title: Synthesis of protoporphyrin-lipids and biological evaluation of micelles and liposomes.
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=151.7-379.9μM) without light irradiation. PL-C17 liposomes (post-inserted liposomes) were readily prepared by adding PL-C17 micelle solution to the liposome solution. The IC50 values of PPIX, PL-C17 micelles, and PL-C17 liposomes toward HeLa cells were 0.53, 5.65, and 12.9μM, respectively, after irradiation with a xenon lamp in the 400-800nm range for 2min. PL-C17 liposomes were selectively accumulated in the Golgi apparatus in cells.
authors: Chemical Research Laboratory, Tokyo Institute of Technology, Nagatsuta-cho, Midori-ku, Yokohama 226-8503, Japan; Department of Life Science, Faculty of Science, Gakushuin University, Mejiro, Toshima-ku, Tokyo 171-8588, Japan.
authors: Shoji
authors: S
authors: Tachikawa
authors: Department of Chemistry, Faculty of Science, Tanta University, 31527 Tanta, Egypt.
authors: Mohamed E
authors: ME
authors: El-Zaria
authors: Department of Life Science, Faculty of Science, Gakushuin University, Mejiro, Toshima-ku, Tokyo 171-8588, Japan.
authors: Ryu
authors: R
authors: Inomata
authors: Chemical Research Laboratory, Tokyo Institute of Technology, Nagatsuta-cho, Midori-ku, Yokohama 226-8503, Japan.
authors: Shinichi
authors: S
authors: Sato
authors: Chemical Research Laboratory, Tokyo Institute of Technology, Nagatsuta-cho, Midori-ku, Yokohama 226-8503, Japan. Electronic address: hiro@res.titech.ac.jp.
authors: Hiroyuki
authors: H
authors: Nakamura
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D049109:Cell Proliferation / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D006367:HeLa Cells; D006801:Humans; D008055:Lipids / Q000737:chemistry / Q000494:pharmacology*; D008081:Liposomes / Q000737:chemistry / Q000494:pharmacology*; D008823:Micelles; D015394:Molecular Structure; D011524:Protoporphyrins / Q000737:chemistry / Q000494:pharmacology*; D017382:Reactive Oxygen Species / Q000032:analysis / Q000378:metabolism; D013329:Structure-Activity Relationship
chemical_list: D000970:Antineoplastic Agents; D008055:Lipids; D008081:Liposomes; D008823:Micelles; D011524:Protoporphyrins; D017382:Reactive Oxygen Species; C028025:protoporphyrin IX
keywords: Drug delivery system (DDS); Lipid; Liposome; Micelle; Photodynamic therapy (PDT); Protoporphyrin IX (PPIX); Reactive oxygen species (ROS)