An inhibitor of respiration
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2-Thenoyltrifluoroacetone

Item No. 15517

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4,4,4-trifluoro-1-(2-thienyl)-1,3-butanedione
CAS Number
326-91-0
Synonyms
  • NSC 66544
  • NSC 405702
  • NSC 405703
  • NSC 405704
  • NSC 405705
  • NSC 405706
  • TTFA
Molecular Formula
C8H5F3O2S
Formula Weight
222.2
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlEthanol: 30 mg/ml
λmax
324, 326, 355 nm
SMILES
O=C(C1=CC=CS1)CC(C(F)(F)F)=O
InChi Code
InChI=1S/C8H5F3O2S/c9-8(10,11)7(13)4-5(12)6-2-1-3-14-6/h1-3H,4H2
InChi Key
TXBBUSUXYMIVOS-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Cayman Chemical
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    Product Description

    2-Thenoyltrifluoroacetone (TTFA) is an inhibitor of respiration in animals and bacteria. In animals, TTFA binds at the quinone reduction site of succinate:ubiquinone oxidoreductase (SQR; Complex II), preventing ubiquinone from binding.1,2 It inhibits NADH fumarate reductase in bacteria.3,4 TTFA also inhibits photosystem II in plants and NADH-ubiquinone oxidoreductase of the virus Vibrio cholerae, decreasing cholera toxin production.5,6 This compound is also a chelator of metals, including lanthanum, zirconium, hafnium, and neodymium.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Sun, F., Huo, X., Zhai, Y., et al. Crystal structure of mitochondrial respiratory membrane protein complex II. Cell 121(7), 1043-1057 (2005).

    2. Horsefield, R., Yankovskaya, V., Sexton, G., et al. Structural and computational analysis of the quinone-binding site of complex II (succinate-ubiquinone oxidoreductase): A mechanism of electron transfer and proton conduction during ubiquinone reduction. The Journal of Biological Chemisty 281(11), 7309-7316 (2006).

    3. Yankovskaya, V., Sablin, S.O., Ramsay, R.R., et al. Inhibitor probes of the quinone binding sites of mammalian complex II and Escherichia coli fumarate reductase. The Journal of Biological Chemisty 271(35), 21020-21024 (1996).

    4. Chen, M., Andersen, L.P., Zhai, L., et al. Characterization of the respiratory chain of Helicobacter pylori. FEMS Immunol. Med. Microbiol. 24(2), 169-174 (1999).

    5. Ikezawa, N., Ifuku, K., Endo, T., et al. Inhibition of photosystem II of spinach by the respiration inhibitors piericidin A and thenoyltrifluoroacetone. Biosci. Biotechnol. Biochem. 66(9), 1925-1929 (2002).

    6. Minato, Y., Fassio, S.R., Reddekopp, R.L., et al. Inhibition of the sodium-translocating NADH-ubiquinone oxidoreductase [Na+-NQR] decreases cholera toxin production in Vibrio cholerae O1 at the late exponential growth phase. Microb. Pathog. 66, 36-39 (2014).

    Product Citations

    Soriano-Castell, D., Currais, A., and Maher, P. Defining a pharmacological inhibitor fingerprint for oxytosis/ferroptosis. Free Radic. Biol. Med. S0891-5849(21), (2021).

    Bai, L., Zhou, H., Xu, R., et al. A potent and selective small-molecule degrader of STAT3 achieves complete tumor regression in vivo. Cancer Cell 36(5), 498-511 (2019).