A bioorthogonally activatable photosensitiser for site-specific photodynamic therapy

• Published in: Chemical communications (Cambridge, England) Vol. 56; no. 7; p. 1078
• Main Authors: Zhou, Yimin, Wong, Roy C H, Dai, Gaole, Ng, Dennis K P
• Format: Journal Article
• Language: English
• Published: England 23-01-2020
• Subjects: Antineoplastic Agents - chemical synthesis; Antineoplastic Agents - pharmacology; Antineoplastic Agents - radiation effects; Biotin - analogs & derivatives; Biotin - chemical synthesis; Biotin - pharmacology; Boron Compounds - chemical synthesis; Boron Compounds - pharmacology; Boron Compounds - radiation effects; Cell Line, Tumor; Cycloaddition Reaction; Cyclooctanes - chemical synthesis; Cyclooctanes - chemistry; Cyclooctanes - pharmacology; Heterocyclic Compounds, 1-Ring - chemical synthesis; Heterocyclic Compounds, 1-Ring - pharmacology; Heterocyclic Compounds, 1-Ring - radiation effects; Humans; Light; Photochemotherapy; Photosensitizing Agents - chemical synthesis; Photosensitizing Agents - pharmacology; Photosensitizing Agents - radiation effects; Singlet Oxygen - metabolism
• ISSN: 1364-548X
• DOI: 10.1039/c9cc07938f

A boron dipyrromethene based photosensitiser substituted with a 1,2,4,5-tetrazine moiety has been prepared of which the photoactivity can be activated upon an inverse-electron-demand Diels-Alder reaction with trans-cyclooctene derivatives. By using a biotin-conjugated trans-cyclooctene to tag the biotin-receptor-positive HeLa cells, this photosensitiser exhibits site-specific activation through cycloaddition, leading to high photocytotoxicity.