New Derivatives of 5-((1-Methyl-Pyrrol-2-yl) Methyl)-4-(Naphthalen-1-yl)-1,2,4-Triazoline-3-Thione and Its Coordination Compounds with Anticancer Activity
A new ligand 5-((1-methyl-pyrrol-2-yl) methyl)-4-(naphthalen-1-yl)-1,2,4-triazoline-3-thione (C15) and its metal complexes with formulae: Mn(C15)Cl<sub>2</sub>MeOH (<b>1</b>), Fe(C15)Cl<sub>2</sub>MeOH (<b>2</b>), Ni(C15)Cl<sub>2</sub>MeOH...
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| Format: | Article |
| Language: | English |
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MDPI AG
2022-08-01
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| Series: | International Journal of Molecular Sciences |
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| Online Access: | https://www.mdpi.com/1422-0067/23/16/9162 |
| _version_ | 1797409792541589504 |
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| author | Agnieszka Czylkowska Suneel Lanka Małgorzata Szczesio Kamila Czarnecka Paweł Szymański Monika Pitucha Aneta Drabińska Bruno Cury Camargo Jacek Szczytko |
| author_facet | Agnieszka Czylkowska Suneel Lanka Małgorzata Szczesio Kamila Czarnecka Paweł Szymański Monika Pitucha Aneta Drabińska Bruno Cury Camargo Jacek Szczytko |
| author_sort | Agnieszka Czylkowska |
| collection | DOAJ |
| description | A new ligand 5-((1-methyl-pyrrol-2-yl) methyl)-4-(naphthalen-1-yl)-1,2,4-triazoline-3-thione (C15) and its metal complexes with formulae: Mn(C15)Cl<sub>2</sub>MeOH (<b>1</b>), Fe(C15)Cl<sub>2</sub>MeOH (<b>2</b>), Ni(C15)Cl<sub>2</sub>MeOH (<b>3</b>), Cu(C15)<sub>2</sub>Cl<sub>2</sub> (<b>4</b>) and Zn(C15)<sub>4</sub>Cl<sub>2</sub> (<b>5</b>) have been synthesized. The C15 ligand and complexes were characterized by NMR, elemental analysis, FT-IR, EPR, magnetic and TGA studies. The anticancer activities of the organic ligand (C15) and complexes (<b>1</b>–<b>5</b>) were evaluated against human colon adenocarcinoma (HT29) and human lung (A549) cancer cell lines. The complex (<b>1</b>) exhibited potential activity at concentration of 794.37 μM (A549) and 654.31 μM (HT29) in both cancer cells. The complex (<b>3</b>) showed significant activity against the HT29 cancer cell line with an IC<sub>50</sub> value of 1064.05 μM. This article highlights some of the metals that have become important in the development of new coordination complexes and the treatment of cancer. Additionally, for C15, the toxicity was predicted by ADMET analysis and molecular docking. |
| first_indexed | 2024-03-09T04:19:51Z |
| format | Article |
| id | doaj.art-222efc68c88249fa92e6f6212e953ee2 |
| institution | Directory Open Access Journal |
| issn | 1661-6596 1422-0067 |
| language | English |
| last_indexed | 2024-03-09T04:19:51Z |
| publishDate | 2022-08-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | International Journal of Molecular Sciences |
| spelling | doaj.art-222efc68c88249fa92e6f6212e953ee22023-12-03T13:48:45ZengMDPI AGInternational Journal of Molecular Sciences1661-65961422-00672022-08-012316916210.3390/ijms23169162New Derivatives of 5-((1-Methyl-Pyrrol-2-yl) Methyl)-4-(Naphthalen-1-yl)-1,2,4-Triazoline-3-Thione and Its Coordination Compounds with Anticancer ActivityAgnieszka Czylkowska0Suneel Lanka1Małgorzata Szczesio2Kamila Czarnecka3Paweł Szymański4Monika Pitucha5Aneta Drabińska6Bruno Cury Camargo7Jacek Szczytko8Institute of General and Ecological Chemistry, Faculty of Chemistry, Lodz University of Technology, Zeromskiego 116, 90-924 Lodz, PolandInstitute of General and Ecological Chemistry, Faculty of Chemistry, Lodz University of Technology, Zeromskiego 116, 90-924 Lodz, PolandInstitute of General and Ecological Chemistry, Faculty of Chemistry, Lodz University of