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Atpenin A5

AG-CN2-0100-C250 250 µg INQ
AG-CN2-0100-M001 1 mg INQ
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Additional Information

Product Data
Synonyms 3-[(2S,4S,5R)-5,6-Dichloro-2,4-dimethyl-1-oxohexyl]-4-hydroxy-5,6-dimethoxy-2(1H)-pyridinone
Properties
Formula C15H21Cl2NO5
MW 366.2
CAS 119509-24-9
RTECS CJ8800000
Source/Host Synthetic. Originally isolated from Penicillium sp. strain FO-125.
Purity ≥95% (HPLC)
Appearance White to off-white solid.
Solubility Soluble in acetone, acetonitrile, chloroform, ethyl acetate, DMSO, methanol or ethanol. Insoluble in water or hexane.
Origin Synthesized by the Organic Chemistry Group of The Kitasato Institute.
InChi Key OVULNOOPECCZRG-CIUDSAMLSA-N
Product Type Chemical
Shipping and Handling
Shipping AMBIENT
Short Term Storage +4°C
Long Term Storage -20°C
Handling Advice After reconstitution, prepare aliquots and store at -20°C.
Use/Stability Stable for at least 3 years after receipt when stored at -20°C.
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Product Description

  • Antibiotic [1-3].
  • Antifungal [1-3].
  • Potent and specific mitochondrial complex II (succinate-ubiquinone oxidoreductase) inhibitor [4, 5, 7].
  • Mitochondrial ATP-sensitive potassium (mK(ATP)) channel activator [6, 8].
  • Cardioprotective [6, 8].
  • Modulates mitochondrial ROS generation during cardioprotection [9].

Product References

  1. 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)
  2. Mechanism of action of atpenin B on Raji cells: K. Oshino, et al.; J. Antibiot. (Tokyo) 43, 1064 (1990)
  3. 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)
  4. Atpenins, potent and specific inhibitors of mitochondrial complex II (succinate-ubiquinone oxidoreductase): H. Miyadera, et al.; PNAS 100, 473 (2003)
  5. 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)
  6. 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)
  7. 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)
  8. 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)
  9. 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)
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