Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C8H5F3O2S |
| Molecular Weight | 222.184 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
FC(F)(F)C(=O)CC(=O)C1=CC=CS1
InChI
InChIKey=TXBBUSUXYMIVOS-UHFFFAOYSA-N
InChI=1S/C8H5F3O2S/c9-8(10,11)7(13)4-5(12)6-2-1-3-14-6/h1-3H,4H2
| Molecular Formula | C8H5F3O2S |
| Molecular Weight | 222.184 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Thenoyltrifluoroacetone (TTFA) is a chelating agent and inhibitor of cellular respiration.
Studies indicate that thenoyltrifluoroacetone is a potent inhibitor of carboxylesterase activity, in addition to its ability to inhibit mitochondrial complex II activity. Thenoyltrifluoroacetone has been shown to specifically inhibit electron transfer from Fe-S centre S-3 (cluster 3) of succinate dehydrogenase to oxidized
ubiquinone and ubisemiquinone pairs.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Mitochondrial dysfunction by complex II inhibition delays overall cell cycle progression via reactive oxygen species production. | 2008-08-01 |
|
| Ionic liquid synergistic cation-exchange system for the selective extraction of lanthanum(III) using 2-thenoyltrifluoroacetone and 18-crown-6. | 2008-06 |
|
| Involvement of hypoxia-triggered endoplasmic reticulum stress in outlet obstruction-induced apoptosis in the urinary bladder. | 2008-05 |
|
| On-line metals preconcentration and simultaneous determination using cloud point extraction and inductively coupled plasma optical emission spectrometry in water samples. | 2008-04-07 |
|
| Reductive dissolution of Pu(IV) by Clostridium sp. under anaerobic conditions. | 2008-04-01 |
|
| Mitochondrial complex I defect induces ROS release and degeneration in trabecular meshwork cells of POAG patients: protection by antioxidants. | 2008-04 |
|
| Improved luminescence properties of europium complexes encapsulated into mesoporous SBA-15. | 2008-03 |
|
| In vivo reactive oxygen species production induced by ischemia in muscle arterioles of mice: involvement of xanthine oxidase and mitochondria. | 2008-02 |
|
| Mitochondrial electron-transport-chain inhibitors of complexes I and II induce autophagic cell death mediated by reactive oxygen species. | 2007-12-01 |
|
| Spectrofluorimetric determination of dopamine using chlorosulfonylthenoyltrifluoroacetone-europium probe. | 2007-11 |
|
| Pro-inflammatory cytokines increase reactive oxygen species through mitochondria and NADPH oxidase in cultured RPE cells. | 2007-10 |
|
| Enhanced luminescence of Eu(3+) by Y(3+) in ternary complexes Eu(X)Y(1-X)(TTA)3Dipy. | 2007-10 |
|
| Dual role of mitochondrial reactive oxygen species in hypoxia signaling: activation of nuclear factor-{kappa}B via c-SRC and oxidant-dependent cell death. | 2007-08-01 |
|
| Target identification of drug induced mitochondrial toxicity using immunocapture based OXPHOS activity assays. | 2007-08 |
|
| A new ion-imprinted silica gel sorbent for on-line selective solid-phase extraction of dysprosium(III) with detection by inductively coupled plasma-atomic emission spectrometry. | 2007-07-30 |
|
| Spectrofluorimetric determination of 5-hydroxytryptamine using chlorosulphonylthenoyltrifluoroacetone-europium probe. | 2007-07-05 |
|
| The environmental carcinogen 3-nitrobenzanthrone and its main metabolite 3-aminobenzanthrone enhance formation of reactive oxygen intermediates in human A549 lung epithelial cells. | 2007-06-01 |
|
| Primary role of superoxide anion generation in the cascade of events leading to endothelial dysfunction and damage in high glucose treated HUVEC. | 2007-05 |
|
| Synthesis, spectral, and thermal characterizations of Ni(II) and Cu(II) beta-diketone complexes with thenoyltrifluoroacetone ligand. | 2007-04 |
|
| Dicoumarol impairs mitochondrial electron transport and pyrimidine biosynthesis in human myeloid leukemia HL-60 cells. | 2007-02-01 |
|
| Chain length dependence of the interactions of bisquaternary ligands with the Torpedo nicotinic acetylcholine receptor. | 2007-02-01 |
|
| Generation of reactive oxygen species is an early event in dolichyl phosphate-induced apoptosis. | 2007-02-01 |
|
| Preconditioning protects endothelium by preventing ET-1-induced activation of NADPH oxidase and xanthine oxidase in post-ischemic heart. | 2007-02 |
|
| ATP depletion does not account for apoptosis induced by inhibition of mitochondrial electron transport chain in human dopaminergic cells. | 2007-02 |
|
| Luminescent Pt(II)(bipyridyl)(diacetylide) chromophores with pendant binding sites as energy donors for sensitised near-infrared emission from lanthanides: structures and photophysics of Pt(II)/Ln(III) assemblies. | 2006-12-13 |
|
| Preliminary evidence on existence of transplasma membrane electron transport in Entamoeba histolytica trophozoites: a key mechanism for maintaining optimal redox balance. | 2006-12 |
