Nitrovin
Nitrovin (Difurazon) is an orally active inhibitor of thioredoxin reductase 1 (TrxR1) with both antibacterial and anticancer activities. Nitrovin induces ROS generation and endoplasmic reticulum stress by targeting and inhibiting TrxR1, which in turn induces cytoplasmic vacuolation, activates MAPK, and inhibits Alix. Nitrovin induces paraptosis-like non-apoptotic cell death, thereby exerting significant cytotoxicity against cancer cells. Nitrovin is used for research on glioblastoma, liver cancer, and bacterial infections.
For research use only. We do not sell to patients.
- CAS No.: 804-36-4
- Formula: C14H12N6O6
- Molecular Weight:360.28
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Storage:
Please store the product under the recommended conditions in the Certificate of Analysis.
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Biological Activity
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Chemical Information
- Protocols
- Purity & Documentation
- References
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Help & FAQs
Biological Activity
Description
IC50 & Target
[1]|
TrxR1 |
In Vitro
Nitrovin (1.25-10 µM; 24 h) decreases cell viability in a concentration-dependent manner, depletes intracellular ATP levels, and induces extensive characteristic cytoplasmic vacuolation in human glioblastoma U251 and U87 cells[1].
Nitrovin (0.625-5 µM; 24 h) downregulates the expression of the paraptosis-specific inhibitory protein Alix in a concentration-dependent manner in human glioblastoma U251 and U87 cells[1].
Nitrovin (1.25-5 µM; 4 h) concentration-dependently inhibits the catalytic activity of intracellular TrxR1 in human glioblastoma U251 and U87 cells[1].
Nitrovin (24 h) activates ARE/Nrf2 reporter gene transcription in human hepatocellular carcinoma HepG2 cells in a bell-shaped curve, activating ARE-bla signaling at low doses and causing cytotoxicity at high doses[5].
Nitrovin (5 µM; 0.5-8 h) time-dependently upregulates the expression of endoplasmic reticulum stress marker proteins BiP, p-eIF2α, ATF4, and CHOP and rapidly induces ERK1/2 and p38 MAPK phosphorylation activation, followed by slightly later induction of JNK1/2 phosphorylation in human glioblastoma U251 cells[1].
Nitrovin (1 μg/dish; 12 h) induces significant frameshift mutations, base substitution mutations, and DNA cross-linking damage in Salmonella typhimurium TA97, TA100, and TA102, and triggers the formation of numerous His+ revertant colonies[6].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Cell Line:U251 and U87 glioblastoma cells
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Concentration:1.25 µM、2.5 µM、5 µM、10 µM
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Incubation Time:24 h
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Result:Induced intracellular ROS formation in a concentration-dependent manner.
NAC or GSH pretreatment significantly reversed Nitrovin hydrochloride-induced ROS and cell death in both cell lines.
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Cell Line:U251 cells
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Concentration:0.625 µM, 1.25 µM, 2.5 µM, 5 µM
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Incubation Time:24 h
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Result:Produced no detectable cleavage of caspase-3 (pro-form 35 kDa; cleaved-forms 19/17 kDa) or caspase-7 (pro-form 35 kDa; cleaved-form 20 kDa).
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Cell Line:U251 cells
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Concentration:0.625 µM, 1.25 µM, 2.5 µM, 5 µM
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Incubation Time:24 h
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Result:Resulted in only a very minor percentage of Annexin V-positive apoptotic cells, confirming that cell death occurred predominantly via a non-apoptotic pathway.
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Cell Line:U251 and U87 cells
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Concentration:0.625 µM, 1.25 µM, 2.5 µM, 5 µM
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Incubation Time:24 h
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Result:Concentration-dependently downregulated the protein expression of Alix.
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Cell Line:U251 cells
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Concentration:0.625 µM, 1.25 µM, 2.5 µM, 5 µM
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Incubation Time:0.5, 1, 2, 4, 8, 24 h
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Result:Caused no statistically significant changes in total TrxR1 protein expression levels across different doses or time intervals.
In Vivo
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Animal Model:wild-type larvae Zebrafish with Glioblastoma multiforme[1]
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Dosage:2.5 μM, 5 μM, 10 μM
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Administration:waterborne exposure; continuous immersion exposure starting at 2 days post-fertilization; 2 days of treatment/observation until 3 days post-microinjection
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Result:Reduced tumor fluorescence area to ~100% of control at 2.5 μM.
Reduced tumor fluorescence area to ~60% of control at 5 μM.
Reduced tumor fluorescence area to ~45% of control at 10 μM.
Showed inhibitory effect at 5 μM comparable to that of 100 μM TMZ.
Chemical Information
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CAS No. 804-36-4
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Molecular Weight 360.28
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Formula C14H12N6O6
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SMILES
O=[N+](C1=CC=C(/C=C/C(/C=C/C2=CC=C([N+]([O-])=O)O2)=N\NC(N)=N)O1)[O-]
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Synonyms
Difurazon
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Shipping
Room temperature in continental US; may vary elsewhere.
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Storage
Please store the product under the recommended conditions in the Certificate of Analysis.
Purity & Documentation
References
[1]. Zhao L, et al. Nitrovin (difurazone), an antibacterial growth promoter, induces ROS-mediated paraptosis-like cell death by targeting thioredoxin reductase 1 (TrxR1). Biochemical pharmacology. 2023 Apr;210:115487. [Content Brief]
[3]. McCalla DR. Nitrofurans. InMechanism of action of antibacterial agents 1979 (pp. 176-213). Berlin.
Calculators
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
Nitrovin Related Classifications
HY-W504391 Related Classifications
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