EF-5
EF-5 Basic information
- Product Name:
- EF-5
- Synonyms:
-
- EF-5
- 1H-Imidazole-1-acetamide, 2-nitro-N-(2,2,3,3,3-pentafluoropropyl)-
- EF5 >=98% (HPLC)
- inhibit,EF 5,EF-5,Inhibitor
- EF-5, 10 mM in DMSO
- CAS:
- 152721-37-4
- MF:
- C8H7F5N4O3
- MW:
- 302.16
- Mol File:
- 152721-37-4.mol
EF-5 Chemical Properties
- Density
- 1.66±0.1 g/cm3(Predicted)
- storage temp.
- Store at -20°C
- solubility
- DMSO : 125 mg/mL (413.69 mM)
- form
- Solid
- pka
- 12.32±0.46(Predicted)
- color
- White to off-white
EF-5 Usage And Synthesis
Uses
EF-5 (EF5; 2-Nitroimidazole) is a hypoxia labeling agent used to identify hypoxia in cells.
Biological Activity
EF5 is a 2-nitroimidazole-based hypoxia marker corresponding to a pentafluorinated derivative of the hypoxic cell-radiation sensitizer etanidazole. Under low oxygen (hypoxic) condition, reductive activation of its 2-nitroimidazole moiety leads to enhanced EF5 adduct formation with protein thiols and reduced glutathione. The pentafluorination derivatization substantially decreases the proportion of low molecular weight hydrolytic fragmentation of the adducts, making EF5 superior to etanidazole when utilized as a hypoxia marker by immunohistological staining.
in vivo
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].
References
[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. DOI:10.1158/1078-0432.CCR-11-2296
[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. DOI:10.1038/bjc.1995.427
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