Bioorthogonal Turn‐On BODIPY‐Peptide Photosensitizers for Tailored Photodynamic Therapy. Issue 44 (23rd July 2020)

• Record Type: Journal Article
• Authors: Linden, Greta; Vázquez, Olalla
• Is Part Of: Chemistry. Volume 26:Issue 44(2020)
• Page Start: 10014
• Page End: 10023
• Publication Date: 2020-07-23
• Subjects: bioorthogonal reactions -- BODIPY -- peptides -- photodynamic therapy -- tetrazine; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.202001718
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: 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 O2 ) generation. Comparing subcellular distribution, PS confined in the cytoplasmic membrane achieved the highest toxicities (IC50 =0.096±0.003 μm ) after activation and without apparent dark toxicity. Our tunable approach will inspire novel probes towards smart PDT. Abstract : Modular peptide‐based platform for organelle‐confinement of the photodynamic effect . We report a general approach capable of directing the bioorthogonal activation of tetrazine‐BODIPY photosensitizers to specific subcellular organelles.