Novel different furoic acid‐linked axial silicon phthalocyanines: Design, syntheses, cholinesterases, tyrosinase inhibitory, and DNA damage studies

Abstract

There is still no specific treatment for Alzheimer's disease, which is a very important public health problem due to the increasing elderly population, especially in developed countries. Acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitors have been used for the treatment of this disease in recent years. Tyrosinase inhibitors are used preventively in Parkinson's disease, pigmentation disorders, and skin aging. Hence, there is a need for novel enzyme inhibitors with desirable properties for the treatment of these diseases. In this study, axial silicon phthalocyanine compounds (FURO‐M‐SiPc, FURO‐Cl‐SiPc, and FURO‐Br‐SiPc) containing different furoic acid derivatives were synthesized, and their structures were elucidated by common spectroscopic methods (FT‐IR, MS, UV‐Vis, and NMR). The inhibitory properties of the compounds were subjected using spectrophotometric methods on AChE, BChE, and tyrosinase enzymes. DNA damage studies were investigated using the agarose electrophoresis gel method to determine whether the compounds cause DNA damage. The IC50 value of FURO‐M‐SiPc (65.57 ± 2.46 μM) was found to be close to that of galantamine (52.82 ± 1.04 μM). As a result of the Lineweaver–Burk plot, FURO‐M‐SiPc inhibited BChE via competitive manner. In tyrosinase inhibitory studies, the IC50 values of FURO‐Br‐SiPc, FURO‐M‐SiPc, and FURO‐Cl‐SiPc were 164.82 ± 10.66 μM, 138.09 ± 8.89 μM, and 149.75 ± 6.71 μM, respectively. Finally, the compounds did not damage DNA under the experimental conditions. All these results showed that the FURO‐M‐SiPc showed a high inhibition effect against the BChE enzyme and was suitable for further studies, since the compounds did not cause DNA damage.