Atpenin A5
Product Code: AG-CN2-0100
Product Group: Natural Products and Extracts
Supplier: AdipoGen Life Sciences
| Code | Size | Price |
|---|
| AG-CN2-0100-C250 | 250 ug | £125.00 |
Quantity:
| AG-CN2-0100-M001 | 1 mg | £340.00 |
Quantity:
Prices exclude any Taxes / VAT
Overview
Regulatory Status: RUO
Shipping:
Ambient
Storage:
-20°C
Documents
Further Information
Alternate Names/Synonyms:
3-[(2S,4S,5R)-5,6-Dichloro-2,4-dimethyl-1-oxohexyl]-4-hydroxy-5,6-dimethoxy-2(1H)-pyridinone
Appearance:
White to off-white solid.
CAS:
119509-24-9
Class:
6.1
EClass:
32160000
Form (Short):
liquid
GHS Symbol:
GHS06
Handling Advice:
After reconstitution, prepare aliquots and store at -20°C.
Hazards:
H301, H311, H330
InChi:
InChI=1S/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
InChiKey:
OVULNOOPECCZRG-CIUDSAMLSA-N
Long Description:
Chemical. CAS: 119509-24-9. Formula: C15H21Cl2NO5. MW: 366.2. Synthetic. Originally isolated from Penicillium sp. strain FO-125. Antibiotic. Antifungal. Potent and specific mitochondrial complex II (succinate-ubiquinone oxidoreductase) inhibitor. Mitochondrial ATP-sensitive potassium (mK(ATP)) channel activator. Cardioprotective. Modulates mitochondrial ROS generation during cardioprotection.
MDL:
MFCD01664873
Molecular Formula:
C15H21Cl2NO5
Molecular Weight:
366.2
Package Type:
Vial
PG:
III
Precautions:
P260, P264, P271, P280, P284, P301, P310. P302, P352, P304, P340
Product Description:
Antibiotic [1-3]. Antifungal [1-3]. Potent and specific mitochondrial complex II (succinate-ubiquinone oxidoreductase) inhibitor [4, 5, 7]. Mitochondrial ATP-sensitive potassium (mK(ATP)) channel activator [6, 8]. Cardioprotective [6, 8]. Modulates mitochondrial ROS generation during cardioprotection [9].
Purity:
>95% (HPLC)
Signal word:
Danger
SMILES:
COC1=C(OC)C(O)=C(C(=O)[C@@H](C)C[C@H](C)[C@@H](Cl)CCl)C(O)=N1
Solubility Chemicals:
Soluble in acetone, acetonitrile, chloroform, ethyl acetate, DMSO, methanol or ethanol. Insoluble in water or hexane.
Source / Host:
Synthetic. Originally isolated from Penicillium sp. strain FO-125.
Transportation:
Excepted Quantity
UN Nummer:
UN 3462
UNSPSC Category:
Natural Products/Extracts
UNSPSC Number:
12352200
Use & Stability:
Stable for at least 3 years after receipt when stored at -20°C.
References
Atpenins, new antifungal antibiotics produced by Penicillium sp. Production, isolation, physico-chemical and biological properties: S. Omura, et al.; J. Antibiot. (Tokyo) 41, 1769 (1988) | Mechanism of action of atpenin B on Raji cells: K. Oshino, et al.; J. Antibiot. (Tokyo) 43, 1064 (1990) | The structures of atpenins A4, A5 and B, new antifungal antibiotics produced by Penicillium sp: H. Kumagai, et al.; J. Antibiot. (Tokyo) 43, 1553 (1990) | Atpenins, potent and specific inhibitors of mitochondrial complex II (succinate-ubiquinone oxidoreductase): H. Miyadera, et al.; PNAS 100, 473 (2003) | Structural and computational analysis of the quinone-binding site of complex II (succinate-ubiquinone oxidoreductase): a mechanism of electron transfer and proton conduction during ubiquinone reduction: R. Horsefield, et al.; J. Biol. Chem. 281, 7309 (2006) | The complex II inhibitor atpenin A5 protects against cardiac ischemia-reperfusion injury via activation of mitochondrial KATP channels.: A. P. Wojtovich & P. S. Brooks; Basic Res. Cardiol. 104, 121 (2009) | Synthetic atpenin analogs: Potent mitochondrial inhibitors of mammalian and fungal succinate-ubiquinone oxidoreductase: T.P. Selby, et al.; Bioorg. Med. Chem. Lett. 20, 1665 (2010) | The mitochondrial complex II and ATP-sensitive potassium channel interaction: quantitation of the channel in heart mitochondria: A.P. Wojtovich, et al.; Acta Biochim. Pol. 57, 431 (2010) | A common mechanism links differently acting complex II inhibitors to cardioprotection: modulation of mitochondrial reactive oxygen species production: S. Drose, et al.; Mol. Pharmacol. 79, 814 (2011)
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