Nadezhda S. Baleeva
Russian Academy of Sciences
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Featured researches published by Nadezhda S. Baleeva.
Science Advances | 2017
Zinaida M. Kaskova; Felipe Augusto Dörr; Valentin N. Petushkov; K. V. Purtov; Aleksandra S. Tsarkova; Natalja S. Rodionova; Konstantin S. Mineev; Elena Guglya; Alexey A. Kotlobay; Nadezhda S. Baleeva; Mikhail S. Baranov; Alexander S. Arseniev; J. I. Gitelson; Sergey Lukyanov; Yoshiki Suzuki; Shusei Kanie; Ernani Pinto; Paolo Di Mascio; Hans E. Waldenmaier; Tatiana A. Pereira; Rodrigo Leal de Paiva Carvalho; Anderson G. Oliveira; Yuichi Oba; Erick L. Bastos; Cassius V. Stevani; Ilia V. Yampolsky
Study of fungal bioluminescence mechanisms generates development of a multicolor enzymatic chemiluminescence system. Bioluminescent fungi are spread throughout the globe, but details on their mechanism of light emission are still scarce. Usually, the process involves three key components: an oxidizable luciferin substrate, a luciferase enzyme, and a light emitter, typically oxidized luciferin, and called oxyluciferin. We report the structure of fungal oxyluciferin, investigate the mechanism of fungal bioluminescence, and describe the use of simple synthetic α-pyrones as luciferins to produce multicolor enzymatic chemiluminescence. A high-energy endoperoxide is proposed as an intermediate of the oxidation of the native luciferin to the oxyluciferin, which is a pyruvic acid adduct of caffeic acid. Luciferase promiscuity allows the use of simple α-pyrones as chemiluminescent substrates.
Chemistry of Heterocyclic Compounds | 2016
Nadezhda S. Baleeva; Mikhail S. Baranov
This microreview presents the key methods of synthesis of 5-methylidene-3,5-dihydro-4H-imidazol-4-ones together with analysis of the relative efficiency for the substituent introduction at different positions of the ring. Also, examples of reactions typical for these compounds presented in the literature over the last seven years are given.
Journal of Physical Chemistry Letters | 2017
Cheng Chen; Weimin Liu; Mikhail S. Baranov; Nadezhda S. Baleeva; Ilia V. Yampolsky; Liangdong Zhu; Yanli Wang; Alexandra Shamir; Kyril M. Solntsev; Chong Fang
Superphotoacidity involves ultrafast proton motions implicated in numerous chemical and biological processes. We used conformational locking and strategic addition of electron-withdrawing substituents to synthesize a new GFP chromophore analogue: p-HO-3,5-diF-BDI:BF2 (diF). It is highly fluorescent and exhibits excited-state proton transfer (ESPT) in various solvents, placing it among the strongest photoacids. Tunable femtosecond stimulated Raman spectroscopy with unique resonance conditions and transient absorption are complementarily employed to elucidate the structural basis for superphotoacidity. We reveal a multistep ESPT reaction from diF to methanol with an initial proton dissociation on the ∼600 fs time scale that forms a charge-separated state, stabilized by solvation, and followed by a diffusion-controlled proton transfer on the ∼350 ps time scale. A ∼1580 cm-1 phenolic ring motion is uncovered to accompany ESPT before 1 ps. This study provides a vivid movie of the photoinduced proton dissociation of a superphotoacid with bright fluorescence, effectively bridging fundamental mechanistic insights to precise control of macroscopic functions.
Journal of Physical Chemistry Letters | 2018
Yulia G. Ermakova; Tirthendu Sen; Yulia Bogdanova; Alexander Yu. Smirnov; Nadezhda S. Baleeva; Anna I. Krylov; Mikhail S. Baranov
Novel fluorogenic dyes based on the GFP chromophore are developed. The compounds contain a pyridinium ring instead of phenolate and feature large Stokes shifts and solvent-dependent variations in the fluorescence quantum yield. Electronic structure calculations explain the trends in solvatochromic behavior in terms of the increase of the dipole moment upon excited-state relaxation in polar solvents associated with the changes in bonding pattern in the excited state. A unique combination of such optical characteristics and lipophilic properties enables using one of the new dyes for imaging the membrane structure of endoplasmic reticulum. An extremely high photostability (due to a dynamic exchange between the free and absorbed states) and selectivity make this compound a promising label for this type of cellular organelles.
