TY - JOUR
T1 - Synthesis of novel cationic bolaamphiphiles from vernonia oil and their aggregated structures
AU - Grinberg, S.
AU - Kolot, V.
AU - Linder, C.
AU - Shaubi, E.
AU - Kas'yanov, V.
AU - Deckelbaum, R. J.
AU - Heldman, E.
N1 - Funding Information:
This study was supported by the Applied Research Fund for Biotechnology Research of BG Negev Technologies Ltd., Ben-Gurion University and by a grant from the United States–Israel Binational Science Foundation No. 2003153. Special thanks are due to Dr. Ina Kalikhman for helpful discussions that facilitated interpretation of NMR spectra.
PY - 2008/6/1
Y1 - 2008/6/1
N2 - 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 α,ω-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, 1H and 13C 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.
AB - 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 α,ω-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, 1H and 13C 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.
KW - Acetylcholine
KW - Acetylcholine esterase
KW - Bolaamphiphiles
KW - Vernonia oil
UR - http://www.scopus.com/inward/record.url?scp=43049175156&partnerID=8YFLogxK
U2 - 10.1016/j.chemphyslip.2008.01.006
DO - 10.1016/j.chemphyslip.2008.01.006
M3 - Article
C2 - 18316039
AN - SCOPUS:43049175156
SN - 0009-3084
VL - 153
SP - 85
EP - 97
JO - Chemistry and Physics of Lipids
JF - Chemistry and Physics of Lipids
IS - 2
ER -