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Thenoyltrifluoroacetone

| NFPA-H = | NFPA-F = | NFPA-R = | NFPA-S =

Thenoyltrifluoroacetone (TTFA) is a chemical compound with the molecular formula C8H5F3O2S. It is used pharmacologically as a chelating agent. It is an inhibitor of cellular respiration by blocking the respiratory chain at complex II.

The first report of TTFA as an inhibitor of respiration was by A. L. Tappel in 1960. Tappel had the erroneous idea that inhibitors such as 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 was published in 2005.

Thenoyltrifluoroacetone can be made in by Claisen condensation of ethyl trifluoroacetate and 2-acetylthiophene.

References

References

  1. [http://www.sigmaaldrich.com/catalog/search/ProductDetail/FLUKA/88302 Sigma-Aldrich product page]
  2. Tappel. (July 1960). "Inhibition of electron transport by antimycin A, alkyl hydroxy naphthoquinones and metal coordination compounds". Biochem. Pharmacol..
  3. (2005). "Crystal Structure of Mitochondrial Respiratory Membrane Protein Complex II". Cell.
  4. {{PDB. 1ZP0
  5. Gergel, Max G.. (March 1977). "Excuse me sir, would you like to buy a kilo of isopropyl bromide?". Pierce Chemical.
  6. (27 December 2018). "A convenient and practical synthesis of β-diketones bearing linear perfluorinated alkyl groups and a 2-thienyl moiety". Beilstein Journal of Organic Chemistry.
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thiophenes diketones chelating-agents trifluoromethyl-ketones
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