A specific inhibitor of mitochondrial complex II enzymes
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Atpenin A5

Item No. 11898

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3-[(2S,4S,5R)-5,6-dichloro-2,4-dimethyl-1-oxohexyl]-4-hydroxy-5,6-dimethoxy-2(1H)-pyridinone
CAS Number
119509-24-9
Synonyms
  • Antibiotic FO-125A5
Molecular Formula
C15H21Cl2NO5
Formula Weight
366.2
Purity
≥95% (mixture of isomers)
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMSO: SolubleEthanol: SolubleMethanol: Soluble
λmax
237, 272, 324 nm
SMILES
COC(NC(O)=C1C([C@H](C[C@H](C)[C@H](CCl)Cl)C)=O)=C(OC)C1=O
InChi Code
InChI=1S/C15H21Cl2NO5/c1-7(9(17)6-16)5-8(2)11(19)10-12(20)13(22-3)15(23-4)18-14(10)21/h7-9H,5-6H2,1-4H3,(H2,18,20,21)/t7-,8-,9-/m0/s1
InChi Key
OVULNOOPECCZRG-CIUDSAMLSA-N
Origin
Synthetic; originally from fungal strain FO-125
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $303

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    Product Description

    Atpenin A5, an antifungal antibiotic isolated from Penicillium sp. found in soil, is a highly specific ubiquinone-binding site inhibitor of succinate dehydrogenase (IC50s = 12 and 3.7 nM in nematode and mammalian mitochondria, respectively, versus IC50s > 100 μM for inhibition of complex I and complex III enzymes).1,2 Atpenin A5 has cardioprotective effects against simulated ischemia-reperfusion injury in cardiomyocytes. Several mechanisms through which this occurs, including activation of mitochondrial ATP-sensitive potassium channels or modulation of mitochondrial reactive oxygen species generation, have been proposed.3,4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Horsefield, R., Yankovskaya, V., Sexton, G., et al. Structural and computational analysis of the quinone-binding site of complex II (succinate-ubiquinone oxidoreductase): A mechanism of electron transfer and proton conduction during ubiquinone reduction. The Journal of Biological Chemisty 281(11), 7309-7316 (2006).

    2. Miyadera, H., Shiomi, K., Ui, H., et al. Atpenins, potent and specific inhibitors of mitochondrial complex II (succinate-ubiquinone oxidoreductase). Proc. Natl. Acad. Sci. USA 100(2), 473-477 (2003).

    3. Wojtovich, A.P., and Brookes, P.S. The complex II inhibitor atpenin A5 protects against cardiac ischemia-reperfusion injury via activation of mitochondrial KATP channels. Basic Res. Cardiol. 104(2), 121-129 (2009).

    4. Dröse, S., Bleier, L., and Brandt, U. A common mechanism links differently acting complex II inhibitors to cardioprotection: Modulation of mitochondrial reactive oxygen species production. Mol. Pharmacol. 79(5), 814-822 (2011).