title: Design, synthesis and in vitro evaluation of d-glucose-based cationic glycolipids for gene delivery.
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 lipids 1-3 with two hydrophobic alkyl chains linked to the glucose ring directly via an ether link. The other contains lipids 4-6 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 lipids 4-6 have better transfection efficiency, in particular lipids 5-6 have similar or better efficiency, compared with the commercial transfection reagent lipofectamine 2000.
authors.affiliation: National & Local Joint Engineering Laboratory for New Petro-chemical Materials and Fine Utilization of Resources, Hunan Normal University, Changsha, Hunan 410081, P. R. China. youlinzengcn@gmail.com.
authors.forename: Chengxi
authors.initials: C
authors.lastname: He
authors.affiliation: Key Laboratory of Protein Chemistry and Developmental Biology of State Education Ministry of China, College of Life Sciences, Hunan Normal University, Changsha, Hunan 410081, P. R. China.
authors.forename: Shang
authors.initials: S
authors.lastname: Wang
authors.affiliation: National & Local Joint Engineering Laboratory for New Petro-chemical Materials and Fine Utilization of Resources, Hunan Normal University, Changsha, Hunan 410081, P. R. China. youlinzengcn@gmail.com.
authors.forename: Meiyan
authors.initials: M
authors.lastname: Liu
authors.affiliation: National & Local Joint Engineering Laboratory for New Petro-chemical Materials and Fine Utilization of Resources, Hunan Normal University, Changsha, Hunan 410081, P. R. China. youlinzengcn@gmail.com.
authors.forename: Chunyan
authors.initials: C
authors.lastname: Zhao
authors.affiliation: Key Laboratory of Protein Chemistry and Developmental Biology of State Education Ministry of China, College of Life Sciences, Hunan Normal University, Changsha, Hunan 410081, P. R. China.
authors.forename: Shuanglin
authors.initials: S
authors.lastname: Xiang
authors.affiliation: National & Local Joint Engineering Laboratory for New Petro-chemical Materials and Fine Utilization of Resources, Hunan Normal University, Changsha, Hunan 410081, P. R. China. youlinzengcn@gmail.com.
authors.forename: Youlin
authors.initials: Y
authors.lastname: Zeng
mesh_terms: D002412:Cations / Q000008:administration & dosage / Q000138:chemical synthesis / Q000737:chemistry; D002470:Cell Survival; D002478:Cells, Cultured; D004247:DNA / Q000008:administration & dosage / Q000235:genetics; D015195:Drug Design; D005947:Glucose / Q000008:administration & dosage / Q000737:chemistry*; D006017:Glycolipids / Q000008:administration & dosage* / Q000138:chemical synthesis / Q000737:chemistry*; D049452:Green Fluorescent Proteins / Q000096:biosynthesis / Q000235:genetics; D057809:HEK293 Cells; D006801:Humans; D018625:Microscopy, Atomic Force; D010957:Plasmids / Q000008:administration & dosage / Q000235:genetics; D013329:Structure-Activity Relationship; D014162:Transfection / Q000379:methods*
chemical_list: D002412:Cations; D006017:Glycolipids; C485184:enhanced green fluorescent protein; D049452:Green Fluorescent Proteins; D004247:DNA; D005947:Glucose