Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C12H13NO4 |
| Molecular Weight | 235.2359 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
COC(=O)CC1CC(=NO1)C2=CC=C(O)C=C2
InChI
InChIKey=AIXMJTYHQHQJLU-UHFFFAOYSA-N
InChI=1S/C12H13NO4/c1-16-12(15)7-10-6-11(13-17-10)8-2-4-9(14)5-3-8/h2-5,10,14H,6-7H2,1H3
| Molecular Formula | C12H13NO4 |
| Molecular Weight | 235.2359 |
| Charge | 0 |
| Count |
|
| Stereochemistry | RACEMIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Optical Activity | ( + / - ) |
DescriptionCurator's Comment: description was created based on several sources, including:
https://www.ncbi.nlm.nih.gov/pubmed/16115897 | https://www.ncbi.nlm.nih.gov/pubmed/20485865 | https://www.ncbi.nlm.nih.gov/pubmed/19592246
Curator's Comment: description was created based on several sources, including:
https://www.ncbi.nlm.nih.gov/pubmed/16115897 | https://www.ncbi.nlm.nih.gov/pubmed/20485865 | https://www.ncbi.nlm.nih.gov/pubmed/19592246
ISO-1 inhibits several Macrophage migration inhibitory factor biological activities. The crystal structure of MIF complexed to (S,R)-3-(4-hydroxyphenyl)-4,5-dihydro-5-isoxazole acetic acid methyl ester (ISO-1) reveals that ISO-1 binds to the same position of the active site as p-hydroxyphenylpyruvic acid, a substrate of MIF. ISO-1 demonstrated significant protection from sepsis in vivo. Moreover, ISO-1 treatment led to the significant suppression observed in the inflammatory responses associated with the allergen-induced lung inflammation and fibrosis in murine asthma model. MIF inhibition by ISO-1 may be a potential therapeutic strategy for diabetic nephropathy.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20177408 | https://www.ncbi.nlm.nih.gov/pubmed/24447830
Curator's Comment: ISO-1, the most tested MIF inhibitor, has already been shown to cross the blood brain barrier.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Antagonism of macrophage migration inhibitory factor decreases cyclophosphamide cystitis in mice. | 2010-11 |
|
| Macrophage migration inhibitory factor regulates interleukin-6 production by facilitating nuclear factor-kappa B activation during Vibrio vulnificus infection. | 2010-10-12 |
|
| The role of macrophage migration inhibitory factor in Alzheimer's disease. | 2010-03 |
|
| Spinal macrophage migration inhibitory factor contributes to the pathogenesis of inflammatory hyperalgesia in rats. | 2010-02 |
|
| Migratory response of mesenchymal stem cells to macrophage migration inhibitory factor and its antagonist as a function of colony-forming efficiency. | 2010-01 |
|
| ISO-1, a macrophage migration inhibitory factor antagonist, inhibits airway remodeling in a murine model of chronic asthma. | 2009-09-16 |
|
| Small-molecule antagonist of macrophage migration inhibitory factor enhances migratory response of mesenchymal stem cells to bronchial epithelial cells. | 2009-09 |
|
| Novel derivatives of ISO-1 as potent inhibitors of MIF biological function. | 2009-08-15 |
|
| A fluorinated analog of ISO-1 blocks the recognition and biological function of MIF and is orally efficacious in a murine model of colitis. | 2009-04-01 |
|
| Role of macrophage migration inhibitory factor in influenza H5N1 virus pneumonia. | 2009 |
|
| Macrophage migration inhibitory factor promotes colorectal cancer. | 2008-10-04 |
|
| A novel, macrophage migration inhibitory factor suicide substrate inhibits motility and growth of lung cancer cells. | 2008-09-15 |
|
| Differential and cell-type specific regulation of responses to Toll-like receptor agonists by ISO-1. | 2008-09 |
|
| Macrophage migration inhibitory factor induces cardiomyocyte apoptosis. | 2008-06-27 |
|
| Hypoxia-inducible factor augments experimental colitis through an MIF-dependent inflammatory signaling cascade. | 2008-06 |
|
| Lung-derived macrophage migration inhibitory factor in sepsis induces cardio-circulatory depression. | 2007-02 |
|
| Inhibition of macrophage migration inhibitory factor or its receptor (CD74) attenuates growth and invasion of DU-145 prostate cancer cells. | 2006-12-15 |
|
| Critical modifications of the ISO-1 scaffold improve its potent inhibition of macrophage migration inhibitory factor (MIF) tautomerase activity. | 2006-07-01 |
|
| ISO-1 binding to the tautomerase active site of MIF inhibits its pro-inflammatory activity and increases survival in severe sepsis. | 2005-11-04 |
|
| Critical role of macrophage migration inhibitory factor activity in experimental autoimmune diabetes. | 2005-07 |
|
| The tautomerase active site of macrophage migration inhibitory factor is a potential target for discovery of novel anti-inflammatory agents. | 2002-07-12 |
Patents
Sample Use Guides
Macrophages were treated with various concentrations of ISO-1 (10–100 μM) for 30 min. The medium was then replaced with ISO-1-free medium. The cells were then lysed and the tautomerase activity determined. ISO-1 applied to the cell cultures inhibited intracellular tautomerase activity in a dose dependent manner, indicating that the exogenous ISO-1 led to suppression of intracellular MIF tautomerase activity.
| Substance Class |
Chemical
Created
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Edited
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| Record UNII |
7QFF3Z0V9X
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| Record Status |
Validated (UNII)
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| Record Version |
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