Specific ligands based on Tröger’s base derivatives for the recognition of glycosaminoglycans

• Tröger’s bases with quinolinium substitution were prepared and characterized.
• High affinity and strong spectroscopic response for the glycosaminoglycans.
• High selectivity for the heparin polysulphated structure motif was observed.

Symmetric Tröger’s base derivatives with quinolinium substitution, 7 and 8, were prepared, and their structures were confirmed by 1H and 13C NMR, 2D NMR and NOE NMR techniques and elemental analysis. These compounds were studied as specific ligands for the recognition of glycosaminoglycans (heparin, heparan sulphate, chondroitin sulphate and hyaluronic acid). They exhibited high affinity and selectivity towards glycosaminoglycans, especially heparin. The conditional binding constants, linear ranges and detection limits were determined by UV–Vis spectroscopy. These values, especially at extremely low limits of detection, showed the high potential of the prepared ligands for the recognition and determination of glycosaminoglycans, especially heparin. For example, the minimum detectable heparin concentrations for 7 and 8 were 0.1 and 0.17 ng/mL (R2 = 0.988 and 0.9938) in media (1 mM NaCl (H2O:MeOH; 7:3, v/v), pH = 7.34), respectively.

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