Evaluation of the influence of ionization states and spacers in the thermotropic phase behaviour of amino acid-based cationic lipids and the transfection efficiency of their assemblies

Satya Ranjan Sarker, Satoshi Arai, Motohide Murate, Hiroshi Takahashi, Masaki Takata, Toshihide Kobayashi, Shinji Takeoka

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

The influence of both the ionization states and the hydrocarbon chain spacer of a series of amino acid-based cationic lipids was evaluated in terms of gene delivery efficiency and cytotoxicity to the COS-7 cell line and compared with that of Lipofectamine™ 2000. We synthesized a series of amino acid-based cationic lipids with different ionization states (i.e., -NH 2, -NH 3 +Cl - or -NH 3 +TFA -) in the lysine head group and different hydrocarbon chain spacers (i.e., 0, 3, 5 or 7 carbon atoms) between the hydrophilic head group and hydrophobic moieties. In the 3-carbon series, the cationic assemblies formed a micellar structure in the presence of -NH 3 +Cl - and a vesicular structure both in the presence of -NH 2 and -NH 3 +TFA -. Differential scanning calorimetry (DSC) data revealed a significantly lower (8.1°C) gel-to-liquid crystalline phase transition temperature for cationic assemblies bearing -NH 3 +TFA - when compared to their -NH 2 counterparts. Furthermore, the zeta potential of cationic assemblies having -NH 3 +TFA - in the hydrophilic head group was maximum followed by -NH 3 +Cl - and -NH 2 irrespective of their hydrocarbon chain spacer length. The gene delivery efficiency in relation to the ionization states of the hydrophilic head group was as follows: -NH 3 +TFA - > -NH 3 +Cl - > -NH 2.

Original languageEnglish
Pages (from-to)364-373
Number of pages10
JournalInternational Journal of Pharmaceutics
Volume422
Issue number1-2
DOIs
Publication statusPublished - 2012 Jan 17

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Hydrocarbons
Transfection
Lipids
Amino Acids
Carbon
Transition Temperature
COS Cells
Phase Transition
Differential Scanning Calorimetry
Genes
Gels
Cell Line

Keywords

  • Cationic lipid
  • Hydrocarbon chain spacer
  • Ionization states
  • Phase transition temperature
  • Transfection efficiency

ASJC Scopus subject areas

  • Pharmaceutical Science

Cite this

Evaluation of the influence of ionization states and spacers in the thermotropic phase behaviour of amino acid-based cationic lipids and the transfection efficiency of their assemblies. / Sarker, Satya Ranjan; Arai, Satoshi; Murate, Motohide; Takahashi, Hiroshi; Takata, Masaki; Kobayashi, Toshihide; Takeoka, Shinji.

In: International Journal of Pharmaceutics, Vol. 422, No. 1-2, 17.01.2012, p. 364-373.

Research output: Contribution to journalArticle

Sarker, Satya Ranjan ; Arai, Satoshi ; Murate, Motohide ; Takahashi, Hiroshi ; Takata, Masaki ; Kobayashi, Toshihide ; Takeoka, Shinji. / Evaluation of the influence of ionization states and spacers in the thermotropic phase behaviour of amino acid-based cationic lipids and the transfection efficiency of their assemblies. In: International Journal of Pharmaceutics. 2012 ; Vol. 422, No. 1-2. pp. 364-373.
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