RESUMO
Photodynamic therapy (PDT) is a minimally invasive procedure that can provide a selective eradication of neoplastic diseases by the combined effect of a photosensitizer, light and oxygen. New amino oligo(phenylene-ethynylene)s (OPEs), bearing hydrophilic glucoside terminations, have been prepared, characterized and tested as photosensitizers in PDT. The effectiveness of these compounds in combination with UVA light has been checked on two tumor cell lines (HEp-2 and HeLa cells, derived from a larynx carcinoma and a cervical carcinoma, respectively). The compounds triggered a mitotic blockage that led to the cell death, being the effect active up to 3 µm concentration. The photophysical properties of OPEs, such as high quantum yield, stability, singlet oxygen production, biocompatibility, easy cell-internalization and very good response even at low concentration, make them promising photosensitizers in the application of PDT.
Assuntos
Alcinos/farmacologia , Materiais Biocompatíveis/farmacologia , Éteres/farmacologia , Glucose/química , Fotoquimioterapia , Fármacos Fotossensibilizantes/farmacologia , Alcinos/síntese química , Alcinos/química , Materiais Biocompatíveis/síntese química , Materiais Biocompatíveis/química , Morte Celular/efeitos dos fármacos , Linhagem Celular Tumoral , Relação Dose-Resposta a Droga , Éteres/síntese química , Éteres/química , Células HeLa , Células Hep G2 , Humanos , Estrutura Molecular , Fármacos Fotossensibilizantes/síntese química , Fármacos Fotossensibilizantes/química , Relação Estrutura-Atividade , Raios UltravioletaRESUMO
A new family of oligo(phenylene ethynylene) (OPE) glucosides has been prepared and characterized. Our results demonstrate that fine-tuning of their photophysical properties can be obtained by acting on the electronics of the core and molecular skeleton. Modulation of the hydrophobic chain length and substituents on the central moieties influences the bioaffinity too. In particular, introducing a NMe2 group on the aromatic central core affords a highly efficient biocompatible fluorescent probe that can be taken up in cytoplasmic vesicles of HEp-2 cells (cells from epidermoid carcinoma larynx tissue). The photophysical behavior, high quantum yield, and stability open the way to the use of the OPE family as stains for cellular imaging analysis by fluorescence microscopy.