title: Dicationic Surfactants with Glycine Counter Ions for Oligonucleotide Transportation.
abstract: Gemini surfactants are good candidates to bind, protect, and deliver nucleic acids. Herein, the concept of amino acids (namely glycine) as counter ions of gemini surfactants for gene therapy application was explored. This study was conducted on DNA and RNA oligomers and two quaternary bis-imidazolium salts, having 2,5-dioxahexane and 2,8-dioxanonane spacer groups. The toxicity level of surfactants was assessed by an MTT assay, and their ability to bind nucleic acids was tested through electrophoresis. The nucleic acid conformation was established based on circular dichroism and infrared spectroscopic analyses. The structures of the formed complexes were characterized by small-angle scattering of synchrotron radiation. Both studied surfactants appear to be suitable for gene therapy; however, although they vary by only three methylene groups in the spacer, they differ in binding ability and toxicity. The tested oligonucleotides maintained their native conformations upon surfactant addition and the studied lipoplexes formed a variety of structures. In systems based on a 2,5-dioxahexane spacer, a hexagonal phase was observed for DNA-surfactant complexes and a micellar phase was dominant with RNA. For the surfactant with a 2,8-dioxanonane spacer group, the primitive cubic phase prevailed.
authors.affiliation: Department of Macromolecular Physics, Faculty of Physics, Adam Mickiewicz University, Umultowska 85, 61-614, Poznan, Poland. zuzannap@amu.edu.pl.
authors.forename: Zuzanna
authors.identifier: http://orcid.org/0000-0003-2990-7047
authors.initials: Z
authors.lastname: Pietralik
authors.affiliation: Institute of Chemical Technology and Engineering, Poznan University of Technology, Berdychowo 4, 60-965, Poznan, Poland.
authors.forename: Andrzej
authors.initials: A
authors.lastname: Skrzypczak
authors.affiliation: Department of Macromolecular Physics, Faculty of Physics, Adam Mickiewicz University, Umultowska 85, 61-614, Poznan, Poland. mkozak@amu.edu.pl.|Joint Laboratory for SAXS Studies, Faculty of Physics, Adam Mickiewicz University, Umultowska 85, 61-614, Poznan, Poland. mkozak@amu.edu.pl.
authors.forename: Maciej
authors.initials: M
authors.lastname: Kozak
mesh_terms: D001692:Biological Transport; D002413:Cations, Divalent / Q000737:chemistry; D004247:DNA / Q000008:administration & dosage* / Q000737:chemistry / Q000493:pharmacokinetics; D018014:Gene Transfer Techniques; D005998:Glycine / Q000031:analogs & derivatives*; D006367:HeLa Cells; D006801:Humans; D007093:Imidazoles / Q000737:chemistry*; D009690:Nucleic Acid Conformation / Q000187:drug effects; D009841:Oligonucleotides / Q000008:administration & dosage* / Q000737:chemistry / Q000493:pharmacokinetics; D012313:RNA / Q000008:administration & dosage* / Q000737:chemistry / Q000493:pharmacokinetics; D013501:Surface-Active Agents / Q000737:chemistry*
chemical_list: D002413:Cations, Divalent; D007093:Imidazoles; D009841:Oligonucleotides; D013501:Surface-Active Agents; D012313:RNA; D004247:DNA; D005998:Glycine
keywords: amino acids; conformation analysis; drug delivery; gene technology; surfactants