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Novel β-cyclodextrin-eosin Conjugates

Novel β-cyclodextrin-eosin Conjugates

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

Beilstein J Org Chem. 2017 Mar 15;13:543-551.

PMID: 28405233

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP548243	Eosin B		548-24-3	Price

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