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Development and Elucidation of a Novel Fluorescent Boron-Sensor for the Analysis of Boronic Acid-Containing Compounds.

ABSTRACT: Novel boron-containing drugs have recently been suggested as a new class of pharmaceuticals. However, the majority of current boron-detection techniques require expensive facilities and/or tedious pretreatment methods. Thus, to develop a novel and convenient detection method for boron-based pharmaceuticals, imine-type boron-chelating-ligands were previously synthesized for use in a fluorescent sensor for boronic acid containing compounds. However, the fluorescence quantum yield of the imine-type sensor was particularly low, and the sensor was easily decomposed in aqueous media. Thus, in this paper, we report the development of a novel, convenient, and stable fluorescent boron-sensor based on O- and N-chelation (i.e., 2-(pyridine-2yl)phenol), and a corresponding method for the quantitative and qualitative detection of boronic acid-containing compounds using this commercially available sensor is presented.

SUBMITTER: Hattori Y

PROVIDER: S-EPMC5677422 | biostudies-literature | 2017 Oct

REPOSITORIES: biostudies-literature

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Development and Elucidation of a Novel Fluorescent Boron-Sensor for the Analysis of Boronic Acid-Containing Compounds.

Hattori Yoshihide Y Ogaki Takuya T Ishimura Miki M Ohta Yoichiro Y Kirihata Mitsunori M

Sensors (Basel, Switzerland) 20171024 10

Novel boron-containing drugs have recently been suggested as a new class of pharmaceuticals. However, the majority of current boron-detection techniques require expensive facilities and/or tedious pretreatment methods. Thus, to develop a novel and convenient detection method for boron-based pharmaceuticals, imine-type boron-chelating-ligands were previously synthesized for use in a fluorescent sensor for boronic acid containing compounds. However, the fluorescence quantum yield of the imine-type ...[more]

PMID: 29064412

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Project description:Simple Summary In boron neutron capture therapy (BNCT), the amount and localization of boron-10 atoms in tumor tissues directly determine the therapeutic effect. This study developed a novel fluorescence sensor, BITQ, to analyze boronic acid agents used for BNCT. Mixing BITQ and a representative 10B-labeled boronoagent, BPA, immediately produced significant fluorescence in a highly quantitative and selective manner. BITQ enabled the visualization of BPA distribution within a living cell and quantified the concentration of BPA in mouse blood to a degree comparable with that of current methods. This study highlights the highly effective properties of BITQ as a versatile fluorescence sensor for analyzing boronic acid agents. Abstract Boron neutron capture therapy (BNCT) is an attractive approach to treating cancers. Currently, only one 10B-labeled boronoagent (Borofalan, BPA) has been approved for clinical BNCT in Japan, and methods for predicting and measuring BNCT efficacy must be established to support the development of next-generation 10B-boronoagents. Fluorescence sensors targeting boronic acids can achieve this because the amount and localization of 10B in tumor tissues directly determine BNCT efficacy; however, current sensors are nonoptimal given their slow reaction rate and weak fluorescence (quantum yield < 0.1). Herein, we designed and synthesized a novel small molecular-weight fluorescence sensor, BITQ, targeting boronic acids. In vitro qualitative and quantitative properties of BITQ were assessed using a fluorophotometer and a fluorescence microscope together with BPA quantification in blood samples. BITQ exhibited significant quantitative and selective fluorescence after reacting with BPA (post-to-pre-fluorescence ratio = 5.6; quantum yield = 0.53); the fluorescence plateaued within 1 min after BPA mixing, enabling the visualization of intracellular BPA distribution. Furthermore, BITQ quantified the BPA concentration in mouse blood with reliability comparable with that of current methods. This study identifies BITQ as a versatile fluorescence sensor for analyzing boronic acid agents. BITQ will contribute to 10B-boronoagent development and promote research in BNCT.

Dataset Information

Development and Elucidation of a Novel Fluorescent Boron-Sensor for the Analysis of Boronic Acid-Containing Compounds.

Publications

Development and Elucidation of a Novel Fluorescent Boron-Sensor for the Analysis of Boronic Acid-Containing Compounds.

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