Peng C.-L.Lai P.-S.MING-JIUM SHIEH2020-02-272020-02-2720081016-2372https://www.scopus.com/inward/record.uri?eid=2-s2.0-46349098954&doi=10.4015%2fS1016237208000556&partnerID=40&md5=b53cf243494968d6c1e978af83223b2chttps://scholars.lib.ntu.edu.tw/handle/123456789/465807The asymmetric porphyrins with different substituents show various bioactivities in biomedical application. In this study, a series of asymmetric porphyrins with varying proportion of substituents, such as hydroxyphenyl and aminophenyl, were synthesized and characterized to evaluate their cell uptake, intracellular localization, cytotoxicities and phototoxicities in vitro. Among these synthesized porphyrins, 5-(4-aminophenyl)-10,15,20-tri-(4-hydroxyphenyl)- 21,23H-porphyrin (porphyrin 5), which was mainly localized in mitochondria and with high quantum yields of singlet oxygen, is a potential candidate for photodynamic therapy. The effective phototoxicity of porphyrin 5 is mainly due to the higher extent in the cells and the selective mitochondria-localization. Comparing the partition coefficients of porphyrin derivatives, the best cellular uptake performs apparently with a partition coefficient (log p) ranging from about 1.7 to 1.9. In summary, higher quantum yields of singlet oxygen, and more specific mitochondrial localization of porphyrin 5 demonstrate its potential application in photodynamic therapy. ? 2008 National Taiwan University.Asymmetric porphyrins; Cancer; Mitochondria; Photodynamic therapy[SDGs]SDG3Derivatives; Medical applications; Mitochondria; Photodynamic therapy; Quantum yield; Asymmetric porphyrins; Biomedical applications; Cancer; Intracellular localization; Intracellular uptake; Partition coefficient; Porphyrin derivatives; Subcellular localizations; Porphyrins; 5 (4 aminophenyl) 10,15,20 tri (4 hydroxyphenyl) 21,23h porphyrin; 5 (4 hydroxyphenyl) 10,15,20 tri (4 aminophenyl) 21,23h porphyrin; 5,10 di (4 aminophenyl) 15,20 (4 hydroxyphenyl) 21,23h porphyrin; 5,10,15,20 tetrakis (4 aminophenyl) 21,23h porphyrin; 5,10,15,20 tetrakis (4 hydroxyphenyl) 21,23h porphyrin; 5,15 di (4 aminophenyl) 10,20 (4 hydroxyphenyl) 21,23h porphyrin; porphyrin derivative; article; cellular distribution; cytotoxicity; dose response; drug synthesis; drug uptake; HeLa cell; human; human cell; in vitro study; partition coefficient; photodynamic therapy; photosensitization; phototoxicity; quantum yield; ultraviolet spectroscopyjournal article10.4015/S10162372080005562-s2.0-46349098954