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Bioorthogonal Turn‐On BODIPY‐Peptide Photosensitizers for Tailored Photodynamic Therapy
Author(s) -
Linden Greta,
Vázquez Olalla
Publication year - 2020
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.202001718
Subject(s) - photodynamic therapy , photosensitizer , singlet oxygen , bodipy , bioorthogonal chemistry , phototoxicity , chemistry , peptide , confocal microscopy , toxicity , biophysics , photochemistry , fluorescence , combinatorial chemistry , biochemistry , click chemistry , microbiology and biotechnology , oxygen , biology , in vitro , physics , organic chemistry , quantum mechanics
Photodynamic therapy (PDT) leads to cancer remission via the production of cytotoxic species under photosensitizer (PS) irradiation. However, concomitant damage and dark toxicity can both hinder its use. With this in mind, we have implemented a versatile peptide‐based platform of bioorthogonally activatable BODIPY‐tetrazine PSs. Confocal microscopy and phototoxicity studies demonstrated that the incorporation of the PS, as a bifunctional module, into a peptide enabled spatial and conditional control of singlet oxygen ( 1 O 2 ) generation. Comparing subcellular distribution, PS confined in the cytoplasmic membrane achieved the highest toxicities (IC 50 =0.096±0.003 μ m ) after activation and without apparent dark toxicity. Our tunable approach will inspire novel probes towards smart PDT.