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Synthesis, characterization, in silico and in vitro biological activity studies of Ru(II) (η6-p-cymene) complexes with novel N-dibenzosuberene substituted aroyl selenourea exhibiting Se type coordination

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Abstract

A series of N-dibenzosuberene substituted aroyl selenourea ligands L1–L3 and their Ru(II) (η6-p-cymene) complexes 1–3, [Ru(II) (η6-p-cymene) L] (L = monodentate aroyl selenourea ligand) were synthesized and characterized. The molecular structures of the ligand L3 and complex 3 were confirmed by single-crystal XRD method. The single-crystal XRD study results revealed that aroyl selenourea ligand coordinates with ruthenium via Se neutral monodentate atom. In vitro DNA interaction studies were investigated by UV–Visible and fluorescence spectroscopic methods which showed that the intercalative mode of binding is in the order of 3 > 2 > 1 with the Ru(II) (η6-p-cymene) complexes. The binding affinity of the bovine serum albumin with complexes was calculated using spectroscopic methods. Quantum chemical computations were made using DFT (density functional theory), BL3YP; LANL2DZ basis set in order to determine the frontier molecular orbital parameters and MESP for the newly synthesized complexes. The complexes 1–3 have shown intensive cytotoxicity against the cancer lines HepG-2 and A549 under in vitro conditions. Complex 3 (IC50 = 62 μM) has shown significant cytotoxic activity against HepG-2 compared to cisplatin standard drug. The complexes also examined for their antimicrobial activity. The complex 2 exhibited good activity against B. subtilis (MIC: 13.60 μg/mL), E. coli (MIC: 8.01 μg/mL) and A. flavus (MIC = 15.60 μg/mL), respectively, compared to reference drugs Streptomycin and Ketoconazole.

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Acknowledgements

The author Moideen Musthafa is thankful to MHRD, Govt. of India for providing Senior Research Fellowship and Ramaiah Konakanchi, and thanks are due to the Malla Reddy Engineering College for Women (Autonomous Institution), Hyderabad, India, for support and encouragement during this research work.

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Authors and Affiliations

  1. Department of Chemistry, National Institute of Technology, Tiruchirappalli, 620015, India

    Moideen Musthafa & Anandaram Sreekanth

  2. Chemistry Division, H&S Department, Malla Reddy Engineering College for Women (Autonomous Institution), Hyderabad, 500014, India

    Ramaiah Konakanchi

  3. Division of Chemistry and Biological Chemistry, Nanyang Technological University, Singapore, 639798, Singapore

    Rakesh Ganguly

  4. Division of Ethnopharmacology, Entomology Research Institute, Loyola College (University of Madras), Chennai, Tamil Nadu, 600034, India

    Perumal Pandikumar

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  1. Moideen Musthafa
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Musthafa, M., Konakanchi, R., Ganguly, R. et al. Synthesis, characterization, in silico and in vitro biological activity studies of Ru(II) (η6-p-cymene) complexes with novel N-dibenzosuberene substituted aroyl selenourea exhibiting Se type coordination. Res Chem Intermed 46, 3853–3877 (2020). https://doi.org/10.1007/s11164-020-04177-w

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