Thenoyltrifluoroacetone

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.

Thenoyltrifluoroacetone[1]
Names
IUPAC name
4,4,4-trifluoro-1-(2-thienyl)-1,3-butanedione
Other names
2-thenoyltrifluoroacetone
Identifiers
3D model (JSmol)
ChemSpider
DrugBank
ECHA InfoCard 100.005.743
UNII
Properties
C8H5F3O2S
Molar mass 222.18 g mol−1
Appearance fine, slightly yellow crystals
Melting point 40 to 44 °C (104 to 111 °F; 313 to 317 K)
Boiling point 96 to 98 °C (205 to 208 °F; 369 to 371 K) 8 mmHg
Hazards
Main hazards Xi
R-phrases (outdated) R36/37/38
S-phrases (outdated) S26 S27 S28 S29 S30 S33 S35 S36
Flash point 12 °C (54 °F; 285 K) (closed cup)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Perhaps the first report of TTFA as an inhibitor of respiration was by A. L. Tappel in 1960.[2] 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 .[3]

References
  1. 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 (4): 289–96. doi:10.1016/0006-2952(60)90094-0. PMID 13836892.
  3. Sun, Fei; Huo, Xia; Zhai, Yujia; Wang, Aojin; Xu, Jianxing; Su, Dan; Bartlam, Mark; Rao, Zihe (2005). "Crystal Structure of Mitochondrial Respiratory Membrane Protein Complex II". Cell. 121 (7): 1043–1047. doi:10.1016/j.cell.2005.05.025. PMID 15989954.


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