Dually directional glycosylated phthalocyanines as extracellular red-emitting fluorescent probes
| Autor: | Miloslav Machacek, Basma Ghazal, Pavel Kubát, Ali Husain, Asaithampi Ganesan, Petr Zimcik, Saad Makhseed, Lukas Cerveny |
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| Rok vydání: | 2020 |
| Předmět: |
Glycosylation
Indoles Photosensitizing Agents Aqueous solution Molecular Structure Cell Survival Isoindoles Chromophore Fluorescence Combinatorial chemistry Madin Darby Canine Kidney Cells Inorganic Chemistry chemistry.chemical_compound Dogs Monomer Microscopy Fluorescence Glucoside chemistry Paracellular transport Monolayer Amphiphile Animals Humans Fluorescent Dyes HeLa Cells |
| Zdroj: | Dalton Transactions. 49:9605-9617 |
| ISSN: | 1477-9234 1477-9226 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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