Thenoyltrifluoroacetone
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| Names | |
|---|---|
| IUPAC name
4,4,4-trifluoro-1-(2-thienyl)-1,3-butanedione | |
| Other names
2-thenoyltrifluoroacetone | |
| Identifiers | |
326-91-0  | |
| ChemSpider | 5399 |
| DrugBank | DB04795 |
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| Jmol-3D images | Image |
| PubChem | 5601 |
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| Properties | |
| C8H5F3O2S | |
| Molar mass | 222.18 g mol−1 |
| Appearance | fine, slightly yellow crystals |
| Melting point | 40 °C (104 °F; 313 K) |
| Boiling point | 96 °C (205 °F; 369 K) 8 mmHg |
| Hazards | |
| Main hazards | Xi |
| R-phrases | R36/37/38 |
| S-phrases | S26 S27 S28 S29 S30 S33 S35 S36 |
| Flash point | 12 °C (54 °F; 285 K) (closed cup) |
| Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa) | |
verify (what is: / ?) | |
| Infobox references | |
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.[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
- ↑ Sigma-Aldrich product page
- ↑ Tappel (July 1960). "Inhibition of electron transport by antimycin A, alkyl hydroxy naphthoquinones and metal coordination compounds". Biochem. Pharmacol. 3: 289–96. doi:10.1016/0006-2952(60)90094-0. PMID 13836892.
- ↑ "Crystal Structure of Mitochondrial Respiratory Membrane Protein Complex II". Cell 121 (7): 1043–1047. 2005. doi:10.1016/j.cell.2005.05.025. PMID 15989954.
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