Article
Chemistry, Multidisciplinary
Subhrakant Jena, Kiran Devi Tulsiyan, Rudhi Ranjan Sahoo, Saiprakash Rout, Akshay Kumar Sahu, Himansu S. Biswal
Summary: Organoselenium compounds have broad applications in organic synthesis, medicinal chemistry, and materials science. A study discovered that selenourea (SeU) significantly enhances fluorescence quenching through a photoinduced electron transfer mechanism and has a fast intrinsic PET lifetime. This research reveals the potential applications of selenourea.
Article
Biochemistry & Molecular Biology
N. S. Baleeva, A. Yu Smirnov, M. S. Baranov
Summary: A novel derivative of the conformationally locked derivative of the green fluorescent protein chromophore is reported. The presence of an additional aryl substituent leads to a decrease in fluorescence intensity without causing absorption and emission spectra shifts. Future research can explore the use of electron-withdrawing groups for more efficient conjugation.
RUSSIAN JOURNAL OF BIOORGANIC CHEMISTRY
(2022)
Article
Environmental Sciences
Dahui Zhu, Yaxin Niu, Keke Fan, Fujun Zhang, Yu Wang, Gejiao Wang, Shixue Zheng
Summary: This study found that the selenium-oxidizing Agrobacterium sp. T3F4 strain can steadily colonize soil and plant tissues, leading to increased absorption of selenium by plants through selenium oxidation in the soil.
SCIENCE OF THE TOTAL ENVIRONMENT
(2021)
Article
Environmental Sciences
Jingxiang Ma, Yi Zhao, Yanan Wei
Summary: A method for oxidation and absorption of selenium dioxide in flue gas emitted from coal-fired power plants was proposed, which significantly reduces the toxicity of selenium to the environment. The study showed that high oxidation efficiency can be achieved by using H2O2 and NaClO2, leading to a decrease in selenium toxicity.
ENVIRONMENTAL SCIENCE AND POLLUTION RESEARCH
(2021)
Article
Biochemistry & Molecular Biology
I. N. Myasnyanko, N. S. Baleeva, M. S. Baranov
Summary: Novel derivatives of the fluorescent protein Kaede's chromophore, (Z)-2-(4-methoxybenzylidene)-6/8-phenylimidazo[1,2-a]pyridine-3(2H)-ones, were reported. The introduction of a phenyl substituent at the 6th and 8th position of the imidazopyridinone fragment did not result in a shift in absorption and emission spectra.
RUSSIAN JOURNAL OF BIOORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Claudius Lenz, Sebastian Doerner, Alexander Sherwood, Dirk Hoffmeister
Summary: Psilocin is the dephosphorylated and psychotropic metabolite of psilocybin, and the blue color stems from the quinoid 7,7'-coupled dimer of psilocin.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Biochemistry & Molecular Biology
Joon-Hwan Lee, Jiduck Kim, Hakwon Kim
Summary: In this study, a kilogram-scale synthesis of a potent TRPV1 antagonist, 1, is described. A scalable Suzuki-Miyaura reaction was developed to obtain a key intermediate, 6'-methyl-3-(trifluoromethyl)-2,3'-bipyridine 4, on a kilogram scale. Two synthetic routes for mass production of bipyridinyl carboxylic acid intermediate 5 or aldehyde intermediate 6 were developed using controlled oxidation reactions. With the developed synthetic procedure, a multi-kilogram-scale bi-pyridinyl benzimidazole derivative 1 can be synthesized.
