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. 2016 Mar 17:12:537-48.
doi: 10.3762/bjoc.12.53. eCollection 2016.

New synthetic strategies for xanthene-dye-appended cyclodextrins

Milo Malanga  1 , Andras Darcsi  2 , Mihaly Balint  1 , Gabor Benkovics  3 , Tamas Sohajda  1 , Szabolcs Beni  2
Affiliations

New synthetic strategies for xanthene-dye-appended cyclodextrins

Milo Malanga et al. Beilstein J Org Chem. .

Abstract

Xanthene dyes can be appended to cyclodextrins via an ester or amide bridge in order to switch the fluorescence on or off. This is made possible through the formation of nonfluorescent lactones or lactams as the fluorophore can reversibly cyclize. In this context we report a green approach for the synthesis of switchable xanthene-dye-appended cyclodextrins based on the coupling agent 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM). By using 6-monoamino-β-cyclodextrin and commercially available inexpensive dyes, we prepared rhodamine- and fluorescein-appended cyclodextrins. The compounds were characterized by NMR and IR spectroscopy and MS spectrometry, their UV-vis spectra were recorded at various pH, and their purity was determined by capillary electrophoresis. Two potential models for the supramolecular assembly of the xanthene-dye-appended cyclodextrins were developed based on the set of data collected by the extensive NMR characterization.

Keywords: DMT-MM; fluorescein; rhodamine; supramolecular assembly.

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Figures

Figure 1
Figure 1
Structures of fluorescent xanthene dyes. Rhodamine B·HCl 1 and fluorescein disodium salt 2.
Figure 2
Figure 2
Reaction scheme for the synthesis of rhodamine-appended β-CD.
Figure 3
Figure 3
TLC plates at different development stages for monitoring the composition of Rho-β-CD crude (left panel) and TLC for evaluating the effectiveness of the work-up (right panels).
Figure 4
Figure 4
1H NMR spectrum of Rho-β-CD with partial assignments (D2O, 500 MHz, 298 K).
Figure 5
Figure 5
Expansion of DEPT-ed-HSQC spectrum of Rho-β-CD with partial assignments (D2O, 500 MHz, 298 K).
Figure 6
Figure 6
Cartoon models for the possible intermolecular inclusion mode of Rho-β-CD in solution (3D perspective view on the left and 3D structural model on the right).
Figure 7
Figure 7
1H NMR spectrum of Flu-β-CD with partial assignments (D2O, 500 MHz, 298 K).
Figure 8
Figure 8
Cartoon models for the possible intermolecular inclusion mode of Flu-β-CD in solution (3D perspective view on the left and 3D structural model on the right).
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