Chemistry of Heterocyclic Compounds | 2015
Svetlana V. Golodukhina; Nadezhda S. Baleeva; Konstantin S. Mineyev; Mikhail S. Baranov
(Z)-1,2-Dimethyl-4-(4-methoxybenzylidene)-1H-imidazol-5(4H)-one underwent a condensation reaction with aromatic acyl chlorides, forming keto derivatives that were structurally similar to chromophores of red fluorescent proteins, as well as to the products of their maturation and/or degradation. The reverse reaction of the obtained products was observed upon treatment with aqueous alkali.
Russian Journal of Bioorganic Chemistry | 2018
Nadezhda S. Baleeva; D. A. Gorbachev; Mikhail S. Baranov
The role of C2-substituents in the imidazolone ring of borated GFP chromophore derivatives (4-(2-(difluoroboryl)benzylidene)-1H-imidazol-5(4H)-ones) in the degradation process was studied. It was found that the nature of this substituent hardly affected their photostability, whereas their sensitivity toward nucleophilic reagents decreased with an increase in size and donating properties of the substituent. The results supported an assumption that the introduction of C2 substituents was not a rate-limiting step of the degradation process of these derivatives and complex C2 substituents were not effective tools for the improvement of their stability.
Chemistry of Heterocyclic Compounds | 2018
Alexander Yu. Smirnov; Nadezhda S. Baleeva; Snezhana O. Zaitseva; Konstantin S. Mineev; Mikhail S. Baranov
A method for the synthesis of 2-amino-4-arylidene-1H-imidazol-5(4H)-ones is proposed based on the reaction of various aromatic isocyanates with phosphazenes derived from azidocinnamic acid amides. The spectral-luminescent properties of the obtained compounds were studied. The products were shown to possess the (Z)-configuration with the help of two-dimensional spectroscopy.
Russian Journal of Bioorganic Chemistry | 2017
Nadezhda S. Baleeva; Mikhail S. Baranov
The Sonogashira reaction was used for modifications of borated green fluorescence protein chromophore derivatives, 4-(2-(difluoroboryl)benzylidene)-1H-imidazol-5(4H)-ones, for the development of new fluorescent dyes. The derivatives bearing an acetylene fragment and a difluoroboryl group were obtained in high yields. The modification resulted in a significant bathochromic shift of the absorption and emission maxima and is a promising method for the development of new fluorescent dyes.
Chemistry of Heterocyclic Compounds | 2017
Nadezhda S. Baleeva; Evgeniya A. Levina; Mikhail S. Baranov
(Z)-4-Arylidene-2-methyl-1H-imidazol-5(4H)-ones containing a substituted aminoethyl group at the N-1 atom can be oxidized with an excess of selenium dioxide, resulting in the closure of additional six-membered ring with the formation of an amide group. The obtained compounds showed a substantial bathochromic shift of the absorption maxima relative to the starting (Z)-4-arylidene-2-methyl-1Himidazol-5(4H)-ones, pointing to potential applications of this method for the synthesis of new fluorescent and fluorogenic dyes.
Russian Journal of Bioorganic Chemistry | 2016
Nadezhda S. Baleeva; Ilia V. Yampolsky; Mikhail S. Baranov
We propose to use the conformationally locked GFP chromophore derivatives (4-(2(difluoroboryl)benzylidene)-1H-imidazol-5(4H)-ones) as potential fluorescent sensors. The model carbamate derivatives were synthesized and their fluorescent properties were studied. It was shown that the introduction/cleavage of the carbamate groups at the nitrogen atom led to the noticeable shifts in the absorption and emission maxima of the resultant derivatives, which makes them promising candidates for new fluorescent sensors.