For research use only. Not for therapeutic Use.
EF-5 (EF5; 2-Nitroimidazole) is a hypoxia labeling agent used to identify hypoxia in cells.
Overexpression of CYPOR induces similar 2- to 4-fold increases in EF-5 binding and metabolic reduction of tirapazamine and CEN-209 in SiHa and HCT116 cell lines, and similar enhancement of γH2AX formation. EF-5 binding and metabolic reduction of the prodrugs are highly correlated in a panel of 14 hypoxic tumor cell lines[1].
EF-5 binding is a promising stratification biomarker for benzotriazine-N-oxide bioreductive prodrugs. In HCT116 xenografts, CYPOR overexpression also significantly increases EF-5 binding and CEN-209 reduction, and modification of tumor hypoxia causes similar changes to the bioreductive activation of both agents, resulting in a strong correlation between EF-5 binding and CEN209-induced DNA damage at the individual tumor level[1]. Following intravenous injection of EF-5, binding and detection using a monoclonal antibody in 9L gliomas is specific and oxygen dependent. Detection of binding using fluorescence microscopy can be performed on frozen tissues; tissue sections can be counterstained with haematoxylin and eosin for light microscopic analysis. Alternatively, the distribution of hypoxia in a tumor can be inferred by examining individual tumor cells using flow cytometric techniques[2].
| Catalog Number | I013365 |
| CAS Number | 152721-37-4 |
| Synonyms | 2-(2-nitroimidazol-1-yl)-N-(2,2,3,3,3-pentafluoropropyl)acetamide |
| Molecular Formula | C8H7F5N4O3 |
| Purity | ≥95% |
| InChI | InChI=1S/C8H7F5N4O3/c9-7(10,8(11,12)13)4-15-5(18)3-16-2-1-14-6(16)17(19)20/h1-2H,3-4H2,(H,15,18) |
| InChIKey | JGGDSDPOPRWSCX-UHFFFAOYSA-N |
| SMILES | C1=CN(C(=N1)[N+](=O)[O-])CC(=O)NCC(C(F)(F)F)(F)F |
| Reference | [1]. Wang J, et al. The 2-nitroimidazole EF5 is a biomarker for oxidoreductases that activate the bioreductive prodrug CEN-209 under hypoxia. Clin Cancer Res. 2012 Mar 15;18(6):1684-95. [2]. Evans SM, et al. Identification of hypoxia in cells and tissues of epigastric 9L rat glioma using EF5 [2-(2-nitro-1H-imidazol-1-yl)-N-(2,2,3,3,3-pentafluoropropyl) acetamide]. Br J Cancer. 1995 Oct;72(4):875-82. |
