Article
Chemistry, Analytical
Yong-Peng Yang, Fu-Jian Qi, Yi-Ping Qian, Xia-Zhen Bao, Han-Chen Zhang, Bin Ma, Fang Dai, Sheng-Xiang Zhang, Bo Zhou
Summary: The newly developed two-photon probe QBMP showed good binding with NQO1 and exhibited superior properties such as rapid response, large Stokes shift, ultra-low detection limit, favorable two-photon cross section, and deep tissue penetration.
ANALYTICAL CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Enric Ros, Marina Bellido, Joan A. Matarin, Albert Gallen, Manuel Martinez, Laura Rodriguez, Xavier Verdaguer, Lluis Ribas de Pouplana, Antoni Riera
Summary: A set of 3-bromo-1,2,4,5-tetrazines with distinct substitutions have been used as reagents for late-stage functionalization. Spectroscopic studies showed that tetrazine ethers are intrinsically fluorescent and this fluorescence can be lost through iEDDA cycloaddition. Tetrazine-phenol ethers can undergo rapid iEDDA reactions with a second order rate constant compatible with bioorthogonal ligations. The coupling of 3-bromo-6-methyl-1,2,4,5-tetrazine with l-tyrosine and octreotide demonstrated the detection and reactivity of intrinsically fluorescent tetrazines in a biologically relevant context. The synthesis and characterization of fluorescent tetrazine ethers with bioorthogonal applicability pave the way for the generation of useful compounds for both detection and bioconjugation in vivo.
Article
Chemistry, Multidisciplinary
Kentaro Nishiyama, Hiroki Akiba, Satoshi Nagata, Kouhei Tsumoto, Haruhiko Kamada, Hiroaki Ohno
Summary: Proximity-induced chemical reactions are rapid and site-specific, taking advantage of high affinity and highly selective interactions with templates. A biepitopic antigen-templated chemical reaction (BATER) is proposed, where reactive functional groups are conjugated to two antibodies that interact with two epitopes of the same antigen to accelerate the reaction. Visualizing the progress of BATER using fluorogenic click chemistry allows for optimal antibody selection and linker design.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Fabien Thoreau, Peter A. Szijj, Michelle K. Greene, Lea N. C. Rochet, Ioanna A. Thanasi, Jaine K. Blayney, Antoine Maruani, James R. Baker, Christopher J. Scott, Vijay Chudasama
Summary: In recent years, there has been growing interest in protein-protein conjugation, especially in the context of bispecific antibodies (bsAbs) and their therapeutic applications. These molecules contain two paratopes capable of binding two distinct epitopes, enabling complex biological functions that monospecific antibodies cannot achieve. While traditional methods for bsAb construction involve protein engineering, recent developments have led to the emergence of chemical methods that offer increased modularity, speed, and the potential for further functionalization. However, most of these approaches lack the inclusion of a fragment crystallizable (Fc) modality, which provides effector function and increased half-life. In this study, a novel method using disulfide rebridging and click-chemistry has been reported for the generation of Fc-containing, IgG-like mono- and bispecific antibodies, referred to as synthetic antibodies (SynAbs). A T cell engager SynAb, FcCD20-(FabHER2)-FabCD3, has been successfully constructed and demonstrated the expected biological functions, including the ability to effectively kill HER2+ target cells in co-culture assays with T cells.
ACS CENTRAL SCIENCE
(2023)
Article
Chemistry, Multidisciplinary
Claudia F. Afonso, Marta C. Marques, Joao P. M. Antonio, Carlos Cordeiro, Pedro M. P. Gois, Pedro M. S. D. Cal, Goncalo J. L. Bernardes
Summary: Post-translational modifications of histones, such as lysine acetylation, play a crucial role in regulating chromatin structure and function. However, studying the individual contribution of single acetylation events has been challenging due to the difficulty in obtaining homogeneous samples of histones with a single acetylation. In this study, the authors developed a click-to-acetylate approach that allows for controlled, site-specific acetylation of a single lysine residue, enabling easier access to and study of acetylated histones.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Review
Chemistry, Multidisciplinary
Dominik Schauenburg, Tanja Weil
Summary: In vivo chemistry refers to chemical reactions taking place within living systems, such as cells, tissues, or the entire organism, while in vitro reactions occur in artificial environments outside living organisms, like test tubes. It is essential to understand which reactions can efficiently occur without producing by-products and how product formation can be characterized in complex living environments. In vivo chemistry offers potential applications in synthesizing drug molecules within cells and enhancing the understanding of living systems and therapeutic strategies. Two guiding principles in this field are identifying translatable chemical reactions from the laboratory to living systems and selecting suitable methods to study reactions and structure formation in complex living environments.
