Inhibitory effects on mitochondrial complex I of semisynthetic mono-Tetrahydrofuran acetogenin derivatives

Modifications in the terminal α,β-unsaturated γ-methyl-γ-lactone moiety or in the alkyl chain that links this terminal γ-lactone with the α,α′-dihydroxylated THF system of the natural mono-tetrahydrofuranic acetogenins, annonacin and annonacinone, led to the preparation of eight semisynthetic deriva...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 2003-11, Vol.13 (22), p.4101-4105
Main Authors: Tormo, José R, Gallardo, Teresa, Peris, Eva, Bermejo, Almudena, Cabedo, Nuria, Estornell, Ernesto, Zafra-Polo, M.Carmen, Cortes, Diego
Format: Article
Language:English
Subjects:
Acetogenins
Antineoplastic agents
Biological and medical sciences
Electron Transport Complex I - antagonists & inhibitors
Enzyme Inhibitors - pharmacology
Fatty Alcohols - chemical synthesis
Fatty Alcohols - pharmacology
Furans - chemical synthesis
Furans - pharmacology
General aspects
Kinetics
Lactones - chemical synthesis
Lactones - pharmacology
Medical sciences
Multienzyme Complexes - antagonists & inhibitors
NADH, NADPH Oxidoreductases - antagonists & inhibitors
Pharmacology. Drug treatments
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Summary:Modifications in the terminal α,β-unsaturated γ-methyl-γ-lactone moiety or in the alkyl chain that links this terminal γ-lactone with the α,α′-dihydroxylated THF system of the natural mono-tetrahydrofuranic acetogenins, annonacin and annonacinone, led to the preparation of eight semisynthetic derivatives. Their inhibitory effects on mitochondrial complex I is discussed and compared with that of the classical complex I inhibitor, rotenone. Graphic
ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2003.08.045