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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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

PDSCL

Deleterious substance

JAN Code

PZ0160-25MG:4.548173308166E12
PZ0160-5MG:4.548173308173E12

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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