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On-off-on relay fluorescence recognition of ferric and fluoride ions based on indicator displacement in living cells
摘要： A new boronic acid derivative functionalized with a 4-(3-(4-(4,5-diphenyl-1H-imidazol-2-yl)phenyl)-1,2,4-oxadiazol-5-yl)phenyl (IOP) moiety was synthesized for use as a sequential “on-off-on”-type relay fluorescence probe for Fe3+ ions and F? ions with high selectivity and sensitivity under physiological conditions. The introduction of Fe3+ to IOP boronic acid (IOPBA) formed an Fe3+-IOPBA complex, which led to quenching of the blue fluorescence intensity at 458 nm. The lowest-energy conformation of IOPBA was theoretically predicted to adopt an extended structure, and the Fe3+ ion in the Fe3+-IOPBA complex was coordinated to two phenyl groups to form a p-complex. Upon addition of F? to the Fe3+-IOPBA complex, the original fluorescence was recovered due to formation of [FeF6]3?, resulting in “on-off-on”-type sensor behavior. IOPBA showed high selectivity towards Fe3+ among other cations. Moreover, the Fe3+-IOPBA complex showed specific selectivity towards F?, with other cations and anions not interfering with detection. Both sensing processes showed 1:1 stoichiometry with binding constants of 6.87 × 106 and 4.49 × 106 mol–1 L for Fe3+ with IOPBA and F? with Fe3+-IOPBA, respectively. The limits of detection for Fe3+ and F? were 10 and 1 nM, respectively. The proposed method was successfully applied in real water samples. Furthermore, the probe had low cytotoxicity and was successfully used as a bioimaging reagent to detect intracellular Fe3+ and F? in living HeLa cells.
关键词： Fluorescence imaging,On-off-on sensor,Probe for Fe3+ ions and F? ions,Living HeLa cells,Boronic acid derivative
更新于2025-11-21 11:08:12
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Selective and Sensitive Sensing of Hydrogen Peroxide by a Boronic Acid Functionalized Metal–Organic Framework and Its Application in Live-Cell Imaging
摘要： A new boronic acid functionalized Zr(IV) metal?organic framework having the capability of sensing H2O2 in live cells is reported. The Zr-MOF bears a UiO-66 structure and contains 2-boronobenzene-1,4-dicarboxylic acid (BDC-B(OH)2) as a framework linker. The activated Zr-UiO-66-B(OH)2 compound (called 1′) is highly selective for the ?uorogenic detection of H2O2 in HEPES bu?er at pH 7.4, even in the presence of interfering ROS (ROS = reactive oxygen species) and other biologically relevant analytes. The ?uorescent probe was found to display extraordinary sensitivity for H2O2 (detection limit 0.015 μM) in HEPES bu?er, which represents a lower value in comparison to those of the MOF probes documented so far for sensing H2O2 using other analytical methods. Taking advantage of its high selectivity and sensitivity for H2O2 in HEPES bu?er, the probe was successfully employed for the imaging of intracellular H2O2. Imaging studies with MDAMB-231 cells revealed the emergence of bright blue ?uorescence after loading with probe 1′ and subsequent treatment with H2O2 solution.
关键词： Zr(IV) metal?organic framework,boronic acid,live-cell imaging,fluorescent probe,H2O2 sensing
更新于2025-09-23 15:21:21
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d-Glucose recognition based on phenylboronic acid-functionalized polyoligomeric silsesquioxane fluorescent probe
摘要： We report a new strategy to synthesize hybrid fluorescent nanosensors consisting of phenylboronic acid-functionalized POSS (POSS–PBA) and diol-modified 8-anilino-1-naphthalenesulfonic acid (ANSA (a fluorescent dye)) for the detection of the biologically important D-glucose. The probe was characterized by FT-IR and 1H-NMR analyses, and the photoluminescence intensity was measured under various conditions to confirm its glucose sensing ability. Our POSS-APBA-dye probe could detect glucose at concentrations of 0–20 mg/mL, with a good linear relationship even at low glucose concentrations of 0–1 mg/mL. The properties of the POSS-APBA-dye probe were evaluated and compared with those of an APBA-dye probe. The glucose sensing ability of our POSS-APBA-dye probe was largely unaffected by the presence of interfering substances. The probe showed high sensing ability in a pH 5 environment and long-term (approximately 40 days) fluorescence stability.
