Insights into Structure and Biological Activity of Copper(II) and Zinc(II) Complexes with Triazolopyrimidine Ligands
In an attempt to increase the biological activity of the 1,2,4-triazolo[1,5-<i>a</i>]pyrimidine scaffold through complexation with essential metal ions, the complexes <i>trans</i>-[Cu(mptp)<sub>2</sub>Cl<sub>2</sub>] (<b>1</b>), [Zn(mptp)Cl...
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| Format: | Article |
| Language: | English |
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MDPI AG
2022-01-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/27/3/765 |
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| author | Aura Argăseală Cătălin Maxim Mihaela Badea Larisa Ioniță Mariana Carmen Chifiriuc Arpad Mihai Rostas Mihaela Bacalum Mina Răileanu Lavinia L. Ruţă Ileana C. Farcaşanu Emilia Elena Iorgulescu Rodica Olar |
| author_facet | Aura Argăseală Cătălin Maxim Mihaela Badea Larisa Ioniță Mariana Carmen Chifiriuc Arpad Mihai Rostas Mihaela Bacalum Mina Răileanu Lavinia L. Ruţă Ileana C. Farcaşanu Emilia Elena Iorgulescu Rodica Olar |
| author_sort | Aura Argăseală |
| collection | DOAJ |
| description | In an attempt to increase the biological activity of the 1,2,4-triazolo[1,5-<i>a</i>]pyrimidine scaffold through complexation with essential metal ions, the complexes <i>trans</i>-[Cu(mptp)<sub>2</sub>Cl<sub>2</sub>] (<b>1</b>), [Zn(mptp)Cl<sub>2</sub>(DMSO)] (<b>2</b>) (mptp: 5-methyl-7-phenyl-1,2,4-triazolo[1,5-<i>a</i>]pyrimidine), [Cu<sub>2</sub>(dmtp)<sub>4</sub>Cl<sub>4</sub>]·2H<sub>2</sub>O (<b>3</b>) and [Zn(dmtp)<sub>2</sub>Cl<sub>2</sub>] (<b>4</b>) (dmtp: 5,7-dimethyl-1,2,4-triazolo[1,5-<i>a</i>]pyrimidine), were synthesized and characterized as new antiproliferative and antimicrobial species. Both complexes (<b>1</b>) and (<b>2</b>) crystallize in the <i>P</i>2<sub>1</sub>/n monoclinic space group, with the tetrahedral surroundings generating a square-planar stereochemistry in the Cu(II) complex and a tetrahedral stereochemistry in the Zn(II) species. The mononuclear units are interconnected in a supramolecular network through π–π interactions between the pyrimidine moiety and the phenyl ring in (<b>1</b>) while supramolecular chains resulting from C-H∙∙∙π interactions were observed in (<b>2</b>). All complexes exhibit an antiproliferative effect against B16 tumor cells and improved antibacterial and antifungal activities compared to the free ligands. Complex (<b>3</b>) displays the best antimicrobial activity against all four tested strains, both in the planktonic and biofilm-embedded states, which can be correlated to its stronger DNA-binding and nuclease-activity traits. |
| first_indexed | 2024-03-09T23:28:59Z |
| format | Article |
| id | doaj.art-219397e786744e42b82f00064c8e5333 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T23:28:59Z |
| publishDate | 2022-01-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-219397e786744e42b82f00064c8e53332023-11-23T17:12:06ZengMDPI AGMolecules1420-30492022-01-0127376510.3390/molecules27030765Insights into Structure and Biological Activity of Copper(II) and Zinc(II) Complexes with Triazolopyrimidine LigandsAura Argăseală0Cătălin Maxim1Mihaela Badea2Larisa Ioniță3Mariana Carmen Chifiriuc4Arpad Mihai Rostas5Mihaela Bacalum6Mina Răileanu7Lavinia L. Ruţă8Ileana C. Farcaşanu9Emilia Elena Iorgulescu10Rodica Olar11Department of Inorganic Chemistry, Faculty of Chemistry, University of Bucharest, 90–92 Panduri Str., 050663 Bucharest, RomaniaDepartment of Inorganic Chemistry, Faculty of Chemistry, University of Bucharest, 90–92 Panduri Str., 050663 Bucharest, RomaniaDepartment of Inorganic Chemistry, Faculty of Chemistry, University of Bucharest, 90–92 Panduri Str., 050663 Bucharest, RomaniaDoping Control Laboratory, 37–39 Basarabia Blvd., 022103 Bucharest, RomaniaDepartment of Microbiology, Faculty of Biology, University of Bucharest, 1–3 Aleea Portocalelor Str., 060101 Bucharest, RomaniaLaboratory of Atomic Structures and Defects in Advanced Materials, National Institute of Materials Physics, 