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New selenonapthaquinone-based copper (II) complexes as the next-generation photochemotherapeutic agents

Devi, LR and Raza, MK and Musib, D and Roy, M (2020) New selenonapthaquinone-based copper (II) complexes as the next-generation photochemotherapeutic agents. In: Anti-Cancer Agents in Medicinal Chemistry, 21 (1). pp. 33-41.

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Official URL: https://doi.org/10.2174/1871520620999200727204237


Background and Objective: Photoactive transition metal complexes like copper complexes find great interest in promoting metal-based photochemotherapeutic agents. In the present study, we explored the photocy-totoxic efficacy of new selenylnaphthoquinone-based copper (II) complexes that provide a phenomenal platform in making an effective photo-chemotherapeutic agent via PDT in the clinical field of cancer therapy. Methods: Three new copper(II) complexes (1-3) were synthesized in 40-60% yield and characterized analyti-cally/spectroscopically. ATCC® Normal Adult Human Primary Epidermal Keratinocytes were grown in Dermal Cell Basal Media supplemented with Keratinocyte Growth Kit components, to propagate keratinocytes in se-rum-free (not animal free) conditions. Anticancer activity of the complexes was studied using MTT (3-[4,5-dimethyltiazol-2-yl]-2,5-diphenyl-tetrazolium bromide) assay. The intracellular ROS (1O2) generation was studied by using Flow Cytometric Analysis (FACS) on HaCaT cells using cell accessible non-polar 2′,7′-Dichlorofluorescein Diacetate (DCFH-DA) dye. The Acridine Orange/Ethidium Bromide (AO/EB) dual staining assay was performed for detecting apoptosis in HaCaT cells. Several photophysical studies probing the generation of singlet oxygen was also carried out. We have performed Time-Dependent Density Functional Theory (TD-DFT) calculations using unrestricted B3LYP to understand the mechanism of type-II process. Results: All the complexes were remarkably cytotoxic in HaCaT cells with IC50, 1-4µM under visible light with comparing lower dark toxicity. The presence of low-lying and long-lived triplet excited state allowed effective intersystem crossing and subsequent generation of singlet oxygen, which was the primary cytotoxic species responsible for oxidative stress and apoptosis. The experimental findings are in good agrrement with the compu-tational analysis (TD-DFT). Conclusion: The remarkably enhanced cytotoxicity of the new selenyl copper (II) complexes under the visible light probed the role of Se in photosensitized generation of singlet oxygen which was responsible for apoptosis in HaCaT cells. The results in the present work are of paramount importance in developing next generation copper(II)-based PDT agents. © 2021 Bentham Science Publishers.

Item Type: Journal Article
Publication: Anti-Cancer Agents in Medicinal Chemistry
Publisher: Bentham Science Publishers
Additional Information: The copyright for this article belongs to Bentham Science Publishers.
Keywords: 2, 3 dichloro 1, 4 napthoquinone; 2,3 bis (methylselenyl)naphthoquinone; arginine; copper complex; dichlorofluorescein; dichlorofluorescein diacetate; ethidium bromide; hydrazine; naphthoquinone; phenanthroline; potassium bromide; potassium hydroxide; propidium iodide; quinone derivative; selenonapthaquinone; unclassified drug; antineoplastic agent; coordination compound; copper; naphthoquinone; photosensitizing agent; reactive oxygen metabolite; selenium derivative, antineoplastic activity; apoptosis; Article; bioassay; cancer therapy; cytotoxicity; density functional theory; drug solubility; drug stability; electrospray mass spectrometry; elemental analysis; flow cytometry; Fourier transform infrared spectroscopy; HaCat cell line; IC50; keratinocyte; MTT assay; oxidative stress; photochemotherapy; photocytotoxicity; skin cell; spectroscopy; time of flight mass spectrometry; chemistry; drug effect; human; metabolism; photochemotherapy; procedures, Antineoplastic Agents; Apoptosis; Coordination Complexes; Copper; Density Functional Theory; HaCaT Cells; Humans; Naphthoquinones; Oxidative Stress; Photochemotherapy; Photosensitizing Agents; Reactive Oxygen Species; Selenium Compounds
Department/Centre: Division of Chemical Sciences > Inorganic & Physical Chemistry
Date Deposited: 07 Feb 2023 10:45
Last Modified: 07 Feb 2023 10:45
URI: https://eprints.iisc.ac.in/id/eprint/80010

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