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C2759

Carbonyl Cyanide m-Chlorophenylhydrazone

Name: Carbonyl Cyanide m-Chlorophenylhydrazone
Brand: SIGMA

≥97% (TLC), powder, mitophagy inducer

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

NACRES:

NA.77

PubChem Substance ID:

24892523

UNSPSC Code:

12352200

EC Number:

209-103-7

MDL number:

MFCD00001848

Beilstein/REAXYS Number:

1842102

Assay:

≥97% (TLC)

Form:

powder

Quality level:

200

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Properties

Product Name

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

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

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.