Metal complex derivatives of bis(pyrazol-1-yl)methane ligands: synthesis, characterization and anti-Trypanosoma cruzi activity
- 36 Downloads
In this work, the synthesis and characterization of seven complexes (1–7) was performed with Zn(II), Cu(II), Co(II) and Ni(II) transition metals and ligands derived from bis(3,5-dimethylpyrazol-1-yl)methane (bdmpzm) and bis(3,5-dimethyl-4-nitro-1H-pyrazolyl)methane (L). The complexes were obtained in high yields, isolated as air-stable solids and characterized by physicochemical and spectroscopic methods. The structures of L and complex 1 were determined by single-crystal X-ray diffraction analysis. The complexes and their respective ligands were evaluated against epimastigotes of Trypanosoma cruzi strains. An increase in the activity of the complexes was observed compared to the free ligands. Greater activities were found for Co(II) complexes than for Cu(II), Ni(II) and Zn(II) complexes. Additionally, complexes 3 and 9 had little effect on erythrocytes, indicating that they are non-toxic. The results obtained in mitochondrial membrane potential analyses suggest a possible mechanism by which complex 3 has a trypanocidal effect through the induction of oxidative stress. The results could provide an interesting contribution to the further design of active complexes against T. cruzi.
Thanks to the Department of Chemistry and the School of Science of the Universidad de los Andes for financial support. O. Triana acknowledges the Universidad de Antioquia, Estrategia de sostenibilidad UdeA. We thank the reviewers and editor for their useful comments.
Conflict of interest
The authors declare no conflicts of interest.
This article does not contain any studies with human participants performed by any of the authors.
CCDC 1586067 and 1586068 contain supplementary crystallographic data for L and 1, respectively. These data can be obtained free of charge via http://www.ccdc.cam.ac.uk/conts/retrieving.html or the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: (+44) 1223-336-033; or e-mail: email@example.com.
- 17.Tarafder MT, Jin KT, Crouse KA et al (2002) Coordination chemistry and bioactivity of Ni2+, Cu2+, Cd2+ and Zn2+ complexes containing bidentate Schiff bases derived from S-benzyldithiocarbazate and the X-ray crystal structure of bis[S-benzyl-β-N-(5-methyl-2-furylmethylene)dithiocarbazato]cadmium(II). Polyhedron 21:2547–2554. https://doi.org/10.1016/S0277-5387(02)01188-9 CrossRefGoogle Scholar
- 21.Sandoval-Rojas AP, Ibarra L, Cortés MT et al (2017) Synthesis and characterization of copper(II) complexes containing acetate and N, N-donor ligands, and their electrochemical behavior in dopamine detection. J Electroanal Chem 805:60–67. https://doi.org/10.1016/j.jelechem.2017.10.018 CrossRefGoogle Scholar
- 32.Urbina JA, Concepcion JL, Montalvetti A et al (2003) Mechanism of action of 4-phenoxyphenoxyethyl thiocyanate (WC-9) against Trypanosoma cruzi, the causative agent of Chagas’ disease. Antimicrob Agents Chemother 47:2047–2050. https://doi.org/10.1128/aac.47.6.2047 CrossRefPubMedPubMedCentralGoogle Scholar