Fluorescent labeling of proteins with amine-specific 1,3,2-(2H)-dioxaborine polymethine dye

Gerasov, Andriy O.; Shandura, Mykola P.; Kovtun, Yuriy P.; Losytskyy, Mykhaylo Yu.; Negrutska, V. V.; Dubey, I. Ya.

doi:10.1016/j.ab.2011.09.018

Cited by 18 publications

(14 citation statements)

References 36 publications

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“…The difluoroboron β-diketonate complex (1,3,2-dioxaborine) is a prominent structural unit of organic dyes, which renders them many appealing photophysical properties, including large molar extinctions, strong and tunable fluorescence both in solutions and in the solid state, and two-photon excited emission . Polymethine dyes comprising the dioxaborine ring are known as highly luminescent and intensely colored fluorophores, widely used in NLO materials, as fluorescent probes for protein, lipid, or DNA labeling, − as fluorescent “turn-on” pH sensors, and molecular rotors. , …”

Section: Introductionmentioning

confidence: 99%

Highly Fluorescent Dianionic Polymethines with a 1,3,2-Dioxaborine Core

et al. 2021

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The difluoroboron β-diketonate ring is ever more used for creating bright polymethine-type fluorophores for the visible and NIR range. Here, we report the synthesis and spectral properties of a series of dianionic cyanine dyes of the rare A1–π–A−π–A1 type, with the central dioxaborine ring (A) embedded into the polymethine chain and various electron-acceptor terminal groups A1. Depending on the nature of the end group, the maxima of their intensive (with molar extinctions up to 380 000 M–1 cm–1) and narrow long-wavelength absorption band lie in the range of 530–770 nm. Their absorption and fluorescence bands are nearly mirror-like and characterized by weak solvatochromism; the marked hypsochromic shifts are observed only when going from polar aprotic solvents to methanol. The designed dianionic dyes have fluorescence quantum yields up to 92 % in the visible range, and even for the NIR dyes, the values of 18–37 % are observed in DMF.

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Section: Introductionmentioning

confidence: 99%

Highly Fluorescent Dianionic Polymethines with a 1,3,2-Dioxaborine Core

et al. 2021

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“…Difluoroboron β‐diketonate complexes, 2,2‐difluoro‐1,3,2‐dioxaborines, are highly luminescent organoboron compounds with many appealing attributes such as large extinction coefficients, bright fluorescence in both solution and the solid state, tunable fluorescent emission, and two‐photon excited fluorescence . Polymethine dyes based on dioxaborines are intensely colored fluorophores widely used in nonlinear optical (NLO) materials, as fluorescence probes for serum albumins, labels for proteins and DNA, and as fluorescent molecular rotors …”

Section: Introductionmentioning

confidence: 99%

D–π–A–π–D Dyes with a 1,3,2‐Dioxaborine Cycle in the Polymethine Chain: Efficient Long‐Wavelength Fluorophores

et al. 2018

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The nitrile group in newly synthesized 5‐cyano‐2,2‐difluoro‐4,6‐dimethyl‐1,3,2‐dioxaborine is shown to significantly increase the acidity of the methyl groups. This allows the cyanine condensation with both methyl groups to form D–π–A–π–D dyes in which the dioxaborine cycle is a part of the polymethine chain. There, the reactivity of the remaining methyl group in the semi‐product is reduced enough to perform the reaction stepwise, giving access to nonsymmetric derivatives. The synthesis of dyes with various electron donor termini [indole, benzothiazole, pyran, 4‐(dialkylamino)phenyl] and with different polymethine chain lengths is reported. The obtained compounds show intense absorption and fluorescence in the red and NIR region, their fluorescence brightness (the product of the molar extinction and the fluorescence quantum yield) attaining a value of 200,000 m–1 cm–1. They are characterized by small‐scale positive solvatochromism, yet their fluorescence quantum yield is much more sensitive to ambient polarity. Time‐dependent (TD)DFT calculations have been performed to study the electronic structure of the new dioxaborines and reveal the nature of the long‐wavelength electronic transitions in those molecules.

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“…Fluorescence techniques are being vastly applied to study proteins, owing to their sensitivity toward the local environment inside the protein. − Tyrosine and tryptophan are the two main fluorescing amino acid residues, which cause intrinsic fluorescence of proteins. In most proteins, the number of these amino acid residues is more than one, and they are located at different parts of the protein.…”

Section: Introductionmentioning

confidence: 99%

Region-Specific Double Denaturation of Human Serum Albumin: Combined Effects of Temperature and GnHCl on Structural and Dynamical Responses

et al. 2018

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In this work, we have investigated the effects of denaturing agents, guanidine hydrochloride (GnHCl) and temperature, on the overall structure, domain-I, and domain-III of human serum albumin (HSA) using circular dichroism (CD) spectroscopy and steady-state, time-resolved fluorescence spectroscopy. We have tagged Cys-34 of HSA, located at domain-I, using N -(7-dimethylamino-4-methylcoumarin-3-yl)iodoacetamide and Tyr-411 of HSA, located at domain-III, using p -nitrophenyl coumarin ester, for this purpose. The CD spectroscopy studies reveal the overall denaturation of the protein. The denaturation follows the expected direction in which the protein is denatured with an increase in the concentration of GnHCl or temperature. The α-helicity of the native state of HSA was found to be 64.2%, and the minimum value of α-helicity was found to be 14.8% in the presence of 6 M GnHCl at room temperature. Steady-state emission studies were carried out on domain-I and domain-III of the protein using site-specific fluorescent tags. The degree of folding of the two domains at different combinations of temperature and GnHCl concentration was calculated and was found to follow a slightly different course of denaturation. Solvation dynamics was found to be quite different for these two domains. The domain-I of HSA has a maximum solvation time of 0.39 ns, and the solvation time tends to decrease with the action of either temperature or GnHCl. On the other hand, the domain-III of HSA showed a much higher solvation time (1.42 ns) and does not show any regular change at higher temperatures or in the presence of GnHCl. This difference could be attributed to the different microenvironment inside the protein cores of the two domains.

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Fluorescent labeling of proteins with amine-specific 1,3,2-(2H)-dioxaborine polymethine dye

Cited by 18 publications

References 36 publications

Highly Fluorescent Dianionic Polymethines with a 1,3,2-Dioxaborine Core

Highly Fluorescent Dianionic Polymethines with a 1,3,2-Dioxaborine Core

D–π–A–π–D Dyes with a 1,3,2‐Dioxaborine Cycle in the Polymethine Chain: Efficient Long‐Wavelength Fluorophores

Region-Specific Double Denaturation of Human Serum Albumin: Combined Effects of Temperature and GnHCl on Structural and Dynamical Responses

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