|
| Evidence for nitrite reductase activity in intact mouse Leydig tumor cells. | 2006-11 |
|
| Hyphal formation of Candida albicans is controlled by electron transfer system. | 2006-09-15 |
|
| Evaluation of the cytotoxic and pro-apoptotic activities of Eu(III) complexes with appended DNA intercalators in a panel of human malignant cell lines. | 2006-09 |
|
| Increasing lanthanide luminescence by use of the RETEL effect. | 2006-08-01 |
|
| Copper-induced stimulation of extracellular signal-regulated kinase in trout hepatocytes: the role of reactive oxygen species, Ca2+, and cell energetics and the impact of extracellular signal-regulated kinase signaling on apoptosis and necrosis. | 2006-08 |
|
| Evidence of ROS generation by mitochondria in cells with impaired electron transport chain and mitochondrial DNA damage. | 2006-07-07 |
|
| Hypoxic vasoconstriction of partial muscular intra-acinar pulmonary arteries in murine precision cut lung slices. | 2006-06-29 |
|
| The sensitive determination of nucleic acids using resonance light scattering quenching method. | 2006-06 |
|
| Analysis of Indian blue ballpoint pen inks tagged with rare-earth thenoyltrifluoroacetonates by inductively coupled plasma-mass spectrometry and instrumental neutron activation analysis. | 2006-05-25 |
|
| The twinned crystal structure of mu-2,2'-bipyrimidine-1kappa2N1,N1':2kappa2N3,N3'-bis{tris[4,4,4-trifluoro-1-(2-thienyl)butane-1,3-dionato-kappa2O,O']terbium(III)} ethyl acetate solvate. | 2006-05 |
|
| The sensitive determination of nucleic acids using a fluorescence-quenching method. | 2006-04-29 |
|
| Synthesis, characterization and application of Ni(tta)2.tmeda to MOCVD of nickel oxide thin films. | 2006-02-28 |
|
| Nitrogenous synergists induced potentiometric response to metal ions with polymeric liquid membranes containing thenoyltrifluoroacetone as an ionophore. | 2006-02 |
|
| Halogen-free water-immiscible ionic liquids based on tetraoctylammonium cation and dodecylsulfate and dodecylbenzenesulfonate anions, and their application as chelate extraction solvent. | 2006-02 |
|
| Homocysteine-induced endothelin-1 release is dependent on hyperglycaemia and reactive oxygen species production in bovine aortic endothelial cells. | 2006 |
|
| Multifunctional cadmium single source precursor for the selective deposition of CdO or CdS by a solution route. | 2005-12-07 |
|
| Intermittent high glucose enhances ICAM-1, VCAM-1 and E-selectin expression in human umbilical vein endothelial cells in culture: the distinct role of protein kinase C and mitochondrial superoxide production. | 2005-12 |
|
| Hypertonic induction of COX-2 in collecting duct cells by reactive oxygen species of mitochondrial origin. | 2005-10-14 |
|
| Selective extraction of naturally occurring radioactive Ra2+. | 2005-09 |
|
| Synthesis, characterization, and luminescence properties of the ternary europium complex covalently bonded to mesoporous SBA-15. | 2005-08-18 |
|
| Iron absorption and oxidant stress during erythropoietin therapy in very low birth weight premature infants: a cohort study. | 2005-08-05 |
|
| Mitochondrial perturbation attenuates bile acid-induced cytotoxicity. | 2004-11-15 |
|
| Location and recycling of mitochondrial alpha-tocopherol. | 2003-08 |
|
| Transfer rate of several tris(beta-diketonato)iron(III) complexes at the bulk aqueous--Triton X-100 micellar interface: effects of substituent groups in the extractants. | 2003-06-01 |
Patents
Sample Use Guides
In Vitro Use Guide
Curator's Comment: Effect of thenoyltrifluoroacetone was assayed on H202 formation
by -antimycin- and uncoupler-supplemented pigeon heart mitochondria.
Thenoyltrifluoroacetone markedly decreased H202 production with a 74% maximal inhibition and a half-maximal effect at about 60uM.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 19:52:40 GMT 2025
by
admin
on
Mon Mar 31 19:52:40 GMT 2025
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| Record UNII |
MYQ9MNW7NI
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| Record Status |
Validated (UNII)
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| Record Version |
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66544
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206-316-7
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DTXSID1059812
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MYQ9MNW7NI
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326-91-0
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5601
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THENOYLTRIFLUOROACETONE
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DB04795
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