Self-organization and lipoplex formation of cationic surfactants with morpholinium head group

• Published in: Journal of molecular liquids 2016-08, Vol.220, p.992-998
• Main Authors: Mirgorodskaya, A.B., Yackevich, E.I., Gabdrakhmanov, D.R., Lukashenko, S.S., Zuev, Yu.F., Zakharova, L.Ya
• Format: Article
• Language: English
• Subjects: Complexation; Gemini; Morpholinium surfactant; Oligonucleotide; Self-assembly
• ISSN: 0167-7322; 1873-3166
• DOI: 10.1016/j.molliq.2016.05.010

A novel dicationic surfactant with morpholinium head groups and hexadecyl tails (MP 16-6-16) has been synthesized. The self-assembly properties of the amphiphile have been evaluated and compared with their monocationic counterpart (MP-16) and trimethylammonium analogs. The critical micelle concentration of gemini (0.01mM) is lower as compared to MP-16 and slightly lower compared to conventional gemini 16-6-16. It was shown that the micelle surface potential increases and the aggregation number decreases upon the transition from a monocationic to a gemini analog. Morpholinium surfactants demonstrate a much higher solubilizing capacity toward the hydrophobic probe Orange OT as compared to the typical trimethylammonium surfactant. Both morpholinium surfactants form lipoplexes with a DNA decamer, which is strongly supported by the ethidium bromide exclusion assay and charge neutralization data. The high solubilizing and complexing activity and the ability to integrate with a lipid bilayer allow us to recommend morpholinium surfactants as candidates for drug and gene carriers. [Display omitted] •Self-assembly of mono- and dicationic morpholinium surfactants is quantified.•Aggregation capacity of gemini is ca.100-fold higher than for monomeric one.•Morpholinium surfactants show higher solubilizing capacity compared to CTAB.•Morpholinium amphiphiles can form lipoplex with DNA decamer.•Morpholinium gemini is capable to integrate with lipid bilayer.