title: Synthesis and biological activities of N-(3-carboxylpropyl)-5-amino-2-hydroxy-3-tridecyl-1,4-benzoquinone and analogues.
abstract: The synthesis of benzoquinone natural product 2 and three analogues is described. The synthesized compounds were tested for their ability to protect Friedreich's ataxia (FRDA) lymphocytes from induced oxidative stress. One of the analogues (3) conferred cytoprotection in a dose-dependent manner in FRDA lymphocytes at micromolar concentrations. The biological assays suggest that the modification of the 2-hydroxy and N-(3-carboxypropyl) groups in the natural product can improve its antioxidant activity and significantly enhance its ability to protect mitochondrial function under conditions of oxidative stress.
authors.affiliation: Center for BioEnergetics, Biodesign Institute, Arizona State University, Tempe, Arizona 85287-2904, USA.
authors.forename: Manikandadas M
authors.initials: MM
authors.lastname: Madathil
authors.forename: Omar M
authors.initials: OM
authors.lastname: Khdour
authors.forename: Jennifer
authors.initials: J
authors.lastname: Jaruvangsanti
authors.forename: Sidney M
authors.initials: SM
authors.lastname: Hecht
mesh_terms: D016227:Benzoquinones / Q000737:chemistry* / Q000494:pharmacology*; D002470:Cell Survival / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D005621:Friedreich Ataxia / Q000378:metabolism; D015227:Lipid Peroxidation / Q000187:drug effects; D008928:Mitochondria / Q000187:drug effects / Q000378:metabolism; D015394:Molecular Structure; D018384:Oxidative Stress / Q000187:drug effects; D017382:Reactive Oxygen Species / Q000494:pharmacology; D013329:Structure-Activity Relationship; D005680:gamma-Aminobutyric Acid / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology
chemical_list: D016227:Benzoquinones; C527465:N-(3-carboxylpropyl)-5-amino-2-hydroxy-3-tridecyl-1,4-benzoquinone; D017382:Reactive Oxygen Species; D005680:gamma-Aminobutyric Acid