BODIPY-attached zinc(II) complexes of curcumin drug for visible light assisted photo-sensitization, cellular imaging and targeted PDT

Bhattacharyya, A and Jameei, A and Karande, AA and Chakravarty, AR (2021) BODIPY-attached zinc(II) complexes of curcumin drug for visible light assisted photo-sensitization, cellular imaging and targeted PDT. In: European Journal of Medicinal Chemistry, 220 .

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Abstract

Boron-dipyrromethene (BODIPY) based photosensitizers as porphyrinoids and curcumin as natural product possess exciting photophysical features suitable for theranostic applications, namely, imaging and photodynamic therapy (PDT). Limited aqueous solubility and insufficient physiological stability, however, reduce their efficacy significantly. We have designed a novel strategy to deliver these two unusable cytotoxins simultaneously in cancer cells and herein, report the synthesis, characterization and imaging-assisted photocytotoxicity of three zinc(II) complexes containing N3-donor dipicolylamine (dpa) ligands (L1-3) and O,O-donor curcumin (Hcur) viz. [Zn(L1)(cur)]Cl (1), [Zn(L2)(cur)]Cl (2) and [Zn(L3)(cur)]Cl (3), where L2 and L3 have pendant fluorescent BODIPY and non-emissive di-iodo-BODIPY moieties. Metal chelation imparted remarkable biological stability (pH ∼7.4) to the respective ligands and induces significant aqueous solubility. These ternary complexes could act as replacements of the existing metalloporphyrin-based PDT photosensitizers as their visible-light photosensitizing ability is reinforced by the dual presence of blue light absorbing curcumin and green light harvesting BODIPY units. Complex 2 having emissive BODIPY unit L2 and curcumin, showed mitochondria selective localization in HeLa, MCF-7 cancer cells and complex 3, the di-iodinated analogue of complex 2, exhibited type-I/II PDT activity via inducing apoptosis through mitochondrial membrane disruption in cancer cells while being significantly nontoxic in dark and to the healthy cells. © 2021 Elsevier Masson SAS

Item Type:	Journal Article
Publication:	European Journal of Medicinal Chemistry
Publisher:	Elsevier Masson s.r.l.
Additional Information:	The copyright for this article belongs to Elsevier Masson s.r.l.
Keywords:	antineoplastic agent; boron; boron dipyrromethene; catalase; cell DNA; cell nucleus DNA; curcumin; cytochrome c; cytotoxin; DNA; metalloporphyrin; mitochondrial DNA; n 3 donor dipicolylamine ligand; o,o donor curcumin; photosensitizing agent; reactive oxygen metabolite; unclassified drug; zinc; zinc complex; 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene; antineoplastic agent; boron derivative; coordination compound; curcumin; photosensitizing agent; zinc, antineoplastic activity; apoptosis; Article; blue light; cell viability assay; chelation; chemical analysis; controlled study; cytotoxicity; diagnostic imaging; drug design; drug formulation; drug stability; drug synthesis; female; fluorescence analysis; green light; HeLa cell line; human; human cell; light exposure; MCF-7 cell line; medicinal chemistry; mitochondrial membrane; mitochondrion; molecular stability; pH; photocytotoxicity; photodynamic therapy; photodynamics; photosensitization; physiological process; water solubility; cell line; cell proliferation; chemical structure; chemistry; dose response; drug effect; fluorescence imaging; light; photochemotherapy; structure activity relation; synthesis, Antineoplastic Agents; Boron Compounds; Cell Line; Cell Proliferation; Coordination Complexes; Curcumin; Dose-Response Relationship, Drug; Humans; Light; Molecular Structure; Optical Imaging; Photochemotherapy; Photosensitizing Agents; Structure-Activity Relationship; Zinc
Department/Centre:	Division of Chemical Sciences > Inorganic & Physical Chemistry
Date Deposited:	20 Feb 2023 11:14
Last Modified:	20 Feb 2023 11:14
URI:	https://eprints.iisc.ac.in/id/eprint/80421

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