Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 21, Issue 2, Pages 386-396Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d2ob01742c
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Here we report the synthesis and biological properties of sugar-conjugated oligophenylene ethynylene (OPE) dyes, which are used as novel photosensitizers for photodynamic treatment (PDT) under blue light. The results show that these dyes effectively penetrate the cytoplasm of cancer cells and exhibit significant photodynamic effect. Localization studies also reveal the organelle targeting of certain dyes and the mechanism of cell death.
Herein we report the synthesis and biological properties of sugar-conjugated oligophenylene ethynylene (OPE) dyes, used as novel photosensitizers (PSs) for photodynamic treatment (PDT) under blue light. The OPE-bearing glycosides at both ends are successfully prepared by a Pd-catalyzed Sonogashira cross-coupling reaction. The live-cell imaging studies have shown that these OPE glycosides (including glucose, mannose and maltose derivatives) efficiently penetrate the cytoplasm of cultured HeLa cancer cells. No dark toxicity was observed, but upon irradiating the cells under blue light an extraordinary photodynamic effect was observed at low concentrations (10(-6)-10(-8) M). The localization studies indicate that OPE-glucose 1 and OPE-mannose 2 have Golgi patterns, whereas OPE-maltose 3 could be in lysosomes. The PDT and morphological studies in HeLa cells treated with sublethal doses of PS 1-3 revealed that cell death occurs by necrosis.
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