New antitumoral acetogenin ‘Guanacone type’ derivatives: Isolation and bioactivity. Molecular dynamics simulation of diacetyl-guanacone

• Published in: Bioorganic & medicinal chemistry Vol. 15; no. 13; pp. 4369 - 4381
• Main Authors: Barrachina, Isabel, Royo, Inmaculada, Baldoni, Héctor A., Chahboune, Nadia, Suvire, Fernando, DePedro, Nuria, Zafra-Polo, M. Carmen, Bermejo, Almudena, El Aouad, Noureddine, Cabedo, Nuria, Saez, Jairo, Tormo, José R., Enriz, Ricardo D., Cortes, Diego
• Format: Journal Article
• Language: English
• Published: Oxford Elsevier Ltd 01.07.2007; Elsevier Science
• Subjects: Acetogenins; Annona - chemistry; Annonaceae acetogenins; Antineoplastic Agents, Phytogenic - biosynthesis; Antineoplastic Agents, Phytogenic - pharmacology; Biological and medical sciences; Cell Line, Tumor; Computer Simulation; Electron Transport - drug effects; Fatty Alcohols - metabolism; Fatty Alcohols - pharmacology; Furans - pharmacology; General pharmacology; Humans; Hydrogen Bonding; Indicators and Reagents; Lactones - metabolism; Lactones - pharmacology; Lipid Bilayers; Magnetic Resonance Spectroscopy; Medical sciences; Mitochondrial complex I; Models, Molecular; Molecular Conformation; Molecular dynamics simulation; Pharmacognosy. Homeopathy. Health food; Pharmacology. Drug treatments; Phosphatidylcholines - chemistry; Seeds - chemistry; Tumor cell lines; Mitochondrial complex I; Molecular dynamics simulation; Tumor cell lines; Annonaceae acetogenins; Antineoplastic agent; Mitochondrial complex 1; Molecular dynamics method; Modeling; Medicinal plant; Respiratory chain; Mitochondria; Dicotyledones; Angiospermae; Annonaceae; Inhibition; Acetogenin; Chemical synthesis; Acylate; Tumor cell; NADH dehydrogenase (ubiquinone); Hemisynthesis; Cell respiration; Enzyme; Bilayer; In vitro; Biological activity; Polyketide; Cell line; Isolation; Spermatophyta; Oxidoreductases; Conformation
• ISSN: 0968-0896; 1464-3391
• DOI: 10.1016/j.bmc.2007.04.039

We describe herein the isolation and semisynthesis of four acetogenin derivatives ( 1– 4) as well as their ability to inhibit the mitochondrial respiratory chain and several tumor cell lines. In addition, we have carried out a four nanoseconds (ns) of MD simulation of compound 4, in a fully hydrated POPC bilayer, as reported. We describe herein the isolation and semisynthesis of four acetogenin derivatives ( 1– 4) as well as their ability to inhibit the mitochondrial respiratory chain and several tumor cell lines. In addition, four nanoseconds (ns) of MD simulation of compound 4, in a fully hydrated POPC bilayer, is reported.