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Keywords: sugar sensing, boronic acid.
The interaction between a boronic acid and a diol is known to be one of the strongest single-pair reversible functional group interactions in an aqueous environment. During the last decade, much effort has been devoted to the development of boronic acid-based sensors for carbohydrates and other diol-containing compounds, and a great deal of progress has been made in this area. However, there are still several fundamental issues that have not been addressed, which hinder the development of such kind of sensors. For example, several factors have long been recognized as important in influencing the binding affinity of boronic acids to diol-containing compound, but there has never been a systematic examination of the relationship among those factors. To address these issues, in Chapter 2 we carefully examined a series of 25 arylboronic acids with various substituents and selected binding affinities with a series of diols at varying pH value. We have found that (1) the pKa of monosubstituted boronic acids can be predicted based on the substituent effect using a Hammet plot; (2) the common belief that boronic acids with lower pKa's have greater binding affinities at neutral pH is not always true; and (3) the optimal pH for binding is not always above the pKa of the boronic acid, instead it is related to the pKa values of both the boronic acid and the diol, although in a manner that cannot be readily predicted. Second, critical to the construction of fluorescent sensors for carbohydrates is the availability of practical fluorescent reporters that respond to the binding event with significant fluorescence intensity changes under physiological conditions. So far a few boronic acid reporters have been described in the literature, but those reporters have undesirable properties such as low water solubility and poor photochemical stability. As described in chapter 2, we have discovered a novel type of fluorescent carbohydrate reporter, 8-quinolineboronic acid (8-QBA). It showed.
The desire to quantify the presence of analytes within diverse physiological, environmental and industrial systems has led to the development of many novel detection methods. In this arena, saccharide analysis has exploited the pair-wise interaction between boronic acids and saccharides. Boronic Acids in Saccharide Recognition provides a comprehensive review and critical analysis of the current developments in this field. It also assesses the potential of this innovative approach, outlining future lines of research and possible applications. Topics include: the molecular recognition of saccharides, the complexation of boronic acids with saccharides, fluorescent sensors and the modular construct of fluorescent sensors, further sensory systems for saccharide recognition and an extensive bibliography. This high level book is ideal for researchers both academic and industrial who require a comprehensive overview of the subject.
This book contains contributions from interdisciplinary scientists to collectively address the issue of targeting carbohydrate recognition for the development of novel therapeutic and diagnostic agents. The book covers (1) biological problems involving carbohydrate recognition, (2) structural factors mediating carbohydrate recognition, (3) design and synthesis of lectin mimics that recognize carbohydrate ligands with high specificity and affinity, and (4) modulation of biological and pathological processes through carbohydrate recognition.
Boronic acid functional group is used widely as a recognition moiety for the development of sensors for saccharides, due to its unique strong and reversible interaction with diols. The fluorescence and/or UV spectroscopic method are the easiest and most common methods to signal the binding event of these receptors (boronic acid compounds) with saccharides. This dissertation consists of three major parts. First, a series of fluorescent diboronic acid compounds with an anthracene PET (photoinduced electron transfer) system were designed and synthesized (Chapter 1). These compounds can be used as sensors for cell surface carbohydrates, such as sialyl Lewis X (sLex), which are known to be biomarkers for certain cancers. Among these diboronic acid compounds, the lead compound was found to fluorescently label cells expressing sLex selectively. The structure of the lead compound was modified and new conformationally constrained analogs were synthesized. Second, the mechanism of the fluorescent photoinduced electron transfer (PET) system, which was used in our design of fluorescent sensors for sLex, was examined in detail using both density functional calculation (DFT) and model compound fluorescence studies. Based on the study, a new hydrolysis mechanism was proposed (Chapter 2 and 3). Third, novel nitrophenol-based boronic acid reporter compounds, which show significant UV spectroscopic changes upon addition of sugars at neutral pH in aqueous solution, were designed and synthesized (Chapter 4). The design took advantage of the ability of a boronic acid functional group to modulate the pKa and/or the electron density of a neighboring group. These reporter compounds can be used as the recognition and signaling unit for the construction of polyboronic acid sensors for selective and specific recognitions of saccharides of biological significance.
An essential reference for any laboratory working in the analytical fluorescence glucose sensing field. The increasing importance of these techniques is typified in one emerging area by developing non-invasive and continuous approaches for physiological glucose monitoring. This volume incorporates analytical fluorescence-based glucose sensing reviews, specialized enough to be attractive to professional researchers, yet appealing to a wider audience of scientists in related disciplines of fluorescence.
In Vivo Glucose Sensing is a key reference for scientists and engineers working on the development of glucose sensing technologies for the management of diabetes and other medical conditions. It discusses the analytical chemistry behind the strategies currently used for measuring glucose in vivo. It focuses on analyzing samples in the real world and discusses the biological complexities that make glucose sensing difficult. Covering current implantable devices, next-generation implantable sensing methods, and non-invasive methods for measuring glucose, this book concludes with an overview of possible applications other than diabetes.
For the first time, the whole field of organoboronic acids is presented in one comprehensive handbook. Professor Dennis Hall, a rising star within the community, covers all aspects of this important substance class, including applications in chemistry, biology and medicine. Starting with an introduction to the structure, properties, and preparation of boronic acid derivatives, together with an overview of their reactions and applications, the book goes on to look at metal-catalyzed borylation of alkanes and arenas, coupling reactions and rhodium-catalyzed additions of boronic acids to alkenes and carbonyl compounds. There follows chapters on copper-promoted C-O and C-N cross-coupling of boronic acids, recent applications in organic synthesis, as well as alpha-haloalkylboronic esters in asymmetric synthesis. Later sections deal with cycloadditions, organoboronic acids, oxazaborolidines as asymmetric inducers, and boronic acid based receptors and sensors. The whole is rounded off with experimental procedures, making this invaluable reading for organic, catalytic and medicinal chemists, as well as those working in organometallics.
A new focus on glycoscience, a field that explores the structures and functions of sugars, promises great advances in areas as diverse as medicine, energy generation, and materials science, this report finds. Glycans-also known as carbohydrates, saccharides, or simply as sugars-play central roles in many biological processes and have properties useful in an array of applications. However, glycans have received little attention from the research community due to a lack of tools to probe their often complex structures and properties. Transforming Glycoscience: A Roadmap for the Future presents a roadmap for transforming glycoscience from a field dominated by specialists to a widely studied and integrated discipline, which could lead to a more complete understanding of glycans and help solve key challenges in diverse fields.
Although noninvasive, continuous monitoring of glucose concentration in blood and tissues is one of the most challenging areas in medicine, a wide range of optical techniques has recently been designed to help develop robust noninvasive methods for glucose sensing. For the first time in book form, the Handbook of Optical Sensing of Glucose in Biological Fluids and Tissues analyzes trends in noninvasive optical glucose sensing and discusses its impact on tissue optical properties. This handbook presents methods that improve the accuracy in glucose prediction based on infrared absorption spectroscopy, recent studies on the influence of acute hyperglycemia on cerebral blood flow, and the correlation between diabetes and the thermo-optical response of human skin. It examines skin glucose monitoring by near-infrared spectroscopy (NIR), fluorescence-based glucose biosensors, and a photonic crystal contact lens sensor. The contributors also explore problems of polarimetric glucose sensing in transparent and turbid tissues as well as offer a high-resolution optical technique for noninvasive, continuous, and accurate blood glucose monitoring and glucose diffusion measurement. Written by world-renowned experts in biomedical optics and biophotonics, this book gives a complete, state-of-the-art treatise on the design and applications of noninvasive optical methods and instruments for glucose sensing.