Synthesis of novel cationic bolaamphiphiles from vernonia oil and their aggregated structures.
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.
Grinberg
S
S
Department of Chemistry, Ben-Gurion University of the Negev, Beer-Sheva, Israel. sarina@bgu.ac.il
Kolot
V
V
Linder
C
C
Shaubi
E
E
Kas'yanov
V
V
Deckelbaum
R J
RJ
Heldman
E
E
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*
D002412:Cations; D008051:Lipid Bilayers; D010938:Plant Oils; D013501:Surface-Active Agents; D002802:Cholinesterases