Novel β-cyclodextrin-eosin conjugates

Gábor Benkovics, Damien Afonso, András Darcsi, S. Béni, Sabrina Conoci, Éva Fenyvesi, Lajos Szente, Milo Malanga, Salvatore Sortino

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)543-551
Number of pages9
JournalBeilstein Journal of Organic Chemistry
Volume13
DOIs
Publication statusPublished - Mar 15 2017

Keywords

  • Fluorescence
  • Photodynamic therapy
  • Photosensitizers
  • Singlet oxygen
  • Xanthene
  • β-cyclodextrins

ASJC Scopus subject areas

  • Organic Chemistry

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  • Cite this

    Benkovics, G., Afonso, D., Darcsi, A., Béni, S., Conoci, S., Fenyvesi, É., Szente, L., Malanga, M., & Sortino, S. (2017). Novel β-cyclodextrin-eosin conjugates. Beilstein Journal of Organic Chemistry, 13, 543-551. https://doi.org/10.3762/bjoc.13.52