A novel series of M(II) complexes of 6‐methylpyridine‐2‐carboxylic acid with 4(5)methylimidazole: Synthesis, crystal structures, α‐glucosidase activity, density functional theory calculations and molecular docking

Abstract

Novel complexes of 6‐methylpyridine‐2‐carboxylic acid and 4(5)methylimidazole, namely [Mn(6‐mpa)2(4(5)MeI)2] (1), [Zn(6‐mpa)2(4(5)MeI)2] (2), [Cd(6‐mpa)2(4(5)MeI)2] (3), [Co(6‐mpa)2(4(5)MeI)2] (4), [Ni(6‐mpa)2(4(5)MeI)(OAc)] (5) and [Cu(6‐mpa)2(4(5)MeI)] (6), were synthesized for the first time. The structures of complexes 1–4 and complexes 5 and 6 were determined using X‐ray diffraction and mass spectrometric techniques, respectively. The experimental spectral analyses for these complexes were performed using Fourier transform infrared and UV–visible techniques. The α‐glucosidase inhibition activity values (IC50) of complexes 1–6 were identified in view of genistein reference compound. Moreover, the DFT/HSEh1PBE/6‐311G(d,p)/LanL2DZ level was used to obtain optimal molecular geometry and vibrational wavenumbers for complexes 1–6. Electronic spectral behaviours and major contributions to the electronic transitions were investigated using TD‐DFT/HSEh1PBE/6‐311G(d,p)/LanL2DZ level with conductor‐like polarizable continuum model and SWizard program. Finally, in order to investigate interactions between the synthesized complexes (1–6) and target protein (template structure S. cerevisiae isomaltase), a molecular docking study was carried out.

Synthesis, spectral properties,in vitroα‐glucosidase inhibitory activity and quantum chemical calculations of novel mixed‐ligand M(II) complexes containing 1,10‐phenanthroline

“…Changing metals for the other complexes 1 and 3 – 5 did not have a notable effect on α‐glucosidase inhibition. It can be stated that this difference arises from the fact that the atomic diameter of Hg metal is greater than that of the other Co, Mn and Ni metals. The variation of metals and coordinating ligands for complexes 1 and 3 – 5 did not have an important effect on inhibitory activity results (IC 50 > 600 μM). For complexes 1 and 4 (IC 50 > 600 μM), moving the methyl group from 3‐position to 6‐position at the mpa showed no change on α‐glucosidase inhibition. The IC 50 values of Cu(pa) 2 , Zn(pa) 2 , VO(pa) 2 and Zn(6mpa‐ma) 2 SO 4 complexes have been observed at 1.28 μM, 15.4 μM, >1 mM and 9.6 μM, respectively. In the last few years, it has been observed that the studies with regard to synthetic or natural α‐glucosidase inhibitors have also increased markedly .…”

“…In addition, the effects of some metal complexes containing heterocyclic picolinic acid and its derivatives on diabetes have been investigated . In other work, the IC 50 values of Zn(pa) 2 , Cu(pa) 2 , Zn(6‐mpa–ma) 2 SO 4 and VO(pa) 2 as α‐glucosidase inhibitors have been measured . To date, no other studies reporting α‐glucosidase inhibition activity of mixed‐ligand–metal complexes containing 6‐mpa except for our studies have been performed …”

Novel Mn(II) and Zn(II) complexes of 6‐bromopicolinic acid as a potential optical material: Synthesis, spectral characterizations, linear, and nonlinear optical properties and density functional theory calculations

“…Many transition metal complexes of these ligands have been extensively studied because of their great coordination potential and biological importance. [4][5][6][7][8][9][10] Recently, the coordination compounds of bromo derivatives of picH to d-block metals (Co(II), Ni(II), Cu(II), and Ru(II)) have been investigated. [11][12][13][14][15] In these studies, the cobalt(II), nickel(II), copper(II), and ruthenium(II) complexes of 6-bromopicolinic acid (6-BrpicH) were synthesized, and generally, their structural, thermal, spectroscopic, and magnetic properties were examined.…”

“…[6,[16][17][18][19][20][21] Furthermore, the metal complexes synthesized with nitrogen-containing ligands have encouraged to research the enzyme activity studies because of their structurally and catalytically similarity with some enzyme-substrate complexes in our body. [7][8][9][10] Due to the ever increasing technological requirements, researching new NLO motifs to meet the needs in these fields is still an important study field. Research of recent NLO materials has focused intensely on metal-organic complex structures.…”

“…Research of recent NLO materials has focused intensely on metal-organic complex structures. [5][6][7][8][9][10][16][17][18][19][20][21] The encouraging situation here is because of the use of strong and versatile metal-ligand bonds and its success in the synthesizing noncentrosymmetric systems in crystal structures. The noncentrosymmetric structures can be designed using the well-defined geometry of metal ions and the coordination ability of ligands.…”