Article
Chemistry, Medicinal
Matt Timmers, Andi Kipper, Raphael Frey, Stef Notermans, Maksym Voievudskyi, Claire Wilson, Nina Hentzen, Michael Ringle, Clara Bovino, Bernhard Stump, Cristianne J. F. Rijcken, Tina Vermonden, Ingrid Dijkgraaf, Rob Liskamp
Summary: The recently developed compound TMTHSI has shown great potential in strain-promoted azide-alkyne cycloaddition (SPAAC), metal-free click chemistry. This research explores the compound's properties in large-scale production, stability in acidic conditions for peptide synthesis, and functionalization of antibodies. The results demonstrate that TMTHSI can be produced on a large scale, is stable against TFA, and efficiently functionalizes antibodies, making it a promising option for diverse bioconjugation applications.
Article
Chemistry, Multidisciplinary
David DiMeglio, Xinqi Zhou, Tatiana Wirth, Frederik Brondsted, Lauren Lesiak, Yuan Fang, Mehrdad Shadmehr, Cliff I. Stains
Summary: A significant barrier inhibiting multiplexed imaging in the near-infrared (NIR) is the extensive trial and error associated with fine-tuning NIR dyes. This study introduces a time-dependent density functional theory (TD-DFT) approach to rapidly estimate absorbance and emission of new dyes, saving significant time compared to synthesis and evaluation of dye derivatives.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Biochemical Research Methods
Alexandra Bristiel, Manon Cadinot, Mathieu Pizzonero, Frederic Taran, Dominique Urban, Raphael Guignard, Dominique Guianvarc'h
Summary: The researchers developed a facile method for conjugating relevant probes, ligands, or delivery agents onto oligonucleotides (ONs), which is important for both fundamental studies in chemical biology and improving the pharmacology of ONs in medicinal chemistry. They introduced novel 2'-functionalized nucleoside phosphoramidite monomers that contain bioorthogonal methylcyclopropene or sydnone moieties for the first time to ON solid-phase synthesis, allowing traceless ON postsynthetic modifications with reactive complementary probes through inverse electron-demand Diels-Alder reactions or strain-promoted sydnone-alkyne cycloaddition. These findings expand the bioorthogonal phosphoramidite building blocks and provide a new method for generating labeled ONs.
BIOCONJUGATE CHEMISTRY
(2023)
Article
Biochemistry & Molecular Biology
Peng Wu
Summary: The Nobel Prize in Chemistry 2022 was awarded to Carolyn R. Bertozzi, Morten Meldal, and K. Barry Sharpless for their contributions to the development of click chemistry and bioorthogonal chemistry. These technologies enable rapid, selective, and nontoxic covalent reactions that link two components together under benign conditions, leading to a paradigm shift in basic research and practical applications.
ACS CHEMICAL BIOLOGY
(2022)
Article
Multidisciplinary Sciences
Kakishi Uno, Ayse Aktalay, Mariano L. Bossi, Masahiro Irie, Vladimir N. Belov, Stefan W. Hell
Summary: This study optimized the performance of fDAEs in fluorescence microscopy and nanoscopy labeling by adjusting the structural design. The complete on-switching of protein labeling was achieved under violet and yellow-green light activation, showing excellent performance in fluorescence imaging. Transient on-off switching of double-labeled nanobodies was induced by irradiation with visible light, allowing for nanoscale superresolution imaging through switching and localization of individual fluorophores.
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA
(2021)
Article
Chemistry, Analytical
Hyun Sun Choi, Ji Hye Yum, Yeonsu Jeong, Soobin Lim, Tomotaka Kumagai, Hyung Joon Cha, Soyoung Park
Summary: Triple negative breast cancer (TNBC) affects young women's health and has a socioeconomic impact. Conventional diagnostic methods have difficulties in detecting TNBC. A fluorescent probe is described here that allows rapid and sensitive visualization of TNBC cells, with potential for extensive therapeutic applications.
SENSORS AND ACTUATORS B-CHEMICAL
(2023)
Article
Engineering, Biomedical
C. T. Moody, A. E. Brown, N. P. Massaro, A. S. Patel, P. A. Agarwalla, A. M. Simpson, A. C. Brown, H. Zheng, J. G. Pierce, Y. Brudno
Summary: Alginate hydrogels are widely used in drug delivery, regenerative medicine, and tissue engineering due to their biocompatibility and chemical versatility. This study proposes a modification method that restores carboxyl groups in alginate, which can improve the gelation, mechanics, tissue retention, and drug-capturing capabilities of the hydrogels.
ACTA BIOMATERIALIA
(2022)
Article
Chemistry, Multidisciplinary
Benjamin K. Raliski, Dong Min Mun, Prof Evan W. Miller
Summary: This study incorporates sulfone rhodamine chromophores into a voltage-sensitive scaffold to generate voltage sensitive fluorophores which absorb and emit above 700 nm. These fluorophores partition into cell membranes and display good sensitivity to membrane potential changes, while also exhibiting excellent photostability.
