THENOYLTRIFLUOROACETONE

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

Structure Search

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

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11992644 | https://www.ncbi.nlm.nih.gov/pubmed/7406888 | https://www.drugbank.ca/drugs/DB04795

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	Potency
superoxide anion generation 11 Target ID: GO:0042554 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11375352	Inhibitor 8297
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial 2 Target ID: CHEMBL5758 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7406888 \| https://www.ncbi.nlm.nih.gov/pubmed/27140478 \| https://www.ncbi.nlm.nih.gov/pubmed/10841308 \| https://www.ncbi.nlm.nih.gov/pubmed/5160697	Inhibitor 8297
fumarate reductase (NADH) activity 1 Target ID: GO:0016156 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10378416 \| https://www.ncbi.nlm.nih.gov/pubmed/7622334	Inhibitor 8297	26.0 µM [EC50]
Carboxylesterase 8 Target ID: CHEMBL3383 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11992644	Inhibitor 8297	0.54 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Prostate cancer 178 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20811696	Preventing		Basic research	Unknown Approved Use Unknown
Diabetes mellitus 91 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28835584 https://www.ncbi.nlm.nih.gov/pubmed/11375352 https://www.ncbi.nlm.nih.gov/pubmed/15111504	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
[Fluorescence spectra of the rare earth complex-PAA-g-PE films].	2001 Feb	12953574
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	11490098
High glucose stimulates angiotensinogen gene expression via reactive oxygen species generation in rat kidney proximal tubular cells.	2002 Aug	12130563
Thenoyltrifluoroacetone, a potent inhibitor of carboxylesterase activity.	2002 Feb 15	11992644
Mitochondrial ROS initiate phosphorylation of p38 MAP kinase during hypoxia in cardiomyocytes.	2002 Jun	12003789
Implication of mitochondria-derived ROS and cardiolipin peroxidation in N-(4-hydroxyphenyl)retinamide-induced apoptosis.	2002 Jun 17	12085192
High glucose-induced oxidative stress and mitochondrial dysfunction in neurons.	2002 Nov	12409316
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	12380826
Inhibition of photosystem II of spinach by the respiration inhibitors piericidin A and thenoyltrifluoroacetone.	2002 Sep	12400692
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	16256601
Mitochondrial cytochrome c release mediates ceramide-induced activator protein 2 activation and gene expression in keratinocytes.	2003 Nov 28	12952965
Sources for superoxide release: lessons from blockade of electron transport, NADPH oxidase, and anion channels in diaphragm.	2003 Oct	14580324
Reactive oxygen species from mitochondria induce cyclooxygenase-2 gene expression in human mesangial cells: potential role in diabetic nephropathy.	2003 Oct	14514642
Control of energy dissipation and photochemical activity in photosystem I by NADP-dependent reversible conformational changes.	2003 Oct 14	14529296
Hypoxic increase in nitric oxide generation of rat sensory neurons requires activation of mitochondrial complex II and voltage-gated calcium channels.	2004	15350645
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	15515888
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	14658024
Mutation in mitochondrial complex I ND6 subunit is associated with defective response to hypoxia in human glioma cells.	2004 Jul 12	15248896
Effect of n-octanesulphonylacetamide (OSA) on ATP and protein expression in Mycobacterium bovis BCG.	2004 Oct	15355939
Effect of ligand radicals on vibrational IR, Raman and vibronic spectra of europium beta-diketonates.	2005 Jan 1	15556438
Increasing lanthanide luminescence by use of the RETEL effect.	2006 Aug 1	16969811
Preliminary evidence on existence of transplasma membrane electron transport in Entamoeba histolytica trophozoites: a key mechanism for maintaining optimal redox balance.	2006 Dec	17039394
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	16991190
Hypoxic vasoconstriction of partial muscular intra-acinar pulmonary arteries in murine precision cut lung slices.	2006 Jun 29	16808843
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	16679578
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	17017982
Mitochondrial electron-transport-chain inhibitors of complexes I and II induce autophagic cell death mediated by reactive oxygen species.	2007 Dec 1	18032788
ATP depletion does not account for apoptosis induced by inhibition of mitochondrial electron transport chain in human dopaminergic cells.	2007 Feb	17027047
Chain length dependence of the interactions of bisquaternary ligands with the Torpedo nicotinic acetylcholine receptor.	2007 Feb 1	17118342
Pro-inflammatory cytokines increase reactive oxygen species through mitochondria and NADPH oxidase in cultured RPE cells.	2007 Oct	17765224
Reductive dissolution of Pu(IV) by Clostridium sp. under anaerobic conditions.	2008 Apr 1	18504965
In vivo reactive oxygen species production induced by ischemia in muscle arterioles of mice: involvement of xanthine oxidase and mitochondria.	2008 Feb	18055522

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Thenoyltrifluoroacetone markedly decreased H202 production with a 74% maximal inhibition and a half-maximal effect at about 60uM.

Name

Type

Language

THENOYLTRIFLUOROACETONE

Systematic Name

English

4,4,4-TRIFLUORO-1-(2-THIENYL)-1,3-BUTANEDIONE

Systematic Name

English

2-THENOYLTRIFLUOROACETONE

Systematic Name

English

NSC-66544

Code

English

Code System Code Type Description

NSC

66544