2-Hydroxy-5-(2-nitrovinyl)benzoic acid
2-Hydroxy-5-(2-nitrovinyl) benzoic acid (SANA) is an orally active pleiotropic anti-inflammatory metabolic modulator. 2-Hydroxy-5-(2-nitrovinyl) benzoic acid inhibits NF-κB, activates Nrf2/Keap1 and AMPK, suppresses inflammasome activity, induces thermogenesis, reverses insulin resistance and alleviates skin graft rejection. 2-Hydroxy-5-(2-nitrovinyl) benzoic acid can be used in research related to obesity, glucose intolerance, skin graft rejection and insulin resistance.
For research use only. We do not sell to patients.
- CAS No.: 42571-07-3
- Formula: C9H7NO5
- Molecular Weight:209.16
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Storage:
Please store the product under the recommended conditions in the Certificate of Analysis.
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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Biological Activity
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Chemical Information
- Purity & Documentation
- References
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Help & FAQs
Biological Activity
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IL-6 |
IL-1β |
2-Hydroxy-5-(2-nitrovinyl) benzoic acid (0.1 mM; 2 h) potently inhibits LPS (HY-D1056)-induced nuclear translocation of NF-κB/p65 in THP-1 macrophages[1].
2-Hydroxy-5-(2-nitrovinyl) benzoic acid (100-200 μM; 5 h) inhibits NF-κB-dependent gene expression of IL-6, TNF-α and MCP-1 in LPS-induced differentiated THP-1 macrophages[1].
2-Hydroxy-5-(2-nitrovinyl) benzoic acid (50-200 μM; 18 h) inhibits LPS-induced NF-κB-dependent IL-6 secretion in RAW 264.7 macrophages in a dose-dependent manner[1].
2-Hydroxy-5-(2-nitrovinyl) benzoic acid (0.1 mM; 5 h) induces Nrf2/Keap1-dependent expression of HO-1, GCLM and NQO1 genes in human hepatoma Hep G2 cells[1].
When co-administered with the initial LPS signal, 2-Hydroxy-5-(2-nitrovinyl) benzoic acid (0.05-0.25 mM; 3.75 h) dose-dependently inhibits inflammasome-mediated IL-1β secretion in differentiated THP-1 macrophages without reducing cell viability[1].
2-Hydroxy-5-(2-nitrovinyl) benzoic acid (0.05-0.25 mM; 3.75 h) exerts a dose-dependent inhibitory effect on inflammasome-mediated IL-1β secretion in differentiated THP-1 macrophages without reducing cell viability when acting in conjunction with a second ATP signal[1].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Cell Line:THP-1 macrophages
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Concentration:0.1 mM
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Incubation Time:2 h (pre-incubation)
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Result:Prevented LPS-induced nuclear translocation of NF-κB/p65, with equivalent effect to 1 mM salicylic acid indicating greater potency.
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Cell Line:differentiated THP-1 macrophages
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Concentration:100-200 μM
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Incubation Time:2 h (pre-incubation); 3 h (LPS stimulation)
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Result:Inhibited LPS-induced NF-κB-dependent expression of IL-6, TNF-α, and MCP-1 genes, while salicylic acid at the same concentrations showed no inhibitory activity.
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Cell Line:murine RAW 264.7 macrophages
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Concentration:50-200 μM
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Incubation Time:2 h (pre-incubation); 16 h (LPS stimulation)
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Result:Dose-dependently inhibited LPS-induced IL-6 secretion, with significant inhibition observed at all tested concentrations (p < 0.05 compared to LPS-DMSO control), and was more potent than 1 mM salicylic acid.
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Cell Line:Hep G2 human liver cells
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Concentration:0.1 mM
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Incubation Time:5 h
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Result:Induced expression of Nrf2/Keap1-dependent phase two enzyme genes (HO-1, GCLM, NQO1), while salicylic acid at 0.2 mM and 5 mM did not induce such expression.
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Cell Line:differentiated THP-1 macrophages
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Concentration:0.05-0.25 mM
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Incubation Time:3 h (co-incubation with LPS); 45 min (ATP stimulation)
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Result:Dose-dependently inhibited LPS/ATP-induced IL-1β secretion, with no reduction in cell viability observed; salicylic acid at 0.25 mM did not inhibit IL-1β secretion.
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Cell Line:differentiated THP-1 macrophages
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Concentration:0.05-0.25 mM
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Incubation Time:3 h (LPS stimulation); 45 min (co-incubation with ATP)
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Result:Dose-dependently inhibited LPS/ATP-induced IL-1β secretion, with no reduction in cell viability observed; salicylic acid at 0.25 mM did not inhibit IL-1β secretion.
SANA (100 mg/kg; i.p.; single administration) significantly inhibits LPS-induced peritoneal IL-1β secretion in mice[1].
SANA (100 mg/kg; p.o.; once daily; for 16 consecutive days) significantly prolongs the survival time of skin allografts in mice[1].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Animal Model:C57BL/6[1]
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Dosage:200 mg/kg (p.o.); 100-400 mg/kg (i.p.)
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Administration:p.o. (gavage; single dose); i.p. (single dose)
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Result:Increased pAMPK levels in mouse liver compared to PBS control.
Increased pAMPK levels in mouse liver, with higher doses showing greater elevation.
Increased pAMPK levels relative to control.
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Animal Model:C57BL/6[1]
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Dosage:100 mg/kg
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Administration:i.p.; single dose (administered 2 hours pre-LPS)
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Result:Reduced LPS-induced IL-1β secretion into the peritoneum, with a statistically significant difference compared to LPS + buffer control.
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Animal Model:C57BL/6 (female recipients, male donors)[1]
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Dosage:100 mg/kg
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Administration:p.o. (gavage); daily; 16 days total (1 pre-transplant day + 15 post-transplant days)
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Result:Prolonged skin allograft survival compared to vehicle control.
Prolonged allograft survival significantly longer than in salicylic acid-treated mice.
Chemical Information
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CAS No. 42571-07-3
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Molecular Weight 209.16
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Formula C9H7NO5
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SMILES
O=C(C1=CC(/C=C/[N+]([O-])=O)=CC=C1O)O
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Synonyms
SANA
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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
Calculators
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
2-Hydroxy-5-(2-nitrovinyl)benzoic acid Related Classifications
HY-184788 Related Classifications
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