SML1961
EF5
≥98% (HPLC)
Synonym(s):
2-(2-Nitro-1H-imidazol-1-yl)-N-(2,2,3,3,3-pentafluoropropyl)acetamide, EF-5, NSC 684681
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About This Item
Empirical Formula (Hill Notation):
C8H7F5N4O3
CAS Number:
Molecular Weight:
302.16
NACRES:
NA.77
UNSPSC Code:
12352200
Assay:
≥98% (HPLC)
Form:
powder
Quality Segment
assay
≥98% (HPLC)
form
powder
color
white to beige
solubility
DMSO: 10 mg/mL, clear
storage temp.
2-8°C
SMILES string
O=C(NCC(F)(F)C(F)(F)F)CN1C=CN=C1[N+]([O-])=O
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)
InChI key
JGGDSDPOPRWSCX-UHFFFAOYSA-N
Biochem/physiol Actions
A 2-nitroimidazole-based hypoxia marker
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.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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