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C2759

Sigma-Aldrich

Carbonyl Cyanide m-Chlorophenylhydrazone

≥97% (TLC), powder, mitophagy inducer

Sinônimo(s):

m-Cl-CCP, CCCP, Mesoxalonitrile 3-chlorophenylhydrazone

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About This Item

Fórmula empírica (Notação de Hill):
C9H5ClN4
Número CAS:
555-60-2
Peso molecular:
204.62
Beilstein:
1842102
Número CE:
209-103-7
Número MDL:
MFCD00001848
Código UNSPSC:
12352200
ID de substância PubChem:
24892523
NACRES:
NA.77

Nome do produto

Carbonyl cyanide 3-chlorophenylhydrazone, ≥97% (TLC), powder

Ensaio

≥97% (TLC)

Formulário

powder

cor

yellow to orange

solubilidade

DMSO: 100 mM

temperatura de armazenamento

−20°C

cadeia de caracteres SMILES

Clc1cccc(N\N=C(\C#N)C#N)c1

InChI

1S/C9H5ClN4/c10-7-2-1-3-8(4-7)13-14-9(5-11)6-12/h1-4,13H

chave InChI

UGTJLJZQQFGTJD-UHFFFAOYSA-N

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Aplicação

Carbonyl cyanide 3-chlorophenylhydrazone (CCCP) has been used:
  • in the inhibition of efflux pump in clinical Pseudomonas aeruginosa
  • to inhibit oxidative phosphorylation activity of mitochondria in human Beas-2B bronchial epithelial cells
  • to prepare carbonyl cyanide m-chlorophenylhydrazone solution for oxidative and mitochondrial stress assay and mitophagy induction in Caenorhabditis elegans

Ações bioquímicas/fisiológicas

Carbonyl cyanide 3-chlorophenylhydrazone (CCCP) induces mitophagy in mammalian cells. CCCP suppresses the expression of few electron transport chain (ETC) proteins. Protonophore (H+ ionophore) and uncoupler of oxidative phosphorylation in mitochondria. Shown to have a number of effects on cellular calcium. Inhibits secretion of hepatic lipase and partially inhibits the pH gradient-activated Cl- uptake and Cl-/Cl- exchange activities in brush-border membrane vesicles.

Outras notas

2024 CiteAb Award Winner for Supplier Succeeding in Parkinson′s Research

Pictogramas

Skull and crossbones
GHS06

Palavra indicadora

Danger

Classificações de perigo

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Órgãos-alvo

Respiratory system

Código de classe de armazenamento

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

Classe de risco de água (WGK)

WGK 3

Equipamento de proteção individual

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

Escolha uma das versões mais recentes:

Certificados de análise (COA)

Lot/Batch Number
MKCQ1261
MKCP5323
MKCP0018
MKCM5342
MKCL3049

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Comparison of Efflux Pump Involvement in Antibiotic Resistance Among Pseudomonas aeruginosa Isolates of Burn and Non-Burn Patients
Azimi L, et al.
Archives of Pediatric Infectious Diseases, 4(3), e36160-e36160 (2016)
In vivo Mitophagy Monitoring in Caenorhabditis elegans to Determine Mitochondrial Homeostasis
Palikaras, Konstantinos and Tavernarakis, Nektarios
Bio-protocol, 7(7), 875-880 (2017)
Impaired oxidative phosphorylation regulates necroptosis in human lung epithelial cells
Koo MJ, et al.
Biochemical and Biophysical Research Communications, 464(3), 875-880 (2015)
Alvin P Joselin et al.
Human molecular genetics, 21(22), 4888-4903 (2012-08-09)
Mutations in several genes, including Parkin, PTEN-induced kinase 1 (Pink1) and DJ-1, are associated with rare inherited forms of Parkinson's disease (PD). Despite recent attention on the function of these genes, the interplay between DJ-1, Pink1 and Parkin in PD
Vimal B Maisuria et al.
Advanced science (Weinheim, Baden-Wurttemberg, Germany), 6(15), 1802333-1802333 (2019-08-14)
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