Thenoyltrifluoroacetone Explained
Thenoyltrifluoroacetone, C8H5F3O2S, is a chemical compound used pharmacologically as a chelating agent. It is an inhibitor of cellular respiration by blocking the respiratory chain at complex II.
Perhaps the first report of TTFA as an inhibitor of respiration was by A. L. Tappel in 1960.[1] Tappel had the (erroneous) idea that inhibitors like antimycin and alkyl hydroxyquinoline-N-oxide might work by chelating iron in the hydrophobic milieu of respiratory membrane proteins, so he tested a series of hydrophobic chelating agents. TTFA was a potent inhibitor, but not because of its chelating ability. TTFA binds at the quinone reduction site in Complex II, preventing ubiquinone from binding. The first x-ray structure of Complex II showing how TTFA binds, 1ZP0, was published in 2005.[2]
Thenoyltrifluoroacetone can be made in a Claisen condensation of ethyl trifluoroacetate and 2-acetylthiophene.[3] [4]
Notes and References
- Tappel. Inhibition of electron transport by antimycin A, alkyl hydroxy naphthoquinones and metal coordination compounds. 13836892 . 3. 4. July 1960. Biochem. Pharmacol.. 289–96. 10.1016/0006-2952(60)90094-0.
- Crystal Structure of Mitochondrial Respiratory Membrane Protein Complex II . 2005 . 121 . 1043–1047 . 10.1016/j.cell.2005.05.025 . Cell . 15989954 . 7. Sun . Fei . Huo . Xia . Zhai . Yujia . Wang . Aojin . Xu . Jianxing . Su . Dan . Bartlam . Mark . Rao . Zihe . 16697879 . free .
- Book: Gergel, Max G.. Excuse me sir, would you like to buy a kilo of isopropyl bromide?. Max Gergel. March 1977. Pierce Chemical. 130.
- Taydakov . Ilya V . Kreshchenova . Yuliya M . Dolotova . Ekaterina P . A convenient and practical synthesis of β-diketones bearing linear perfluorinated alkyl groups and a 2-thienyl moiety . Beilstein Journal of Organic Chemistry . 27 December 2018 . 14 . 3106–3111 . 10.3762/bjoc.14.290. 30643588 . 6317410 .
