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Key Documents

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PZ0160

Sigma-Aldrich

UK-5099

≥98% (HPLC), powder, mitochondrial pyruvate carrier inhibitor

Sinónimos:

2-Cyano-3-(1-phenyl-1H-indol-3-yl)-2-propenoic acid, PF-1005023

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About This Item

Fórmula empírica (notación de Hill):
C18H12N2O2
Número de CAS:
56396-35-1
Peso molecular:
288.30
MDL number:
MFCD19443867
UNSPSC Code:
12352200
PubChem Substance ID:
329823742
NACRES:
NA.77

product name

UK-5099, ≥98% (HPLC)

Quality Level

100

assay

≥98% (HPLC)

form

powder

color

yellow to tan

solubility

DMSO: >20 mg/mL

storage temp.

2-8°C

SMILES string

OC(=O)\C(=C\c1cn(-c2ccccc2)c3ccccc13)C#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+

InChI key

BIZNHCWFGNKBBZ-JLHYYAGUSA-N

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. 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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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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
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
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
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)
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