Using Quenching Kinetics and Thermodynamics of Amino-Fluorophores as Empirical Tools for Predicting Boronic Acid Sensors Suitable for Use in Physiological Conditions

2011 ◽  
Vol 64 (11) ◽  
pp. 1438 ◽  
Author(s):  
Nicholas McGregor ◽  
Christophe Pardin ◽  
W. G. Skene
Keyword(s):  
Electron Transfer ◽  
Fluorescence Quenching ◽  
Boronic Acid ◽  
Sulfonic Acid ◽  
Phenylboronic Acid ◽  
Water Soluble ◽  
Time Resolved ◽  
Diffusion Limited ◽  
Phenylboronic Acids ◽  
Acid Sensors

A series of water-soluble 1-amino-naphthalenes and 2-amino-fluorenes are prepared. These serve as model fluorophores for measuring the thermodynamics and kinetics of fluorescence quenching with phenylboronic acids and aliphatic amines. Steady-state and time-resolved fluorescence quenching kinetics are investigated using the Stern–Volmer method. Diffusion limited quenching constants and exergonic thermodynamics of electron transfer are derived for the 5-amino-1-napthol and 2-aminofluorene derivatives with phenylboronic acid and/or an aliphatic imine. No quenching and endergonic thermodynamics or electron transfer are observed for 5-sulfonamide, 5-sulfonic acid, or 5-hydroxy-7-sulfonic acid aminonaphthalene derivatives. Boronic acid sensors synthesized from these aminofluorophores by reductive amination with 2-formylphenylboronic acid undergo fluorescence revival in the presence of saccharides only when the fluorophore demonstrates diffusion limited quenching kinetics and exergonic thermodynamics of electron transfer with the boronic acid or imine quenchers. Thus, these two properties are suitable empirical tools for predicting saccharide-induced fluorescence revival of boronic acid sensors.

scholarly journals The Role of Electron Transfer in the Fragmentation of Phenyl and Cyclohexyl Boronic Acids

2019 ◽  
Vol 20 (22) ◽  
pp. 5578 ◽  
Author(s):  
Ana Lozano ◽  
Beatriz Pamplona ◽  
Tymon Kilich ◽  
Marta Łabuda ◽  
Mónica Mendes ◽  
...  
Keyword(s):  
Electron Transfer ◽  
Boronic Acid ◽  
Theoretical Calculations ◽  
Phenylboronic Acid ◽  
Negative Ions ◽  
Potassium Atom ◽  
Negative Ion ◽  
Fragmentation Pattern ◽  
Unimolecular Decomposition ◽  
Wide Range

In this study, novel measurements of negative ion formation in neutral potassium-neutral boronic acid collisions are reported in electron transfer experiments. The fragmentation pattern of phenylboronic acid is comprehensively investigated for a wide range of collision energies, i.e., from 10 to 1000 eV in the laboratory frame, allowing some of the most relevant dissociation channels to be probed. These studies were performed in a crossed molecular beam set up using a potassium atom as an electron donor. The negative ions formed in the collision region were mass analysed with a reflectron time-of-flight mass spectrometer. In the unimolecular decomposition of the temporary negative ion, the two most relevant yields were assigned to BO− and BO2−. Moreover, the collision-induced reaction was shown to be selective, i.e., at energies below 100 eV, it mostly formed BO−, while at energies above 100 eV, it mostly formed BO2−. In order to further our knowledge on the complex internal reaction mechanisms underlying the influence of the hybridization state of the boron atom, cyclohexylboronic acid was also investigated in the same collision energy range, where the main dissociation channel yielded BO2−. The experimental results for phenyl boronic acid are supported by ab initio theoretical calculations of the lowest unoccupied molecular orbitals (LUMOs) accessed in the collision process.

scholarly journals Fast and Sensitive Bacteria Detection by Boronic Acid Modified Fluorescent Dendrimer

Sensors ◽  
2021 ◽  
Vol 21 (9) ◽  
pp. 3115
Author(s):  
Ayame Mikagi ◽  
Riho Tsurufusa ◽  
Yuji Tsuchido ◽  
Takeshi Hashimoto ◽  
Takashi Hayashita
Keyword(s):  
Boronic Acid ◽  
Electrostatic Interactions ◽  
Detection Method ◽  
Phenylboronic Acid ◽  
Bacteria Detection ◽  
Gram Negative Bacteria ◽  
Recognition Method ◽  
Dansyl Group ◽  
Colony Forming Units ◽  
Phenylboronic Acids

This study reports a novel, fast, easy, and sensitive detection method for bacteria which is urgently needed to diagnose infections in their early stages. Our work presents a complex of poly(amidoamine) dendrimer modified by phenylboronic acid and labeled by a fluorescent dansyl group (Dan-B8.5-PAMAM). Our system detects bacteria in 20 min with a sensitivity of approximately 104 colony-forming units (CFU)·mL−1. Moreover, it does not require any peculiar technical skills or expensive materials. The driving force for bacteria recognition is the binding between terminal phenylboronic acids on the probe and bacteria’s surface glycolipids, rather than electrostatic interactions. The aggregation caused by such binding reduces fluorescence. Even though our recognition method does not distinguish between live or dead bacteria, it shows selective antibacterial activity towards Gram-negative bacteria. This study may potentially contribute a new method for the convenient detection and killing of bacteria.

scholarly journals Amination-reduction reaction as simple protocol for potential boronic molecular receptors. Insight in supramolecular structure directed by weak interactions

