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Near‐IR Absorbing BODIPY Derivatives as Glutathione‐Activated Photosensitizers for Selective Photodynamic Action
Author(s) -
Turan Ilke Simsek,
Cakmak Fatma Pir,
Yildirim Deniz Cansen,
CetinAtalay Rengul,
Akkaya Engin U.
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201405450
Subject(s) - bodipy , singlet oxygen , photosensitizer , photodynamic therapy , glutathione , chemistry , internalization , selectivity , photochemistry , reactive oxygen species , cytotoxicity , sensitization , combinatorial chemistry , biophysics , fluorescence , oxygen , cell , biochemistry , organic chemistry , in vitro , biology , immunology , physics , quantum mechanics , enzyme , catalysis
Enhanced spatiotemporal selectivity in photonic sensitization of dissolved molecular oxygen is an important target for improving the potential and the practical applications of photodynamic therapy. Considering the high intracellular glutathione concentrations within cancer cells, a series of BODIPY‐based sensitizers that can generate cytotoxic singlet oxygen only after glutathione‐mediated cleavage of the electron‐sink module were designed and synthesized. Cell culture studies not only validate our design, but also suggest an additional role for the relatively hydrophobic quencher module in the internalization of the photosensitizer.