Article
Chemistry, Multidisciplinary
Arnaud de Zordo-Banliat, Kevin Grollier, Nicolas Vanthuyne, Sebastien Floquet, Thierry Billard, Guillaume Dagousset, Bruce Pegot, Emmanuel Magnier
Summary: This study presents a method for the selective synthesis of perfluoroalkyl selenoxides and selenones using Oxone (R) as an oxidant or a Polyoxometalate-based Ionic Liquid (POM-IL) as a catalyst. The reaction provides satisfactory to excellent yields for various perfluoroalkyl chains and substituents. Perfluoroalkyl selenoxides are obtained through a two-step one-pot reaction from selenocyanates, and the previously unknown perfluoroalkyl selenoximines family is prepared with good yields. Two strategies for the synthesis of fluoroalkylated Se-IV and Se-VI compounds are explored, and the lipophilicity parameters of these compounds are evaluated. Additionally, the absolute configurations of asymmetric aryl perfluoroalkyl selenoximines are determined through resolution.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Galina Selivanova, Alexandrina Skolyapova, Jiaying Wang, Elena Karpova, Inna Shundrina, Irina Bagryanskaya, Evgeny Amosov
Summary: New 1,3,4-thiadiazole derivatives with a diazenyl group and an imino group were synthesized and their optical and thermal properties were studied. The compounds were characterized by spectral and X-ray analyses.
NEW JOURNAL OF CHEMISTRY
(2022)
Letter
Biochemistry & Molecular Biology
A. M. Bogdanov, D. A. Gorbachev, E. R. Zaitseva, A. Yu. Smirnov, N. S. Baleeva, M. S. Baranov
Summary: The solvatochromic behavior of a model compound mimicking the chromophore of cyan fluorescent protein (CFP) was studied, showing that the lipophilic environment promotes an increase in fluorescence lifetime, while aromatic solvents and tertiary amines lead to a decrease. This study proposed a possible rational design of CFP-like proteins based on the findings.
RUSSIAN JOURNAL OF BIOORGANIC CHEMISTRY
(2021)
Article
Engineering, Environmental
Qiyu Weng, Yingli Gong, Xiongwei Tian, Yuqun Zhuo, Shujuan Wang, Pengbo Hu, Tao Lyu
Summary: The research found that selenite in simulated slurry can be reduced by SO2 to form amorphous elemental selenium, while selenate remains unaffected. Increasing SO2 concentration in flue gas accelerates the reduction of selenite, and the reduction reaction is exothermic. Additionally, the oxidation effect of S2O82- competes with the reduction effect of SO2.
JOURNAL OF HAZARDOUS MATERIALS
(2021)
Article
Plant Sciences
Muhammad Sayyar Khan, Anna Soyk, Ingo Wolf, Miriam Peter, Andreas J. Meyer, Thomas Rausch, Markus Wirtz, Ruediger Hell
Summary: This study analyzed the effects of selenite and selenate on Arabidopsis development, selenium partitioning, and redox environment. Selenate was predominantly deposited in leaves, causing chlorosis and impaired plant morphology, and triggering sulfur accumulation. Selenate also resulted in vigorous oxidation of the cytosolic glutathione pool, while selenite primarily affected the plastidic redox environment.
FRONTIERS IN PLANT SCIENCE
(2022)
Article
Chemistry, Multidisciplinary
Ibakyntiew D. Marpna, O. Risuklang Shangpliang, Kmendashisha Wanniang, Baskhemlang Kshiar, Tyrchain Mitre Lipon, Badaker M. Laloo, Bekington Myrboh
Summary: A novel method for the synthesis of fused 1,3-dioxolanes was developed, involving the self-condensation of glyoxal generated in situ by oxidation of acetophenones with SeO2 in the presence of trifluoroacetic acid. This reaction allows for the construction of four C-O bonds simultaneously, resulting in architecturally novel oxygen-containing heterocycles from readily available ketones using affordable shelf reagents and simple reaction conditions.
