Chlorophyllin Derivatives as Photosensitizers: Synthesis and Photodynamic Properties

Adjaci F. Uchoa, Aaron M. Konopko, Maurício S. Baptista
2015 Journal of the Brazilian Chemical Society  
Two new photosensitizers (PSs) derived from copper-chlorophyllin were designed to have excitation wavelengths appropriate for the use in photodynamic therapy (PDT) and to have amphiphilic character with positive charge, which favors binding to cell membranes and walls and the intracellular localization in mitochondria. Herein we describe the synthesis and characterization of several properties of these two new PS, i.e., photophysical (absorption, fluorescence and singlet oxygen emission quantum
more » ... en emission quantum yields, Φ f and Φ Δ , respectively), physical-chemical (aggregation) and photobiological (binding, incorporation and cell killing). As expected, the aggregation affected not only the absorption spectra but also lowered considerably the values of Φ f and Φ Δ , which could be controlled by the interaction of the PS with aqueous micelles. In vitro studies were performed in cells, mitochondria, and vesicles to determine uptake, membrane binding, cytotoxicity, phototoxicity, and intracellular localization. The positively charged derivatives showed to be considerably more efficient for cell killing than methylene blue.
doi:10.5935/0103-5053.20150290 fatcat:4ztlmwoazrdwpaebpkw3ubtqoi