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...
Saved in:
| Main Authors: | , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2024-12-01
|
| Series: | Inorganics |
| Subjects: | |
| Online Access: | https://www.mdpi.com/2304-6740/13/1/6 |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| _version_ | 1832588336046276608 |
|---|---|
| author | Leonardo Sandin-Mazzondo Jesús M. Martínez-Ilarduya Jesús A. Miguel Camino Bartolomé Concepción Alonso |
| author_facet | Leonardo Sandin-Mazzondo Jesús M. Martínez-Ilarduya Jesús A. Miguel Camino Bartolomé Concepción Alonso |
| author_sort | Leonardo Sandin-Mazzondo |
| collection | DOAJ |
| description | 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. |
| format | Article |
| id | doaj-art-39f31d4b784c4b1c8205a378b2733b5c |
| institution | Kabale University |
| issn | 2304-6740 |
| language | English |
| publishDate | 2024-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Inorganics |
| spelling | doaj-art-39f31d4b784c4b1c8205a378b2733b5c2025-01-24T13:35:27ZengMDPI AGInorganics2304-67402024-12-01131610.3390/inorganics130100061,10-Phenanthroline and 4,5-Diazafluorene Ketones and Their Silver(I) and Platinum(II) Complexes: Syntheses and Biological Evaluation as Antiproliferative AgentsLeonardo Sandin-Mazzondo0Jesús M. Martínez-Ilarduya1Jesús A. Miguel2Camino Bartolomé3Concepción Alonso4IU CINQUIMA/Química Inorgánica, Facultad de Ciencias, Universidad de Valladolid, 47071 Valladolid, SpainIU CINQUIMA/Química Inorgánica, Facultad de Ciencias, Universidad de Valladolid, 47071 Valladolid, SpainIU CINQUIMA/Química Inorgánica, Facultad de Ciencias, Universidad de Valladolid, 47071 Valladolid, SpainIU CINQUIMA/Química Inorgánica, Facultad de Ciencias, Universidad de Valladolid, 47071 Valladolid, SpainDepartamento de Química Orgánica I, Facultad de Farmacia, Universidad del País Vasco, 01006 Vitoria-Gasteiz, SpainUsing 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.https://www.mdpi.com/2304-6740/13/1/6antiproliferativecytotoxicityphenanthroline4,5-diazafluoreneplatinum complexessilver complexes |
| spellingShingle | Leonardo Sandin-Mazzondo Jesús M. Martínez-Ilarduya Jesús A. Miguel Camino Bartolomé Concepción Alonso 1,10-Phenanthroline and 4,5-Diazafluorene Ketones and Their Silver(I) and Platinum(II) Complexes: Syntheses and Biological Evaluation as Antiproliferative Agents Inorganics antiproliferative cytotoxicity phenanthroline 4,5-diazafluorene platinum complexes silver complexes |
| title | 1,10-Phenanthroline and 4,5-Diazafluorene Ketones and Their Silver(I) and Platinum(II) Complexes: Syntheses and Biological Evaluation as Antiproliferative Agents |
| title_full | 1,10-Phenanthroline and 4,5-Diazafluorene Ketones and Their Silver(I) and Platinum(II) Complexes: Syntheses and Biological Evaluation as Antiproliferative Agents |
| title_fullStr | 1,10-Phenanthroline and 4,5-Diazafluorene Ketones and Their Silver(I) and Platinum(II) Complexes: Syntheses and Biological Evaluation as Antiproliferative Agents |
| title_full_unstemmed | 1,10-Phenanthroline and 4,5-Diazafluorene Ketones and Their Silver(I) and Platinum(II) Complexes: Syntheses and Biological Evaluation as Antiproliferative Agents |
| title_short | 1,10-Phenanthroline and 4,5-Diazafluorene Ketones and Their Silver(I) and Platinum(II) Complexes: Syntheses and Biological Evaluation as Antiproliferative Agents |
| title_sort | 1 10 phenanthroline and 4 5 diazafluorene ketones and their silver i and platinum ii complexes syntheses and biological evaluation as antiproliferative agents |
| topic | antiproliferative cytotoxicity phenanthroline 4,5-diazafluorene platinum complexes silver complexes |
| url | https://www.mdpi.com/2304-6740/13/1/6 |
| work_keys_str_mv | AT leonardosandinmazzondo 110phenanthrolineand45diazafluoreneketonesandtheirsilveriandplatinumiicomplexessynthesesandbiologicalevaluationasantiproliferativeagents AT jesusmmartinezilarduya 110phenanthrolineand45diazafluoreneketonesandtheirsilveriandplatinumiicomplexessynthesesandbiologicalevaluationasantiproliferativeagents AT jesusamiguel 110phenanthrolineand45diazafluoreneketonesandtheirsilveriandplatinumiicomplexessynthesesandbiologicalevaluationasantiproliferativeagents AT caminobartolome 110phenanthrolineand45diazafluoreneketonesandtheirsilveriandplatinumiicomplexessynthesesandbiologicalevaluationasantiproliferativeagents AT concepcionalonso 110phenanthrolineand45diazafluoreneketonesandtheirsilveriandplatinumiicomplexessynthesesandbiologicalevaluationasantiproliferativeagents |