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Key Documents

SML1961

Sigma-Aldrich

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
UNSPSC Code:
12352200
NACRES:
NA.77
Pricing and availability is not currently available.

Quality Level

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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