Remote loading of aloe emodin in gemini-based cationic liposomes

Langmuir. 2015;31(1):76-82. doi: 10.1021/la5038074. Epub 2014 Dec 23.

Abstract

Anthraquinone compound aloe-emodin (AE) has shown antineoplastic, antibacterial, antiviral, and anti-inflammatory properties and scavenging activity on free radicals. Because of these therapeutic features, AE has been attracting increasing interest and could be applied in the curing of many diseases. However, until now the physicochemical features of this compound have not been fully investigated; furthermore, its wide application might be hindered by its scarce solubility in aqueous media (∼19 μM). The inclusion of AE in nanocarriers, such as cationic liposomes, could allow its delivery effectively and selectively to target sites, reducing side effects in the remaining tissues. In this work, the weak acid nature of AE, because of its two phenolic functions, was exploited to load it remotely in the internal aqueous phase of liposomes in response to a difference in pH between the inside and outside of the liposomes, pHin > pHout. The inclusion of AE in gemini-based cationic liposomes by the acetate gradient method was obtained at high AE/lipid ratios (up to 1:30).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anthraquinones / chemistry*
  • Hydrogen-Ion Concentration
  • Liposomes / chemistry*
  • Membranes, Artificial
  • Quaternary Ammonium Compounds / chemistry*
  • Water / chemistry

Substances

  • 2,3-dimethoxy-1,4-bis(N-hexadecyl-N,N-dimethylammonium)butane
  • Anthraquinones
  • Liposomes
  • Membranes, Artificial
  • Quaternary Ammonium Compounds
  • Water
  • aloe emodin