关键词： polyhedral oligomeric silsesquioxane,glucose sensor,fluorescence probe,boronic acid derivative
更新于2025-09-23 15:21:01
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Towards Detection of Glycoproteins Using Molecularly Imprinted Nanoparticles and Boronic Acid-Modified Fluorescent Probe
摘要： Glycoproteins represent a group of important biomarkers for cancer and other life-threatening diseases. Selective detection of specific glycoproteins is an important step for early diagnosis. Traditional glycoprotein assays are mostly based on lectins, antibodies, and enzymes, biochemical reagents that are costly and require special cold chain storage and distribution. To address the shortcomings of the existing glycoprotein assays, we propose a new approach using protein-imprinted nanoparticles to replace the traditional lectins and antibodies. Protein-imprinted binding sites were created on the surface of silica nanoparticles by copolymerization of dopamine and aminophenylboronic acid. The imprinted nanoparticles were systematically characterized by dynamic light scattering, scanning and transmission electron microscopy, thermogravimetric analysis, Fourier transform infrared spectroscopy, and elemental analysis. A boronic acid-modified fluorescent probe was used to detect the target glycoprotein captured by the imprinted nanoparticles. Using horseradish peroxidase as a model glycoprotein, we demonstrated that the proposed method can be applied to detect target protein containing multiple glycosylation sites. Because of their outstanding stability and low cost, imprinted nanoparticles and synthetic probes are attractive replacements of traditional biochemical reagents to develop simpler, faster, and more cost-effective analytical methods for glycoproteins.
关键词： glycoprotein,molecular imprinting,boronic acid,fluorescent probe
更新于2025-09-19 17:15:36
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Photo-Switchable Boronic Acid Derived Salicylidenehydrazone Enabled by Photochromic Spirooxazine and Fulgide Moieties: Multiple Responses of Optical Absorption, Fluorescence Emission, and Quadratic Nonlinear Optics
摘要： A novel protocol of the boronic acid derived salicylidenehydrazone (BASHY) core being sandwiched by photochromic spirooxazine and fulgide moieties was proposed here to design multistate fluorescent photoswitches with variable nonlinear optical (NLO) responses. Systematic investigations on their optical absorption, fluorescence emission, and static first hyperpolarizabilities (β) were performed using density functional theory (DFT). It was found that the BASHY-based sandwiched series exhibited significant differences of absorption and emission properties between three photoisomers, which were essentially ascribed to the massive changes of corresponding electron transition characteristics quantified by hole–electron descriptors and visualized by electron density difference (EDD) plots. However, the isomerization of fulgide parts in the merocyanine (MC) form of spirooxazine failed to greatly shift maximum absorption/emission wavelengths, due to their high similarity of intrinsic transition features. Furthermore, large β contrasts between three photoisomers were observed, which resulted from significant variations of contributions of spirooxazine and/or fulgide moieties to the total β upon photoisomerization according to β densities. Although the fulgide moiety contributes negatively and positively to spirooxazine (SO) isomers when fulgide switches from close (C-) to open (E-) forms, respectively, their dominant βxxx values with opposite signs are still similar in magnitude, leading to quite close quadratic NLO responses. Therefore, the captivating ternary photoswitches with multiple responses of absorption, emission, and NLO were elaborately built in this context, promising to be applied as multifunctional optical materials in various scientific and technological fields.
关键词： photochromic spirooxazine,fulgide moieties,nonlinear optical (NLO) responses,density functional theory (DFT),boronic acid derived salicylidenehydrazone (BASHY)
更新于2025-09-12 10:27:22