Insights into Structure and Biological Activity of Copper(II) and Zinc(II) Complexes with Triazolopyrimidine Ligands

Laboratory of Atomic Structures and Defects in Advanced Materials, National Institute of Materials Physics, 405A Atomiştilor Str., 077125 Măgurele-Ilfov, Romania

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National Institute for Research and Development of Isotopic and Molecular Technologies, 67–103 Donat, 400293 Cluj-Napoca, Romania

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Department of Life and Environmental Physics, Horia Hulubei National Institute for Physics and Nuclear Engineering, 30 Reactorului Str., 077125 Măgurele-Ilfov, Romania

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Department of Electricity, Solid State and Biophysics, Faculty of Physics, University of Bucharest, 405A Atomiştilor Str., 077125 Măgurele-Ilfov, Romania

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Department of Organic Chemistry, Biochemistry and Catalysis, Faculty of Chemistry, University of Bucharest, 90–92 Panduri Str., 050663 Bucharest, Romania

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Department of Analytical Chemistry, Faculty of Chemistry, University of Bucharest, 90–92 Panduri Str., 050663 Bucharest, Romania

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Academic Editor: Mauro Ravera

Molecules 2022, 27(3), 765; https://doi.org/10.3390/molecules27030765

Received: 24 December 2021 / Revised: 16 January 2022 / Accepted: 22 January 2022 / Published: 24 January 2022

(This article belongs to the Special Issue New Trends in Developing Complexes as Biological Active Species)

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Abstract

In an attempt to increase the biological activity of the 1,2,4-triazolo[1,5-a]pyrimidine scaffold through complexation with essential metal ions, the complexes trans-[Cu(mptp)₂Cl₂] (1), [Zn(mptp)Cl₂(DMSO)] (2) (mptp: 5-methyl-7-phenyl-1,2,4-triazolo[1,5-a]pyrimidine), [Cu₂(dmtp)₄Cl₄]·2H₂O (3) and [Zn(dmtp)₂Cl₂] (4) (dmtp: 5,7-dimethyl-1,2,4-triazolo[1,5-a]pyrimidine), were synthesized and characterized as new antiproliferative and antimicrobial species. Both complexes (1) and (2) crystallize in the P2₁/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 (1) while supramolecular chains resulting from C-H∙∙∙π interactions were observed in (2). All complexes exhibit an antiproliferative effect against B16 tumor cells and improved antibacterial and antifungal activities compared to the free ligands. Complex (3) 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. View Full-Text

Keywords: complex; 1,2,4-triazolo[1,5-a]pyrimidine; cytotoxicity; biofilm; metallonuclease activity

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MDPI and ACS Style

Argăseală, A.; Maxim, C.; Badea, M.; Ioniță, L.; Chifiriuc, M.C.; Rostas, A.M.; Bacalum, M.; Răileanu, M.; Ruţă, L.L.; Farcaşanu, I.C.; Iorgulescu, E.E.; Olar, R. Insights into Structure and Biological Activity of Copper(II) and Zinc(II) Complexes with Triazolopyrimidine Ligands. Molecules 2022, 27, 765. https://doi.org/10.3390/molecules27030765

AMA Style

Argăseală A, Maxim C, Badea M, Ioniță L, Chifiriuc MC, Rostas AM, Bacalum M, Răileanu M, Ruţă LL, Farcaşanu IC, Iorgulescu EE, Olar R. Insights into Structure and Biological Activity of Copper(II) and Zinc(II) Complexes with Triazolopyrimidine Ligands. Molecules. 2022; 27(3):765. https://doi.org/10.3390/molecules27030765

Chicago/Turabian Style

Argăseală, Aura, 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, and Rodica Olar. 2022. "Insights into Structure and Biological Activity of Copper(II) and Zinc(II) Complexes with Triazolopyrimidine Ligands" Molecules 27, no. 3: 765. https://doi.org/10.3390/molecules27030765

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Insights into Structure and Biological Activity of Copper(II) and Zinc(II) Complexes with Triazolopyrimidine Ligands

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