Dually Directional Glycosylated Phthalocyanines as Extracellular Red-Emitting Fluorescent Probes

The development of new non-aggregated phthalocyanines bearing multivalent saccharide moieties on their macrocyclic rims is of a great interest. Many belongings, including, water-solubility, non-toxicity and others, can be feasibly obtained by these amphiphiles which can be considered as a key-solution for demonstrating highly efficient photoactive materials in water. Herein, a family of five newly prepared dually directional Zn(II) containing phthalocyanines (PcG1-4) and azaphthalocyanine (AzaPcG1) glycoconjugatesis described. The unique spatial arrangement of the glucoside units based on peripherally hexadeca- (PcG1) and nonperipherally octa-(PcG4) macrocycles, provides a fully monomeric behaviour along with a high fluorescence (ΦF~ 0.21) in aqueous solution. These amphiphiles were characterized by low toxicity and extremely low cellular uptake was obtained due to the highly polar nature of the glucoside substituents. Accordingly, their potentialsas suitable photoactive chromophores for red-emitting extracellular fluorescent probes has been confirmed upon the evaluation of paracellular transport using layer of MDCKII cells with permeability coefficient fully comparable with an established evaluator of the integrity of the monolayer.