아트페닌A5

아트페닌A5
아트페닌A5 구조식 이미지
카스 번호:
119509-24-9
한글명:
아트페닌A5
동의어(한글):
아트페닌A5
상품명:
atpenin A5
동의어(영문):
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
분자식:
C15H21Cl2NO5
포뮬러 무게:
366.24
MOL 파일:
119509-24-9.mol

아트페닌A5 속성

녹는점
83-85℃
끓는 점
538.3±50.0 °C(Predicted)
밀도
1.31±0.1 g/cm3(Predicted)
저장 조건
-20°C Freezer, Under inert atmosphere
용해도
클로로포름 (약간 용해됨), 에탄올 (약간 용해됨), 메탄올 (약간 용해됨,초음파처리)
산도 계수 (pKa)
4.50±1.00(Predicted)
물리적 상태
백색 내지 회백색 분말.
색상
흰색에서 황백색까지
안전
  • 위험 및 안전 성명
그림문자(GHS): GHS hazard pictograms
신호 어: Danger
유해·위험 문구:
암호 유해·위험 문구 위험 등급 범주 신호 어 그림 문자 P- 코드
예방조치문구:
NFPA 704
0
4 0

아트페닌A5 C화학적 특성, 용도, 생산

개요

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.

정의

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.

생물학적 활성

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.

아트페닌A5 준비 용품 및 원자재

원자재

준비 용품


아트페닌A5 공급 업체

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