Peripheral or nonperipheral tetra-[4-(9H-carbazol-9-yl)phenoxy] substituted cobalt(II), manganese(III) phthalocyanines: Synthesis, acetylcholinesterase, butyrylcholinesterase, and α-glucosidase inhibitory effects and anticancer activities

In this work, peripheral or nonperipheral tetra-[4-(9H-carbazol-9-yl)phenoxy] substituted cobalt(II), manganese (III) phthalocyanines were synthesized for the first time. Their acetylcholinesterase fromElectrophorus electricus(AChE), butyrylcholinesterase equine serum (BuChE), and alpha-glucosidaseSaccharomyces cerevisiaeinhibition were investigated spectrophotometrically. Finally, in vitro cytotoxicities of the compounds were investigated on human neuroblastoma (SH-SY5Y) cell line using MTT cell viability assay. The compounds inhibited to enzymes in the range of 7.39 +/- 0.25-35.29 +/- 2.49 mu M with IC(50)values for AChE and 14.38 +/- 0.66-58.02 +/- 4.94 mu M for BuChE as compared with galantamine, which used as a positive control. For alpha-glucosidase, all compounds had stronger inhibition action than acarbose according to the IC(50)values. The IC(50)values of N-Co and N-Mn were found to be 3.05 +/- 0.10 and 15.82 +/- 1.85 mu M, respectively. The results of cytotoxicity showed that the IC(50)values were above 100 mu M showing the compounds had low cytotoxic action against SH-SY5Y cell line for 24 h. Overall, carbazole substituted nonperipheral compounds can be considered as a potential agent for the treatment of Alzheimer's diseases and diabetes mellitus.

Automated summary

Novel compounds with carbazole substitution showed potential for the treatment of Alzheimer's diseases and diabetes mellitus by inhibiting enzyme activity and exhibiting low cytotoxicity in in vitro cell experiments.