2-cyano-3-(1-phenylindol-3-yl)acrylate

Product Name: 2-cyano-3-(1-phenylindol-3-yl)acrylate
CAS No.: 56396-35-1
Chemical Name: 2-cyano-3-(1-phenylindol-3-yl)acrylate
Synonyms: CS-748;UK 5099;PF-1005023;PF-06340678;UK-5099 (PF-1005023);BIZNHCWFGNKBBZ-JLHYYAGUSA-N;2-cyano-3-(1-phenylindol-3-yl)acrylate;2-Cyano-3-(1-phenyl-1H-indol-3-yl)acrylic acid;Mitochondrial Pyruvate Carrier Inhibitor, UK5099;(E)-2-cyano-3-(1-phenylindol-3-yl)prop-2-enoicaci
CBNumber: CB11396725
Molecular Formula: C18H12N2O2
Formula Weight: 288.3
MOL File: 56396-35-1.mol

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2-cyano-3-(1-phenylindol-3-yl)acrylate Property

Melting point:: 235-238°C
Boiling point:: 448.6±45.0 °C(Predicted)
Density: 1.20
storage temp.: 2-8°C
solubility: DMSO: >20mg/mL
form: powder
pka: 1.49±0.19(Predicted)
color: yellow to tan
Stability:: Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 1 month.
InChIKey: BIZNHCWFGNKBBZ-JLHYYAGUSA-M

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Safety

WGK Germany: 3

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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: PZ0160
Product name: UK-5099
Purity: ≥98% (HPLC)
Packaging: 5mg
Price: $139
Updated: 2024/03/01

Sigma-Aldrich

Product number: PZ0160
Product name: UK-5099
Purity: ≥98% (HPLC)
Packaging: 25mg
Price: $519
Updated: 2024/03/01

Sigma-Aldrich

Product number: 5.04817
Product name: Mitochondrial Pyruvate Carrier Inhibitor, UK5099 - CAS 56396-35-1 - Calbiochem
Packaging: 5mg
Price: $111
Updated: 2024/03/01

Sigma-Aldrich

Product number: 5.04817
Product name: Mitochondrial Pyruvate Carrier Inhibitor, UK5099 - CAS 56396-35-1 - Calbiochem
Packaging: 25MG
Price: $378
Updated: 2024/03/01

Cayman Chemical

Product number: 16980
Product name: UK 5099
Purity: ≥95%
Packaging: 1mg
Price: $32
Updated: 2024/03/01

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2-cyano-3-(1-phenylindol-3-yl)acrylate Chemical Properties,Usage,Production

Description

UK-5099 (56396-35-1) is a potent inhibitor of the mitochondrial pyruvate carrier (MPC).1?Rapidly increases glucose uptake in human monocytes.2?Attenuates mitochondrial oxidative phosphorylation and increases glycolysis creating greater stem-like properties in LnCap prostate cancer cells.3?Blocks the neuroprotective action of L-lactate or pyruvate during glutamate-induced excitotoxicity.4?Inhibits pyruvate transport across the plasma membrane of trypanosomes (Ki=49 μM).5

Chemical Properties

Yellow Solid

Uses

Pyruvate transport into mitochondria is facilitated by mitochondrial pyruvate carrier (MPC) 1 and 2, two small transmembrane proteins that are part of a larger 150 kDa protein transport complex in the inner mitochondrial membrane. UK 5099 is a specific and potent inhibitor of MPC carrier activity. It potently inhibits pyruvate-dependent oxygen consumption by rat heart mitochondria with an IC50 value of 50 nM.

Uses

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

Uses

Inhibitor of plasma membrane monocarboxylate transporters (MCTs) and the mitochondrial pyruvate carrier (MPC).

Biochem/physiol Actions

UK-5099 induces lactate generation.

storage

Store at +4°C

References

1) Shearman and Halestrap (1984), The concentration of the mitochondrial pyruvate carrier in rat liver and heart mitochondria determined with alpha-cyano-beta-(1-phenylindol-3-yl)acrylate; Biochem. J.,?223?673 2) Divakaruni?et al.?(2013),?Thiazolidinediones are acute, specific inhibitors of the mitochondrial pyruvate carrier.; Proc. Natl. Acad. Sci. USA,?110?5422 3) Zhong?et al. (2015),?Application of mitochondrial pyruvate carrier blocker UK5099 creates metabolic reprogram and greater stem-like properties in LnCap prostate cancer cells in vitro; Oncotarget,?6?37758 4) Jourdain?et al. (2016),?L-Lactate protects neurons against excitotoxicity: implication of an ATP-mediated signaling cascade; Sci. Rep.,?6?21250 5) Wiemer?et al.?(1995),?The inhibition of pyruvate transport across the plasma membrane of the bloodstream form of Trypanosoma brucei and its metabolic implications; Biochem. J.,?312?479

2-cyano-3-(1-phenylindol-3-yl)acrylate Preparation Products And Raw materials

Raw materials

Preparation Products

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2-cyano-3-(1-phenylindol-3-yl)acrylate Suppliers

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View Lastest Price from 2-cyano-3-(1-phenylindol-3-yl)acrylate manufacturers

Career Henan Chemical Co

Product: 2-cyano-3-(1-phenylindol-3-yl)acrylate 56396-35-1
Price: US $1.00/KG
Min. Order: 1KG
Purity: 40%-99%
Supply Ability: 1000kg
Release date: 2018-08-20

56396-35-1, 2-cyano-3-(1-phenylindol-3-yl)acrylateRelated Search:

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2-cyano-3-(1-phenylindol-3-yl)acrylate

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UK 5099

(E)-2-cyano-3-(1-phenyl-1H-indol-3-yl)acrylic acid

BIZNHCWFGNKBBZ-JLHYYAGUSA-N

Mitochondrial Pyruvate Carrier Inhibitor, UK5099

PF-1005023; UK5099; UK 5099; PF1005023; PF 1005023

CS-748

Mitochondrial Pyruvate Carrier Inhibitor, UK5099 - CAS 56396-35-1 - Calbiochem

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2-Cyano-3-(1-phenyl-1H-indol-3-yl)acrylic acid

UK-5099 (PF-1005023)

(E)-2-cyano-3-(1-phenylindol-3-yl)prop-2-enoicaci

56396-35-1

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