Molecular structure of Atpenin A5, CAS Number: 119509-24-9
Atpenin A5 (CAS 119509-24-9)
See product citations (17)
Alternate Names:
3-[(2S,4S,5R)-5,6-Dichloro-2,4-dimethyl-1-oxohexyl]-4-hydroxy-5,6-dimethoxy-2(1H)-pyridinone
Application:
Atpenin A5 is a mitochondrial complex II inhibitor able to protect against cardiac-reperfusion
CAS Number:
119509-24-9
Purity:
≥95%
Molecular Weight:
366.20
Molecular Formula:
C15H21Cl2NO5
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.
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SDS & Certificate of Analysis
Atpenin A5 belongs to a class of antifungal antibiotics found in Penicillium sp. The atpenins are effective against filamentous fungi, particularly Trichophyton sp., and are specific and potent inhibitors of the succinate-ubiquinone reducatase activity of the mitochondrial complex II. Atpenin A5 is the most effective inhibitor against complex II from all the atpenins and may act to protect against cardiac-reperfusion injury in rat studies through the stimulation of mitochondrial KATP channels. Atpenin A5 is an inhibitor of SDHB, SDHC and SDHD.
Atpenin A5 (CAS 119509-24-9) References
- Atpenins, potent and specific inhibitors of mitochondrial complex II (succinate-ubiquinone oxidoreductase). | Miyadera, H., et al. 2003. Proc Natl Acad Sci U S A. 100: 473-7. PMID: 12515859
- The complex II inhibitor atpenin A5 protects against cardiac ischemia-reperfusion injury via activation of mitochondrial KATP channels. | Wojtovich, AP. and Brookes, PS. 2009. Basic Res Cardiol. 104: 121-9. PMID: 19242645
- Enantioselective total synthesis of atpenin A5. | Ohtawa, M., et al. 2009. J Antibiot (Tokyo). 62: 289-94. PMID: 19373276
- Mitochondrial complex II can generate reactive oxygen species at high rates in both the forward and reverse reactions. | Quinlan, CL., et al. 2012. J Biol Chem. 287: 27255-64. PMID: 22689576
- The structures of atpenins A4, A5 and B, new antifungal antibiotics produced by Penicillium sp. | Kumagai, H., et al. 1990. J Antibiot (Tokyo). 43: 1553-8. PMID: 2276974
- Production of superoxide/H2O2 by dihydroorotate dehydrogenase in rat skeletal muscle mitochondria. | Hey-Mogensen, M., et al. 2014. Free Radic Biol Med. 72: 149-55. PMID: 24746616
- Ubiquinone-binding site mutagenesis reveals the role of mitochondrial complex II in cell death initiation. | Kluckova, K., et al. 2015. Cell Death Dis. 6: e1749. PMID: 25950479
- Manganese ions induce H2O2 generation at the ubiquinone binding site of mitochondrial complex II. | Bonke, E., et al. 2015. Arch Biochem Biophys. 580: 75-83. PMID: 26116786
- Bioisosteric Exchange of Csp3 -Chloro and Methyl Substituents: Synthesis and Initial Biological Studies of Atpenin A5 Analogues. | Krautwald, S., et al. 2016. Angew Chem Int Ed Engl. 55: 4049-53. PMID: 26891236
- Mitochondrial complex II regulates a distinct oxygen sensing mechanism in monocytes. | Sharma, S., et al. 2017. Hum Mol Genet. 26: 1328-1339. PMID: 28204537
- Synthesis and Antineoplastic Evaluation of Mitochondrial Complex II (Succinate Dehydrogenase) Inhibitors Derived from Atpenin A5. | Wang, H., et al. 2017. ChemMedChem. 12: 1033-1044. PMID: 28523727
- TMEM126B deficiency reduces mitochondrial SDH oxidation by LPS, attenuating HIF-1α stabilization and IL-1β expression. | Fuhrmann, DC., et al. 2019. Redox Biol. 20: 204-216. PMID: 30368040
- Atpenins, new antifungal antibiotics produced by Penicillium sp. Production, isolation, physico-chemical and biological properties. | Omura, S., et al. 1988. J Antibiot (Tokyo). 41: 1769-73. PMID: 3209470
- Computational Modeling Analysis of Generation of Reactive Oxygen Species by Mitochondrial Assembled and Disintegrated Complex II. | Markevich, NI., et al. 2020. Front Physiol. 11: 557721. PMID: 33178032
- Crystallographic investigation of the ubiquinone binding site of respiratory Complex II and its inhibitors. | Huang, LS., et al. 2021. Biochim Biophys Acta Proteins Proteom. 1869: 140679. PMID: 34089891
Inhibitor of:
ETFDH, LYRM2, MT-ND (mitochondrial NADH dehydrogenase), ND6, NDH II, PTRH2, QCR10, RFESD, SDHA, SDHAF1, SDHAF2, SDHB, SDHC, SDHD, SQRDL, Uqcr, UQCRHL, V-ATPase A1, V-ATPase A2, and Vacuolar ATPase (V-ATPase; ATP6).Activator of:
MTFmt.Ordering Information
| Product Name | Catalog # | UNIT | Price | Qty | FAVORITES | |
Atpenin A5, 250 µg | sc-202475 | 250 µg | $195.00 | |||
Atpenin A5, 1 mg | sc-202475A | 1 mg | $540.00 | |||
Atpenin A5, 10 mg | sc-202475B | 10 mg | $2905.00 | |||
Atpenin A5, 50 mg | sc-202475C | 50 mg | $12885.00 |