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Sigma-Aldrich

Rotenone

A mitochondrial toxin and a potent, reversible, and competitive inhibitor of complex I (NADH-CoQ reductase) of the respiratory chain.

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Synonym(s):
Rotenone
Empirical Formula (Hill Notation):
C23H22O6
CAS Number:
83-79-4
Molecular Weight:
394.42
MDL number:
MFCD09025614
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
protect from light

color

white to off-white

solubility

ethanol: 5 mg/mL
DMSO: 50 mg/mL
chloroform: 50 mg/mL

shipped in

ambient

storage temp.

10-30°C

InChI

1S/C23H22O6/c1-11(2)16-8-14-15(28-16)6-5-12-22(24)21-13-7-18(25-3)19(26-4)9-17(13)27-10-20(21)29-23(12)14/h5-7,9,16,20-21H,1,8,10H2,2-4H3/t16-,20-,21+/m1/s1

InChI key

JUVIOZPCNVVQFO-HBGVWJBISA-N

General description

A mitochondrial toxin and a potent, reversible and competitive inhibitor of complex I (NADH-CoQ reductase) of the respiratory chain. Also inhibits cellular proliferation in mouse liver.
A mitochondrial toxin and a potent, reversible, and competitive inhibitor of complex I (NADH-CoQ reductase) of the respiratory chain. Also inhibits cellular proliferation in mouse liver.

Biochem/physiol Actions

Cell permeable: no
Primary Target
NADH-CoQ reductase
Product does not compete with ATP.
Reversible: yes

Packaging

Packaged under inert gas

Warning

Toxicity: Toxic (F)

Reconstitution

Following reconstitution, aliquot, flush with nitrogen, and store at -70°C. Stock solutions are stable for up to 1 month at -70°C.

Other Notes

Due to the nature of the Hazardous Materials in this shipment, additional shipping charges may be applied to your order. Certain sizes may be exempt from the additional hazardous materials shipping charges. Please contact your local sales office for more information regarding these charges.
Kopustinskiene, D.M., et al. 2001. Eur. J. Pharmacol.428, 311.
Higgins, D.S., Jr. and Greenamyre, J.T. 1996. J. Neurosci. 16, 3807.
Cunningham, M.L., et al. 1995. Cancer Lett. 95, 93.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Pictograms

Skull and crossbonesEnvironment
GHS06,GHS09

Signal Word

Danger

Hazard Classifications

Acute Tox. 1 Inhalation - Acute Tox. 2 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 3

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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Measuring ATP levels within the cytosol of living cells in animals is important to understand how cellular activities are energetically supported, but is challenging because of tissue complexity and ATP sensor limitations. In this protocol, we describe how to quantify
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The specific functional properties of a tissue are distributed amongst its component cell types. The various cells act coherently, as an ensemble, in order to execute a physiologic response. Modern approaches for identifying and dissecting novel physiologic mechanisms would benefit
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In this study, we employed proteomics to identify mechanisms of posttranslational regulation on cell survival signaling proteins. We focused on Cu-Zn superoxide dismutase (SOD1), which protects cells from oxidative stress. We found that acylation of K122 on SOD1, while not
Localized glucose import, glycolytic processing, and mitochondria generate a focused ATP burst to power basement-membrane invasion.
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Frontiers in physiology, 14, 1164287-1164287 (2023-08-31)
Introduction: Mitochondrial disease is a spectrum of debilitating disorders caused by mutations in the mitochondrial DNA (mtDNA) or nuclear DNA that compromises the respiratory chain. Mitochondrial 3243A>G (m.3243 A>G) is the most common mutation showing great heterogeneity in phenotype. Previous
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