Boronic acids for fluorescence imaging of carbohydrates

Abstract

"Fluorescence imaging" is a particularly exciting and rapidly developing area of research; the annual number of publications in the area has increased ten-fold over the last decade. The rapid increase of interest in fluorescence imaging will necessitate the development of an increasing number of molecular receptors and binding agents in order to meet the demand in this rapidly expanding area. Carbohydrate biomarkers are particularly important targets for fluorescence imaging given their pivotal role in numerous important biological events, including the development and progression of many diseases. Therefore, the development of new fluorescent receptors and binding agents for carbohydrates is and will be increasing in demand. This review highlights the development of fluorescence imaging agents based on boronic acids a particularly promising class of receptors given their strong and selective binding with carbohydrates in aqueous media.

Glucose‐Sensitive Hydrogel Optical Fibers Functionalized with Phenylboronic Acid

“…[13c] In contrast to the photonic crystal sensors that only expand in z-direction, hydrogel optical fibers expand isotropically. [26] Unlike enzymatic reactions involving glucose oxidase or hexokinase-glucose-6-phosphate dehydrogenase, [34] 3-APBA competitively bind cis diols of carbohydrates ( e.g.…”

“…[6] One of the promising approaches for optical glucose sensors is to covalently incorporate glucose-sensitive chelating agents such as phenylboronic acid (PBA) derivatives [7] into matrixes such as or micro- and nanostructures including holographic thin films, [8] crystalline colloidal arrays, [9] plasmonic nanoantennas, [10] Fabry-Perot cavities, [11] fluorescent dyes, [12] and quantum dots (QDs). [13] Optical monitoring systems have also been developed in the form of solid-state optodes that report on the glucose concentration via refractive index (RI) changes. [14] Recently, solid-state optical fiber glucose sensors comprising of fluorescent diboronic acid receptors have been clinically tested for continuous intravascular glucose monitoring.…”

Coordination Networks Based on Boronate and Benzoxaborolate Ligands

“…For phenylboronic acid (C 6 H 5 -B(OH) 2 ), the pK a is~8.9 (and thus similar to that of boric acid B(OH) 3 ), while for methylboronic acid it is~10.4 [1,18]. The pK a of the benzoxaborole/benzoxaborolate couple is~7.3 due to the cyclic form of the organoboron function.…”

“…Their main use is as reagents in the Miyaura-Suzuki coupling reaction (2010 Nobel Prize), for the formation of C-C bonds. Their reactivity is also of great interest for other fields [2][3][4][5][6], like in organocatalysis [2] and for the development of sensors (detection of carbohydrates, H 2 O 2 , fluoride anions, etc.) [3].…”

“…Their reactivity is also of great interest for other fields [2][3][4][5][6], like in organocatalysis [2] and for the development of sensors (detection of carbohydrates, H 2 O 2 , fluoride anions, etc.) [3]. It has also been shown that some boronic acids can play the role of enzyme inhibitors [6], as is the case for bortezomib (Velcade ® ), an anticancer molecule used for the treatment of multiple myeloma ( Figure 1).…”