Synthesis of Zinc Phthalocyanine Complex Containing Tetra Propanoic Acid Groups: Electronic Properties and Inhibitory Effects on Some Metabolic Enzymes

Abstract

In the new study, first the synthesis and characterization of 2, 10, 16, 24-Tetrakis-3-(phenoxy) propanoic acid phthalocyaninato zinc (II)(4) and its starting compound are presented. The aggregation properties of compound (4) were investigated with the UV-visible spectrum, and the excitation and emission properties were investigated with the fluorescence spectra. The new compounds were characterized by IR, UV-visible, Mass and 1H NMR spectroscopy. These 3-(3,4-dicyanophenoxy) propanoic acid (3) and compound (4) had effective inhibition against alpha-glycosidase, alpha-amylase, butyrylcholinesterase and acetylcholinesterase. IC50 values were found as 4.21-6.57 mu M for AChE, 0.32-1.88 mu M for BChE, 47.14-62.07 mu M for alpha-amylase, and 13.41-21.82 mu M for alpha-glycosidase. By molecular docking study, compared to reference compounds (tacrine and acarbose) of compound (4) [-9.25 kcal/mol for AChE; -9.30 kcal/mol for BChE; -6.50 kcal/mol for alpha-amylase and -8.49 kcal/mol for alpha-glycosidase seem to be more effective and promising. Drug development for the treatment of diabetes, hyperglycemia, and obesity has as one of its design goals the creation of molecules that are alpha-amylase and alpha-glycosidase inhibitors. As a result, compound (4) can have promising anti Alzheimer drug potential and record as novel anti-diabetic inhibitors.