A series of tert-butyl- and tert-butylthio-substituted phthalocyanine derivatives: biological activities, DFT calculations and molecular docking studies
Abstract
In this study, the biological activities, including amylolytic, antimicrobial, antimicrobial photodynamic therapy (aPDT), antibiofilm, DNA cleavage, and microbial cell viability inhibition activities, of a series of tert-butyl-substituted phthalocyanines (tBuH2Pc, tBuZnPc, tBuNiPc, and tBuCuPc) and their tert-butylthio-substituted derivatives (S-tBuH2Pc, S-tBuZnPc, S-tBuNiPc, and S-tBuCuPc) were systematically evaluated and compared. In addition, density functional theory (DFT) calculations and molecular docking studies targeting α-amylase were conducted for all the compounds. All of the phthalocyanines (Pcs) demonstrated effective amylolytic inhibition activity, especially at 50 and 100 mg L-1, indicating that the test compounds may be effective antidiabetic agents. Among the tested molecules, S-tBuZnPc and S-tBuCuPc exhibited superior antibiofilm activity against S. aureus and P. aeruginosa, achieving complete inhibition at 15 mg L-1 under both dark and LED light conditions. DNA cleavage experiments showed that all the Pc derivatives except tBuH2Pc and tBuNiPc induced complete cleavage at all tested concentrations. Microbial viability assays revealed that tBuZnPc, tBuCuPc, S-tBuZnPc and S-tBuCuPc achieved 100% inhibition of E. coli viability at just 10 mg L-1. DFT calculations confirmed favorable electronic distributions and molecular electrostatic potential maps, while molecular docking results demonstrated strong binding affinities of the S-tBuPc compounds to α-amylase,…
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