Red‐Shifted Fluorescent Aminated Derivatives of a Conformationally Locked GFP Chromophore

Баранов, Михаил С.; Solntsev, Kyril M.; Балеева, Надежда С.; Mishin, Alexander S.; Lukyanov, Sergey; Lukyanov, Konstantin A.; Yampolsky, Ilia V.

doi:10.1002/chem.201403678

Cited by 71 publications

(75 citation statements)

References 63 publications

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“…Studying the emission spectra of 6b in different solvents revealed no dual emission, which suggests that the ICT state of 6b undergoes nonradiative relaxation to the ground state, as shown earlier for aminated derivatives of the GFP chromophore15 and for some arylacetylenes 21. Also, the solvatochromic behavior of 6b is in good agreement with a Kamlet–Taft model, which provides additional support of this hypothesis (see below).…”

Section: Resultssupporting

confidence: 57%

“…Double‐locked chromophores 6 possessed FQYs that were increased relative to those of single‐locked analogues 4 , and the brightest fluorescence was observed for compounds 6a (FQY = 0.53 in MeCN) and 6b (FQY = 0.66 in dioxane, Table 2). Similarly to other diethylamine‐substituted derivatives of GFP chromophores,15,18 compound 6b demonstrated significant variability in the FQY in different solvents. However, this dependence was not that strong and reached only a ca.…”

Section: Resultsmentioning

confidence: 90%

“…Compounds 4 as conformationally locked analogues of the Kaede chromophore were synthesized by condensation of borylated GFP chromophore 1 13 with aminated analogues 2 and 3 15 with a range of aromatic aldehydes (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

“…We recently developed an approach to increase the FQY of GFP‐like chromophores dramatically by introducing a difluoroboryl substituent, which provides a conformational lock at the double bond responsible for nonradiative relaxation of the excited state13 (Figure 1). Conformationally locked analogues of the chromophore of GFP show favorable properties, such as small size, high solubility, and tunable spectral properties, all of which allow their use in the covalent fluorescent labeling of proteinases14 and in the staining of cellular membranes 15…”

Section: Introductionmentioning

confidence: 99%

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Bioinspired Fluorescent Dyes Based on a Conformationally Locked Chromophore of the Fluorescent Protein Kaede

et al. 2015

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A novel class of fluorescent dyes based on the conformationally locked heterocyclic core of the chromophore of the fluorescent protein Kaede was discovered. Introduction of a single conformational lock at the benzylidene fragment of the Kaede chromophore resulted in an increase in the fluorescence quantum yield (FQY) by one order of magnitude and a redshift of ca. 60 nm in the emission spectrum. Imposing the second lock at the ethylene fragment of the Kaede chromophore provided a further increase in the FQY. Locked analogues demonstrated bright and redshifted emission in a broad range of solvents, which makes them good candidates for a wide spectrum of fluorescent‐labeling applications.

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Section: Resultssupporting

confidence: 57%

Section: Resultsmentioning

confidence: 90%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Bioinspired Fluorescent Dyes Based on a Conformationally Locked Chromophore of the Fluorescent Protein Kaede

et al. 2015

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“…Some of the compounds synthesized along this line showed relatively bright fluorescence (Wu and Burgess 2008;Baranov et al 2014). Of special interest was the design of fluorophores exhibiting the excited-state reactions, particularly ESIPT (Chen et al 2007).…”

