Synthesis of protoporphyrin-lipids and biological evaluation of micelles and liposomes

Shoji Tachikawa, Mohamed E. El-Zaria, Ryu Inomata, Shinichi Sato, Hiroyuki Nakamura

Research output: Contribution to journalArticlepeer-review

22 Citations (Scopus)

Abstract

Protoporphyrin IX (PPIX) lipids were synthesized by introducing a long alkyl chain, such as C13, C15, and C17, at each vinyl group on PPIX via hydrobromination. The PPIX lipids exhibited a water-soluble property by forming their micelles in water and the PPIX-lipid micelles showed relatively low cytotoxicity toward HeLa cells (IC50 = 151.7-379.9 μM) without light irradiation. PL-C17 liposomes (post-inserted liposomes) were readily prepared by adding PL-C17 micelle solution to the liposome solution. The IC 50 values of PPIX, PL-C17 micelles, and PL-C17 liposomes toward HeLa cells were 0.53, 5.65, and 12.9 μM, respectively, after irradiation with a xenon lamp in the 400-800 nm range for 2 min. PL-C17 liposomes were selectively accumulated in the Golgi apparatus in cells.

Original languageEnglish
Pages (from-to)4745-4751
Number of pages7
JournalBioorganic and Medicinal Chemistry
Volume22
Issue number17
DOIs
Publication statusPublished - 2014 Sep 1
Externally publishedYes

Keywords

  • Drug delivery system (DDS)
  • Lipid
  • Liposome
  • Micelle
  • Photodynamic therapy (PDT)
  • Protoporphyrin IX (PPIX)
  • Reactive oxygen species (ROS)

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

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