119509-24-9 Usage
Description
Atpenin A5 is a potent mitochondrial complex II (succinate-ubiquinone oxidoreductase) inhibitor that belongs to a class of antifungal antibiotics isolated from Penicillium sp. It is effective against filamentous fungi, particularly Trichophyton sp., and is a specific inhibitor of the succinate-ubiquinone reductase activity of the mitochondrial complex II. Atpenin A5 is the most effective inhibitor against complex II from all the atpenins and has been shown to protect against cardiac-reperfusion injury in rat studies through the stimulation of mitochondrial KATP channels. It is an inhibitor of SDHB, SDHC, and SDHD.
Uses
Used in Pharmaceutical Industry:
Atpenin A5 is used as an antifungal agent for its effectiveness against filamentous fungi, particularly Trichophyton sp. Its potent inhibitory action on the succinate-ubiquinone reductase activity of the mitochondrial complex II makes it a valuable compound in the development of antifungal drugs.
Used in Cardiology:
Atpenin A5 is used as a protective agent against cardiac-reperfusion injury. It has been shown to protect against such injury in rat studies through the stimulation of mitochondrial KATP channels, making it a potential candidate for the development of treatments to reduce damage during reperfusion events in cardiac conditions.
Used in Enantioselective Total Synthesis:
Atpenin A5 is used as a target compound in the development of enantioselective total synthesis methods. The convergent approach through a coupling reaction between 5-iodo-2,3,4,6-tetraalkoxypyridine and a side-chain aldehyde, along with key segment syntheses involving ortho-metalation/boronation, ortho-iodination, halogen dance reaction, Sharpless epoxidation, and regioselective epoxide-opening reaction, highlights its potential in the synthesis of complex molecules with specific chiral properties.
Biological Activity
Mitochondrial complex II (succinate dehydrogenase or succinate:ubiquinone oxidoreductase) is a functional member of the Krebs cycle and the aerobic respiratory chain that couples the oxidation of succinate to fumarate with the reduction of quinone to quinol. Atpenin A5, an antifungal antibiotic isolated from Penicillium sp. found in soil, is a highly specific ubiquinone-binding site inhibitor of succinate dehydrogenase (IC50s = 12 and 3.7 nM in nematode and mammalian mitochondria, respectively, versus IC50s > 100 μM for inhibition of complex I and complex III enzymes). Atpenin A5 has cardioprotective effects against simulated ischemia-reperfusion injury in cardiomyocytes. Several mechanisms through which this occurs, including activation of mitochondrial ATP-sensitive potassium channels or modulation of mitochondrial reactive oxygen species generation, have been proposed.
in vitro
Highly selective, potent ubiquinone-binding site mitochondrial complex II inhibitor (IC50 values are 12 and 3.7 nM for nematode and mammalian mitochondria respectively). Stimulates mitochondrial KATP channels. Shows anti-ischemic and cardioprotective effects in vivo.
Check Digit Verification of cas no
The CAS Registry Mumber 119509-24-9 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,1,9,5,0 and 9 respectively; the second part has 2 digits, 2 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 119509-24:
(8*1)+(7*1)+(6*9)+(5*5)+(4*0)+(3*9)+(2*2)+(1*4)=129
129 % 10 = 9
So 119509-24-9 is a valid CAS Registry Number.
InChI:InChI=1/C15H21Cl2NO5/c1-7(9(17)6-16)5-8(2)11(19)10-12(20)13(22-3)15(23-4)18-14(10)21/h7-9H,5-6H2,1-4H3,(H2,18,20,21)/t7-,8-,9-/m0/s1
