Design, synthesis and in vitro evaluation of d-glucose-based cationic glycolipids for gene delivery. Issue 5 (16th December 2015)

• Record Type: Journal Article
• Authors: He, Chengxi; Wang, Shang; Liu, Meiyan; Zhao, Chunyan; Xiang, Shuanglin; Zeng, Youlin
• Is Part Of: Organic & biomolecular chemistry. Volume 14:Issue 5(2016)
• Page Start: 1611
• Page End: 1622
• Publication Date: 2015-12-16
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c5ob02107c
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Two novel series of cationic cyclic glycolipids were synthesized and the gene transfection efficiencies of these glycolipids were investigeted. Abstract : A cationic lipid consists of a hydrophilic headgroup, backbone and hydrophobic tails which have an immense influence on the transfection efficiency of the lipid. In this paper, two novel series of cationic cyclic glycolipids with a quaternary ammonium headgroup and different-length hydrophobic tails (dodecyl, tetradecyl, hexadecyl) have been designed and synthesized for gene delivery. One contains lipids1–3 with two hydrophobic alkyl chains linked to the glucose ring directly via an ether link. The other contains lipids4–6 with two hydrophobic chains on the positively charged nitrogen atoms. All of the lipids were characterized for their ability to bind to DNA, size, ζ-potential, and toxicity. Atomic force microscopy showed that the lipids and DNA–lipid complexes were sphere-like forms. The lipids were used to transfer enhanced green fluorescent protein (EGFP-C3) to HEK293 cells without a helper lipid, the results indicated that lipids4–6 have better transfection efficiency, in particular lipids5–6 have similar or better efficiency, compared with the commercial transfection reagent lipofectamine 2000.