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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:
152721-37-4
Molecular Weight:
302.16
UNSPSC Code:
12352200
NACRES:
NA.77
Pricing and availability is not currently available.

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

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

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Show Differences

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EF5 ≥98% (HPLC)

SML1961

EF5

AP-C5 ≥98% (HPLC)

SML2552

AP-C5

OB-1 ≥98% (HPLC)

SML2560

OB-1

I-BET469 ≥98% (HPLC)

SML2825

I-BET469

form

powder

form

powder

form

powder

form

powder

assay

≥98% (HPLC)

assay

≥98% (HPLC)

assay

≥98% (HPLC)

assay

≥98% (HPLC)

Quality Level

100

Quality Level

100

Quality Level

-

Quality Level

100

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

solubility

DMSO: 10 mg/mL, clear

solubility

DMSO: 2 mg/mL, clear

solubility

DMSO: 2 mg/mL, clear

solubility

DMSO: 2 mg/mL, clear

color

white to beige

color

white to beige

color

white to very dark brown

color

white to beige

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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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