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

Abstract

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 from Electrophorus electricus (AChE), butyrylcholinesterase equine serum (BuChE), and α-glucosidase Saccharomyces cerevisiae inhibition 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 μM with IC 50 values for AChE and 14.38 ± 0.66-58.02 ± 4.94 μM for BuChE as compared with galantamine, which used as a positive control. For α-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 μM, respectively. The results of cytotoxicity showed that the IC 50 values were above 100 μM 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.

A review on α-glucosidase inhibitory activity of first row transition metal complexes: a futuristic strategy for treatment of type 2 diabetes

“…3) have shown good to weak α-glucosidase inhibitory activity based on different phthalocyanine derivatives ( L64 , L67–L74 , Table 7, entries 5 and 8–15). 108–114 Considering the results revealed that Co( ii ) complex 162 (IC 50 = 0.006 μM, acarbose = 22.80 μM) having 5-amino-4-aryl-3-methyl-1-oxylethyl pyrazole group ( L73 , Table 7, entry 14) 114 had the best inhibitory activity. Complexes 160 ( L70 , Table 7, entry 11) 113 and 161 ( L71 , Table 7, entry 12) 113 containing carbazole-phenoxy were also studied and the corresponding IC 50 values were calculated as 26.57 and 3.05 μM, respectively comparing with acarbose (IC 50 = 58.47 μM).…”

“… 108–114 Considering the results revealed that Co( ii ) complex 162 (IC 50 = 0.006 μM, acarbose = 22.80 μM) having 5-amino-4-aryl-3-methyl-1-oxylethyl pyrazole group (L73, Table 7 , entry 14) 114 had the best inhibitory activity. Complexes 160 (L70, Table 7 , entry 11) 113 and 161 (L71, Table 7 , entry 12) 113 containing carbazole-phenoxy were also studied and the corresponding IC 50 values were calculated as 26.57 and 3.05 μM, respectively comparing with acarbose (IC 50 = 58.47 μM). It showed that the position of connection of phenoxy carbazole moiety to the phthalocyanines ring is important as complexes 161 having the substituent at 3-position was more potent than complexe 160 having the same group at 4-position.…”

“…3) with various substituted phthalocyanines ( L60 , L62–L67 , L72 , Table 7, entries 1, 3–8, 13) has been recently reported. 105–114 Among them, complex 143 containing sodium 2-mercaptoethanesulfonate moiety ( L66 , Table 7, entry 7) with IC 50 value of 1.93 μM showed the best inhibitory effect comparing with acarbose as the reference drug (IC 50 = 22.80 μM). 110 It should be noted that complex 142 (IC 50 = 111.63 μM, acarbose = 189.20 μM) which had sodium 3-mercaptoethanesulfonate moiety ( L65 ), 110 depicted 198-fold lower activity than 143 , indicating the effect of the position of substituents.…”

“…3) bearing phthalocyanine derivatives ( L60 , L64 , L70 , L71 , and L73 , Table 7, entries 1, 5, 11, 12, and 14) has been reported in the literature and the IC 50 values were obtained in the range of 0.002–695.37 μM comparing with acarbose as the standard drug. 106,108,113,114 Complex 168 containing 5-amino-4-aryl-3-methyl-1-oxylethyl pyrazole group ( L73 , Table 7, entry 14) 114 showed the most potent activity (IC 50 = 0.002 μM, acarbose = 22.80 μM), while complex 164 having oxy methyl furan moiety ( L60, Table 7, entry 1) 106 was the weakest inhibitor (IC 50 = 695.37 μM, acarbose = 0.38 μM) among those Mn( ii ) phthalocyanines. Complexes 165 (IC 50 = 30.01 μM, acarbose = 51.54 μM) having phenyl 1,2,3-triazole ligand ( L64 , Table 7, entry 5) 108 as well as 166 (IC 50 = 25.93 μM, acarbose = 58.47 μM) ( L70 , Table 7, entry 11) 113 and 167 (IC 50 = 15.82 μM, acarbose = 58.47 μM) ( L71 , Table 7, entry 12) 113 bearing carbazole-phenoxy group showed no significant difference in the inhibitory activity.…”

Recent progress in organometallic porphyrin‐based molecular materials for optical sensing, light conversion, and magnetic cooling

“…Just as no review can claim an absolute coverage of available data in the area under consideration, our review did not consider the results for some specific very important results for MPXs/MPcXs as molecular materials. We are here obliged to cite significant works on the study and the application of the porphyrin/phthalocyanine sensitizers for PDT/diagnostics, [ 180–187 ] the catalysts based on the porphyrin/phthalocyanine complexes of rhenium [ 188–191 ] and iridium [ 192,193 ] for redox reactions that are beyond the scope of our review, and the shift reagents based on REE porphyrin complexes in NMR. [ 194–196 ]…”