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Increased Lipophilicity of Halogenated Ruthenium(II) Polypyridyl Complexes Leads to Decreased Phototoxicity in vitro when Used as Photosensitizers for Photodynamic Therapy
Author(s) -
Roy Saonli,
Colombo Elisa,
Vinck Robin,
Mari Cristina,
Rubbiani Riccardo,
Patra Malay,
Gasser Gilles
Publication year - 2020
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.202000289
Subject(s) - phototoxicity , lipophilicity , ruthenium , photodynamic therapy , chemistry , combinatorial chemistry , phenazine , cytotoxicity , ligand (biochemistry) , in vitro , stereochemistry , photochemistry , biochemistry , organic chemistry , receptor , catalysis
In the fight against cancer, photodynamic therapy is generating great interest thanks to its ability to selectively kill cancer cells without harming healthy tissues. In this field, ruthenium(II) polypyridyl complexes, and more specifically, complexes with dipyrido[3,2‐ a :2’,3’‐ c ]phenazine (dppz) as a ligand are of particular interest due to their DNA‐binding and photocleaving properties. However, ruthenium(II) polypyridyl complexes can sometimes suffer from low lipophilicity, which hampers cellular internalisation through passive diffusion. In this study, four new [Ru(dppz‐X 2 ) 3 ] 2+ complexes (X=H, F, Cl, Br, I) were synthesized and their lipophilicity (log P ), cytotoxicity and phototoxicity on cancerous and noncancerous cell lines were assessed. This study shows that, counterintuitively, the phototoxicity of these complexes decreases as their lipophilicity increases; this could be due solely to the atomic radius of the halogen substituents.