Rotenone

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Cat.No. 3616 - Rotenone | C23H22O6 | CAS No. 83-79-4
Description: Inhibits complex I of the mitochondrial electron transport chain
Chemical Name: (2R,6aS,12aS)-1,2,12,12a-Tetrahydro-8,9-dimethoxy-2-(1-methylethenyl)-[1]benzopyrano[3,4-b]furo[2,3-h][1]benzopyran-6(6aH)-one
Purity: ≥95% (HPLC)
Datasheet
Citations (7)
Reviews

Biological Activity

Mitochondrial electron transport chain inhibitor (IC50 = 1.7 - 2.2 μM at complex I). Inhibits NADH oxidation by cardiac sarcoplasmic reticulum (IC50 = 3.4 nM). Commonly used pesticide and induces Parkinsonism in animal models. May also inhibit autophagy induction; blocks lysosomal degradation of autophagic vacuoles. Cell-permeable and brain penetrant.

Technical Data

M. Wt 394.42
Formula C23H22O6
Storage Store at RT
Purity ≥95% (HPLC)
CAS Number 83-79-4
PubChem ID 6758
InChI Key JUVIOZPCNVVQFO-HBGVWJBISA-N
Smiles C=[C@](C)[C@@H](C5)OC4=C5C(O3)=C(C=C4)C([C@@]([C@@]3([H])CO2)([H])C1=C2C=C(OC)C(OC)=C1)=O

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.

Tocris products are intended for laboratory research use only, unless stated otherwise.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 39.44 100
ethanol 1.97 5

Preparing Stock Solutions

The following data is based on the product molecular weight 394.42. Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 2.54 mL 12.68 mL 25.35 mL
5 mM 0.51 mL 2.54 mL 5.07 mL
10 mM 0.25 mL 1.27 mL 2.54 mL
50 mM 0.05 mL 0.25 mL 0.51 mL

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References

References are publications that support the biological activity of the product.

Cherednichenko et al (2004) NADH oxidase activity of rat cardiac sarcoplasmic reticulum regulates calcium-induced calcium release. Circ.Res. 94 478 PMID: 14699012

Uversky (2004) Neurotoxicant-induced animal models of Parkinson's disease: understanding the role of rotenone, maneb and paraquat in neurodegeneration. Cell Tissue Res. 318 225 PMID: 15258850

Gomez et al (2007) Pesticides and impairment of mitochondrial function in relation with the parkinsonian syndrome. Front.Biosci. 12 1079 PMID: 17127363

Mader et al (2012) Rotenone inhibits autophagic flux prior to inducing cell death. ACS Chem.Neurosci. 3 1063 PMID: 23259041


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Keywords: Rotenone, Rotenone supplier, inhibitors, inhibits, complex, I, mitochondrial, electron, transport, chain, Oxidative, phosphorylation, parkinson's, parkinsons, parkinsonism, Phosphorylation, 3616, Tocris Bioscience

7 Citations for Rotenone

Citations are publications that use Tocris products. Selected citations for Rotenone include:

Banh et al (2016) PTP1B controls non-mitochondrial oxygen consumption by regulating RNF213 to promote tumour survival during hypoxia. Nat Cell Biol 18 803 PMID: 27323329

Moloney et al (2017) Subcellular localization of the FLT3-ITD oncogene plays a significant role in the production of NOX- and p22(phox)-derived reactive oxygen species in acute myeloid leukemia. Leuk Res 52 34 PMID: 27870947

Battefeld et al (2019) High-Frequency Microdomain Ca2+ Transients and Waves during Early Myelin Internode Remodeling. Cell Rep 26 182 PMID: 30605675

Martin et al (2017) A Role for Mitochondrial Translation in Promotion of Viability in K-Ras Mutant Cells. Cell Rep 20 427 PMID: 28700943


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