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C2759

Sigma-Aldrich

Carbonyl cyanide 3-chlorophenylhydrazone

≥97% (TLC), powder

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C9H5ClN4
CAS Number:
555-60-2
Molecular Weight:
204.62
Beilstein:
1842102
EC Number:
209-103-7
MDL number:
MFCD00001848
UNSPSC Code:
12352200
PubChem Substance ID:
24892523
NACRES:
NA.77

Quality Level

200

Assay

≥97% (TLC)

form

powder

color

yellow to orange

solubility

DMSO: 100 mM

storage temp.

−20°C

SMILES string

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

InChI key

UGTJLJZQQFGTJD-UHFFFAOYSA-N

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Application

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

Biochem/physiol Actions

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.

Other Notes

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

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

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

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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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)
Antibiotic resistance is spreading at an alarming rate among pathogenic bacteria in both medicine and agriculture. Interfering with the intrinsic resistance mechanisms displayed by pathogenic bacteria has the potential to make antibiotics more effective and decrease the spread of acquired
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