Applications of triarylborane materials in cell imaging and sensing of bio-relevant molecules such as DNA, RNA, and proteins

Berger, Sarina M.; Marder, Todd B.

doi:10.1039/d1mh00696g

Cited by 51 publications

(16 citation statements)

References 61 publications

(138 reference statements)

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“…In addition, NIR-absorbing organic π-conjugated materials hold great promise as photothermal agents (PTAs) for photothermal therapy (PTT) owing to their favorable biocompatibility, potential biodegradability, high reproducibility, and accessible structure–property relationships . In this respect, the functionalization of π-conjugated systems with main group elements such as boron is attractive because it offers a means to easily tune the electronic structures and optoelectronic properties . Substitution of carbon–carbon (C–C) covalent bonds with isoelectronic dative B ← N units has emerged as a versatile strategy to adjust the energy levels and band gap of conjugated materials. , In addition, the reversibility of the B ← N dative bonds in such systems is an attractive feature for development of stimuli-responsive materials and molecular switches .…”

Section: Introductionmentioning

confidence: 99%

Near-Infrared-Absorbing B–N Lewis Pair-Functionalized Anthracenes: Electronic Structure Tuning, Conformational Isomerism, and Applications in Photothermal Cancer Therapy

et al. 2022

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B–N-fused dianthracenylpyrazine derivatives are synthesized to generate new low gap chromophores. Photophysical and electrochemical, crystal packing, and theoretical studies have been performed. Two energetically similar conformers are identified by density functional theory calculations, showing that the core unit adopts a curved saddle-like shape (x-isomer) or a zig-zag conformation (z-isomer). In the solid state, the z-isomer is prevalent according to an X-ray crystal structure of a C6F5-substituted derivative (4-Pf), but variable-temperature nuclear magnetic resonance studies suggest a dynamic behavior in solution. B–N fusion results in a large decrease of the HOMO–LUMO gap and dramatically lowers the LUMO energy compared to the all-carbon analogues. 4-Pf in particular shows significant absorbance at greater than 700 nm while being almost transparent throughout the visible region. After encapsulation in the biodegradable polymer DSPE-mPEG2000, 4-Pf nanoparticles (4-Pf-NPs) exhibit good water solubility, high photostability, and an excellent photothermal conversion efficiency of ∼41.8%. 4-Pf-NPs are evaluated both in vitro and in vivo as photothermal therapeutic agents. These results uncover B–N Lewis pair functionalization of PAHs as a promising strategy toward new NIR-absorbing materials for photothermal applications.

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Section: Introductionmentioning

confidence: 99%

Near-Infrared-Absorbing B–N Lewis Pair-Functionalized Anthracenes: Electronic Structure Tuning, Conformational Isomerism, and Applications in Photothermal Cancer Therapy

et al. 2022

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“…Hence, such compounds are good π-acceptors and display interesting photophysical and electrochemical properties, which lead to many different applications, [1][2][3][4][5][6][7][8] e. g., optoelectronics, [9][10][11] sensors for anions or small molecules, [12][13][14][15][16][17] and cell-imaging agents and biomolecule sensors. [15,[18][19][20][21][22][23][24][25][26][27][28][29][30][31][32][33] For the latter applications, which were summarized very recently by Berger and Marder, [34] focusing on triarylboranes, water-stable and soluble compounds are required. In 2009, Gabbaï and coworkers reported water-soluble triarylboranes bearing at least two trimethylammonium groups at positions para to the boron center.…”

Section: Introductionmentioning

confidence: 99%

Bithiophene‐Cored,mono‐,bis‐, andtris‐(Trimethylammonium)‐Substituted,bis‐Triarylborane Chromophores: Effect of the Number and Position of Charges on Cell Imaging and DNA/RNA Sensing

