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.
Highlights
The problems related to drug resistance in cancer and microbial infections are complex and lead to thousands of deaths each year
Complexes (1) and (2) were fully characterized by single X-ray diffraction, a method that evidenced a square-planar stereochemistry in the Cu(II) complex and tetrahedral in the Zn(II) compound, and a supramolecular network generated by π–π or C-H···π interactions
The complexes exhibited a moderate antiproliferative effect against the B16 tumor cells since the viability was reduced by 80% at concentrations higher than 75 μM
Summary
The problems related to drug resistance in cancer and microbial infections are complex and lead to thousands of deaths each year. The complexes bearing essential elements represent an alternative strategy to overcome these shortcomings, considering the human body’s ability to manage their excess, either by storage or by excretion [5] Among these species, complexes with Cu(II) and Zn(II) proved to be valuable in developing bioactive compounds with potential applications in several biomedical fields due to their antimicrobial [6,7,8], antitumor [8,9,10,11,12,13,14,15,16], antiparasitic [17], or anti-inflammatory [8] activities. New complexes of copper(II) and zinc(II) with 5-methyl-7-phenyl-1,2,4-triazolo[1,5 a]pyrimidine (mptp) were synthesized by the ligand direct reaction with metal chlorides in an ethanol–dimethylsulfoxide (DMSO) mixture, as presented in Scheme 1.
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