1. Highly Efficient Singlet Oxygen Generators Based on Ruthenium Phthalocyanines: Synthesis, Characterization and in vitro Evaluation for Photodynamic Therapy
- Author
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Joana T. Ferreira, M. Salomé Rodríguez-Morgade, João Pina, João P. C. Tomé, Tomás Torres, Carlos Fontes Ribeiro, and Rosa Fernandes
- Subjects
Light ,Cell Survival ,medicine.medical_treatment ,Urinary Bladder ,chemistry.chemical_element ,Photodynamic therapy ,010402 general chemistry ,01 natural sciences ,Catalysis ,chemistry.chemical_compound ,Cell Line, Tumor ,PEG ratio ,medicine ,Organometallic Compounds ,Humans ,Photosensitizing Agents ,Singlet Oxygen ,010405 organic chemistry ,Singlet oxygen ,Ligand ,Organic Chemistry ,General Chemistry ,Combinatorial chemistry ,0104 chemical sciences ,Ruthenium ,Photochemotherapy ,Urinary Bladder Neoplasms ,chemistry ,Spectrophotometry ,Phthalocyanine ,Isoindole ,Phototoxicity - Abstract
The synthesis of ruthenium(II) phthalocyanines (RuPcs) endowed with one carbohydrate unit-that is, glucose, galactose and mannose-and a dimethylsulfoxide (DMSO) ligand at the two axial coordination sites, respectively, is described. Two series of compounds, one unsubstituted at the periphery, and the other one bearing eight PEG chains at the isoindole meta-positions, have been prepared. The presence of the axial DMSO unit significantly increases the phthalocyanine singlet oxygen quantum yields, related to other comparable RuPcs. The compounds have been evaluated for PDT treatment in bladder cancer cells. In vitro studies have revealed high phototoxicity for RuPcs unsubstituted at their periphery. The phototoxicity of PEG-substituted RuPcs has been considerably improved by repeated light irradiation. The choice of the axial carbohydrate introduced little differences in the cellular uptake for both series of photosensitizers, but the phototoxic effects were considerably higher for compounds bearing mannose units.
- Published
- 2019