Chemical Structure| 56-57-5 Chemical Structure| 56-57-5

Structure of 4-Nitroquinoline N-oxide
CAS No.: 56-57-5

Chemical Structure| 56-57-5

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4-Nitroquinoline N-oxide is a chemical carcinogen that induces DNA damage and promotes apoptosis in cells through the p53 pathway. It is significant for cancer mechanism research.

Synonyms: 4-NQO; Nitrochin

4.5 *For Research Use Only !

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Product Citations

Product Citations

Boyao Zhang ; George-Eugen Maftei ; Bartosz Bartmanski ; Michael Zimmermann ;

Abstract: Organic carcinogens, in particular DNA-reactive compounds, contribute to the irreversible initiation step of tumorigenesis through introduction of genomic instability. Although carcinogen bioactivation and detoxification by human enzymes has been extensively studied, carcinogen biotransformation by human-associated bacteria, the microbiota, has not yet been systematically investigated. We tested the biotransformation of 68 mutagenic carcinogens by 34 bacterial species representative for the upper and lower human gastrointestinal tract and found that the majority (41) of the tested carcinogens undergo bacterial biotransformation. To assess the functional consequences of microbial carcinogen metabolism, we developed a pipeline to couple gut bacterial carcinogen biotransformation assays with Ames mutagenicity testing and liver biotransformation experiments. This revealed a bidirectional crosstalk between gut microbiota and host carcinogen metabolism, which we validated in gnotobiotic mouse models. Overall, the systematic assessment of gut microbiota carcinogen biotransformation and its interplay with host metabolism highlights the gut microbiome as an important modulator of exposome-induced tumorigenesis.

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Product Details of 4-Nitroquinoline N-oxide

CAS No. :56-57-5
Formula : C9H6N2O3
M.W : 190.15
SMILES Code : O=[N+](C1=C2C=CC=CC2=[N+]([O-])C=C1)[O-]
Synonyms :
4-NQO; Nitrochin
MDL No. :MFCD00006738
InChI Key :YHQDZJICGQWFHK-UHFFFAOYSA-N
Pubchem ID :5955

Safety of 4-Nitroquinoline N-oxide

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H350
Precautionary Statements:P201-P308+P313
Class:6.1
UN#:2811
Packing Group:

Isoform Comparison

Biological Activity

In Vitro:

Cell Line
Concentration Treated Time Description References
Human dysplastic oral keratinocytes (DOK) 2.6 μM 3 h DOK cells were transformed by 4-NQO to generate DOK-4-NQO cell line for in vitro and in vivo tumorigenicity studies. Redox Biol. 2024 Oct;76:103335

In Vivo:

Species
Animal Model
Administration Dosage Frequency Description References
Mice 4-NQO-induced ESCC mouse model Drinking water 100 mg/L 16 weeks To study the effect of SENP3 deletion on ESCC progression, results showed increased tumor numbers in Senp3 cKO mice. Cell Commun Signal. 2024 Aug 9;22(1):395
Mice 4-NQO-induced oral carcinogenesis model Drinking water 100 μg/mL Weekly for 16 weeks Assessed the effect of 4-NQO on oral carcinogenesis, showing that 4-NQO treatment significantly promotes the occurrence and development of oral cancer. Redox Biol. 2024 Oct;76:103335
Mice IP6K2 knockout mice Drinking water 100 μg/ml Continuous for 23 weeks To evaluate the carcinogenic effect of 4-NQO on IP6K2 knockout mice, results showed a fourfold increased incidence of invasive squamous cell carcinoma in the oral cavity and esophagus of KO mice compared to wild-type littermates Oncogene. 2009 Jun 25;28(25):2383-92
Mice CD24-deficient and CD24-heterozygous mice Drinking water 50 µg/mL 16 weeks To investigate the role of CD24 in oral cancer development. Results showed that CD24-deficient mice were more susceptible to 4-NQO-induced oral carcinogenesis with significantly increased tumor burden. Oncoimmunology. 2016 Sep 26;5(10):e1226719
Mice Grhl2 conditional knockout mouse model Drinking water 30 μg/ml 16 weeks of 4-NQO exposure followed by 6 weeks of drug-free drinking water To investigate the role of GRHL2 in oral carcinogenesis, results showed that Grhl2 KO mice completely abolished 4-NQO-induced tongue tumor formation. Oncogenesis. 2018 May 8;7(5):38
BALB/C nude mice 4-NQO-induced HNSCC model Drinking water 50 μg/mL 16 weeks Establish an HNSCC tumorigenesis model, results showed that the protein expression of PSMD14 was significantly higher in low-grade dysplasia (Week 24) and high-grade dysplasia/carcinoma (Week 28) than in normal tissue (Week 16). Theranostics. 2021 Jan 1;11(6):2655-2669
BALB/c nude mice 4-NQO-induced ESCC model Oral administration via drinking water 50 μg/mL 16 weeks of exposure followed by 12 weeks of normal drinking water To induce a murine ESCC model and investigate the expression of PSMD14 in esophageal tumorigenesis Theranostics. 2021 Apr 3;11(12):5847-5862
C57BL/6J mice Oral squamous cell carcinoma model Drinking water 0.1 mg/mL Once a week for 16 weeks To induce the development and progression of oral squamous cell carcinoma for evaluating the therapeutic effects of TGF-β inhibitors and anti-PD-L1 antibodies. Mol Cancer Ther. 2021 Jun;20(6):1102-1111
C57BL/6J mice 4-NQO-induced spontaneous ESCC mouse model Drinking water 100 μg/mL 16 weeks To induce spontaneous esophageal squamous cell carcinoma and verify the antitumor activity of the CCL18-blocking peptide Pep3. J Exp Clin Cancer Res. 2023 Feb 27;42(1):51

Protocol

Bio Calculators
Preparing Stock Solutions 1mg 5mg 10mg

1 mM

5 mM

10 mM

5.26mL

1.05mL

0.53mL

26.30mL

5.26mL

2.63mL

52.59mL

10.52mL

5.26mL

 

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