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044573 Atpenin A5 CAS: 119509-24-9

Specifications
References
CAS Number
119509-24-9
Grade
Highly Purified
Molecular Formula
C15H21Cl2NO5
Molecular Weight
366.2
EU Commodity Code
38220090
Shipping Temp
Blue Ice
Storage Temp
4°C/-20°C
3-[(2S,4S,5R)-5,6-Dichloro-2,4-dimethyl-1-oxohexyl]-4-hydroxy-5,6-dimethoxy-2(1H)-pyridinone

Antibiotic. Antifungal. Potent and specific mitochondrial complex II (succinate-ubiquinone oxidoreductase) inhibitor. Mitochondrial ATP-sensitive potassium (mK(ATP)) channel activator. Cardioprotective. Modulates mitochondrial ROS generation during cardioprotection.

The IC50 value against bovine heart complex II is 3.6nM (which is ~300-fold lower than the IC50 value of carboxin (1.1uM)). It also inhibits fumarate reductase of Ascaris suum (IC50 = 12nM). Inhibition of E. coli succinate dehydrogenase is less potent (IC50 = 5uM). 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.
Synonyms
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
Source
Synthetic. Originally isolated from Penicillium sp. strain FO-125.
Molecular Weight
366.2
Molecular Formula
C15H21Cl2NO5
Solubility
Acetone, acetonitrile, chloroform, ethyl acetate, DMSO, methanol or ethanol. Insoluble in water or hexane.
Appearance
Supplied as a white to off-white solid.
Purity
≥95% (HPLC)
Storage and Stability
Store at 4°C. For maximum recovery of product, centrifuge the original vial prior to removing the cap.
References
Product Reference: |●Atpenins, new antifungal antibiotics produced by Penicillium sp. Production, isolation, physico-chemical and biological properties: S. Omura, et al.; J. Antibiot. (Tokyo) 41, 1769 (1988)|●Mechanism of action of atpenin B on Raji cells: K. Oshino, et al.; J. Antibiot. (Tokyo) 43, 1064 (1990)|●The structures of atpenins A4, A5 and B, new antifungal antibiotics produced by Penicillium sp: H. Kumagai, et al.; J. Antibiot. (Tokyo) 43, 1553 (1990)|●Atpenins, potent and specific inhibitors of mitochondrial complex II (succinate-ubiquinone oxidoreductase): H. Miyadera, et al.; PNAS 100, 473 (2003)|●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)|●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)|●Synthetic atpenin analogs: Potent mitochondrial inhibitors of mammalian and fungal succinate-ubiquinone oxidoreductase: T.P. Selby, et al.; Bioorg. Med. Chem. Lett. 20, 1665 (2010)|●The mitochondrial complex II and ATP-sensitive potassium channel interaction: quantitation of the channel in heart mitochondria: A.P. Wojtovich, et al.; Acta Biochim. Pol. 57, 431 (2010)|●A common mechanism links differently acting complex II inhibitors to cardioprotection: modulation of mitochondrial reactive oxygen species production: S. Drose, et al.; Mol. Pharmacol. 79, 814 (2011)
USBio References
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