Eosin B (EoB) and eosin Y (EoY), two xanthene dye derivatives with photosensitizing ability were prepared in high purity through an improved synthetic route. The dyes were grafted to a 6-monoamino-β-cyclodextrin scaffold under mild reaction conditions through a stable amide linkage using the coupling agent 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride. The molecular conjugates, well soluble in aqueous medium, were extensively characterized by 1D and 2D NMR spectroscopy and mass spectrometry. Preliminary spectroscopic investigations showed that the β-cyclodextrin-EoY conjugate retains both the fluorescence properties and the capability to photogenerate singlet oxygen of the unbound chromophore. In contrast, the corresponding β-cyclodextrin-EoB conjugate did not show either relevant emission or photosensitizing activity probably due to aggregation in aqueous medium, which precludes any response to light excitation.

CycloLab Cyclodextrin R and D Ltd Budapest H 1097 Illatos út 7 Hungary

CycloLab Cyclodextrin R and D Ltd Budapest H 1097 Illatos út 7 Hungary; Department of Organic Chemistry Faculty of Science Charles University Prague Hlavová 8 128 43 Prague 2 Czech Republic

Department of Pharmacognosy Semmelweis University H 1085 Üllői út 26 Hungary

Laboratory of Photochemistry Department of Drug Sciences University of Catania 1 95125 Viale A Doria 6 Italy

STMicroelectronics Stradale Primosole 50 1 95121 Catania Italy

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