BODIPY-linked: Cis -dichlorido zinc(ii) conjugates: The strategic design of organelle-specific next-generation theranostic photosensitizers

Bhattacharyya, A and Jameei, A and Saha, R and Garai, A and Karande, AA and Chakravarty, AR (2021) BODIPY-linked: Cis -dichlorido zinc(ii) conjugates: The strategic design of organelle-specific next-generation theranostic photosensitizers. In: Dalton Transactions, 50 (1). pp. 103-115.

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Abstract

Dipicolylamine (dpa) based cis-dichlorido zinc(ii) complexes Zn(L1-3)Cl2 (1-3), where L2 and L3 are non-iodo and di-iodo BODIPY-appended dpa in 2 and 3, and L1 is dpa in control complex 1, were prepared and characterized and their photocytotoxicity was studied. Complexes 2 and 3 were developed as potential substitutes for zinc(ii)-porphyrins/phthalocyanines that are photodynamic therapeutic agents with moderate activity owing to their inherent hydrophobicity and aggregation-induced deactivation mechanism. In our approach, we strategically designed hybrid inorganic-organic zinc-BODIPY conjugates as theranostic photosensitizers. The structurally characterized diamagnetic Zn(ii) cis-dichlorido complexes mimic cisplatin and serve as new-generation photosensitizers with enhanced aqueous solubility and mito-DNA targeting propensity while imparting significant physiological stability to the heavy atom tethered BODIPY ligand, L3. The BODIPY complexes showed a visible band near 500 nm (ϵ � 34�000-44�000 dm3 mol-1 cm-1) and an emission band at 507 nm for 2 in 1% DMSO-Dulbecco's phosphate buffered saline. The labile chlorido ligands (�M � 200 S m2 mol-1 in 9�:�1 H2O-DMSO) generated positively charged complexes inside the cellular medium enabling them to cross the mitochondrial membrane for this organelle-selective localization and singlet oxygen-mediated apoptotic photocytotoxicity at nanomolar concentrations for 3 in HeLa and MCF-7 cells in light (400-700 nm), while being less active in the dark. © The Royal Society of Chemistry.

Item Type:	Journal Article
Publication:	Dalton Transactions
Publisher:	Royal Society of Chemistry
Additional Information:	The copyright of this article belongs to Royal Society of Chemistry
Department/Centre:	Division of Biological Sciences > Biochemistry Division of Chemical Sciences > Inorganic & Physical Chemistry
Date Deposited:	22 Jan 2021 10:37
Last Modified:	22 Jan 2021 10:37
URI:	http://eprints.iisc.ac.in/id/eprint/67680

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