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PZ0160

Sigma-Aldrich

UK-5099

≥98% (HPLC)

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C18H12N2O2
CAS Number:
56396-35-1
Molecular Weight:
288.30
MDL number:
MFCD19443867
UNSPSC Code:
12352200
PubChem Substance ID:
329823742
NACRES:
NA.77

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘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
B J Dezube et al.
Journal of acquired immune deficiency syndromes and human retrovirology : official publication of the International Retrovirology Association, 14(1), 13-17 (1997-01-01)
Interleukin-6 (IL-6) may be important in the pathogenesis of HIV-1 because of its ability to induce HIV-1 expression in infected cells in vitro. Tenidap, a structurally and functionally novel antirheumatic drug affecting diverse biologic processes, has been shown to reduce
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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Discover Bioactive Small Molecules for Apoptosis

Apoptosis, or programmed cell death (PCD), is a selective process for the removal of unnecessary, infected or transformed cells in various biological systems. As it plays a role in the homeostasis of multicellular organisms, apoptosis is tightly regulated through two principal pathways by a number of regulatory and effector molecules.

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