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C2759

Carbonyl Cyanide m-Chlorophenylhydrazone

≥97% (TLC), powder, mitophagy inducer

Synonym(s):

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

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100 mg
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$40.00
250 mg
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$115.00
1 g
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$201.00

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

$40.00

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Product Name

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

Quality Segment

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

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

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This Item
215911112968
Carbonyl cyanide 3-chlorophenylhydrazone ≥97% (TLC), powder

Sigma-Aldrich

C2759

Carbonyl cyanide 3-chlorophenylhydrazone

Carbonyl Cyanide m-Chlorophenylhydrazone Protonophore. Uncoupling agent for oxidative phosphorylation that inhibits mitochondrial function. Approximately 100 times more effective than 2,4-dinitrophenol.

Sigma-Aldrich

215911

Carbonyl Cyanide m-Chlorophenylhydrazone

Methylhydroquinone 99%

Sigma-Aldrich

112968

Methylhydroquinone

description

≥97% (TLC), powder

description

Protonophore. Uncoupling agent for oxidative phosphorylation that inhibits mitochondrial function. Approximately 100 times more effective than 2,4-dinitrophenol.

description

99%

form

powder

form

solid

form

solid

assay

≥97% (TLC)

assay

≥95% (HPLC)

assay

99%

Quality Level

200

Quality Level

100

Quality Level

100

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

-

solubility

DMSO: 100 mM

solubility

DMSO: 5 mg/mL, ethanol: 1 mg/mL

solubility

-

color

yellow to orange

color

yellow

color

-

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

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

WGK

WGK 3

PPE (personal protective equipment)

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

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Questions

1–3 of 3 Questions  

  1. What is the suggested incubation time and concentration of CCCP suggested for Hepg2 cells for a mitochondrial membrane potential assay?

    1 answer

    1. This product has not been specifically tested for use with HepG2 cells. However, based on published literature, see the general protocol below:

      Begin with 10 µM carbonyl cyanide m-chlorophenyl hydrazone
      Incubate for 30 minutes at 37 °C
      Measure mitochondrial membrane potential the fluorescent probe of choice.
      Prepare a 100 mM stock solution in dimethyl sulfoxide, dilute freshly in culture medium and include a vehicle control.
      Optimize with 5–20 µM for 15–60 minutes.
      Note that this is a general protocol, optimization may be required.

      Helpful?

  2. What is the solubility of CCCP in ethanol?

    1 answer

    1. This material is soluble in ethanol at 50 mg/mL, heating may be required. The product is tested for solubility in Acetone at 50 mg/mL and is also soluble at 100 mM in DMSO.

      Helpful?

  3. What is the shelf life of C2759 in cell culture media?

    1 answer

    1. Product C2759 has not undergone cell culture testing. However, information about storage after reconstitution is available. It states, "Following reconstitution, store in the refrigerator (4°C). Stock solutions are stable for up to 1 month at 4°C."

      Helpful?

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