1,10-Phenanthroline and 4,5-Diazafluorene Ketones and Their Silver(I) and Platinum(II) Complexes: Syntheses and Biological Evaluation as Antiproliferative Agents

1,10-Phenanthroline and 4,5-Diazafluorene Ketones and Their Silver(I) and Platinum(II) Complexes: Syntheses and Biological Evaluation as Antiproliferative Agents

Using non-classical polyfluorophenyl ligands in Pt(II) complexes and other transition metals such as silver is a promising approach in the search for more effective and safer antitumoral drugs. In this work, a series of chelating <i>N</i>-donor ligands with 1,10-phenanthroline and 4,5-di...

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Bibliographic Details
Main Authors: Leonardo Sandin-Mazzondo, Jesús M. Martínez-Ilarduya, Jesús A. Miguel, Camino Bartolomé, Concepción Alonso
Format: Article
Language:English
Published: MDPI AG 2024-12-01
Series:Inorganics
Subjects:
antiproliferative
cytotoxicity
phenanthroline
4,5-diazafluorene
platinum complexes
silver complexes
Online Access:https://www.mdpi.com/2304-6740/13/1/6
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Summary:Using non-classical polyfluorophenyl ligands in Pt(II) complexes and other transition metals such as silver is a promising approach in the search for more effective and safer antitumoral drugs. In this work, a series of chelating <i>N</i>-donor ligands with 1,10-phenanthroline and 4,5-diazafluorene backbones and ketone groups were synthesized (1,10-phenanthroline-5,6-dione, <b>1</b>; (R/S)-6-hydroxy-6-(2-oxypropyl)-1,10-phenanthroline-5(6<i>H</i>)-one, <b>2</b>; 4,5-diazafluoren-9-one, <b>3</b>; 9-hydroxy-9-(2-oxypropyl)-4,5-diazafluorene, <b>4</b>). The corresponding [Ag(N,N)<sub>2</sub>]NO<sub>3</sub> (<b>1Ag</b>–<b>4Ag</b>) and [Pt(C<sub>6</sub>F<sub>5</sub>)<sub>2</sub>(N,N)] (<b>1Pt</b>–<b>4Pt</b>) complexes were prepared. The stability of these complexes in DMSO solution was studied, showing no dissociation over 48 h for almost all complexes, except <b>3Pt</b>. The compounds were characterized by NMR (<sup>1</sup>H, <sup>13</sup>C, and <sup>19</sup>F), MS, and X-ray diffraction (<b>2</b>, <b>4</b>, <b>1Ag</b>, <b>3Ag</b>, <b>1Pt</b>, and <b>3Pt</b>). A study of the cytotoxicity of the compounds in lung carcinoma (A-549) and fetal lung fibroblast (MRC-5) cell lines was performed. Compounds <b>1</b>, <b>2</b>, <b>1Ag</b>, <b>2Ag</b>, <b>3Ag</b>, <b>1Pt</b>, <b>3Pt</b>, and <b>4Pt</b> were more active against A-549 cells than cisplatin. Complexes <b>3Ag</b> and <b>1Pt</b> showed an acceptable SI and better selectivity than cisplatin, proving that silver(I) complexes and Pt(polyfluorophenyl) complexes are valuable options in searching for new antitumoral drugs.
ISSN:2304-6740

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