Technology, Zeromskiego 116, 90-924 Lodz, PolandDepartment of Pharmaceutical Chemistry, Drug Analyses and Radiopharmacy, Faculty of Pharmacy, Medical University of Lodz, Muszynskiego 1, 90-151 Lodz, PolandDepartment of Pharmaceutical Chemistry, Drug Analyses and Radiopharmacy, Faculty of Pharmacy, Medical University of Lodz, Muszynskiego 1, 90-151 Lodz, PolandIndependent Radiopharmacy Unit, Faculty of Pharmacy, Medical University of Lublin, Chodzki 4A, 20-093 Lublin, PolandFaculty of Physics, University of Warsaw, Pasteura 5, 02-093 Warszawa, PolandInstitute of Experimental Physics, Faculty of Physics, University of Warsaw, Pasteura 5, 02-093 Warszawa, PolandInstitute of Experimental Physics, Faculty of Physics, University of Warsaw, Pasteura 5, 02-093 Warszawa, PolandA new ligand 5-((1-methyl-pyrrol-2-yl) methyl)-4-(naphthalen-1-yl)-1,2,4-triazoline-3-thione (C15) and its metal complexes with formulae: Mn(C15)Cl<sub>2</sub>MeOH (<b>1</b>), Fe(C15)Cl<sub>2</sub>MeOH (<b>2</b>), Ni(C15)Cl<sub>2</sub>MeOH (<b>3</b>), Cu(C15)<sub>2</sub>Cl<sub>2</sub> (<b>4</b>) and Zn(C15)<sub>4</sub>Cl<sub>2</sub> (<b>5</b>) have been synthesized. The C15 ligand and complexes were characterized by NMR, elemental analysis, FT-IR, EPR, magnetic and TGA studies. The anticancer activities of the organic ligand (C15) and complexes (<b>1</b>–<b>5</b>) were evaluated against human colon adenocarcinoma (HT29) and human lung (A549) cancer cell lines. The complex (<b>1</b>) exhibited potential activity at concentration of 794.37 μM (A549) and 654.31 μM (HT29) in both cancer cells. The complex (<b>3</b>) showed significant activity against the HT29 cancer cell line with an IC<sub>50</sub> value of 1064.05 μM. This article highlights some of the metals that have become important in the development of new coordination complexes and the treatment of cancer. Additionally, for C15, the toxicity was predicted by ADMET analysis and molecular docking.https://www.mdpi.com/1422-0067/23/16/9162coordination compoundsanticancer activitiesADMETmolecular docking |
| spellingShingle | Agnieszka Czylkowska Suneel Lanka Małgorzata Szczesio Kamila Czarnecka Paweł Szymański Monika Pitucha Aneta Drabińska Bruno Cury Camargo Jacek Szczytko New Derivatives of 5-((1-Methyl-Pyrrol-2-yl) Methyl)-4-(Naphthalen-1-yl)-1,2,4-Triazoline-3-Thione and Its Coordination Compounds with Anticancer Activity International Journal of Molecular Sciences coordination compounds anticancer activities ADMET molecular docking |
| title | New Derivatives of 5-((1-Methyl-Pyrrol-2-yl) Methyl)-4-(Naphthalen-1-yl)-1,2,4-Triazoline-3-Thione and Its Coordination Compounds with Anticancer Activity |
| title_full | New Derivatives of 5-((1-Methyl-Pyrrol-2-yl) Methyl)-4-(Naphthalen-1-yl)-1,2,4-Triazoline-3-Thione and Its Coordination Compounds with Anticancer Activity |
| title_fullStr | New Derivatives of 5-((1-Methyl-Pyrrol-2-yl) Methyl)-4-(Naphthalen-1-yl)-1,2,4-Triazoline-3-Thione and Its Coordination Compounds with Anticancer Activity |
| title_full_unstemmed | New Derivatives of 5-((1-Methyl-Pyrrol-2-yl) Methyl)-4-(Naphthalen-1-yl)-1,2,4-Triazoline-3-Thione and Its Coordination Compounds with Anticancer Activity |
| title_short | New Derivatives of 5-((1-Methyl-Pyrrol-2-yl) Methyl)-4-(Naphthalen-1-yl)-1,2,4-Triazoline-3-Thione and Its Coordination Compounds with Anticancer Activity |
| title_sort | new derivatives of 5 1 methyl pyrrol 2 yl methyl 4 naphthalen 1 yl 1 2 4 triazoline 3 thione and its coordination compounds with anticancer activity |
| topic | coordination compounds anticancer activities ADMET molecular docking |
| url | https://www.mdpi.com/1422-0067/23/16/9162 |
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