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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
Le tarif et la disponibilité ne sont pas disponibles actuellement.

Nom du produit

UK-5099, ≥98% (HPLC)

Niveau de qualité

100

Essai

≥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[1]
  • in dimethyl sulfoxide (DMSO) stock,[2] to study the effect of inhibiting pyruvate transport into mitochondria on pro-inflammatory responses in lipopolysaccharide activated macrophages[3]
  • in topical treatment in order to study its effect on hair cycle induction in experimental mice[4]

Actions biochimiques/physiologiques

UK-5099 induces lactate generation.[4]
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.

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

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Certificats d'analyse (COA)

Lot/Batch Number
0000294170
0000216472
0000216471
0000202685
021M4729V

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Retrouvez la documentation relative aux produits que vous avez récemment achetés dans la Bibliothèque de documents.

Consulter la Bibliothèque de documents

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
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
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
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)
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