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AdipoGen Life Sciences
Atpenin A5
160
CHF
CHF 160.00
In stock
AG-CN2-0100-C250250 µgCHF 160.00
AG-CN2-0100-M0011 mgCHF 450.00
| 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 |
| Smiles | COC1=C(OC)C(O)=C(C(=O)[C@@H](C)C[C@H](C)[C@@H](Cl)CCl)C(O)=N1 |
| 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 |
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
- 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)
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