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Recent development of boronic acid-based fluorescent sensors.

ABSTRACT: As Lewis acids, boronic acids can bind with 1,2- or 1,3-diols in aqueous solution reversibly and covalently to form five or six cyclic esters, thus resulting in significant fluorescence changes. Based on this phenomenon, boronic acid compounds have been well developed as sensors to recognize carbohydrates or other substances. Several reviews in this area have been reported before, however, novel boronic acid-based fluorescent sensors have emerged in large numbers in recent years. This paper reviews new boron-based sensors from the last five years that can detect carbohydrates such as glucose, ribose and sialyl Lewis A/X, and other substances including catecholamines, reactive oxygen species, and ionic compounds. And emerging electrochemically related fluorescent sensors and functionalized boronic acid as new materials including nanoparticles, smart polymer gels, and quantum dots were also involved. By summarizing and discussing these newly developed sensors, we expect new inspiration in the design of boronic acid-based fluorescent sensors.

SUBMITTER: Fang G

PROVIDER: S-EPMC9084483 | biostudies-literature | 2018 Aug

REPOSITORIES: biostudies-literature

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Recent development of boronic acid-based fluorescent sensors.

Fang Guiqian G Wang Hao H Bian Zhancun Z Sun Jie J Liu Aiqin A Fang Hao H Liu Bo B Yao Qingqiang Q Wu Zhongyu Z

RSC advances 20180820 51

As Lewis acids, boronic acids can bind with 1,2- or 1,3-diols in aqueous solution reversibly and covalently to form five or six cyclic esters, thus resulting in significant fluorescence changes. Based on this phenomenon, boronic acid compounds have been well developed as sensors to recognize carbohydrates or other substances. Several reviews in this area have been reported before, however, novel boronic acid-based fluorescent sensors have emerged in large numbers in recent years. This paper revi ...[more]

PMID: 35548017

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Project description:Photophysical data and orbital energy levels (from electrochemistry) were compared for molecules with the same BODIPY acceptor part (red) and perpendicularly oriented xanthene or BODIPY donor fragments (green). Transfer of energy, hence the photophysical properties of the cassettes, including the pH dependent fluorescence in the xanthene-containing molecules, correlates with the relative energies of the frontier orbitals in these systems. Intracellular sensing of protons is often achieved via sensors that switch off completely at certain pH values, but probes of this type are not easy to locate inside cells in their "off-state". A communication from these laboratories (J. Am. Chem. Soc., 2009, 131, 1642-3) described how the energy transfer cassette 1 could be used for intracellular imaging of pH. This probe is fluorescent whatever the pH, but its exact photophysical properties are governed by the protonation states of the xanthene donors. This work was undertaken to further investigate correlations between structure, photophysical properties, and pH for energy transfer cassettes. To achieve this, three other cassettes 2-4 were prepared: another one containing pH-sensitive xanthene donors (2) and two "control cassettes" that each have two BODIPY-based donors (3 and 4). Both the cassettes 1 and 2 with xanthene-based donors fluoresce red under slightly acidic conditions (pH < ?6) and green when the medium is more basic (>?7), whereas the corresponding cassettes with BODIPY donors give almost complete energy transfer regardless of pH. The cassettes that have BODIPY donors, by contrast, show no significant fluorescence from the donor parts, but the overall quantum yields of the cassettes when excited at the donor (observation of acceptor fluorescence) are high (ca. 0.6 and 0.9). Electrochemical measurements were performed to elucidate orbital energy level differences between the pH-fluorescence profiles of cassettes with xanthene donors, relative to the two with BODIPY donors. These studies confirm energy transfer in the cassettes is dramatically altered by analytes that perturb relative orbital levels. Energy transfer cassettes with distinct fluorescent donor and acceptor units provide a new, and potentially useful, approach to sensors for biomedical applications.

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Recent development of boronic acid-based fluorescent sensors.

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Recent development of boronic acid-based fluorescent sensors.

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