405A Atomiştilor Str., 077125 Măgurele-Ilfov, RomaniaDepartment of Life and Environmental Physics, Horia Hulubei National Institute for Physics and Nuclear Engineering, 30 Reactorului Str., 077125 Măgurele-Ilfov, RomaniaDepartment of Life and Environmental Physics, Horia Hulubei National Institute for Physics and Nuclear Engineering, 30 Reactorului Str., 077125 Măgurele-Ilfov, RomaniaDepartment of Organic Chemistry, Biochemistry and Catalysis, Faculty of Chemistry, University of Bucharest, 90–92 Panduri Str., 050663 Bucharest, RomaniaDepartment of Organic Chemistry, Biochemistry and Catalysis, Faculty of Chemistry, University of Bucharest, 90–92 Panduri Str., 050663 Bucharest, RomaniaDepartment of Analytical Chemistry, Faculty of Chemistry, University of Bucharest, 90–92 Panduri Str., 050663 Bucharest, RomaniaDepartment of Inorganic Chemistry, Faculty of Chemistry, University of Bucharest, 90–92 Panduri Str., 050663 Bucharest, RomaniaIn an attempt to increase the biological activity of the 1,2,4-triazolo[1,5-<i>a</i>]pyrimidine scaffold through complexation with essential metal ions, the complexes <i>trans</i>-[Cu(mptp)<sub>2</sub>Cl<sub>2</sub>] (<b>1</b>), [Zn(mptp)Cl<sub>2</sub>(DMSO)] (<b>2</b>) (mptp: 5-methyl-7-phenyl-1,2,4-triazolo[1,5-<i>a</i>]pyrimidine), [Cu<sub>2</sub>(dmtp)<sub>4</sub>Cl<sub>4</sub>]·2H<sub>2</sub>O (<b>3</b>) and [Zn(dmtp)<sub>2</sub>Cl<sub>2</sub>] (<b>4</b>) (dmtp: 5,7-dimethyl-1,2,4-triazolo[1,5-<i>a</i>]pyrimidine), were synthesized and characterized as new antiproliferative and antimicrobial species. Both complexes (<b>1</b>) and (<b>2</b>) crystallize in the <i>P</i>2<sub>1</sub>/n monoclinic space group, with the tetrahedral surroundings generating a square-planar stereochemistry in the Cu(II) complex and a tetrahedral stereochemistry in the Zn(II) species. The mononuclear units are interconnected in a supramolecular network through π–π interactions between the pyrimidine moiety and the phenyl ring in (<b>1</b>) while supramolecular chains resulting from C-H∙∙∙π interactions were observed in (<b>2</b>). All complexes exhibit an antiproliferative effect against B16 tumor cells and improved antibacterial and antifungal activities compared to the free ligands. Complex (<b>3</b>) displays the best antimicrobial activity against all four tested strains, both in the planktonic and biofilm-embedded states, which can be correlated to its stronger DNA-binding and nuclease-activity traits.https://www.mdpi.com/1420-3049/27/3/765complex1,2,4-triazolo[1,5-<i>a</i>]pyrimidinecytotoxicitybiofilmmetallonuclease activity |
| spellingShingle | Aura Argăseală Cătălin Maxim Mihaela Badea Larisa Ioniță Mariana Carmen Chifiriuc Arpad Mihai Rostas Mihaela Bacalum Mina Răileanu Lavinia L. Ruţă Ileana C. Farcaşanu Emilia Elena Iorgulescu Rodica Olar Insights into Structure and Biological Activity of Copper(II) and Zinc(II) Complexes with Triazolopyrimidine Ligands Molecules complex 1,2,4-triazolo[1,5-<i>a</i>]pyrimidine cytotoxicity biofilm metallonuclease activity |
| title | Insights into Structure and Biological Activity of Copper(II) and Zinc(II) Complexes with Triazolopyrimidine Ligands |
| title_full | Insights into Structure and Biological Activity of Copper(II) and Zinc(II) Complexes with Triazolopyrimidine Ligands |
| title_fullStr | Insights into Structure and Biological Activity of Copper(II) and Zinc(II) Complexes with Triazolopyrimidine Ligands |
| title_full_unstemmed | Insights into Structure and Biological Activity of Copper(II) and Zinc(II) Complexes with Triazolopyrimidine Ligands |
| title_short | Insights into Structure and Biological Activity of Copper(II) and Zinc(II) Complexes with Triazolopyrimidine Ligands |
| title_sort | insights into structure and biological activity of copper ii and zinc ii complexes with triazolopyrimidine ligands |
| topic | complex 1,2,4-triazolo[1,5-<i>a</i>]pyrimidine cytotoxicity biofilm metallonuclease activity |
| url | https://www.mdpi.com/1420-3049/27/3/765 |
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