atpenin A5

Product Name: atpenin A5
CAS No.: 119509-24-9
Chemical Name: atpenin A5
Synonyms: FO 125A5;atpenin A5;Antibiotic FO 125A5;Atpenin A5 (Synthetic);(2S,4S,5R)-5,6-Dichloro-1-(2,4-dihydroxy-5,6-dimethoxypyridin-3-yl)-2,4-dimethyl-1-hexanone;(2S,4S,5R)-1-(2,4-Dihydroxy-5,6-dimethoxy-3-pyridinyl)-2,4-dimethyl-5,6-dichloro-1-hexanone;3-[(2S,4S,5R)-5,6-Dichloro-2,4-dimethyl-1-oxohexyl]-4-hydroxy-5,6-dimethoxy-2(1H)-pyridinone;2(1H)-Pyridinone, 3-[(2S,4S,5R)-5,6-dichloro-2,4-dimethyl-1-oxohexyl]-4-hydroxy-5,6-dimethoxy-;preconditioning,sensitive,mKATP,Atpenin A 5,Atpenin A5,ischemia,potassium,complex II,Inhibitor,cardioprotective,channel,mitochondrial,Potassium Channel,KcsA,ATP,inhibit,reperfusion,Atpenin A-5
CBNumber: CB71388223
Molecular Formula: C15H21Cl2NO5
Formula Weight: 366.24
MOL File: 119509-24-9.mol

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atpenin A5 Property

Melting point:: 83-85℃
Boiling point:: 538.3±50.0 °C(Predicted)
Density: 1.31±0.1 g/cm3(Predicted)
storage temp.: -20°C Freezer, Under inert atmosphere
solubility: Chlroform (Slightly), Ethanol (Slightly), Methanol (Slightly, Sonicated)
pka: 4.50±1.00(Predicted)
form: White to off-white powder.
color: White to Off-White

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word: Danger

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N-Bromosuccinimide Price

Cayman Chemical

Product number: 11898
Product name: Atpenin A5
Purity: ≥95%
Packaging: 1mg
Price: $235
Updated: 2024/03/01

TRC

Product number: A794643
Product name: AtpeninA5
Packaging: 5mg
Price: $300
Updated: 2021/12/16

Usbiological

Product number: 169935
Product name: Atpenin A5
Packaging: 250ug
Price: $315
Updated: 2021/12/16

Usbiological

Product number: 044573
Product name: Atpenin A5
Packaging: 250ug
Price: $368
Updated: 2021/12/16

TRC

Product number: A794643
Product name: AtpeninA5
Packaging: 10mg
Price: $450
Updated: 2021/12/16

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atpenin A5 Chemical Properties,Usage,Production

Description

Enantioselective total synthesis of atpenin A5, a potent mitochondrial complex II (succinate-ubiquinone oxidoreductase) inhibitor, has been achieved by a convergent approach through a coupling reaction between 5-iodo-2,3,4,6-tetraalkoxypyridine and a side-chain aldehyde. The two key segments were synthesized through ortho-metalation/boronation with (MeO)3B/oxidation with mCPBA, ortho-iodination, halogen dance reaction, Sharpless epoxidation and regioselective epoxide-opening reaction.

Uses

Atpenin A5 is a mitochondrial complex II inhibitor able to protect against cardiac-reperfusion.

Definition

Atpenin A5 belongs to a class of antifungal antibiotics isolated from 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 has been shown 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.

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.

storage

+4°C

atpenin A5 Preparation Products And Raw materials

Raw materials

Preparation Products

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atpenin A5 Suppliers

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119509-24-9, atpenin A5Related Search:

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atpenin A5

(2S,4S,5R)-1-(2,4-Dihydroxy-5,6-dimethoxy-3-pyridinyl)-2,4-dimethyl-5,6-dichloro-1-hexanone

(2S,4S,5R)-5,6-Dichloro-1-(2,4-dihydroxy-5,6-dimethoxypyridin-3-yl)-2,4-dimethyl-1-hexanone

3-[(2S,4S,5R)-5,6-Dichloro-2,4-dimethyl-1-oxohexyl]-4-hydroxy-5,6-dimethoxy-2(1H)-pyridinone

Antibiotic FO 125A5

FO 125A5

Atpenin A5 (Synthetic)

2(1H)-Pyridinone, 3-[(2S,4S,5R)-5,6-dichloro-2,4-dimethyl-1-oxohexyl]-4-hydroxy-5,6-dimethoxy-

preconditioning,sensitive,mKATP,Atpenin A 5,Atpenin A5,ischemia,potassium,complex II,Inhibitor,cardioprotective,channel,mitochondrial,Potassium Channel,KcsA,ATP,inhibit,reperfusion,Atpenin A-5

119509-24-9