Cat. No.: HY-W504391

Nitrovin

Name: Nitrovin
Brand: MedChemExpress
SKU: HY-W504391
Availability: PreOrder

(Synonyms: Difurazon)

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.

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CAS No.: 804-36-4
화학식: C₁₄H₁₂N₆O₆
분자량:360.28

보관:

Please store the product under the recommended conditions in the Certificate of Analysis.

Data Sheet (293 KB)

Nitrovin Chemical Structure

CAS No.: 804-36-4

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Use of MCE Products

Fluorescent Dye

Strong Fluorescence Signal / Multi-Disciplinary Applications / High Fluorescence Specificity

Biological Activity
- 제품 설명
- IC₅₀ & Target
- In Vitro
- In Vivo
Chemical Information
순도&문서
References
Calculators
Help & FAQs
Classifications
Bioz

Biological Activity

제품 설명

IC₅₀ & Target

^[1]

TrxR1

All TrxR Isoforms :

TrxR1
TrxR2

All p38 MAPK Isoforms :

In Vitro

Anti-cancerApoptosisOxidative StressMitochondrial FunctionEndoplasmic Reticulum StressBacterial InfectionOthers

Anti-cancer

Nitrovin (Difurazon) (1.25-10 µM; 24 h) inhibits cell viability in a concentration-dependent manner and exhibits significant cytotoxicity in 16 human tumor cell lines and 2 normal cell lines^[1].
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].

Anti-cancer

Apoptosis

Nitrovin (0.625-5 µM; 24 h) does not cause significant changes in Caspase-3 activity, does not induce cleavage activation of Caspase-3 and Caspase-7, does not cause typical apoptotic nuclear morphological changes such as nuclear condensation and nuclear fragmentation, and only induces a very low proportion of cells to be positive for Annexin V/7AAD apoptosis staining in human glioblastoma U251 cells^[1].

Oxidative Stress

Mitochondrial Function

Anti-cancer

Nitrovin (1.25-5 µM; 4 h) concentration-dependently induces significant accumulation of total intracellular ROS and a significant increase in mitochondrial superoxide levels in human glioblastoma U251 and U87 cells^[1].

Oxidative Stress

Anti-cancer

Nitrovin (5 µM; 2-24 h) induces cytoplasmic vacuolation and ROS generation and inhibits cell viability in human glioblastoma U251 cells transfected with control vector or overexpressing Alix, and Alix overexpression fails to reverse this cell death and does not alter ROS production levels^[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].

Endoplasmic Reticulum Stress

Anti-cancer

Nitrovin (5 µM; 24 h) induces significant large vacuole formation derived from endoplasmic reticulum swelling in human glioblastoma U251 and U87 cells^[1].
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].

Anti-cancer

Oxidative Stress

Nitrovin (5 µM; 24 h) induces cytoplasmic vacuolation and death and induces ROS generation in human glioblastoma U251 cells transfected with control plasmid or overexpressing TrxR1; TrxR1 overexpression significantly inhibits vacuole accumulation and reverses cell death and significantly inhibits ROS generation^[1].

Bacterial Infection

Nitrovin (1-100 μg/mL; 2 days) inhibits most chicken cecal anaerobes at 100 μg/mL, whereas B. hypermegas (2 of 3 strains), Coprococcus sp. NE1/97, and Budding bacteria NE3/209 remain resistant^[2].
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].

Others

Nitrovin (0.625-5 µM; 0.5-24 h) does not alter the total expression level of TrxR1 protein in human glioblastoma U251 cells^[1].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Cell Cytotoxicity Assay^[1]

Cell Line:

U251 and U87 glioblastoma cells
Concentration:

1.25 µM、2.5 µM、5 µM、10 µM
Incubation Time:

24 h
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.

Western Blot Analysis^[1]

Cell Line:

U251 cells
Concentration:

0.625 µM, 1.25 µM, 2.5 µM, 5 µM
Incubation Time:

24 h
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).

Apoptosis Analysis^[1]

Cell Line:

U251 cells
Concentration:

0.625 µM, 1.25 µM, 2.5 µM, 5 µM
Incubation Time:

24 h
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.

Western Blot Analysis^[1]

Cell Line:

U251 and U87 cells
Concentration:

0.625 µM, 1.25 µM, 2.5 µM, 5 µM
Incubation Time:

24 h
Result:

Concentration-dependently downregulated the protein expression of Alix.