Berger

Rühe

Schwarzmann

et al. 2021

Chemistry A European J

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The synthesis, photophysical, and electrochemical properties of selectively mono-, bis-and tris-dimethylaminoand trimethylammonium-substituted bis-triarylborane bithiophene chromophores are presented along with the water solubility and singlet oxygen sensitizing efficiency of the cationic compounds Cat 1 + , Cat 2 + , Cat(i) 2 + , and Cat 3 + . Comparison with the mono-triarylboranes reveals the large influence of the bridging unit on the properties of the bistriarylboranes, especially those of the cationic compounds.Based on these preliminary investigations, the interactions of Cat 1 + , Cat 2 + , Cat(i) 2 + , and Cat 3 + with DNA, RNA, and DNApore were investigated in buffered solutions. The same compounds were investigated for their ability to enter and localize within organelles of human lung carcinoma (A549) and normal lung (WI38) cells showing that not only the number of charges but also their distribution over the chromophore influences interactions and staining properties.

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“…Push–pull fluorescent dyes, which feature electron-donating (D) substituents connected to electron-accepting (A) substituents, have been investigated − as environmentally sensitive fluorophores. The design and synthesis of fluorescent organic compounds containing push–pull chromophores have emerged as an active area of research over the past two decades as a result of their potential applications in the fields of photovoltaics, − non-linear optics, , organic light emitting diodes, − fluorescent sensors, , and bioimaging. − Although quadrupolar chromophores, − which contain symmetrical structures, have no permanent dipole moment, experimental data − ,− point to the existence of polar excited states. Time-resolved fluorescence (TRF) anisotropy measurements suggest that the initially delocalized excitation can be localized on the picosecond time-scale over one branch of the chromophore, leading to the formation of a polar state.…”

Section: Introductionmentioning

confidence: 99%

Alkoxy-Substituted Quadrupolar Fluorescent Dyes

et al. 2022

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Polar and polarizable π-conjugated organic molecules containing push−pull chromophores have been investigated extensively in the past. Identifying unique backbones and building blocks for fluorescent dyes is a timely exercise. Here, we report the synthesis and characterization of a series of fluorescent dyes containing quadrupolar A−D−A constitutions (where A = acceptor and D = donor), which exhibit fluorescence emission at a variety of different wavelengths. We have investigated the effects of different electron-withdrawing groups, located at both termini of a para-terphenylene backbone, by steady-state UV/vis and fluorescence spectroscopy. Pyridine and substituted pyridinium units are also introduced during the construction of the quadrupolar backbones. Depending on the quadrupolarity, fluorescence emission wavelengths cover from 380 to 557 nm. Time-resolved absorption and emission spectroscopy reveal that the photophysical properties of those quadrupolar dyes result from intramolecular charge transfer. One of the dyes we have investigated is a symmetrical box-like tetracationic cyclophane. Its water-soluble tetrachloride, which is non-cytotoxic to cells up to a loading concentration of 1 μM, has been employed in live-cell imaging. When taken up by cells, the tetrachloride emits a green fluorescence emission without any hint of photobleaching or disruption of normal cell behavior. We envision that our design strategy of modifying molecules through the functionalization of the quadrupolar building blocks as chromophores will lead to future generations of fluorescent dyes in which these A−D−A constitutional fragments are incorporated into more complex molecules and polymers for broader photophysical and biological applications.

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Applications of triarylborane materials in cell imaging and sensing of bio-relevant molecules such as DNA, RNA, and proteins

Abstract: Triarylboranes have been known for more than 100 years and have found potential applications in various fields such as anion sensors and optoelectronics, for example in organic light emitting diodes...

Cited by 51 publications

References 61 publications

Near-Infrared-Absorbing B–N Lewis Pair-Functionalized Anthracenes: Electronic Structure Tuning, Conformational Isomerism, and Applications in Photothermal Cancer Therapy

Near-Infrared-Absorbing B–N Lewis Pair-Functionalized Anthracenes: Electronic Structure Tuning, Conformational Isomerism, and Applications in Photothermal Cancer Therapy

Bithiophene‐Cored,mono‐,bis‐, andtris‐(Trimethylammonium)‐Substituted,bis‐Triarylborane Chromophores: Effect of the Number and Position of Charges on Cell Imaging and DNA/RNA Sensing

Alkoxy-Substituted Quadrupolar Fluorescent Dyes

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