6463-21-4Relevant academic research and scientific papers
A novel class of ethacrynic acid derivatives as promising drug-like potent generation of anticancer agents with established mechanism of action
Mignani, Serge,El Brahmi, Nabil,El Kazzouli, Sa?d,Eloy, Laure,Courilleau, Delphine,Caron, Joachim,Bousmina, Mosto M.,Caminade, Anne-Marie,Cresteil, Thierry,Majoral, Jean-Pierre
, p. 656 - 673 (2016/07/22)
The well-known diuretic Ethacrynic acid (EA, Edecrin), showing low anti-proliferative activities, was chemically modified at different positions. The new EA derivatives have been tested in?vitro in anti-proliferative assays on both tumor KB (epidermal carcinoma) and leukemia HL60 (promyelocytic) cells suitable targets for anticancer activity. Reduction of the α-β double bond of EA completely abolished anti-cancer activities, whereas introduction of either 2-(4-substituted phenyl)ethanamine (series A) or 4-(4-substituted phenyl)piperazine (series B) moieties generated compounds showing moderate to strong anti-proliferative activities against human cancer cell lines. Several substitutions on the phenyl of these two moieties are tolerated. The mechanism of action of the EA derivatives prepared in this study is more complex than the inhibition of glutathione S-transferase π ascribed as unique effect to EA and might help to overcome tumor resistances.
Synthesis and evaluation of [18F]Fluorobutyl ethacrynic amide: A potential PET tracer for studying glutathione transferase
Huang, Ho-Lien,Yeh, Chun-Nan,Chang, Kang-Wei,Chen, Jenn-Tzong,Lin, Kun-Ju,Chiang, Li-Wu,Jeng, Kee-Ching,Wang, Wei-Ting,Lim, Ken-Hong,Chen, Caleb Gonshen,Lin, Kun-I,Huang, Ying-Cheng,Lin, Wuu-Jyh,Yen, Tzu-Chen,Yu, Chung-Shan
supporting information; experimental part, p. 3998 - 4003 (2012/07/13)
[18F]Flurobutyl ethacrynic amide ([18F]FBuEA) was prepared from the precursor tosylate N-Boc-N-[4-(toluenesulfonyloxy)butyl] ethacrynic amide with a radiochemical yield of 3%, a specific activity of 48 GBq/μmol and radiochemical purity of 98%. Chemical conjugation of [ 18F]FBuEA with glutathione (GSH) via a self-coupling reaction and enzymatic conjugation under catalysis of glutathiontransferase alpha (GST-α) and π provided about 41% yields of radiochemical conjugated product [18F]FBuEA-GSH, 85% and 5-16%, respectively. The catalytic selectivity of this tracer toward GST-alpha was addressed. Positron emission tomography (PET) imaging of [18F]FBuEA in normal rats showed that a homogeneous pattern of radioactivity was distributed in the liver, suggesting a catalytic role of GST. By contrast, PET images of [18F]FBuEA in rats with thioacetamide-induced cholangiocarcinoma displayed a heterogeneous pattern of radioactive accumulation with cold spots in tumor lesions. PET imaging with [18F]FBuEA could be used for early diagnosis of hepatic tumor with a low GST activity as well as liver function.
Method and precursor for production of no-carrier-added N-(4-[18F] fluorobutyl)-Ethacrynic amide
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Page/Page column 2-3, (2011/04/19)
The present invention is related to a precursor for no-carrier-added fluorine-18 labeled ethacrynic acid, N-(4-[18F]fluorobutyl)-Ethacrynic amide([18F]FBuEA) and the preparation method for HPLC non-radioactive standards. Its chemical structure is shown in the following: In the precursor, R1 represents a protective group for the amide functional group; R2 represents leaving group; or R1 represents carboxyl group, R2 represents p-tosyloxy, methane sulfonyloxy group or trifluoromethane sulfonyloxy group or bromine (Br). For the HPLC non-radioactive standards, R1 represents a protective group for the amide functional group and hydrogen, R2 represents fluorine.
