Synthesis of novel cationic bolaamphiphiles from vernonia oil and their aggregated structures

S. Grinberg, V. Kolot, C. Linder, E. Shaubi, V. Kas'yanov, R. J. Deckelbaum, E. Heldman

Research output: Contribution to journalArticlepeer-review

36 Scopus citations

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 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.

Original languageEnglish
Pages (from-to)85-97
Number of pages13
JournalChemistry and Physics of Lipids
Volume153
Issue number2
DOIs
StatePublished - 1 Jun 2008

Keywords

  • Acetylcholine
  • Acetylcholine esterase
  • Bolaamphiphiles
  • Vernonia oil

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry
  • Cell Biology

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