Pyridine substituted BODIPYs: synthesis, characterization and cholinesterease, α-glucosidase inhibitory, DNA hydrolytic cleavage effects

Abstract

In this study, the synthesis of new monostyryl (BDPY-2) and distyryl BODIPY dyes (BDPY-4, BDPY-5) containing pyridine groups to has been reported for the first time. The acetylcholinesterase from Electrophorus electricus (AChE), butyrylcholinesterase from equine serum (BuChE), α-glucosidase from Saccharomyces cerevisiae and DNA hydrolytic cleavage actions of BDPY-2, BDPY-4, BDPY-5 were investigated using various techniques.The results indicated that the compounds had varying inhibition properties against AChE, BuChE, and α-glucosidase. BDPY-4 was the most potent compound on AChE with IC 50 of 54.78 ± 4.51 µM and Lineweaver-Burk plots indicated that the compound is bound to a site other than the active site as a noncompetitive inhibitor. The compound-protein binding experiment showed that BDPY-4 changed the microenvironment around AChE. On the other hand, the compounds showed lower α-glucosidase inhibition than the positive control. The DNA hydrolytic cleavage effects were not observed on supercoiled plasmid DNA in the presence of the compounds as compared to negative controls. These findings results suggested that BDPY-4 might be a promising compound to treat Alzheimer's diseases.

Synthesis, anticholinesterase activity, molecular docking, and molecular dynamic simulation studies of 1,3,4‐oxadiazole derivatives

“…[37][38][39] Furthermore, different moieties reported the development of new pyridine hybrids for the cholinesterase inhibitory activity. [40][41][42][43][44][45][46] Various pyridine-based drugs have been or are used in the treatment of AD, such as tacrine (AChEI) and umibecestat (BACE-1 inhibitor). [42,47] In addition, there has been a lot of interest in the development of pyridine scaffolds for the treatment of AD.…”

Non‐aggregated and water soluble axially disubstituted silicon phthalocyanines: Synthesis and inhibitory effect on acetylcholinesterase enzyme

“…In medicinal chemistry, pyridine groups one the most important heterocyclic compounds because of their various pharmacological and biological activities such as antiviral, [ 24 ] anticancer, [ 25 ] antidiabetic, [ 26 ] and anticholinesterase. [ 27 ] For this reason, we wondered how the presence of phthalocyanines in the axial positions of the [3,5‐bis(3‐pyridin‐3‐ylpropoxy)phenyl]methoxy and [4‐(3‐pyridin‐3‐ylpropoxy)phenyl]methoxy groups affect the in vitro cholinesterases inhibitory properties of phthalocyanine compounds. Therefore, in this study, axially pyridine groups substituted silicon (IV) phthalocyanines and their water soluble derivatives were designed as target ligands against AD; thus, it was focused on the inhibition activity of acetylcholinesterase.…”