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ISO-1 - 99%, high purity , CAS No.478336-92-4

Item Number
I303791
Grouped product items
SKUSizeAvailabilityPrice Qty
I303791-5mg
5mg
In stock
$208.90
I303791-25mg
25mg
In stock
$940.90
I303791-100mg
100mg
In stock
$1,654.90

Potent, cell-permeable MIF antagonist

Basic Description

Synonyms4,5-DIHYDRO-3-(4-HYDROXYPHENYL)-5-ISOXAZOLEACETIC ACID, METHYL ESTER; ISO-1 | 4,5-dihydro-3-(4-hydroxyphenyl)-5-isoxazoleacetic acid, methyl ester | Methyl 2-[3-(4-Hydroxyphenyl)-4,5-dihydroisoxazol-5-yl]acetate | SY245019 | CS-3224 | CCG-266827 | AC-3608
Specifications & PurityMoligand™, ≥99%
Biochemical and Physiological MechanismsPotent, cell-permeable MIF (migration inhibitory factor) antagonist (IC 50 = 25 μM). Targets catalytic pocket of MIF. Inhibits TNF release from macrophages.
Storage TempStore at -20°C,Argon charged
Shipped InIce chest + Ice pads
GradeMoligand™
NoteWherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.
Product Description

A cell-permeable isoxazoline compound that displays anti-inflammatory properties. Inhibits MIF dopachrome tautomerase activity by binding to its catalytic active site (IC50 = 7 µM for D-dopachrome tautomerase) and suppresses the production of TNFα, PGE2 and COX-2 in human monocytes and arachidonic acid in RAW 264.7 macrophages. Shown to exhibit antidiabetogenic properties in immunoinflammatory diabetic mouse model.

Associated Targets(Human)

MIF Tchem Macrophage migration inhibitory factor (979 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DU-145 (51482 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
A549 (127892 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PBMC (10003 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Sigmar1 Sigma opioid receptor (160 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Hdac6 Histone deacetylase 6 (222 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Mechanisms of Action

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Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Names and Identifiers

IUPAC Name methyl 2-[3-(4-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]acetate
INCHI 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
InChi Key AIXMJTYHQHQJLU-UHFFFAOYSA-N
Canonical SMILES COC(=O)CC1CC(=NO1)C2=CC=C(C=C2)O
Isomeric SMILES COC(=O)CC1CC(=NO1)C2=CC=C(C=C2)O
PubChem CID 4633677
Molecular Weight 235.24

Certificates

Certificate of Analysis(COA)

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Find and download the COA for your product by matching the lot number on the packaging.

3 results found

Lot NumberCertificate TypeDateItem
I2128242Certificate of AnalysisJul 12, 2024 I303791
I2128273Certificate of AnalysisJul 12, 2024 I303791
I2128274Certificate of AnalysisJul 12, 2024 I303791

Chemical and Physical Properties

SolubilitySoluble in DMSO
Sensitivitylight、Moisture、heat sensitive
Melt Point(°C)112.0 - 116.0 °C

Related Documents

References

1. Lubetsky JB, Dios A, Han J, Aljabari B, Ruzsicska B, Mitchell R, Lolis E, Al-Abed Y.  (2002)  The tautomerase active site of macrophage migration inhibitory factor is a potential target for discovery of novel anti-inflammatory agents..  J Biol Chem,  277  (28): (24976-82).  [PMID:11997397] [10.1021/op500134e]
2. Zapatero MC, Pérez P, Vázquez MJ, Colmenarejo G, de Los Frailes M, Ramón F.  (2016)  Discovery of Novel Inhibitors of the Tautomerase Activity of Macrophage Migration Inhibitory Factor (MIF)..  J Biomol Screen,  21  (5): (446-58).  [PMID:26933127] [10.1021/op500134e]
3. Vujicic M, Nikolic I, Krajnovic T, Cheng KF, VanPatten S, He M, Stosic-Grujicic S, Stojanovic I, Al-Abed Y, Saksida T.  (2014)  Novel inhibitors of macrophage migration inhibitory factor prevent cytokine-induced beta cell death..  Eur J Pharmacol,  740  (13): (683-9).  [PMID:24967533] [10.1021/op500134e]
4. Cisneros JA, Robertson MJ, Valhondo M, Jorgensen WL.  (2016)  Irregularities in enzyme assays: The case of macrophage migration inhibitory factor..  Bioorg Med Chem Lett,  26  (12): (2764-2767).  [PMID:27156768] [10.1021/op500134e]
5. Bloom J, Metz C, Nalawade S, Casabar J, Cheng KF, He M, Sherry B, Coleman T, Forsthuber T, Al-Abed Y.  (2016)  Identification of Iguratimod as an Inhibitor of Macrophage Migration Inhibitory Factor (MIF) with Steroid-sparing Potential..  J Biol Chem,  291  (51): (26502-26514).  [PMID:27793992] [10.1021/op500134e]
6. Ito N et al..  (2020)  Biphasic MIF and SDF1 expression during podocyte injury promote CD44-mediated glomerular parietal cell migration in focal segmental glomerulosclerosis..  Am J Physiol Renal Physiol,  318  (3): (F741-F753).  [PMID:32068458]
7. Becker-Herman S et al..  (2021)  CD74 is a regulator of hematopoietic stem cell maintenance..  PLoS Biol,  19  (3): (e3001121).  [PMID:33661886]
8. Adzavon YM et al..  (2018)  Macrophage migration inhibitory factor contributes to the pathogenesis of benign lymphoepithelial lesion of the lacrimal gland..  Cell Commun Signal,  16  (70).  [PMID:30348174]
9. Yamamoto Y et al..  (2022)  Neutrophils delay repair process in Wallerian degeneration by releasing NETs outside the parenchyma..  Life Sci Alliance,  (10):   [PMID:35961782]

Solution Calculators