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Ruthenium(II) Conjugates of Boron-Dipyrromethene and Biotin for Targeted Photodynamic Therapy in Red Light

Paul, S and Kundu, P and Bhattacharyya, U and Garai, A and Maji, RC and Kondaiah, P and Chakravarty, AR (2020) Ruthenium(II) Conjugates of Boron-Dipyrromethene and Biotin for Targeted Photodynamic Therapy in Red Light. In: Inorganic Chemistry, 59 (1). pp. 913-924.

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Official URL: https://doi.org/10.1021/acs.inorgchem.9b03178


The ruthenium(II) complexes [RuCl(L1)(L3)]Cl (1), [RuCl(L1)(L4)]Cl (2), [RuCl(L2)(L4)]Cl (3), [RuCl(L1)(L5)]Cl (4), and [RuCl(L2)(L5)]Cl (5) of NNN-donor dipicolylamine (dpa) bases (L4, L5) having BODIPY (boron-dipyrromethene) moieties, NN-donor phenanthroline derivatives (L1, L2), and benzyldipicolylamine (bzdpa, L3) were prepared and characterized by spectroscopic techniques and their cellular localization/uptake and photocytotoxicity studied. Complex 1, as its PF6 salt (1a), has been structurally characterized with help of a single-crystal X-ray diffraction technique. It has a RuN5Cl core with the Cl bonded trans to the amine nitrogen atom of bzdpa. The complexes showed intense absorption spectral bands near 500 nm (ϵ ≈ 58000 M-1 cm-1) in 2 and 3 and 654 nm (ϵ ≈ 80000 M-1 cm-1) in 4 and 5 in 1/1 DMSO/DPBS (v/v). Complex 5 having biotin and PEGylated-disteryl BODIPY gave a singlet oxygen quantum yield (φÎ") of â¼0.65 in DMSO. Complex 5 exhibited remarkable PDT (photodynamic therapy) activity (IC50 ≈ 0.02 μM) with a photocytotoxicity index (PI) value of >5000 in red light of 600-720 nm in A549 cancer cells. The biotin-conjugated complexes showed better photocytotoxicity in comparison to nonbiotinylated analogues in A549 cells. The complexes displayed less toxicity in HPL1D normal cells in comparison to A549 cancer cells. The emissive BODIPY complexes 3 and 5 (φF ≈ 0.07 in DMSO) showed significant mitochondrial localization.

Item Type: Journal Article
Publication: Inorganic Chemistry
Publisher: American Chemical Society
Additional Information: The copyright for this article belongs to American Chemical Society.
Keywords: antineoplastic agent; biotin; boron; coordination compound; dipyrromethene; photosensitizing agent; porphobilinogen; ruthenium, A-549 cell line; cell line; cell proliferation; cell survival; chemistry; density functional theory; DNA cleavage; drug effect; drug screening; fluorescence imaging; human; light; molecular model; photochemotherapy; synthesis, A549 Cells; Antineoplastic Agents; Biotin; Boron; Cell Line; Cell Proliferation; Cell Survival; Coordination Complexes; Density Functional Theory; DNA Cleavage; Drug Screening Assays, Antitumor; Humans; Light; Models, Molecular; Optical Imaging; Photochemotherapy; Photosensitizing Agents; Porphobilinogen; Ruthenium
Department/Centre: Division of Biological Sciences > Molecular Reproduction, Development & Genetics
Division of Chemical Sciences > Inorganic & Physical Chemistry
Date Deposited: 06 Feb 2023 10:15
Last Modified: 06 Feb 2023 10:15
URI: https://eprints.iisc.ac.in/id/eprint/79939

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