Western Blot Analysis^[1]

Cell Line:

U251 cells
Concentration:

0.625 µM, 1.25 µM, 2.5 µM, 5 µM
Incubation Time:

0.5, 1, 2, 4, 8, 24 h
Result:

Caused no statistically significant changes in total TrxR1 protein expression levels across different doses or time intervals.

In Vivo

Anti-cancerBacterial InfectionOthers

Anti-cancer

Nitrovin (Difurazon) (2.5-10 μM; waterborne exposure; continuous immersion exposure starting at 2 days post-fertilization; 2 days of treatment/observation until 3 days post-microinjection) dose-dependently inhibits tumor growth and reduces tumor fluorescence area in a wild-type zebrafish embryo yolk sac microinjection model xenotransplanted with DiI-labeled human glioblastoma U251 cells^[1].

Bacterial Infection

Nitrovin (10 mg/kg; p.o.; free access; continuous administration) eliminates Gram-negative non-spore-forming anaerobes that constitute a major component of the cecal microbiota, while maintaining sufficient VFA concentrations and low pH to inhibit Salmonella typhimurium proliferation^[2].

Others

Nitrovin (10 mg/kg; p.o.; free access; continuous administration) significantly promotes the growth and development of neonatal healthy male Warren chicks in a 1-day-old rearing model, accompanied by a moderate increase in feed consumption and improved feed conversion ratio^[4].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Animal Model:

wild-type larvae Zebrafish with Glioblastoma multiforme^[1]
Dosage:

2.5 μM, 5 μM, 10 μM
Administration:

waterborne exposure; continuous immersion exposure starting at 2 days post-fertilization; 2 days of treatment/observation until 3 days post-microinjection
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.

Related Protocols :

Chemical Information

CAS No. 804-36-4
분자량 360.28
화학식 C₁₄H₁₂N₆O₆
SMILES

O=[N+](C1=CC=C(/C=C/C(/C=C/C2=CC=C([N+]([O-])=O)O2)=N\NC(N)=N)O1)[O-]
Synonyms

Difurazon
선적

Room temperature in continental US; may vary elsewhere.
보관

Please store the product under the recommended conditions in the Certificate of Analysis.

순도&문서

Select Batch:

Purity: 99.98%

Assay: 99.98%

ee.: 99.98%

Data Sheet (293 KB)
COA (2659 KB)
Elemental Analysis Report (2659 KB)
HNMR (2659 KB)
CNMR (2659 KB)
RP-HPLC (2659 KB)
NP-HPLC (2659 KB)
MS (2659 KB)
LCMS (2659 KB)
IR (2659 KB)
GC (2659 KB)
OR (2659 KB)
SDS-PAGE (2659 KB)
SEC-HPLC (2659 KB)
Other Report (2659 KB)
Handling Instructions (2659 KB)

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]

[2]. Barnes EM, et al. Factors affecting the incidence and anti-salmonella activity of the anaerobic caecal flora of the young chick. J Hyg (Lond). 1979;82(2):263-283.

[3]. McCalla DR. Nitrofurans. InMechanism of action of antibacterial agents 1979 (pp. 176-213). Berlin.

[4]. Bunyan J, et al. Antimicrobial substances and chick growth promotion: the growth-promoting activities of antimicrobial substances, including fifty-two used either in therapy or as dietary additives. Br Poult Sci. 1977;18:283-294.

[5]. Thorne N, et al. High-Throughput Phenotypic Screening of Human Astrocytes to Identify Compounds That Protect Against Oxidative Stress. Stem Cells Transl Med. 2016 May;5(5):613-27.

[6]. Onuska KD, et al. Antimutagenic and bacteriostatic activities of Schiff-base compounds derived from aminoguanidine, semicarbazone and thiosemicarbazone and a copper(II)-coordination complex. Toxicol Environ Chem. 1996;57(1-4):163-170.

Calculators

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Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

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Help & FAQs

How should lyophilized recombinant proteins be reconstituted and stored?

1. Before opening the cap, centrifuge the vial at 13000 rpm for 20-30 seconds. This step will ensure that any lyophilized powder that may have adhered to the cap or walls is collected at the bottom of the vial, minimizing the risk of product loss.

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Nitrovin

All TrxR Isoforms

All p38 MAPK Isoforms