TY - JOUR
T1 - Synthesis of protoporphyrin-lipids and biological evaluation of micelles and liposomes
AU - Tachikawa, Shoji
AU - El-Zaria, Mohamed E.
AU - Inomata, Ryu
AU - Sato, Shinichi
AU - Nakamura, Hiroyuki
N1 - Funding Information:
This work was supported by the Ministry of Education, Science, Sports, Culture and Technology, Grant-in-Aid for Scientific Research (B) (No. 23390018) from Japan. We thank Professor Kunio Mochida for his kind support of irradiation experiments using a xenon lamp.
PY - 2014/9/1
Y1 - 2014/9/1
N2 - 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.
AB - 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.
KW - Drug delivery system (DDS)
KW - Lipid
KW - Liposome
KW - Micelle
KW - Photodynamic therapy (PDT)
KW - Protoporphyrin IX (PPIX)
KW - Reactive oxygen species (ROS)
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U2 - 10.1016/j.bmc.2014.07.003
DO - 10.1016/j.bmc.2014.07.003
M3 - Article
C2 - 25066052
AN - SCOPUS:84906939213
SN - 0968-0896
VL - 22
SP - 4745
EP - 4751
JO - Bioorganic and Medicinal Chemistry
JF - Bioorganic and Medicinal Chemistry
IS - 17
ER -