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A Family of Potent Ru( II ) Photosensitizers with Enhanced DNA Intercalation: Bimodal Photokillers
Author(s) -
Pefkianakis Eleftherios K.,
Theodossiou Theodossis A.,
Toubanaki Dimitra K.,
Karagouni Evdokia,
Falaras Polycarpos,
Papadopoulos Kyriakos,
Vougioukalakis Georgios C.
Publication year - 2015
Publication title -
photochemistry and photobiology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.818
H-Index - 131
eISSN - 1751-1097
pISSN - 0031-8655
DOI - 10.1111/php.12485
Subject(s) - chemistry , singlet oxygen , intercalation (chemistry) , counterion , ruthenium , moiety , phenazine , photochemistry , du145 , photodynamic therapy , stereochemistry , combinatorial chemistry , cancer cell , organic chemistry , oxygen , medicine , ion , cancer , lncap , catalysis
A new family of Ru( II )‐based photosensitizers was synthesized and systematically characterized. The ligands employed to coordinate the ruthenium metal center were the commercially available 2,2′‐bipyridine and a pyridine‐quinoline hybrid bearing an anthracene moiety. The complexes obtained carry either PF 6 − or Cl − counterions. These counterions determine the complexes' hydrophobic or hydrophilic character, respectively, therefore dictating their solubility in biologically related media. All photosensitizers exhibit characteristic, relatively strong and wide UV –Vis absorption spectral profiles. Their high efficiency in generating cytotoxic singlet oxygen was established (up to Φ Δ ~0.8). Moreover, the interaction of these photosensitizers with double‐stranded DNA was studied fluoro‐ and photospectroscopically and their binding affinities were found to be of the order of 3 × 10 7 M −1 . All complexes are photocytotoxic to DU 145 human prostate cancer cells. The highest light‐induced toxicity was conferred by the photosensitizers bearing Cl − counterions, probably due to the looser ionic “chaperoning” of Cl − , in comparison to PF 6 − , leading to higher cell internalization.