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Synthesis, Crystallographic Structure, Theoretical Analysis, Molecular Docking Studies, and Biological Activity Evaluation of Binuclear Ru(II)-1-Naphthylhydrazine Complex
Ruthenium(II)–arene complexes have gained significant research interest due to their possible application in cancer therapy. In this contribution two new complexes are described, namely [{RuCl(η(6)-p-cymene)}(2)(μ-Cl)(μ-1-N,N′-naphthyl)]X (X = Cl, 1; PF(6), 2), which were fully characterized by IR,...
Autores principales: | , , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2022
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9821167/ https://www.ncbi.nlm.nih.gov/pubmed/36614131 http://dx.doi.org/10.3390/ijms24010689 |
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author | Eichhorn, Thomas Kolbe, Franz Mišić, Stefan Dimić, Dušan Morgan, Ibrahim Saoud, Mohamad Milenković, Dejan Marković, Zoran Rüffer, Tobias Dimitrić Marković, Jasmina Kaluđerović, Goran N. |
author_facet | Eichhorn, Thomas Kolbe, Franz Mišić, Stefan Dimić, Dušan Morgan, Ibrahim Saoud, Mohamad Milenković, Dejan Marković, Zoran Rüffer, Tobias Dimitrić Marković, Jasmina Kaluđerović, Goran N. |
author_sort | Eichhorn, Thomas |
collection | PubMed |
description | Ruthenium(II)–arene complexes have gained significant research interest due to their possible application in cancer therapy. In this contribution two new complexes are described, namely [{RuCl(η(6)-p-cymene)}(2)(μ-Cl)(μ-1-N,N′-naphthyl)]X (X = Cl, 1; PF(6), 2), which were fully characterized by IR, NMR, and elemental microanalysis. Furthermore, the structure of 2 in the solid state was determined by a single crystal X-ray crystallographic study, confirming the composition of the crystals as 2·2MeOH. The Hirshfeld surface analysis was employed for the investigation of interactions that govern the crystal structure of 2·2MeOH. The structural data for 2 out of 2·2MeOH was used for the theoretical analysis of the cationic part [{RuCl(η(6)-p-cymene)}(2)(μ-Cl)(μ-1-N,N′-naphthyl)](+) (2a) which is common to both 1 and 2. The density functional theory, at B3LYP/6-31+G(d,p) basis set for H, C, N, and Cl atoms and LanL2DZ for Ru ions, was used for the optimization of the 2a structure. The natural bond orbital and quantum theory of atoms in molecules analyses were employed to quantify the intramolecular interactions. The reproduction of experimental IR and NMR spectra proved the applicability of the chosen level of theory. The binding of 1 to bovine serum albumin was examined by spectrofluorimetry and molecular docking, with complementary results obtained. Compound 1 acted as a radical scavenger towards DPPH(•) and HO(•) radicals, along with high activity towards cancer prostate and colon cell lines. |
format | Online Article Text |
id | pubmed-9821167 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-98211672023-01-07 Synthesis, Crystallographic Structure, Theoretical Analysis, Molecular Docking Studies, and Biological Activity Evaluation of Binuclear Ru(II)-1-Naphthylhydrazine Complex Eichhorn, Thomas Kolbe, Franz Mišić, Stefan Dimić, Dušan Morgan, Ibrahim Saoud, Mohamad Milenković, Dejan Marković, Zoran Rüffer, Tobias Dimitrić Marković, Jasmina Kaluđerović, Goran N. Int J Mol Sci Article Ruthenium(II)–arene complexes have gained significant research interest due to their possible application in cancer therapy. In this contribution two new complexes are described, namely [{RuCl(η(6)-p-cymene)}(2)(μ-Cl)(μ-1-N,N′-naphthyl)]X (X = Cl, 1; PF(6), 2), which were fully characterized by IR, NMR, and elemental microanalysis. Furthermore, the structure of 2 in the solid state was determined by a single crystal X-ray crystallographic study, confirming the composition of the crystals as 2·2MeOH. The Hirshfeld surface analysis was employed for the investigation of interactions that govern the crystal structure of 2·2MeOH. The structural data for 2 out of 2·2MeOH was used for the theoretical analysis of the cationic part [{RuCl(η(6)-p-cymene)}(2)(μ-Cl)(μ-1-N,N′-naphthyl)](+) (2a) which is common to both 1 and 2. The density functional theory, at B3LYP/6-31+G(d,p) basis set for H, C, N, and Cl atoms and LanL2DZ for Ru ions, was used for the optimization of the 2a structure. The natural bond orbital and quantum theory of atoms in molecules analyses were employed to quantify the intramolecular interactions. The reproduction of experimental IR and NMR spectra proved the applicability of the chosen level of theory. The binding of 1 to bovine serum albumin was examined by spectrofluorimetry and molecular docking, with complementary results obtained. Compound 1 acted as a radical scavenger towards DPPH(•) and HO(•) radicals, along with high activity towards cancer prostate and colon cell lines. MDPI 2022-12-30 /pmc/articles/PMC9821167/ /pubmed/36614131 http://dx.doi.org/10.3390/ijms24010689 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Eichhorn, Thomas Kolbe, Franz Mišić, Stefan Dimić, Dušan Morgan, Ibrahim Saoud, Mohamad Milenković, Dejan Marković, Zoran Rüffer, Tobias Dimitrić Marković, Jasmina Kaluđerović, Goran N. Synthesis, Crystallographic Structure, Theoretical Analysis, Molecular Docking Studies, and Biological Activity Evaluation of Binuclear Ru(II)-1-Naphthylhydrazine Complex |
title | Synthesis, Crystallographic Structure, Theoretical Analysis, Molecular Docking Studies, and Biological Activity Evaluation of Binuclear Ru(II)-1-Naphthylhydrazine Complex |
title_full | Synthesis, Crystallographic Structure, Theoretical Analysis, Molecular Docking Studies, and Biological Activity Evaluation of Binuclear Ru(II)-1-Naphthylhydrazine Complex |
title_fullStr | Synthesis, Crystallographic Structure, Theoretical Analysis, Molecular Docking Studies, and Biological Activity Evaluation of Binuclear Ru(II)-1-Naphthylhydrazine Complex |
title_full_unstemmed | Synthesis, Crystallographic Structure, Theoretical Analysis, Molecular Docking Studies, and Biological Activity Evaluation of Binuclear Ru(II)-1-Naphthylhydrazine Complex |
title_short | Synthesis, Crystallographic Structure, Theoretical Analysis, Molecular Docking Studies, and Biological Activity Evaluation of Binuclear Ru(II)-1-Naphthylhydrazine Complex |
title_sort | synthesis, crystallographic structure, theoretical analysis, molecular docking studies, and biological activity evaluation of binuclear ru(ii)-1-naphthylhydrazine complex |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9821167/ https://www.ncbi.nlm.nih.gov/pubmed/36614131 http://dx.doi.org/10.3390/ijms24010689 |
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