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Synthesis and characterization of the new ligand, 1,2,4-triazino[5,6-b]indol-3-ylimino methyl naphthalene-2-ol and its Ni(II) and Cu(II) complexes: comparative studies of their in vitro DNA and HSA Binding

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Abstract

A new ligand 1,2,4-triazino[5,6-b]indol-3-ylimino methyl naphthalene-2-ol (HL) was derived from 5H-[1,2,4]triazino[5,6-b]indol-3-amine and 2-hydroxy-1-naphthaldehyde. The metal complexes of the type [Ni(L)(Bipy)]1/2SO4 (1), [Cu(L)(Bipy)(H2O)2]1/2SO4 (2), [Ni(L)(Phen)]1/2SO4 (3) and [Cu(L)(Phen)(H2O)2]1/2SO4 (4) were synthesized. The ligand (HL) and complexes 14 were thoroughly characterized by elemental analysis and spectroscopic methods (FT-IR, ToF-MS, 1H NMR, 13C NMR), molar conductance and magnetic moment determination. The Ni(II) complexes 1 and 3 adopt the square planar geometry and Cu(II) complexes 2 and 4 acquire distorted octahedral arrangement. In vitro DNA binding behavior of ligand (HL) and metal complexes 14 was explored by fluorescence spectral and ethidium bromide studies. The outcomes reveal that the complexes interact with DNA via non-covalent groove binding and electrostatic interactions. The higher binding constant (K) values of 4.35 × 104 and 9.12 × 104 M−1 for complexes 2 and 4 indicate stronger binding ability with DNA. Moreover, in vitro human serum albumin (HSA) binding experiment with HL and complexes 14 reveals conformational modulations in the Trp-214 microenvironments in the subdomain IIA pocket.

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Acknowledgements

Dr. Mehvash Zaki and Dr. Wafa A. Bawazir acknowledge with thanks King Abdulaziz University and King Fahad Medical Research Center for technically supporting this work. The author Reem Alanazi is grateful to Hafr Al-Batin University for its financial support. The authors are highly thankful to Dr. Mohd Afzal, King Saud University, Saudi Arabia for his valuable suggestions during the whole process of this manuscript. The authors are also highly grateful to potential reviewers for their valuable suggestions and consistently guiding us throughout the revision process.

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RLBA: Data curation, Investigation. MZ: Conceptualization, Methodology, Validation, Visualization, Formal analysis, Supervision, Writing—Original draft preparation, Writing—Reviewing and Editing. WAB: Methodology, Resources, Project administration.

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Correspondence to Mehvash Zaki.

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Alanazi, R.L.B., Zaki, M. & Bawazir, W.A. Synthesis and characterization of the new ligand, 1,2,4-triazino[5,6-b]indol-3-ylimino methyl naphthalene-2-ol and its Ni(II) and Cu(II) complexes: comparative studies of their in vitro DNA and HSA Binding. Biometals 35, 1199–1223 (2022). https://doi.org/10.1007/s10534-022-00437-x

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  • DOI: https://doi.org/10.1007/s10534-022-00437-x

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