Boronic acid complexes with amino phenolic N,O-ligands and their use for non-covalent protein fluorescence labeling

Martínez‐Aguirre, Mayte A.; Álamo, Marcos Flores; Trejo-Huizar, Karla Elisa; Yatsimirsky, Anatoly K.

doi:10.1016/j.bioorg.2021.104993

Cited by 5 publications

(3 citation statements)

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“…The decrease in K tet for 1 as compared to PBA means that the relative affinity of alkoxide groups of diols to the boron atom in comparison with hydroxide anions is smaller in 1 than in PBA. An opposite tendency was observed for tetrahedral complexes of amino phenolic N,O-ligands with boronic acids, which demonstrated a larger K tet for 1 than for PBA . Thus, the Lewis acidity of 1 is manifested differently for different ligands, which is a common situation with stability of Lewis acid–base pairs, and one of the aspects of this study is to find out how the Lewis acidity of 1 is manifested toward anions of variable basicity and structure.…”

Section: Introductionmentioning

confidence: 89%

“…An opposite tendency was observed for tetrahedral complexes of amino phenolic N,O-ligands with boronic acids, which demonstrated a larger K tet for 1 than for PBA. 12 Thus, the Lewis acidity of 1 is manifested differently for different ligands, which is a common situation with stability of Lewis acid−base pairs, 13 and one of the aspects of this study is to find out how the Lewis acidity of 1 is manifested toward anions of variable basicity and structure. It appeared also that 1 still was able to bind many anions through the hydrogen bonding via its single B-OH group without any contribution from the coordinate bonding to the boron atom.…”

Section: ■ Introductionmentioning

confidence: 99%

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Anion Recognition by Benzoxaborole

et al. 2022

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The binding types (H-bonding or coordinate) and stability constants for complexes of 11 mono- and di-anions with benzoxaborole (1) were determined by 1H and 11B NMR titrations in DMSO or MeCN. Compared to phenylboronic acid (PBA), 1 is a stronger Lewis acid and a poorer H-bond donor with only one B-OH group, which is expected therefore to recognize anions mostly through the coordinate bonding. This is the case however only with F–, HPO4 2–, and PhPO3 2– anions, which are coordinately bonded to 1, and partially with SO4 2–, which forms only the H-bonded complex with PBA, but both H-bonded and coordinate complexes with 1. The majority of tested anions (AcO–, PhPO3H–, (PhO)2PO2 –, Cl–, and Br–) form H-bonded complexes with both 1 and PBA, whereas H2PO4 – changes the binding mode from coordinate for PBA to H-bonded for 1. The preferable binding type for each anion is confirmed by calculations of DFT-optimized structures of the anion complexes of 1. The preferable binding type can be rationalized considering the effects of the steric hindrance, more significant for the coordinate bonding, and of increased anion basicity, which is favorable for both binding types, but enhances the strength of coordinate bonding more significantly than the strength of H-bonding.

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Section: Introductionmentioning

confidence: 89%

Section: ■ Introductionmentioning

confidence: 99%

Anion Recognition by Benzoxaborole

et al. 2022

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“…Herein, we aimed to develop a novel sensor compound that emits strong fluorescence with a high quantum yield immediately after reacting with boronic acid. Specifically, we selected 2-(2-hydroxyphenyl)-1 H -benzimidazole (HPBI), which rapidly reacts with boronic acid and emits strong fluorescence regardless of forming a complex with boronic acid [ 23 , 24 ] as the skeleton of a fluorescence sensor. To achieve an off/on fluorescence property, we introduced an electron-donating moiety to the skeleton to suppress the fluorescence before complexation with boronic acid [ 25 ].…”

Section: Introductionmentioning

confidence: 99%

Development of a 2-(2-Hydroxyphenyl)-1H-benzimidazole-Based Fluorescence Sensor Targeting Boronic Acids for Versatile Application in Boron Neutron Capture Therapy

Kondo

Takada

Hagimori

et al. 2023

Cancers

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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.

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