Article
Chemistry, Applied
Yafeng Liu, Fengkai Sun, Zhenyu An, Man Miao, Xin Guo, Chonglong Li
Summary: A regioselective synthesis of multi-substituted furans has been achieved using SeO2-mediated intermolecular cyclization. The developed methodology utilized commercially available starting materials and provided various 2,3,5-triarylfurans.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Ivan N. Myasnyanko, Alexey S. Gavrikov, Snizhana O. Zaitseva, Alexander Yu. Smirnov, Elvira R. Zaitseva, Anatolii I. Sokolov, Kseniya K. Malyshevskaya, Nadezhda S. Baleeva, Alexander S. Mishin, Mikhail S. Baranov
Summary: By using benzylidene imidazolone core, a range of color-shifted fluorogenic ligands for FAST protein were developed without compromising binding efficiency or utility for live-cell protein labeling. This study emphasizes the potential of benzylidene imidazolone derivatives for rapidly expanding live-cell fluorogenic labeling tools.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Organic
Elvira R. Zaitseva, Alexander Yu Smirnov, Vladimir Timashev, Vadim Malyshev, Ekaterina A. Zhigileva, Andrey A. Mikhaylov, Michael G. Medvedev, Nadezhda S. Baleeva, Mikhail S. Baranov
Summary: In this study, researchers discovered that 2-(2-(benzylthio)benzylidene)malonates can undergo controlled 1,5-hydride shift triggered cyclization, resulting in the formation of thiachromanes. Boron trifluoride played a key role as a reaction promotor. Experimental and theoretical comparison revealed that sulfur derivatives have the highest activation barrier for hydride transfer due to unfavorable transition state geometry, explaining the lack of previous reports on 1,5-hydride shifts in (alkylthio)styrenes.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Dmitry S. Ivanov, Elvira R. Zaitseva, Alexander Yu Smirnov, Nadezhda S. Baleeva, Mikhail S. Baranov
Summary: This methodology offers a straightforward approach to synthesize the targeted compound, which is achieved by reacting 2-alkylaminobenzaldehydes with hydrogen chloride solution in dioxane at room temperature.
CHEMISTRY OF HETEROCYCLIC COMPOUNDS
(2022)
Article
Biology
Marina Goncharuk, Nadezhda S. Baleeva, Dmitry E. Nolde, Alexey S. Gavrikov, Alexey Mishin, Alexander S. Mishin, Andrey Y. Sosorev, Alexander S. Arseniev, Sergey A. Goncharuk, Valentin Borshchevskiy, Roman G. Efremov, Konstantin S. Mineev, Mikhail S. Baranov
Summary: This study describes the rational design of enhanced FAST mutants optimized for the N871b fluorogen. Through structural analysis, NMR relaxation analysis, and computer simulations, the study identifies mobile regions in the complex and suggests mutations that could stabilize both the protein and the ligand. The experimental results show that the mutants exhibit higher brightness and provide up to 35% enhancement for several other fluorogens of similar structure, both in vitro and in vivo.
COMMUNICATIONS BIOLOGY
(2022)
Article
Chemistry, Organic
Elvira R. Zaitseva, Anatolii Sokolov, Andrey A. Mikhaylov, Nadezhda S. Baleeva, Mikhail S. Baranov, Alexander Yu Smirnov
Summary: A methodology was developed for the synthesis of phenylspiro[imidazole-4,3'-thiochroman]ones by treating [2-(benzylsulfanyl)-benzylidene]imidazolones with titanium tetrachloride. The reaction proceeded via a [1,5]-hydride shift mechanism followed by thiochromane ring closure.
CHEMISTRY OF HETEROCYCLIC COMPOUNDS
(2022)
Article
Biochemistry & Molecular Biology
Vladislav A. Lushpa, Nadezhda S. Baleeva, Sergey A. Goncharuk, Marina Goncharuk, Alexander S. Arseniev, Mikhail S. Baranov, Konstantin S. Mineev
Summary: NanoFAST is a fluorogen-activating protein and the deletion of the N-terminus of FAST destabilizes the C-terminal domain in the apo state, affecting ligand binding propensity. The structure of the nanoFAST/HBR-DOM2 complex reveals atomistic details of nanoFAST interactions with ligands and explains ligand specificity.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2022)
Article
Chemistry, Organic
Semen E. E. Nikolaev, Anatolii I. I. Sokolov, Andrey A. A. Mikhaylov, Alexander A. A. Korlyukov, Nadezhda S. S. Baleeva, Mikhail S. S. Baranov, Ivan N. N. Myasnyanko
Summary: The interaction between imidazol-5-one-based donor-acceptor cyclopropanes and thiourea and thioacetamide was investigated, resulting in the formation of previously undescribed spirocyclic 2-amino and 2-iminotetrahydrothiophenes.