Section: Finding Analogs Of Fluorescent Protein Fluorophoresmentioning

confidence: 99%

Molecular-Size Fluorescence Emitters

Demchenko

2015

Introduction to Fluorescence Sensing

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A variety of fluorescent and luminescent materials in the form of molecules, their complexes and nanoparticles are available for implementation as response units into sensing and imaging technologies and we discuss their general properties that are essential for these applications. Organic dyes were the first and remain to be the most popular emitters used with these purposes. Their labeling and responsive properties are overviewed. Natural fluorescent proteins and their engineered analogues incorporate organic fluorophores that are synthesized spontaneously from the polypeptide chain inside the living cells without the need of their intrusion, as the gene products. They resulted in revolutionary advancement in cell imaging and show good prospects in sensing and reporting on cellular processes. Organic heterocyclic compounds can incorporate metal ions generating long-living luminescence. Moreover, noble metal particles of a very small size exhibit unique light-absorbing and fluorescent emission properties. In this Chapter we focus on these types of fluorophores that possess subnanometer dimensions and display single type of absorption-emission cycle. The more complex nanostructures and nanocomposites will be overviewed in Chaps. 5 and 6 that follow. Fluorophores and Their Characteristics General Properties of Fluorescent DyesIn view of tremendous diversity of structures, chemical reactivities and spectroscopic properties, one needs certain practically useful criteria for the dye selection for the purpose of sensing and imaging. They can be formulated in the form of spectroscopic parameters that have to be optimized. It is the parameter describing the ability of molecule to absorb light at a particular wavelength. The absorbance E measured at any wavelength on spectrophotometer is proportional to the dye concentration c (in mol/l) and the light path length in a sample l (in cm). In this relation, ε plays the role of coefficient of proportionality, so that E = εcl. The value of molar absorbance is obtained by purifying and drying the dye, dissolving it at low concentration and measuring E on a spectrophotometer. The broadly used term extinction includes absorbance and light scattering. Absorbance is a unique characteristic of a molecule under certain environmental conditions. In general, the bigger the fluorophore size, the greater is the probability that the photon will be absorbed.The value of ε max at the maximum of absorption band is the common characteristic of the light-absorbing power of the dye. The dye 'brightness' that determines the absolute sensitivity of fluorescence detection (Wetzl et al. 2003) is the product of molar absorbance and quantum yield, Φ. The absorbance is related to optical cross-section and for organic dyes, ε max varies from ca. 10 3 l mol −1 cm −1 for small dyes, such as coumarins to ca. 10 5 l mol −1 cm −1 for larger fluorophores such as cyanines and phthalocyanines (Lavis and Raines 2008). It should be selected as high as possible, but the limiting factor is the fluorophore size. Us...

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Rational Design of Heterogeneous Silver Catalysts by Exploitation of Counteranion‐Induced Coordination Geometry

Singh

Ramanathan

2016

Asian J Org Chem

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The coordination geometry of silver complexes of the green fluorescencep rotein chromophorei sh ighly diverse and dependentonthe size and shape of the counteranion in the complexes. Only complexes that have vacancies at the silver atom prove to be heterogeneous catalysts in the "green"s ynthesis of 1,4-benzodioxines.T he results reveala ni nteresting strategy of exploiting crystal packing forces to enhance catalytic efficiency by just changing the counteranion.The design of less hazardous and environmental friendly catalysts with high selectivitya nd increased efficiency is always ag reat challenge. In recent years, heterogeneous catalysts are becomingi ncreasingly popular due to easy product separation, recyclability,a nd the reusable nature of the insoluble catalyst. [1] The surface of ah eterogeneousc atalyst providesadefined shape with as uitable functionality to achieve the desired selectivity. [2] Thus, the geometry of the catalyst plays ap ivotal role in its function. Moreover,i ti sm ore attractive when ac atalytic reaction is performed under green conditions. [3] In order to design new heterogeneousc atalysts, we have synthesized new coordinationc omplexes of the green fluorescence protein (GFP) chromophore. Several GFP chromophorea nalogues [4] and two complexes [5] (with zinc and boron) have been reported previously with the aim of understandingt heir photophysical properties. GFP chromophoreanalogues have also been exploited as chemidosensors, [6] biosensors [7] and organic materials in solar cells. [8] Detailed crystallographic studies by our group have found that synthetic mimics of the GFP chromophore are stabilized by p···p stacking, hydrogen bonding, and other supramolecular interactions. [9] Nevertheless, the coordination behavior and catalytic activity has never been investigated. Keepingt his in mind, we have explored the coordination and catalytic behavior of the silver complexes of GFP chromophorea nalogue (Z)-4-(4-methoxybenzylidene)-1,2-d imethyl-1 H-imidazol-5(4 H)-one [a] A.Supporting information and the ORCID identification number(s) for the author(s) of this article can be found under http://dx.

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Red‐Shifted Fluorescent Aminated Derivatives of a Conformationally Locked GFP Chromophore

Cited by 71 publications

References 63 publications

Bioinspired Fluorescent Dyes Based on a Conformationally Locked Chromophore of the Fluorescent Protein Kaede

Bioinspired Fluorescent Dyes Based on a Conformationally Locked Chromophore of the Fluorescent Protein Kaede

Molecular-Size Fluorescence Emitters

Rational Design of Heterogeneous Silver Catalysts by Exploitation of Counteranion‐Induced Coordination Geometry

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