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Merck
모든 사진(1)

주요 문서

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SML1961

Sigma-Aldrich

EF5

≥98% (HPLC)

동의어(들):

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

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모든 사진(1)

About This Item

실험식(Hill 표기법):
C8H7F5N4O3
CAS Number:
152721-37-4
Molecular Weight:
302.16
UNSPSC 코드:
12352200
NACRES:
NA.77

Quality Level

100

분석

≥98% (HPLC)

양식

powder

색상

white to beige

solubility

DMSO: 10 mg/mL, clear

저장 온도

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

생화학적/생리학적 작용

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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시험 성적서(COA)

Lot/Batch Number

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문서 라이브러리 방문

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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