Synthesis, characterization and distinct butyrylcholinesterase activities of transition metal complexes of 2-[(E)-(quinolin-3-ylimino)methyl]phenol

Abstract

2-[(E)-(Quinolin-3-ylimino)methyl]phenol (H-QMP) was synthesized by condensing salicylaldehyde with 2-aminoquinoline and fully characterized by mass spectrometry, 1H and 13C{1H}NMR, and IR spectroscopies. The metal complexes [M(QMP)(OAc)]H2O where M=Cu(II) and Zn(II) and [M(QMP)2] where M=Ni and Co(II) were prepared from the metal acetates. All transition metal complexes were assigned geometries based on the UV–Vis spectra, conductivity and magnetic susceptibilities. [M(QMP)2], {where M=Ni and Co(II)}, were further characterized by single crystal X-ray diffraction and were found to be pseudo-octahedral with interquinoline interaction to the metal center. The complexes were screened for acetylcholinesterase (AChE) and butyrylcholinesterase (BChE). Only cobalt and copper containing complexes were found to be active against BChE with IC50=69±0.0112 and 5±0.0004μM±SEM, respectively. Surprisingly no activity was observed for AChE, therefore selective BChE inhibition was observed for copper and cobalt complexes only.