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C2759 Sigma-Aldrich

Carbonyl cyanide 3-chlorophenylhydrazone

≥97% (TLC), powder

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

  • CAS Number 555-60-2

  • Empirical Formula (Hill Notation) C9H5ClN4

  • Molecular Weight 204.62

  •  Beilstein/REAXYS Number 1842102

  •  EC Number 209-103-7

  •  MDL number MFCD00001848

  •  PubChem Substance ID 24892523

  •  NACRES NA.77

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Properties

Related Categories Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, C-CH, Cell Biology, Cell Signaling and Neuroscience,
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

Description

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

Packaging

1 g in glass bottle

250 mg in glass bottle

100 mg in glass insert

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.

Safety & Documentation

Safety Information

Symbol 
GHS06  GHS06
Signal word 
Danger
Target organs 
Respiratory system
RIDADR 
UN 2811 6.1 / PGIII
WGK Germany 
WGK 3
RTECS 
FG5600000

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

Articles

Discover Bioactive Small Molecules for Nitric Oxide & Cell Stress Research

Exposure to harsh conditions, cellular damage, and other factors can cause stress on cells. Stress attributed directly and indirectly to oxygen is referred to as oxidative stress, which is imposed on...
Keywords: Antimicrobials, Bioactive small molecules, Cancer, Diseases, Neurodegenerative Diseases, Oxidations

Peer-Reviewed Papers
15

References

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