EMAIL THIS PAGE TO A FRIEND
SML1961 Sigma-Aldrich

EF5

≥98% (HPLC)

Synonym: 2-(2-Nitro-1H-imidazol-1-yl)-N-(2,2,3,3,3-pentafluoropropyl)acetamide, EF-5, NSC 684681

  • CAS Number 152721-37-4

  • Empirical Formula (Hill Notation) C8H7F5N4O3

  • Molecular Weight 302.16

  •  NACRES NA.77

Purchase

Properties

Related Categories Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, Cell Biology, E
Quality Level   100
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

Description

Biochem/physiol Actions

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.

Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

Please Enter a Lot Number
Protocols & Articles
Peer-Reviewed Papers
15

References

Related Products

Technical Service:

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Bulk Ordering & Pricing:

Need larger quantities for your development, manufacturing or research applications?