Thermal behaviour of some biological active perchlorate complexes with a triazolopyrimidine derivative

Badea, Mihaela; Calu, Larisa; Korošin, Nataša Čelan; David, Iulia Gabriela; Chifiriuc, Mariana Carmen; Bleoţu, Coralia; Ioniţă, Gabriela; Silvestro, Luigi; Maurer, Martin; Olar, Rodica

doi:10.1007/s10973-018-7134-x

Cited by 7 publications

(13 citation statements)

References 34 publications

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“…In the complexes’ spectra, the band associated with the triazolopyrimidine core (1603 and 1605 cm −1 ) is shifted to lower wavenumbers in comparison with the free ligand (1612 cm −1 ). This behavior was also observed for other complexes with pmtp coordinated through N 3 from triazole ring [ 28 , 29 , 30 ]. The characteristic bands for overlapping ν(C=N) and ν(C=C) stretching vibrations of N-N-chelating heterocycle ring appear in the 1625–1635 cm −1 range.…”

Section: Resultssupporting

confidence: 72%

“…The chemicals for synthesis of the complexes were purchased from Sigma-Aldrich (Darmstadt, Germany) (copper(II) perchlorate hexahydrate (≥99.99% trace metals basis), 2,2′-bipyridine (bpy, 99%), 1,10-phenanthroline (phen, 99%), 1-phenyl-1,3-butanedione (99%) and 3-amino-4H-1,2,4-triazole (96%)) and Merck (Darmstadt, Germany) (dibenzo-18-crown-6-ether, potassium superoxide) as reagent grade and were used as received, without further purification. The 5-phenyl-7-methyl-1,2,4-triazolo[1,5- a ]pyrimidine (pmtp) was synthesized by a method reported in the literature [ 30 ].…”

Section: Methodsmentioning

confidence: 99%

“…Single-crystal X-ray diffraction evidenced its ability to establish both hydrogen and π-π stacking interactions [ 27 ]. Moreover, for Cu(II) complexes with this ligand a good antimicrobial activity was evidenced for chloride [ 28 ], acetate [ 29 ] and perchlorate [ 30 ] species on a wide range of pathogenic strains, both in planktonic and biofilm growth state. Furthermore, the [Cu(pmtp)(CH 3 COO) 2 ]·0.5H 2 O complex exhibits a dose-dependent antiproliferative effect on human colon adenocarcinoma (HT 29) cell and an anti-inflammatory effect similar with diclofenac [ 29 ].…”

Section: Introductionmentioning

confidence: 99%

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Copper(II) Complexes with Mixed Heterocycle Ligands as Promising Antibacterial and Antitumor Species

et al. 2020

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Complexes with mixed ligands [Cu(N-N)2(pmtp)](ClO4)2 ((1) N-N: 2,2′-bipyridine; (2) L: 1,10-phenanthroline and pmpt: 5-phenyl-7-methyl-1,2,4-triazolo[1,5-a]pyrimidine) were synthesized and structurally and biologically characterized. Compound (1) crystallizes into space group Pa and (2) in P-1. Both complexes display an intermediate stereochemistry between the two five-coordinated ones. The biological tests indicated that the two compounds exhibited superoxide scavenging capacity, intercalative DNA properties, and metallonuclease activity. Tests on various cell systems indicated that the two complexes neither interfere with the proliferation of Saccharomyces cerevisiae or BJ healthy skin cells, nor cause hemolysis in the active concentration range. Nevertheless, the compounds showed antibacterial potential, with complex (2) being significantly more active than complex (1) against all tested bacterial strains, both in planktonic and biofilm growth state. Both complexes exhibited a very good activity against B16 melanoma cells, with a higher specificity being displayed by compound (1). Taken together, the results indicate that complexes (1) and (2) have specific biological relevance, with potential for the development of antitumor or antimicrobial drugs.

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Section: Resultssupporting

confidence: 72%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Copper(II) Complexes with Mixed Heterocycle Ligands as Promising Antibacterial and Antitumor Species

et al. 2020

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“…A broad spectrum of antimicrobial activity was demonstrated by [Cu 2 (pmtp) 2 Cl 4 (OH 2 ) 2 ] [26], [Cu(pmtp)(CH 3 COO) 2 ]0.5H 2 O [27] and [Cu(pmtp)(OH 2 ) 3 ](ClO 4 )3H 2 O (pmtp: 5-phenyl-7methyl-1,2,4-triazolo [1,5-a]pyrimidine) [28] against both planktonic and biofilm-embedded strains. It is worth mentioning the activity of all complexes against methicillin-resistant S. aureus (MRSA).…”

Section: Introductionmentioning

confidence: 99%

Biological Activity of Triazolopyrimidine Copper(II) Complexes Modulated by an Auxiliary N-N-Chelating Heterocycle Ligands

et al. 2021

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Novel complexes of type [Cu(N-N)(dmtp)2(OH2)](ClO4)2·dmtp ((1) N-N: 2,2′-bipyridine; (2) L: 1,10-phenantroline and dmtp: 5,7-dimethyl-1,2,4-triazolo[1,5-a]pyrimidine) were designed in order to obtain biologically active compounds. Complexes were characterized as mononuclear species that crystallized in the space group P-1 of the triclinic system with a square pyramidal geometry around the copper (II). In addition to the antiproliferative effect on murine melanoma B16 cells, complex (1) exhibited low toxicity on normal BJ cells and did not affect membrane integrity. Complex (2) proved to be a more potent antimicrobial in comparison with (1), but both compounds were more active in comparison with dmtp—both against planktonic cells and biofilms. A stronger antimicrobial and antibiofilm effect was noticed against the Gram-positive strains, including methicillin-resistant Staphylococcus aureus (MRSA). Both electron paramagnetic resonance (EPR) and Saccharomyces cerevisiae studies indicated that the complexes were scavengers rather than reactive oxygen species promoters. Their DNA intercalating capacity was evidenced by modifications in both absorption and fluorescence spectra. Furthermore, both complexes exhibited nuclease-like activity, which increased in the presence of hydrogen peroxide.

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“…A broad spectrum of antimicrobial activity against both planktonic and biofilm-embedded strains, including methicillin-resistant Staphylococcus aureus (MRSA), was demonstrated by a series of complexes of 5-methyl-7-phenyl-1,2,4-triazolo[1,5-a]pyrimidine (pmtp) with the M(pmtp)X 2 moiety (M: Cu, Zn; X: Cl [ 30 ], CH 3 COO [ 31 ] and ClO 4 [ 32 ]). Furthermore, the Cu(II) species with mixed ligands, pmtp or dmtp and 2,2’-bipyridine (bpy) or 1,10-phenanthroline, showed enhanced activity in comparison with both ligands against several planktonic and biofilm-embedded bacterial strains [ 21 , 33 ].…”

Section: Introductionmentioning

confidence: 99%

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

et al. 2022

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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.

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Thermal behaviour of some biological active perchlorate complexes with a triazolopyrimidine derivative

Cited by 7 publications

References 34 publications

Copper(II) Complexes with Mixed Heterocycle Ligands as Promising Antibacterial and Antitumor Species

Copper(II) Complexes with Mixed Heterocycle Ligands as Promising Antibacterial and Antitumor Species

Biological Activity of Triazolopyrimidine Copper(II) Complexes Modulated by an Auxiliary N-N-Chelating Heterocycle Ligands

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

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