Atpenin A5

CHF 185.00
In stock
AG-CN2-0100-C250250 µgCHF 185.00
AG-CN2-0100-M0011 mgCHF 500.00
More Information
Product Details
Synonyms 3-[(2S,4S,5R)-5,6-Dichloro-2,4-dimethyl-1-oxohexyl]-4-hydroxy-5,6-dimethoxy-2(1H)-pyridinone
Product Type Chemical
Properties
Formula

C15H21Cl2NO5

MW 366.2
CAS 119509-24-9
RTECS CJ8800000
Source/Host Chemicals Synthetic. Originally isolated from Penicillium sp. strain FO-125.
Purity Chemicals ≥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.
InChi Key OVULNOOPECCZRG-CIUDSAMLSA-N
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.
Documents
MSDS Download PDF
Product Specification Sheet
Datasheet Download PDF
  • 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)
© 2017 Adipogen Life Sciences. Pictures: © 2012 Martin Oeggerli. All Rights Reserved.