2011 ◽  
Vol 9 (2) ◽  
pp. 199-205 ◽  
Author(s):  
Agnieszka Adamczyk-Woźniak ◽  
Izabela Madura ◽  
Alicja Pawełko ◽  
Andrzej Sporzyński ◽  
Anna Żubrowska ◽  
...  
Keyword(s):  
Boronic Acid ◽  
Weak Interactions ◽  
Layer Structure ◽  
Phenylboronic Acid ◽  
Reduction Reaction ◽  
Significant Rise ◽  
Molecular Receptors ◽  
Simple Protocol ◽  
Phenylboronic Acids ◽  
Insight Into

AbstractThe synthesis of the potential molecular receptors in the amination-reduction reaction has been investigated within the model system comprising (2-formylphenyl)boronic acid and morpholine. The 3-amine substituted benzoxaborole was identified to be the intermediate of the synthesis and the unsubstituted benzoxaborole as the by-product resulting from reduction of the starting material. The insight into the reactivity of the starting materials as well as the intermediate benzoxaborole enabled significant rise in the yield of 2-(aminomethyl) phenylboronic acids synthesis. The solid state structure of 2-(piperidylmethyl)phenylboronic acid has been re-determined, and the description of the molecule and the crystal is given. The supramolecular layer structure directed by the weak C-H…O and C-H…π interactions was identified and scrutinized based on the geometry and Hirshfeld surface analyses

A diboronic acid fluorescent sensor for selective recognition of d-ribose via fluorescence quenching

2019 ◽  
Vol 43 (11) ◽  
pp. 4385-4390 ◽  
Author(s):  
Hao Wang ◽  
Guiqian Fang ◽  
Hongxiao Wang ◽  
Jindi Dou ◽  
Zhancun Bian ◽  
...  
Keyword(s):  
Fluorescence Quenching ◽  
Boronic Acid ◽  
Fluorescent Sensor ◽  
Water Soluble ◽  
Selective Recognition

Herein we reported a novel boronic acid-based water-soluble sensor. It decreased the fluorescence by 50% when combined with 0.0146 M of d-ribose, while increased or not changed obviously after binding to other carbohydrates.

scholarly journals Fluorescence Quenching Studies on the Interactions between Chosen Fluoroquinolones and Selected Stable TEMPO and PROXYL Nitroxides

2021 ◽  
Vol 22 (2) ◽  
pp. 885
Author(s):  
Krzysztof Żamojć ◽  
Irena Bylińska ◽  
Wiesław Wiczk ◽  
Lech Chmurzyński
Keyword(s):  
Fluorescence Quenching ◽  
Rate Constants ◽  
Quenching Rate ◽  
Time Resolved ◽  
Radiative Processes ◽  
Diffusion Limited ◽  
Fluoroquinolone Antibiotics ◽  
Quenching Efficiency ◽  
Bimolecular Quenching ◽  
The Impact

The influence of the stable 2,2,6,6-tetramethylpiperidinyl-N-oxyl (TEMPO) nitroxide and its six C4-substituted derivatives, as well as two C3-substituted analogues of 2,2,5,5-tetramethylpyrrolidynyl-N-oxyl (PROXYL) nitroxide on the chosen fluoroquinolone antibiotics (marbofloxacin, ciprofloxacin, danofloxacin, norfloxacin, enrofloxacin, levofloxacin and ofloxacin), has been examined in aqueous solutions by UV absorption as well as steady-state and time-resolved fluorescence spectroscopies. The mechanism of fluorescence quenching has been specified and proved to be purely dynamic (collisional) for all the studied systems, which was additionally confirmed by temperature dependence experiments. Moreover, the selected quenching parameters—that is, Stern–Volmer quenching constants and bimolecular quenching rate constants—have been determined and explained. The possibility of electron transfer was ruled out, and the quenching was found to be diffusion-limited, being a result of the increase in non-radiative processes. Furthermore, as the chosen nitroxides affected the fluorescence of fluoroquinolone antibiotics in different ways, an influence of the structure and the type of substituents in the molecules of both fluoroquinolones and stable radicals on the quenching efficiency has been determined and discussed. Finally, the impact of the solvent’s polarity on the values of bimolecular quenching rate constants has been explained. The significance of the project comes from many applications of nitroxides in chemistry, biology and industry.

Fluorescence quenching of a biologically active boronic acid derivative by aniline in different solvents

2018 ◽  
Vol 96 (6) ◽  
pp. 603-609 ◽  
Author(s):  
Raveendra M. Melavanki
Keyword(s):  
Fluorescence Quenching ◽  
Boronic Acid ◽  
Biologically Active ◽  
Fluorescent Properties ◽  
Quenching Rate ◽  
Diffusion Limited ◽  
Fluorescence Measurements ◽  
Wide Range ◽  
Boronic Acid Derivatives ◽  
Fluorescent Molecules

Boronic acid derivatives are novel biologically active fluorescent molecules with numerous applications in various fields. A study of their fluorescent properties reveals some information that can be utilized in sensor design. One such study is fluorescence quenching. Here fluorescence quenching of 2-methoxypyridin-3-yl-3-boronic acid (2MPBA) in different solvents of a wide range of polarities has been carried out at room temperature by steady state fluorescence measurements. Aniline is used as the quencher. The positive deviation observed in Stern–Volmer (S-V) plots is analyzed using different quenching models. Various quenching parameters like S-V constant (KSV), quenching rate parameter (kq), volume constant (V), and kinetic distance (r) have been estimated using extended S-V equations. KSV is found to vary from 12.94 to 62.49 (mol/L)−1 with respect to solvents. From the calculated values of these parameters it is concluded that the static quenching mechanism is active in the studied system. However the reactions are diffusion-limited, which is confirmed by invoking the finite sink approximation model.

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