Dually directional glycosylated phthalocyanines as extracellular red-emitting fluorescent probes

0532313 - ÚFCH JH 2021 RIV GB eng J - Journal Article
Husain, A. - Ganesan, A. - Macháček, M. - Červený, L. - Kubát, Pavel - Ghazal, B. - Zimčík, P. - Makhseed, S.
Dually directional glycosylated phthalocyanines as extracellular red-emitting fluorescent probes.
Dalton Transactions. Roč. 49, č. 28 (2020), s. 9605-9617. ISSN 1477-9226. E-ISSN 1477-9234
Institutional support: RVO:61388955
Keywords : zinc(ii) phthalocyanine * photodynamic therapy * singlet oxygen * in-vitro * transporters * glycoconjugation * photosensitizers * permeability * absorption * inhibitors
OECD category: Physical chemistry
Impact factor: 4.390, year: 2020
Method of publishing: Limited access

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 (Phi((sic)) similar to 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.
Permanent Link: http://hdl.handle.net/11104/0310834