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PZ0160

Sigma-Aldrich

UK-5099

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

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C18H12N2O2
Numéro CAS:
56396-35-1
Poids moléculaire :
288.30
Numéro MDL:
MFCD19443867
Code UNSPSC :
12352200
ID de substance PubChem :
329823742
Nomenclature NACRES :
NA.77

product name

UK-5099, ≥98% (HPLC)

Pureté

≥98% (HPLC)

Forme

powder

Couleur

yellow to tan

Solubilité

DMSO: >20 mg/mL

Température de stockage

2-8°C

Chaîne SMILES 

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+

Clé InChI

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

Actions biochimiques/physiologiques

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.

Caractéristiques et avantages

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.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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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)
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
Application of mitochondrial pyruvate carrier blocker UK5099 creates metabolic reprogram and greater stem-like properties in LnCap prostate cancer cells in vitro
Zhong Y, et al.
Testing, 6(35), 37758-37758 (2015)
Y Hamon et al.
Blood, 90(8), 2911-2915 (1997-10-24)
The production of interleukin-1beta (IL-1beta), a powerful mediator of inflammation, is tightly regulated at several levels. However, in some pathologic conditions, a pharmacologic treatment is required to control the toxicity of excessive extracellular IL-1beta. Because of the heavy side effects
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
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