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Atpenin A5 (synthetic)

Mitochondrial complex II inhibitor
ALX-380-313-M001 1 mg Inquire for pricing
ALX-380-313-MC25 0.25 mg Inquire for pricing
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Replaces Prod. #: ALX-380-108

Antibiotic. Potent and specific inhibitor of mitochondrial complex II (succinate-ubiquinone oxidoreductase).

Product Details

Alternative Name:3-[(2S,4S,5R)-5,6-Dichloro-2,4-dimethyl-1-oxohexyl]-4-hydroxy-5,6-dimethoxy-2(1H)-pyridinone
Source:Synthetic. Originally isolated from Penicillium sp. strain FO-125.
Purity:≥95% (HPLC)
Appearance:White to off-white powder.
Solubility:Soluble in acetone, acetonitrile, chloroform, ethyl acetate, DMSO, methanol or 100% ethanol; insoluble in water or hexane.
Shipping:Ambient Temperature
Long Term Storage:-20°C
Technical Info/Product Notes:The IC50 value against bovine heart complex II is 3.6nM (which is ~300-fold lower than the IC50 value of carboxin (1.1μM)). It also inhibits fumarate reductase of Ascaris suum (IC50 = 12nM). Inhibition of E. coli succinate dehydrogenase is less potent (IC50 = 5μM).By co-crystallization studies of atpenin A5 and complex II, the binding site of atpenin A5 was found to be the quinone-binding site of complex II. Additionally, atpenin A5 has been shown to have a protective action against ischemia-reperfusion via the activation of mitochondrial KATP channels.
Regulatory Status:RUO - Research Use Only
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Product Literature References

Ym155 localizes to the mitochondria leading to mitochondria dysfunction and activation of AMPK that inhibits BMP signaling in lung cancer cells: A. Mondal, et al.; Sci. Rep. 12, 13135 (2022), Abstract;
BCPP compounds, PET probes for early therapeutic evaluations, specifically bind to mitochondrial complex I: S. Kazami, et al.; Mitochondrion 46, 97 (2019), Abstract;
Dual loss of succinate dehydrogenase (SDH) and complex I activity is necessary to recapitulate the metabolic phenotype of SDH mutant tumors: D. Lorendeau, et al.; Metab. Eng. 43(Pt B), 187 (2017), Abstract;
Ubiquinone-binding site mutagenesis reveals the role of mitochondrial complex II in cell death initiation: K. Kluckova, et al.; Cell Death Dis. 6, e1749 (2015), Application(s): Cell Culture, Abstract; Full Text
Enantioselective total synthesis of atpenin A5: M. Ohtawa et al.; J. Antibiot. 62, 289 (2009), Abstract;
The complex II inhibitor atpenin A5 protects against cardiac ischemia-reperfusion injury via activation of mitochondrial KATP channels: A. P. Wojtovich & P. S. Brooks; Basic Res. Cardiol. 104, 121 (2009), Abstract;
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: R. Horsefield, et al.; J. Biol. Chem. 281, 7309 (2006), Abstract; Full Text
Atpenins, potent and specific inhibitors of mitochondrial complex II (succinate-ubiquinone oxidoreductase): H. Miyadera, et al.; PNAS 100, 473 (2003), Abstract;
Mechanism of action of atpenin B on Raji cells: K. Oshino, et al.; J. Antibiot. 43, 1064 (1990), Abstract;
The structures of atpenins A4, A5 and B, new antifungal antibiotics produced by Penicillium sp: H. Kumagai, et al.; J. Antibiot. 43, 1553 (1990), Abstract;
Atpenins, new antifungal antibiotics produced by Penicillium sp. Production, isolation, physico-chemical and biological properties: S. Omura, et al.; J. Antibiot. 41, 1769 (1988), Abstract;