Synthesis of protoporphyrin–lipids and biological evaluation of micelles and liposomes |
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| Institution: | 1. Chemical Research Laboratory, Tokyo Institute of Technology, Nagatsuta-cho, Midori-ku, Yokohama 226-8503, Japan;2. Department of Life Science, Faculty of Science, Gakushuin University, Mejiro, Toshima-ku, Tokyo 171-8588, Japan;3. Department of Chemistry, Faculty of Science, Tanta University, 31527 Tanta, Egypt;1. Academy of Scientific and Innovative Research, CSIR-Indian Institute of Integrative Medicine, Jammu 180 001, India;2. Medicinal Chemistry Division, CSIR-Indian Institute of Integrative Medicine, Jammu 180 001, India;1. Organic Chemistry Division, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune 411008, India;2. Academy of Scientific and Innovative Research (AcSIR), New Delhi 110 025, India;1. National Engineering Research Center for Biomaterials, Sichuan University, Chengdu 610065, China;2. College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325027, China |
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| 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 IC50 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. |
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| Keywords: | Photodynamic therapy (PDT) Reactive oxygen species (ROS) Liposome Protoporphyrin IX (PPIX) Lipid Micelle Drug delivery system (DDS) |
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