Synthesis of 2-morpholinetetraphenylporphyrins and their photodynamic activities |
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| Affiliation: | 1. College of Pharmacy, Nanjing University of Chinese Medicine, Nanjing, Jiangsu Province 210023, People’s Republic of China;2. Laboratory of Translational Medicine, Jiangsu Province Academy of Traditional Chinese Medicine, Nanjing, Jiangsu Province 210028, People’s Republic of China;3. Department of Nuclear Medicine, The First Affiliated Hospital of Nanjing Medical University, Nanjing, Jiangsu Province 210029, People’s Republic of China;4. Bijie Institute of Traditional Chinese Medicine, Bijie, Guizhou Province 551700, People’s Republic of China;5. Department of Natural Medicinal Chemistry and State Key Laboratory of Natural Medicines, China Pharmaceutical University, Nanjing, Jiangsu Province 210009, People’s Republic of China;6. Shandong Academy of Medical Sciences, Jinan, Shandong 250062, People’s Republic of China;7. Theragnostic LaboratoryCampus Gasthuisberg, KU LeuvenLeuven3000Belgium;1. Beckman Laser Institute and Medical Clinic, University of California, Irvine, Irvine, California, USA;2. Department of Dermatology, University of California, Irvine, Irvine, California, USA;3. Department of Surgery, University of California, Irvine, Irvine, California, USA;4. Department of Biomedical Engineering, University of California, Irvine, Irvine, California, USA;5. Department of Medicine, Virginia Commonwealth University, Richmond, Virginia, USA;6. Department of Medicine, University of California, Irvine, Irvine, California, USA;7. Edwards Lifesciences Center for Advanced Cardiovascular Technology, University of California, Irvine, Irvine, California, USA |
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| Abstract: | A series of 2-morpholinetetraphenylporphyrins functionalized with various substituents (Cl, Me, MeO group) at 4-phenyl position were prepared via nucleophilic substitution of 2-nitroporphyrin copper derivatives with morpholine by refluxing under a nitrogen atmosphere and then demetalization. Their basic photophysical properties, intracellular localization, cytotoxicities in vitro and in vivo were also investigated. All synthesized photosensitizers exhibited longer maxima absorption wavelengths than Hematoporphyrin monomethyl ether (HMME). They showed low dark cytotoxicity compared with that of HMME and were more phototoxic than HMME against Eca-109 cells in vitro. M3 also exhibited better photodynamic antitumor efficacy on BALB/c nude mice at a lower concentration. Therefore, M3 is a promising antitumor photosensitizer in photodynamic therapy application. |
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| Keywords: | Photosensitizer Photodynamic therapy Porphyrin Antitumor |
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