期刊
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
卷 13, 期 -, 页码 543-551出版社
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.13.52
关键词
beta-cyclodextrins; fluorescence; photodynamic therapy; photosensitizers; singlet oxygen; xanthene
资金
- Marie Curie Program [CYCLON-HIT 608407]
- NKFIH [109373]
- Ministry of Human Capacities [UNKP-16-4]
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-beta-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 beta-cyclodextrin-EoY conjugate retains both the fluorescence properties and the capability to photogenerate singlet oxygen of the unbound chromophore. In contrast, the corresponding beta-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.
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