Conditional Singlet Oxygen Generation through a Bioorthogonal DNA-targeted Tetrazine Reaction.
Angew Chem Int Ed Engl
; 58(37): 12868-12873, 2019 09 09.
Article
em En
| MEDLINE
| ID: mdl-31291504
ABSTRACT
We report the use of bioorthogonal reactions as an original strategy in photodynamic therapy to achieve conditional phototoxicity and specific subcellular localization simultaneously. Our novel halogenated BODIPY-tetrazine probes only become efficient photosensitizers (ΦΔ ≈0.50) through an intracellular inverse-electron-demand Diels-Alder reaction with a suitable dienophile. Abâ
initio computations reveal an activation-dependent change in decay channels that controls 1 O2 generation. Our bioorthogonal approach also enables spatial control. As a proof-of-concept, we demonstrate the feasibility of the selective activation of our dormant photosensitizer in cellular nuclei, causing cancer cell death upon irradiation. Thus, our dual biorthogonal, activatable photosensitizers open new venues to combat current limitations of photodynamic therapy.
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Texto completo:
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Base de dados:
MEDLINE
Assunto principal:
Compostos de Boro
/
Fármacos Fotossensibilizantes
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Oxigênio Singlete
Limite:
Humans
Idioma:
En
Ano de publicação:
2019
Tipo de documento:
Article