Cu(ii) flavonoids as potential photochemotherapeutic agents

Das, N and Bora, B and Upadhyay, A and Das, D and Bera, A and Goswami, TK (2024) Cu(ii) flavonoids as potential photochemotherapeutic agents. In: Dalton Transactions .

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Abstract

Flavonoids, naturally derived polyphenolic compounds, have received significant attention due to their remarkable biochemical properties that offer substantial health benefits to humans. In this work, a series of six Cu(ii) flavonoid complexes of the formulation Cu(L1)(L2)(ClO4) where L1 is 3-hydroxy flavone (HF1, 1 and 4), 4-fluoro-3-hydroxy flavone (HF2, 2 and 5), and 2,6-difluoro-3-hydroxy flavone (HF3, 3 and 6); L2 is 1,10-phenanthroline (phen, 1-3) and 2-(anthracen-1-yl)-1H-imidazo4,5-f1,10phenanthroline (aip, 4-6) were successfully synthesized, fully characterized and also evaluated for their in vitro photo-triggered cytotoxicity in cancer cells. The single-crystal X-ray diffraction structure of complex 2 shows square pyramidal geometry around the Cu(ii) center. The complexes 1-6 showed quasi-reversible cyclic voltammetric responses for the Cu(ii)/Cu(i) couple at ��0.230 V with a very large �Ep value of �350-480 mV against the Ag/AgCl reference electrode in DMF-0.1 M tetrabutylammonium perchlorate (TBAP) at a scan rate of 50 mV s�1. The complexes were found to have considerable binding propensity for human serum albumin (HSA) and calf thymus DNA (ct-DNA). The complexes displayed remarkable dose-dependent photocytotoxicity in visible light (400-700 nm) in both A549 (human lung cancer) and MCF-7 (human breast cancer) cell lines while remaining significantly less toxic in darkness. They were found to be much less toxic to HPL1D (immortalized human peripheral lung epithelial) normal cells compared to A549 and MCF-7 cancer cells. Upon exposure to visible light, they generate reactive oxygen species, which are thought to be the main contributors to the death of cancer cells. In the presence of visible light, the complexes predominantly elicit an apoptotic mode of cell death. Complex 6 preferentially localizes in the mitochondria of A549 cells. © 2024 The Royal Society of Chemistry.

Item Type:	Journal Article
Publication:	Dalton Transactions
Publisher:	Royal Society of Chemistry
Additional Information:	The copyright for this article belongs toRoyal Society of Chemistry.
Keywords:	Biological organs; Cell culture; Cell death; Computerized tomography; Copper compounds; Crystal structure; Diseases; Flavonoids; Inorganic compounds; Single crystals; Synthesis (chemical), Biochemical properties; Cancer cells; Flavonoid; Health benefits; In-vitro; Phenanthrolines; Square-pyramidal geometry; Synthesised; Visible light; X-ray diffraction structure, Cancer cells
Department/Centre:	Division of Chemical Sciences > Inorganic & Physical Chemistry
Date Deposited:	04 Mar 2024 07:02
Last Modified:	04 Mar 2024 07:02
URI:	https://eprints.iisc.ac.in/id/eprint/84199

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