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
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
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: GO:0042554 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11375352 |
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Target ID: GO:0016156 |
26.0 µM [EC50] | ||
Target ID: CHEMBL3383 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11992644 |
0.54 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Preventing | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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[Fluorescence spectra of the rare earth complex-PAA-g-PE films]. | 2001 Feb |
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Tumour necrosis factor induced an early release of superoxide and a late mitochondrial membrane depolarization in L929 cells. Increase in the production of superoxide is not sufficient to mimic the action of TNF. | 2001 Sep-Oct |
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High glucose stimulates angiotensinogen gene expression via reactive oxygen species generation in rat kidney proximal tubular cells. | 2002 Aug |
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Thenoyltrifluoroacetone, a potent inhibitor of carboxylesterase activity. | 2002 Feb 15 |
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Mitochondrial ROS initiate phosphorylation of p38 MAP kinase during hypoxia in cardiomyocytes. | 2002 Jun |
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Implication of mitochondria-derived ROS and cardiolipin peroxidation in N-(4-hydroxyphenyl)retinamide-induced apoptosis. | 2002 Jun 17 |
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High glucose-induced oxidative stress and mitochondrial dysfunction in neurons. | 2002 Nov |
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Magnetophoretic velocimetry of manganese(II) in a single microdroplet in a flow system under a high gradient magnetic field generated with a superconducting magnet. | 2002 Oct 1 |
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Inhibition of photosystem II of spinach by the respiration inhibitors piericidin A and thenoyltrifluoroacetone. | 2002 Sep |
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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 Jun 1 |
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Mitochondrial cytochrome c release mediates ceramide-induced activator protein 2 activation and gene expression in keratinocytes. | 2003 Nov 28 |
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Sources for superoxide release: lessons from blockade of electron transport, NADPH oxidase, and anion channels in diaphragm. | 2003 Oct |
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Reactive oxygen species from mitochondria induce cyclooxygenase-2 gene expression in human mesangial cells: potential role in diabetic nephropathy. | 2003 Oct |
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Control of energy dissipation and photochemical activity in photosystem I by NADP-dependent reversible conformational changes. | 2003 Oct 14 |
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Hypoxic increase in nitric oxide generation of rat sensory neurons requires activation of mitochondrial complex II and voltage-gated calcium channels. | 2004 |
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Growth inhibition dependent on reactive oxygen species generated by C9-UK-2A, a derivative of the antifungal antibiotic UK-2A, in Saccharomyces cerevisiae. | 2004 Aug |
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Low-temperature electrothermal vaporization of thenoyltrifluoroacetone complex of Sc(III) and Y(III) for sample introduction in an inductively coupled plasma atomic emission spectrometry, and their determination in biological samples. | 2004 Jan |
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Mutation in mitochondrial complex I ND6 subunit is associated with defective response to hypoxia in human glioma cells. | 2004 Jul 12 |
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Effect of n-octanesulphonylacetamide (OSA) on ATP and protein expression in Mycobacterium bovis BCG. | 2004 Oct |
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Effect of ligand radicals on vibrational IR, Raman and vibronic spectra of europium beta-diketonates. | 2005 Jan 1 |
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Increasing lanthanide luminescence by use of the RETEL effect. | 2006 Aug 1 |
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Preliminary evidence on existence of transplasma membrane electron transport in Entamoeba histolytica trophozoites: a key mechanism for maintaining optimal redox balance. | 2006 Dec |
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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 Dec 13 |
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Hypoxic vasoconstriction of partial muscular intra-acinar pulmonary arteries in murine precision cut lung slices. | 2006 Jun 29 |
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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 May |
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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 Sep |
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Mitochondrial electron-transport-chain inhibitors of complexes I and II induce autophagic cell death mediated by reactive oxygen species. | 2007 Dec 1 |
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ATP depletion does not account for apoptosis induced by inhibition of mitochondrial electron transport chain in human dopaminergic cells. | 2007 Feb |
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Chain length dependence of the interactions of bisquaternary ligands with the Torpedo nicotinic acetylcholine receptor. | 2007 Feb 1 |
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Pro-inflammatory cytokines increase reactive oxygen species through mitochondria and NADPH oxidase in cultured RPE cells. | 2007 Oct |
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Reductive dissolution of Pu(IV) by Clostridium sp. under anaerobic conditions. | 2008 Apr 1 |
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In vivo reactive oxygen species production induced by ischemia in muscle arterioles of mice: involvement of xanthine oxidase and mitochondria. | 2008 Feb |
Patents
Sample Use Guides
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7406888
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.
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206-316-7
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DTXSID1059812
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5601
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THENOYLTRIFLUOROACETONE
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DB04795
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SUBSTANCE RECORD