atpenin A5

atpenin A5 Chemische Eigenschaften,Einsatz,Produktion Methoden

Beschreibung

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.

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.

Biologische Aktivität

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.

atpenin A5 Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte

atpenin A5 Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

Firmenname	Telefon	E-Mail	Land	Produktkatalog	Edge Rate
Fuxin Pharmaceutical	+86-021-021-50872116 +8613122107989	contact@fuxinpharm.com	China	10297	58
BOC Sciences	+1-631-485-4226	inquiry@bocsci.com	United States	19553	58
SHANGHAI T&W PHARMACEUTICAL CO., LTD.	+86-021-61551413 +8618813727289	contact@trustwe.com	China	5738	58
Zhejiang Huida Biotech Co., LTD	008613515763466 8615669048680	wendy@huidabiotech.com	CHINA	87	58
Henan Alfa Chemical Co., Ltd	+8618339805032	alfa4@alfachem.cn	China	13512	58
Alfa Chemistry		Info@alfa-chemistry.com	United States	24072	58
TargetMol Chemicals Inc.	+1-781-999-5354	support@targetmol.com	United States	19973	58
LEAPCHEM CO., LTD.	+86-852-30606658	market18@leapchem.com	China	43348	58
Aladdin Scientific	+1-+1(833)-552-7181	sales@aladdinsci.com	United States	57511	58
T&W GROUP	021-61551611 13296011611	contact@trustwe.com	China	9900	58

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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