Chemical Structure
Atpenin A5 [119509-24-9]
AG-CN2-0100
Overview
- SupplierAdipoGen Life Sciences
- Product NameAtpenin A5
- Delivery Days Customer10
- ADR Class6.1
- CAS Number119509-24-9
- CertificationResearch Use Only
- Estimated Purity>95%
- Hazard InformationDanger,Excepted quantity
- Molecular FormulaC15H21Cl2NO5
- Molecular Weight366.2
- Scientific DescriptionAntibiotic [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.
- SMILESCOC1=C(OC)C(O)=C(C(=O)[C@@H](C)C[C@H](C)[C@@H](Cl)CCl)C(O)=N1
- Storage Instruction-20°C,2°C to 8°C
- UN NumberUN 3462
- UNSPSC12352200
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)