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Chemical Structure
Chemical Structure
Chemical Structure

Atpenin A5 [119509-24-9]

Research Use Only
AG-CN2-0100
AdipoGen Life Sciences
CAS Number119509-24-9
Product group Chemicals
Estimated Purity>95% (HPLC)
Molecular Weight366.2
Price on request
Packing Size
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Overview

  • Supplier
    AdipoGen Life Sciences
  • Product Name
    Atpenin A5 [119509-24-9]
  • Delivery Days Customer
    10
  • ADR Class
    6.1
  • CAS Number
    119509-24-9
  • Certification
    Research Use Only
  • Estimated Purity
    >95% (HPLC)
  • Hazard Information
    Danger,Excepted quantity
  • Molecular Formula
    C15H21Cl2NO5
  • Molecular Weight
    366.2
  • Scientific 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]. - Chemical. CAS: 119509-24-9. Formula: C15H21Cl2NO5. MW: 366.2. Synthetic. Originally isolated from Penicillium sp. strain FO-125. 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.
  • SMILES
    COC1=C(OC)C(O)=C(C(=O)[C@@H](C)C[C@H](C)[C@@H](Cl)CCl)C(O)=N1
  • Storage Instruction
    2°C to 8°C,-20°C
  • UN Number
    UN 3462
  • UNSPSC
    12352200

References

  • 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)