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Merck

SML1961

Sigma-Aldrich

EF5

≥98% (HPLC)

別名:

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

実験式(ヒル表記法):
C8H7F5N4O3
CAS番号:
分子量:
302.16
UNSPSCコード:
12352200
NACRES:
NA.77

品質水準

アッセイ

≥98% (HPLC)

フォーム

powder

white to beige

溶解性

DMSO: 10 mg/mL, clear

保管温度

2-8°C

SMILES記法

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

生物化学的/生理学的作用

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.

保管分類コード

11 - Combustible Solids

WGK

WGK 3

引火点(°F)

Not applicable

引火点(℃)

Not applicable


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S M Evans et al.
British journal of cancer, 72(4), 875-882 (1995-10-01)
One of the most sensitive hypoxia detection methods is based on the observation that binding of nitroimidazoles to cellular macromolecules occurs as a result of hypoxia-dependent bioreduction by cellular nitroreductases. Nitroimidazole-binding techniques provide measurements of hypoxia to virtually any degree
E M Lord et al.
Cancer research, 53(23), 5721-5726 (1993-12-01)
Hypoxic cells in tissue pose many medical problems, and there is a need for more accurate measurements of tissue hypoxia. However, measurement of the pO2 and the extent of hypoxia within normal and tumor tissue have proven difficult. One of
Sung Hoon Cho et al.
Nature, 537(7619), 234-238 (2016-08-09)
Germinal centres (GCs) promote humoral immunity and vaccine efficacy. In GCs, antigen-activated B cells proliferate, express high-affinity antibodies, promote antibody class switching, and yield B cell memory. Whereas the cytokine milieu has long been known to regulate effector functions that

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