Novel macrocyclic and acyclic cationic lipids for gene transfer: Synthesis and in vitro evaluation

William P D Goldring, Emile Jubeli, Rachael A Downs, Adam J S Johnston, Nada Abdul Khalique, Liji Raju, Deena Wafadari, Michael D Pungente

Research output: Contribution to journalArticlepeer-review

10 Citations (Scopus)


The synthesis and in vitro evaluation of four cationic lipid gene delivery vectors, characterized by acyclic or macrocyclic, and saturated or unsaturated hydrophobic regions, is described. The synthesis employed standard protocols, including ring-closing metathesis for macrocyclic lipid construction. All lipoplexes studied, formulated from plasmid DNA and a liposome composed of a synthesized lipid, 1,2-dimyristoyl-sn-glycero-3-ethylphosphocholine (EPC), and either 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (DOPE) or cholesterol as co-lipid, exhibited plasmid DNA binding and protection from DNase I degradation, and concentration dependent cytotoxicity using Chinese hamster ovary-K1 cells. The transfection efficiency of formulations with cholesterol outperformed those with DOPE, and in many cases the EPC/cholesterol control, and formulations with a macrocyclic lipid (+/- 10:1) outperformed their acyclic counterparts (+/- 3:1).
Original languageEnglish
Pages (from-to)4686-4692
Number of pages7
JournalBioorganic & Medicinal Chemistry Letters
Issue number14
Publication statusPublished - 15 Jul 2012

ASJC Scopus subject areas

  • Pharmaceutical Science
  • Drug Discovery
  • Organic Chemistry
  • Molecular Medicine
  • Molecular Biology
  • Clinical Biochemistry
  • Biochemistry


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