title: Synthesis of novel cationic bolaamphiphiles from vernonia oil and their aggregated structures.
abstract: The present study describes the synthesis of a novel class of vesicle-forming bolaamphiphiles with choline ester head groups. These bolaamphiphiles were derived from vernonia oil, whose main constituent is vernolic acid, a fatty acid with a unique combination of epoxy, carboxy and unsaturated double bonds. A series of bolaamphiphiles containing amido or ester groups within the hydrophobic domain were synthesized from N,N'-alkylenebis (vernolamides) and alpha,omega-alkylene divernolate ester in a two-stage synthesis comprising opening of the epoxy ring with chloroacetic acid, followed by quaternization with N,N-dimethylaminoethyl acetate to form choline ester head groups. The products were characterized by FT-IR, (1)H and (13)C NMR, and ESI-MS. Vesicles prepared from these bolaamphiphiles have the potential to serve as a targeted drug delivery systems with selective decapsulation in the presence of the enzyme acetylcholine esterase, resulting in site-specific release of the drug.
authors.affiliation: Department of Chemistry, Ben-Gurion University of the Negev, Beer-Sheva, Israel. sarina@bgu.ac.il
authors.forename: S
authors.initials: S
authors.lastname: Grinberg
authors.forename: V
authors.initials: V
authors.lastname: Kolot
authors.forename: C
authors.initials: C
authors.lastname: Linder
authors.forename: E
authors.initials: E
authors.lastname: Shaubi
authors.forename: V
authors.initials: V
authors.lastname: Kas'yanov
authors.forename: R J
authors.initials: RJ
authors.lastname: Deckelbaum
authors.forename: E
authors.initials: E
authors.lastname: Heldman
mesh_terms: D002412:Cations / Q000138:chemical synthesis; D002802:Cholinesterases / Q000378:metabolism; D008051:Lipid Bilayers / Q000138:chemical synthesis*; D019906:Nuclear Magnetic Resonance, Biomolecular; D010938:Plant Oils / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization; D017550:Spectroscopy, Fourier Transform Infrared; D013501:Surface-Active Agents / Q000138:chemical synthesis* / Q000378:metabolism; D035741:Vernonia / Q000737:chemistry*
chemical_list: D002412:Cations; D008051:Lipid Bilayers; D010938:Plant Oils; D013501:Surface-Active Agents; D002802:Cholinesterases