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Dually directional glycosylated phthalocyanines as extracellular red-emitting fluorescent probes

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Abstract

The development of new non-aggregated phthalocyanines bearing multivalent saccharide moieties on their macrocyclic rims is of great interest. Many characteristics, 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) glycoconjugates is 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 an extremely low cellular uptake was obtained due to the highly polar nature of the glucoside substituents. Accordingly, their potential as suitable photoactive chromophores for red-emitting extracellular fluorescent probes has been confirmed upon the evaluation of paracellular transport using a layer of MDCKII cells with the permeability coefficient fully comparable with an established evaluator of the integrity of the monolayer.

Graphical abstract: Dually directional glycosylated phthalocyanines as extracellular red-emitting fluorescent probes

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Supplementary files

Article information


Submitted
29 Mar 2020
Accepted
27 May 2020
First published
28 May 2020

Dalton Trans., 2020, Advance Article
Article type
Paper

Dually directional glycosylated phthalocyanines as extracellular red-emitting fluorescent probes

A. Husain, A. Ganesan, M. Machacek, L. Cerveny, P. Kubat, B. Ghazal, P. Zimcik and S. Makhseed, Dalton Trans., 2020, Advance Article , DOI: 10.1039/D0DT01180K

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