PZ0160
UK-5099
≥98% (HPLC), powder, mitochondrial pyruvate carrier inhibitor
Synonym(s):
2-Cyano-3-(1-phenyl-1H-indol-3-yl)-2-propenoic acid, PF-1005023
Sign In to View Organizational & Contract Pricing.
Select a Size
About This Item
Empirical Formula (Hill Notation):
C18H12N2O2
CAS Number:
Molecular Weight:
288.30
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
MDL number:
Product Name
UK-5099, ≥98% (HPLC)
SMILES string
OC(=O)\C(=C\c1cn(-c2ccccc2)c3ccccc13)C#N
InChI key
BIZNHCWFGNKBBZ-JLHYYAGUSA-N
InChI
1S/C18H12N2O2/c19-11-13(18(21)22)10-14-12-20(15-6-2-1-3-7-15)17-9-5-4-8-16(14)17/h1-10,12H,(H,21,22)/b13-10+
assay
≥98% (HPLC)
form
powder
color
yellow to tan
solubility
DMSO: >20 mg/mL
storage temp.
2-8°C
Quality Level
Application
UK-5099 has been used:
- as a mitochondrial pyruvate blocker to reduce pyruvate transportation into mitochondria in Roswell park memorial institute (RPMI) 1640 medium for prostatic cancer cell line culture
- in dimethyl sulfoxide (DMSO) stock, to study the effect of inhibiting pyruvate transport into mitochondria on pro-inflammatory responses in lipopolysaccharide activated macrophages
- in topical treatment in order to study its effect on hair cycle induction in experimental mice
Biochem/physiol Actions
UK-5099 induces lactate generation.
UK-5099 is a potent inhibitor of the mitochondrial pyruvate transporter.
UK-5099 is a potent inhibitor of the mitochondrial pyruvate transporter. In rat heart mitochondria, UK-5099 inhibits pyruvate-dependent O2 consumption with an IC50 of 50 nM.
Features and Benefits
This compound is a featured product for Apoptosis research. Click here to discover more featured Apoptosis products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
Choose from one of the most recent versions:
Already Own This Product?
Find documentation for the products that you have recently purchased in the Document Library.
M S Shearman et al.
The Biochemical journal, 223(3), 673-676 (1984-11-01)
alpha-Cyano-beta-(1-phenylindol-3-yl)acrylate inhibited pyruvate transport into both liver and heart mitochondria approximately linearly with respect to its concentration until 65% inhibition was achieved. The extent of inhibition was dependent on the mitochondrial protein concentration. By extrapolation of plots of inhibition versus
M O Proudlove et al.
The Biochemical journal, 247(2), 441-447 (1987-10-15)
1. Mitochondria isolated from the thermogenic spadices of Arum maculatum and Sauromatum guttatum plants oxidized external NADH, succinate, citrate, malate, 2-oxoglutarate and pyruvate without the need to add exogenous cofactors. 2. Oxidation of substrates was virtually all via the alternative
Ajit S Divakaruni et al.
Proceedings of the National Academy of Sciences of the United States of America, 110(14), 5422-5427 (2013-03-21)
Facilitated pyruvate transport across the mitochondrial inner membrane is a critical step in carbohydrate, amino acid, and lipid metabolism. We report that clinically relevant concentrations of thiazolidinediones (TZDs), a widely used class of insulin sensitizers, acutely and specifically inhibit mitochondrial
A P Halestrap et al.
The Biochemical journal, 223(3), 677-685 (1984-11-01)
The inhibitor of mitochondrial pyruvate transport alpha-cyano-beta-(1-phenylindol-3-yl)-acrylate was used to inhibit progressively pyruvate carboxylation by liver mitochondria from control and glucagon-treated rats. The data showed that, contrary to our previous conclusions [Halestrap (1978) Biochem. J. 172, 389-398], pyruvate transport could
Oleic acid stimulates glucagon-like peptide-1 release from enteroendocrine cells by modulating cell respiration and glycolysis
Clara R, et al.
Metabolism and Disease, 65(3), 8-17 (2016)
Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.
Contact Technical Service