Amino-OPE glycosides and blue light: a powerful synergy in photodynamic therapy. Issue 2 (16th December 2022)

• Record Type: Journal Article
• Authors: Lara-Pardo, Andrea; Mancuso, Aurora; Simón-Fuente, Silvia; Bonaccorsi, Paola M.; Gangemi, Chiara M. A.; Moliné, María Ángeles; Puntoriero, Fausto; Ribagorda, Maria; Barattucci, Anna; Sanz-Rodriguez, Francisco
• Is Part Of: Organic & biomolecular chemistry. Volume 21:Issue 2(2023)
• Page Start: 386
• Page End: 396
• Publication Date: 2022-12-16
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d2ob01742c
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Amino-OPE glycosides have been synthesized and tested as PSs in PDT under blue light. Abstract : 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.