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Photodynamic Therapy with Targeted Release of Boron-Dipyrromethene Dye from Cobalt(III) Prodrugs in Red Light

Jana, A and Sahoo, S and Paul, S and Sahoo, S and Jayabaskaran, C and Chakravarty, AR (2024) Photodynamic Therapy with Targeted Release of Boron-Dipyrromethene Dye from Cobalt(III) Prodrugs in Red Light. In: Inorganic Chemistry, 63 (15). pp. 6822-6835.

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Official URL: https://doi.org/10.1021/acs.inorgchem.4c00244


Boron-dipyrromethene (BODIPY) dyes are promising photosensitizers for cellular imaging and photodynamic therapy (PDT) owing to their excellent photophysical properties and the synthetically tunable core. Metalation provides a convenient way to overcome the drawbacks arising from their low aqueous solubility. New photo-/redox-responsive Co(III) prodrug chaperones are developed as anticancer PDT agents for efficient cellular delivery of red-light-active BODIPY dyes. The photobiological activity of heteroleptic Co(III) complexes derived from tris(2-pyridylmethyl)amine (TPA) and acetylacetone-conjugated PEGylated distyryl BODIPY (HL1) or its dibromo analogue (HL2), CoIII(TPA)(L1/L2)(ClO4)2 (1 and 2), are investigated. The Co(III)/Co(II) redox potential is tuned using the Co(III)-TPA scaffold. Complex 1 displays the in vitro release of BODIPY on red light irradiation. Complex 2, having good singlet oxygen quantum yield (Φ� � 0.28 in DMSO), demonstrates submicromolar photocytotoxicity to HeLa cancer cells (IC50 � 0.23 μM) while being less toxic to HPL1D normal cells in red light. Cellular imaging using the emissive complex 1 shows mitochondrial localization and significant penetration into the HeLa tumor spheroids. Complex 2 shows supercoiled DNA photocleavage activity and apoptotic cell death through phototriggered generation of reactive oxygen species. The Co(III)-BODIPY prodrug conjugates exemplify new type of phototherapeutic agents with better efficacy than the organic dyes alone in the phototherapeutic window. © 2024 American Chemical Society

Item Type: Journal Article
Publication: Inorganic Chemistry
Publisher: American Chemical Society
Additional Information: The copyright for this article belongs to American Chemical Society.
Keywords: Boron; Cancer cells; Cell death; Cobalt compounds; Dies; Lanthanum compounds; Oxygen; Photodynamic therapy; Photosensitizers; Redox reactions, Aqueous solubility; Boron dipyrromethene; Cellular imaging; Complex 1; Metalations; Photophysical properties; Photosensitiser; Prodrugs; Red light; Tunables, Acetone, 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene; antineoplastic agent; boron; boron derivative; cobalt; coloring agent; dipyrromethene; photosensitizing agent; porphobilinogen; prodrug; singlet oxygen, human; light; metabolism; photochemotherapy; radiation response; red light, Antineoplastic Agents; Boron; Boron Compounds; Cobalt; Coloring Agents; Humans; Light; Photochemotherapy; Photosensitizing Agents; Porphobilinogen; Prodrugs; Red Light; Singlet Oxygen
Department/Centre: Division of Biological Sciences > Biochemistry
Division of Chemical Sciences > Inorganic & Physical Chemistry
Date Deposited: 21 May 2024 05:18
Last Modified: 21 May 2024 05:18
URI: https://eprints.iisc.ac.in/id/eprint/84781

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