AChE/BuChE inhibitory, DNA nuclease and cytotoxic properties of axially 5-[6-(benzyloxy)-2H-1,3-benzoxazin-3(4H)-yl]pentanoxy and 5-[6-(hexyloxy)-2H-1,3-benzoxazin-3(4H)-yl]pentanoxy substituted silicon phthalocyanines

Abstract

In this work, axially di-5-[6-(benzyloxy)-2H-1,3-benzoxazin-3(4H)-yl]pentanoxy and 5-[6-(hexyloxy)-2H-1,3-benzoxazin-3(4H)-yl]pentanoxy substituted silicon phthalocyanines were synthesized and characterized for the first time. Then, AChE/BuChE inhibitory, supercoiled plasmid pR322 DNA nuclease and cytotoxic properties of the A1-C5-Si and A2-C5-Si were investigated using different methods. The results showed that A1-C5-Si and A2-C5-Si inhibited AChE and BuChE in a concentration-dependent manner whereas galantamine showed higher inhibitory effects that of the compounds. DNA nuclease experiments showed that both compounds did not damage to plasmid DNA when exposed for 30, 60 and 90 min. Both compounds exhibited a concentration-dependent cytotoxicity against SH-SY5Y cells for 24 and 48 h. The cell viabilities were 63.14±12.63% and 54.95±10.38% in the presence of A1-C5-Si at 50 and 100 µM for 24 h. Moreover, the cell viabilities were found to be 53.07±5.83% and 52.33±3.68% for A1-C5-Si and A2-C5-Si at 100 µM, respectively for 48 h.