Development of a quinoxaline-based fluorescent probe for quantitative estimation of protein binding site polarity

Kudo, Keiei; Momotake, Atsuya; Kanna, Yoko; Nishimura, Yukio

doi:10.1039/c1cc10183h

Cited by 60 publications

(36 citation statements)

References 23 publications

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“…This pronounced effect is explained by better stabilization of the excited state with increasings olventp olarity. [31] Thee mission spectra of 1a-d only become the mirror image of their absorption spectra in cyclohexane. These findings suggest that solvation relaxation of the singlet excited states of 1a-d does not occur in hexane, whereas it does occur in other solvents.…”

Section: Photophysical Propertiesmentioning

confidence: 99%

Dibenzocarbazolediimides: Synthesis, Solid Structure, Self‐Assembly Behavior, and Optoelectronic Properties

Zhang

et al. 2015

Chemistry An Asian Journal

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Both planar and nonplanar polycyclic aromatic hydrocarbons (PAHs) have attracted attention owing to their potential applications in optoelectronic materials. Four twist benzopicenediimides with good optoelectronic properties have been reported previously. Following on from this work, four functionalized dibenzocarbazoles have been synthesized and reported herein. The fluorescence quantum yields of these compounds were high in dichloromethane and moderate in the solid state. They have interesting self-assembling behavior and tunable packing motifs in single crystals obtained by introducing different functional groups. Their good optoelectronic properties make them potential candidates for organic devices, bioimaging, and biolabeling.

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Section: Photophysical Propertiesmentioning

confidence: 99%

Dibenzocarbazolediimides: Synthesis, Solid Structure, Self‐Assembly Behavior, and Optoelectronic Properties

Zhang

et al. 2015

Chemistry An Asian Journal

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“…[24,25] Apart from their luminescence, they also display pronounceds olvatochromic shifts of the emissionb ands. Solvatochromic quinoxaline-based push-pull systemsw ere employed as emissive probes for the bindingsite polarity of bovine serum albumin, [26] for exploring site-dependentf luorescence in HEp-2 cells, [27] and as chromophores for DSSCs. [28] Onlyr ecently,w e [27,29] and Jiang et al [30] described the synthesis of emission-solvatochromic indole-substituted quinoxaline derivatives.…”

Section: Introductionmentioning

confidence: 99%

Three‐Component Activation/Alkynylation/Cyclocondensation (AACC) Synthesis of Enhanced Emission Solvatochromic 3‐Ethynylquinoxalines

Merkt

Höwedes

Gers-Panther

et al. 2018

Chemistry A European J

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2-Substituted 3-ethynylquinoxaline chromophores can be readily synthesized by a consecutive activation-alkynylation-cyclocondensation (AACC) one-pot sequence in a three-component manner. In comparison with the previously published four-component glyoxylation starting from electron-rich π-nucleophiles, the direct activation of (hetero)aryl glyoxylic acids allows the introduction of substituents that cannot be directly accessed by glyoxylation. By introducing N,N-dimethylaniline as a strong donor in the 2-position, the emission solvatochromicity of 3-ethynylquinoxalines can be considerably enhanced to cover the spectral range from blue-green to deep red-orange with a single chromophore in a relatively narrow polarity window. The diversity-oriented nature of the synthetic multicomponent reaction concept enables comprehensive investigations of structure-property relationships by Hammett correlations and Lippert-Mataga analysis, as well as the elucidation of the electronic structure of the emission solvatochromic π-conjugated donor-acceptor systems by DFT and time-dependent DFT calculations with the PBEh1PBE functional for a better reproduction of the dominant charge-transfer character of the longest wavelength absorption band.

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“…Prominently, BSA–dye conjugates have been used to estimate protease activity . Squarines , diphenyl ether , quinoxaline, dicyanomethylene, indolo‐quinolizine, pyrazoles, benzothiazole and phenanthrolinone, and functionalized fluorescent probes have been used to recognize BSA. Fluorescently labelled proteins can have some advantages as well as adverse effects over intact proteins.…”

Section: Introductionmentioning

confidence: 99%

“…[16,17] Prominently, BSA-dye conjugates have been used to estimate protease activity. [18--20] Squarines [21] , diphenyl ether [22] , quinoxaline [23] , dicyanomethylene [24] , indolo-quinolizine [25] , pyrazoles [26] , benzothiazole [27] and phenanthrolinone [28] , and functionalized fluorescent probes have been used to recognize BSA.…”

Section: Introductionmentioning

confidence: 99%

Design and synthesis of the BODIPY–BSA complex for biological applications

Vedamalai

Gupta

2017

Luminescence

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A quinoxaline-functionalized styryl-BODIPY derivative (S1) was synthesized by microwaveassisted Knoevenagel condensation. It exhibited fluorescence enhancement upon microencapsulation into the hydrophobic cavity of bovine serum albumin (BSA). The S1-BSA complex was characterized systematically using ultraviolet (UV)-visible absorption, fluorescence emission, kinetics, circular dichroism and time-resolved lifetime measurements. The binding nature of BSA towards S1 was strong, and was found to be stable over a period of days. The studies showed that the S1-BSA complex could be used as a new biomaterial for fluorescence-based highthroughput assay for kinase enzymes.

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Development of a quinoxaline-based fluorescent probe for quantitative estimation of protein binding site polarity

Cited by 60 publications

References 23 publications

Dibenzocarbazolediimides: Synthesis, Solid Structure, Self‐Assembly Behavior, and Optoelectronic Properties

Dibenzocarbazolediimides: Synthesis, Solid Structure, Self‐Assembly Behavior, and Optoelectronic Properties

Three‐Component Activation/Alkynylation/Cyclocondensation (AACC) Synthesis of Enhanced Emission Solvatochromic 3‐Ethynylquinoxalines

Design and synthesis of the BODIPY–BSA complex for biological applications

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