CHEMISTRY OF HETEROCYCLIC COMPOUNDS
(2023)
Article
Chemistry, Organic
Dmitry S. Ivanov, Elvira R. Zaitseva, Alexander Yu. Smirnov, Alexey V. Nizovtsev, Nadezhda S. Baleeva, Mikhail S. Baranov
Summary: A simple procedure was developed to synthesize 2H-pyrido[3,4-c][1,2]benzoxazine-2,4(3H)-diones from o-fluorophenyl-substituted 6-oxo-6H-1,2-oxazine-3-carboxylates using primary amines. The reaction followed a previously described mechanism for the formation of 3-(hydroxyimino)pyridine-2,6-diones, followed by intramolecular nucleophilic substitution to form the 1,2-oxazine ring.
CHEMISTRY OF HETEROCYCLIC COMPOUNDS
(2023)
Article
Biochemistry & Molecular Biology
Maxim M. Perfilov, Elvira R. Zaitseva, Nadezhda S. Baleeva, Vadim S. Kublitski, Alexander Yu. Smirnov, Yulia A. Bogdanova, Svetlana A. Krasnova, Ivan N. Myasnyanko, Alexander S. Mishin, Mikhail S. Baranov
Summary: In this work, we demonstrated that the addition of a trifluoromethyl group to the meta-position of arylidene imidazolones (GFP chromophore core) significantly enhances their fluorescence intensity in nonpolar and aprotic solvents. The solvent-dependent modulation of fluorescence intensity allows these compounds to be used as fluorescent polarity sensors. Specifically, we identified a compound suitable for selective labeling of the endoplasmic reticulum in living cells.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2023)
Article
Biochemistry & Molecular Biology
Yulia A. Bogdanova, Elvira R. Zaitseva, Alexander Yu. Smirnov, Nadezhda S. Baleeva, Alexey S. Gavrikov, Ivan N. Myasnyanko, Sergey A. Goncharuk, Erik F. Kot, Konstantin S. Mineev, Alexander S. Mishin, Mikhail S. Baranov
Summary: In this study, we demonstrated that NanoLuc luciferase, a well-known enzyme, can serve as a fluorogen activating protein for arylidene-imidazolones analogs of the Kaede protein chromophore. We showed that these compounds can be utilized as fluorescent sensors for this particular protein and can also be employed alongside it as a genetically encoded tag in fluorescent microscopy.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2023)
Article
Chemistry, Multidisciplinary
Nadezhda S. Baleeva, Alexander Yu. Smirnov, Elvira R. Zaitseva, Dmitrii S. Ivanov, Anatolii I. Sokolov, Andrey A. Mikhaylov, Ivan N. Myasnyanko, Mikhail S. Baranov
Summary: ortho-Dialkylaminoarylidene malonates undergo hydrogen transfer mediated cyclization in the absence of a catalyst under LED irradiation. This activation mode is relatively general and can be applied to a number of other acceptor motifs in the arylidene substrates tested. Variation of the light source wavelength provides an extra option for fine tuning of the reaction conditions, making the described method almost universal.
NEW JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Organic
Elvira R. Zaitseva, Victoria E. Opryshko, Dmitrii S. Ivanov, Andrey A. Mikhaylov, Alexander Yu. Smirnov, Mikhail S. Baranov
Summary: In this study, it was found that 2-Allyloxybenzaldehydes readily undergo [2 + 1] cycloadditions under 365 nm LED irradiation to form chroman-fused cyclopropanols. This reaction occurs without the need for any catalysts or additives in dimethyl sulfoxide.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
