Synthesizing and evaluating the photodynamic efficacy of asymmetric heteroleptic A7B type novel lanthanide bis-phthalocyanine complexes

Abstract

In this study heteroleptic A₇B type novel Lu(III) and Eu(III) lanthanide phthalocyanines (LnPc(Pox)[Pc′(AB₃SH)]) with high extinction coefficients have been synthesized as candidate photosensitizers with reaction yields higher than 33%. The singlet oxygen quantum yields of LuPc(Pox)[Pc′(AB₃SH)] and EuPc(Pox)[Pc′(AB₃SH)], respectively, were measured 17% and 1.4% by the direct method in THF. The singlet oxygen quantum yield of LuPc(Pox)[Pc′(AB₃SH)] in THF is the highest among lutetium(III) bis-phthalocyanine complexes to date. The photodynamic efficacy of the heteroleptic lanthanide phthalocyanines was evaluated by measuring cell viabilities of A549 and BEAS-2B lung cells, selected to representing in vitro models for testing cancer and normal cells against potential drugs. The cell viabilities demonstrated concentration dependent behavior and were varied by the type of phthalocyanines complexes. Irradiation of the cells for 30 minutes with LED array at 660 nm producing flux of 0.036 J cm⁻² s⁻¹ increased cell death for LuPcPox-OAc, LuPc(Pox)[Pc′(AB₃SH)] and ZnPc. The IC₅₀ concentrations of LuPc(Pox)[Pc′(AB₃SH)] and ZnPc were determined to be below 10 nM for both cell lines, agreeing very well with the singlet oxygen quantum yield measurements. These findings suggest that LuPc(Pox)[Pc′(AB₃SH)] and particularly LuPcPox-OAc are promising drug candidates enabling lowered dose and shorter irradiation time for photodynamic therapy.