| Identification | Back Directory | [Name]
MIF Antagonist, ISO-1 | [CAS]
478336-92-4 | [Synonyms]
ISO-1
CS-1195
ISO-1
(ISO 1
MIF Antagonist
MIF Antagonist, ISO-1
ISO-1, MIF Antagonist
ISO 1;ISO1;MIF ANTAGONIST
Methyl 2-(3-(4-hydroxyphenyl)-4,5-dihydroisoxazol-5-yl)acetate
4,5-Dihydro-3-(4-hydroxyphenyl)-5-isoxazoleacetic acid methyl ester
5-Isoxazoleacetic acid, 4,5-dihydro-3-(4-hydroxyphenyl)-, methyl ester
2-[3-(4-Hydroxyphenyl)-4,5-dihydroisoxazol-5-yl]acetic Acid Methyl Ester | [Molecular Formula]
C12H13NO4 | [MDL Number]
MFCD22376813 | [MOL File]
478336-92-4.mol | [Molecular Weight]
235.24 |
| Chemical Properties | Back Directory | [Melting point ]
114 °C | [Boiling point ]
365.0±48.0 °C(Predicted) | [density ]
1.30±0.1 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Sealed in dry,Store in freezer, under -20°C | [solubility ]
Soluble in DMSO. | [form ]
Light yellow crystalline solid. | [pka]
9.22±0.30(Predicted) | [color ]
Off-white | [Sensitive ]
Light Sensitive | [Stability:]
Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 2 months. | [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 | [InChIKey]
AIXMJTYHQHQJLU-UHFFFAOYSA-N | [SMILES]
O1C(CC(OC)=O)CC(C2=CC=C(O)C=C2)=N1 |
| Hazard Information | Back Directory | [Description]
ISO-1 (478336-92-4) is an antagonist of macrophage migration inhibitory factor (MIF, a pro-inflammatory cytokine). Displays anti-inflammatory activity. Increases survival in severe sepsis.1 Inhibits airway remodeling in mouse asthma model.2 ISO-1 also blocks MIF-induced autophagy.3?Active in cellular and mouse models. | [Uses]
MIF Antagonist, ISO-1 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. MIF Antagonist, ISO-1 has been shown to exhibit antidiabetogenic properties in immunoinflammatory diabetic mouse model. | [in vivo]
ISO-1 (injected intraperitoneally; 3.5-35 mg/kg; twice daily; 2 weeks) improves the survival rate from lethal endotoxemia and shows the anti-inflammatory effect[2].
ISO-1 (intraperitoneal injection; 35 mg/kg; twice daily; 3 days) causes a significant reduction in average implant size and decreases Flk1 expression in implants[3]. | Animal Model: | C57Bl/6 MIF+/+ and MIF–/– mice[2] | | Dosage: | 3.5-35 mg/kg | | Administration: | Injected intraperitoneally; 3.5-35 mg/kg; twice a day ; 2 weeks | | Result: | Was protective against lethal sepsis. |
| Animal Model: | Female C57BL/6-Tg(ACTB-EGFP)1Osb/J mice[3] | | Dosage: | 35 mg/kg | | Administration: | Intraperitoneal injection; 35 mg/kg; twice daily; 3 days | | Result: | Reduced average endometriotic implant size. |
| [storage]
Store at +4°C | [References]
1) Al-Abed et al. (2005), ISO-1 binding to the tautomerase active site of MIF inhibits its pro-inflammatory activity and increases survival in severe sepsis; J. Biol. Chem., 280
2) Chen et al. (2010), ISO-1, a macrophage migration inhibitory factor antagonist, inhibits airway remodeling in a murine model of chronic asthma; Mol. Med., 16 400
3) Chuang et al. (2012), Macrophage migration inhibitory factor induces autophagy via reactive oxygen species generation; PLoS One, 7 e37613 |
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