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

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

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
Enhancement of oxidative damage to cultured cells and Caenorhabditis elegans by mitochondrial electron transport inhibitors.	2001 Apr	11569921
Hyperglycemia potentiates collagen-induced platelet activation through mitochondrial superoxide overproduction.	2001 Jun	11375352
Mitochondrial electron transport inhibitors cause lipid peroxidation-dependent and -independent cell death: protective role of antioxidants.	2001 Sep 1	11516165
High glucose stimulates angiotensinogen gene expression via reactive oxygen species generation in rat kidney proximal tubular cells.	2002 Aug	12130563
Role of mitochondrial complexes I and II, reactive oxygen species and arachidonic acid metabolism in deoxycholate-induced apoptosis.	2002 Mar 28	11825660
High glucose-induced oxidative stress and mitochondrial dysfunction in neurons.	2002 Nov	12409316
Inhibition of photosystem II of spinach by the respiration inhibitors piericidin A and thenoyltrifluoroacetone.	2002 Sep	12400692
Location and recycling of mitochondrial alpha-tocopherol.	2003 Aug	16120342
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
Glucose regulates monocyte adhesion through endothelial production of interleukin-8.	2003 Mar 7	12600878
Essential role of complex II of the respiratory chain in hypoxia-induced ROS generation in the pulmonary vasculature.	2003 May	12676762
Mutation in mitochondrial complex I ND6 subunit is associated with defective response to hypoxia in human glioma cells.	2004 Jul 12	15248896
Catalase protects cardiomyocyte function in models of type 1 and type 2 diabetes.	2004 May	15111504
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 Dec	16285992
Hypertonic induction of COX-2 in collecting duct cells by reactive oxygen species of mitochondrial origin.	2005 Oct 14	16024921
Selective extraction of naturally occurring radioactive Ra2+.	2005 Sep	16100615
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
Halogen-free water-immiscible ionic liquids based on tetraoctylammonium cation and dodecylsulfate and dodecylbenzenesulfonate anions, and their application as chelate extraction solvent.	2006 Feb	16512407
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
Target identification of drug induced mitochondrial toxicity using immunocapture based OXPHOS activity assays.	2007 Aug	17346924
Enhanced luminescence of Eu(3+) by Y(3+) in ternary complexes Eu(X)Y(1-X)(TTA)3Dipy.	2007 Oct	17329150
Spectrofluorimetric determination of 5-hydroxytryptamine using chlorosulphonylthenoyltrifluoroacetone-europium probe.	2007 Sep-Oct	17610298
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
Ionic liquid synergistic cation-exchange system for the selective extraction of lanthanum(III) using 2-thenoyltrifluoroacetone and 18-crown-6.	2008 Jun	18544855
Involvement of hypoxia-triggered endoplasmic reticulum stress in outlet obstruction-induced apoptosis in the urinary bladder.	2008 May	18347581

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.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 19:39:48 GMT 2023` Edited by `admin` on `Fri Dec 15 19:39:48 GMT 2023`
Record UNII	MYQ9MNW7NI
Record Status	`Validated (UNII)`
Record Version

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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