A highly selective fluorescent sensor for glucosamine

Abstract

A new fluorescent chemical sensor for glucosamine is reported. The sensor is based on a boronic acid-containing coumarin aldehyde and shows excellent selectivity for glucosamine by forming a boronic ester with the sugar diol as well as an iminium ion with the amine group of glucosamine. The sensor successfully discriminates glucosamine over other similar biomolecules in terms of both fluorescence intensity and binding affinity. This method provides a new concept for the design and synthesis of very selective turn-on optical sensors for selective detection of multi-functional biomolecules.

Recent development of boronic acid-based fluorescent sensors

“… 4 The selectivity of glucose can be achieved via molecular design, 38 and this technology is maturing, 13 and recent developments tend to produce glucose optical responses by inducing nanoscale self-assembly of boronic acid-containing amphiphiles or other materials. 39 This section will briefly introduce fluorescent sensors that were fabricated with anthracene, pyrene, heterocyclic ring as fluorescent units, and then the analysis of ribose, 40 sialic acids, 25,41 glucosamine, 42 α-hydroxy carboxylate, 43 ATP, 44,45 amyloid-β plaques 46 fluorescent sensors are followed. This paper summarized the unique design ideas of these fluorescent sensors, the luminescence response mechanisms and the development perspective in the future.…”

Targeting biomolecules with reversible covalent chemistry

“…Incorporating a phenylboronic acid moiety into the coumarin 3-aldehyde scaffold affords a highly selective fluorescent sensor for dopamine[29] and glucosamine. [30] The sensor-analyte pairs give K a values over 4000 M −1 , reflecting the additional thermodynamic stabilization provided by the boronate ester formation (Figure 4c). Also based on the coumarin 3-aldehyde scaffold, a clever design by Buccella and coworkers exploits imine formation in an intramolecular setting (Figure 4d), which allows facile detection of histone deacetylase activity in live cells.…”

A novel boronic acid-based fluorescent sensor for selectively recognizing Fe3+ ion in real time

“…Due to the simple operation, high sensitivity and selectivity, uorescence spectroscopy has been widely applied to detect various ions (Cu 2+ , [9][10][11][12][13][14][15] Cr 3+ , 16 Hg 2+ , [17][18][19][20][21] Al 3+ , 22,23 etc. ), carbohydrates [24][25][26][27] and so on. Compared with sensing other transition metals such as Cu 2+ and Hg 2+ , there are relatively less uorescent sensors of Fe 3+ ion, which are based on derivatives of macrocyclic molecules, 2,28 rhodamines, [29][30][31][32][33][34] coumarin, [35][36][37] quinoline, 1,[38][39][40] etc.…”

“…Due to the obvious changes in uorescence aer binding, rapid recognition, good selectivity, etc. boronic acid-based uorescent sensors have been developed widely in the recognition of carbohydrates, [24][25][26][27] etc. In addition, boronic acid can also be used to sense ions, 11,17 such as Cu 2+ , Hg 2+ and so on.…”