Sensitive and specific detection of saccharide species based on fluorescence: update from 2016

Abstract

Increasing evidence supports the critical role of saccharides in various pathophysiological steps of tumor progression, where they regulate tumor proliferation, invasion, hematogenic metastasis, and angiogenesis. The identification and recognition of these saccharides provide a solid foundation for the development of targeted drug preparations, which are however not fully understood due to their complex and similar structures. In order to achieve fluorescence sensing of saccharides, extensive research has been conducted to design molecular probes and nanoparticles made of different materials. This paper aims to provide in-depth discussion of three main topics that cover the current status of the carbohydrate sensing based on the fluorescence sensing mechanism, including a phenylboronic acid-based sensing platform, non-boronic acid entities, as well as an enzyme-based sensing platform. It also highlights efforts made to understand the recognition mechanisms and improve the sensing properties of these systems. Finally, we present the challenge of achieving high selectivity and sensitivity recognition of saccharides, and suggest possible future avenues for exploration. Graphical Abstract

Recent advances in nanopore-based analysis for carbohydrates and glycoconjugates

“…Saccharides, also known as carbohydrates, are the primary source of energy for most living systems and are the basic building blocks of glycans, polysaccharides, nucleic acids, glycopeptides, and glycolipids. 144 Glucose detection has an important application in the diagnosis of diabetes. Glycans play an important role in physiology and pathology such as bacterial and viral infections, inflammation, Alzheimer's disease, etc.…”

Molecular two-point recognition of fructosyl valine and fructosyl glycyl histidine in water by fluorescent Zn(ii)-terpyridine complexes bearing boronic acids

“…28 In the last few decades, phenylboronic acid fluorophores have been demonstrated to be an outstanding tool for recognizing and sensing monosaccharides, 36 catechol-based neurotransmitters, 37 nucleotides, 38 sialic acid, 39 glucosamine, 40 ginsenosides, 41 glycated hemoglobin, 42 and in general, 1,2-dihydroxy-substituted derivatives. 33,43 However, the recognition of fructosyl amino acids (Amadori products) 44 remains largely unexplored. In principle, it should be possible to have a selective optical chemosensor for FV by using a fluorescent receptor with multiple and high-affinity binding sites for FV or target derivatives.…”

Water-soluble fluorescent chemosensor for sorbitol based on a dicationic diboronic receptor. Crystal structure and spectroscopic studies

“…In recent decades, the use of boronic acid derivatives has been proven to be an outstanding strategy for the recognition of saccharides, 12–17 glucosamine, 18 catecholamines, 19 nucleotides, 20 ginsenosides, 21 sialic acid, 22 glycated hemoglobin 23 and in general, 1,2-dihydroxy-substituted compounds. 24 …”

“…11 In recent decades, the use of boronic acid derivatives has been proven to be an outstanding strategy for the recognition of saccharides, [12][13][14][15][16][17] glucosamine, 18 catecholamines, 19 nucleotides, 20 ginsenosides, 21 sialic acid, 22 glycated hemoglobin 23 and in general, 1,2-dihydroxy-substituted compounds. 24 The affinity of phenylboronic acids towards 1,2-diol derivatives is primarily induced by the reversible formation of diol-boronic ester in an sp 2 hybridization, which results in increasing the Lewis acidity of the boron atom and subsequent fast conversion to the diol-boronate ester with an sp 3 hybridization. 25,26 In principle, the binding strength of boronic acid-diol ester depends on the orientation of the target analyte's hydroxyl groups, 27 the acidity of the boronic acid, 2 and the inuence of substituent groups that can stabilize the sp 3 -boronate ester.…”