CHEMISTRY-AN ASIAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Xin-Jing Zhao, Yang-Yang Ju, Yu-Ming Su, Chun Tang, Qi Zeng, Liubin Feng, Cheng Wang, Klaus Muellen, Yuan-Zhi Tan
Summary: The study shows a new strategy involving the use of hexa-branched nanographenes to design molecules with large two-photon absorption (TPA) capabilities.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
M. Dobrynin, S. O. Kasatkina, S. Baykov, P. Yu Savko, N. S. Antonov, A. S. Mikherdov, V. P. Boyarskiy, R. M. Islamova
Summary: C,N-Chelate deprotonated diaminecarbene platinum(II) complexes were studied as catalysts for hydrosilylation in polysiloxane systems, leading to the synthesis of phenyl-containing silicone rubbers.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY
(2022)
Article
Chemistry, Applied
Svetlana O. Kasatkina, Kirill K. Geyl, Sergey V. Baykov, Mikhail S. Novikov, Vadim P. Boyarskiy
Summary: A protocol for synthesizing unsymmetrical ureas substituted by pyridyl/quinolinyl moieties has been developed. This method is metal- and base-free and allows for the reamination of N,N-dimethyl-N'-hetaryl ureas with a wide range of aryl and alkyl amines. The method is applicable to over 50 examples and can be easily scaled up to gram quantities.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Inorganic & Nuclear
Haritha Rajasekaran, Peter Jerome, V. Eugene Eliseenkov, Vadim P. Boyarskiy, Nattamai Bhuvanesh, Ramasamy Karvembu
Summary: Four Ru(II)-arene thioamide complexes have been synthesized and characterized, and their catalytic performance in the synthesis of 1,5-diketones has been investigated. The complexes exhibit different catalytic activities, producing either 1,5-diketones or alkylated ketones.
JOURNAL OF ORGANOMETALLIC CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Kirill K. Geyl, Sergey V. Baykov, Stanislav A. Kalinin, Alexandr S. Bunev, Marina A. Troshina, Tatiana V. Sharonova, Mikhail Yu. Skripkin, Svetlana O. Kasatkina, Sofia I. Presnukhina, Anton A. Shetnev, Mikhail Yu. Krasavin, Vadim P. Boyarskiy
Summary: In this study, twelve previously unknown Cu(II) complexes were synthesized using a newly suggested protocol for conveniently accessing variously substituted 2-pyridyl ureas. The structures of the complexes were evaluated using elemental analysis, HRMS, IR spectroscopy, and X-ray diffraction study. Two structural motifs were identified based on the substitution pattern on the 2-pyridine fragment. The antiproliferative activity of the synthesized complexes against lung cancer cell lines was investigated, along with their non-specific cytotoxicity against healthy cells. Certain complexes showed enhanced activity against drug-resistant cells with moderate selectivity towards normal cells. The mechanism of antiproliferative effect was studied through additional experiments, including cell cycle analysis and apoptosis induction test. The findings suggest that these 2-pyridyl urea-based Cu(II) complexes have potential as starting points for further exploration of their anticancer properties.
Article
Chemistry, Inorganic & Nuclear
Roman A. Popov, Alexander S. Mikherdov, Vadim P. Boyarskiy
Summary: A method for obtaining C,S-cyclometalated deprotonated diaminocarbene complexes has been extended to reactions with pyridine-2(1H)-thione by adding a bifunctional N,S-nucleophile's endocyclic nitrogen atom to a coordinated isocyanide. The coupling of Pd-II- and Pt-II-bis(arylisocyanide) complexes with pyridine-2(1H)-thione leads to the formation of mononuclear C,S-cyclometalated deprotonated diaminocarbene complexes in high yield. The obtained complexes were characterized by various analytical techniques.
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY
(2022)
Article
Chemistry, Physical
Sergey V. Baykov, Marina V. Tarasenko, Artem V. Semenov, Evgeniy A. Katlenok, Anton A. Shetnev, Vadim P. Boyarskiy
Summary: A series of cyclohexane and cyclohexene carboxylic acids bearing 1,2,4-oxadiazole substituent were prepared via condensation reactions. The compounds were characterized by HRMS, 1 H and 13 C NMR, and the crystal structures of five acids were determined using X-ray diffraction analysis. Computational investigations revealed previously undescribed noncovalent interactions between the oxadiazole ring and carboxylic group, which were found to be caused by packing effects and have electrostatic and dispersive nature.
JOURNAL OF MOLECULAR STRUCTURE
(2022)
Article
Chemistry, Physical
Sergey Baykov, Artem Semenov, Sofia Presnukhina, Alexander S. Novikov, Anton A. Shetnev, Vadim P. Boyarskiy
Summary: The competition between hydrogen bonding and halogen bonding in crystal structures of 2,5-dibromothiophene-3-carboxylic acid derivatives was studied. It was found that the oxygen atom of the carbonyl group forms preferential interaction with the acidic protons of the amide moieties. Theoretical calculations confirmed the presence of these interactions and clarified their noncovalent nature.
JOURNAL OF MOLECULAR STRUCTURE
(2022)
Article
Chemistry, Multidisciplinary
Sergey Baykov, Marina Tarasenko, Valentina Kotlyarova, Anton Shetnev, Lev E. Zelenkov, Irina A. Boyarskaya, Vadim P. Boyarskiy
Summary: This study synthesized and studied a series of organic luminophores with different structures under specific conditions. The results showed that 2-(ortho-aminophenyl) 1,2,4-oxadiazoles are the best luminophores.
Article
Chemistry, Multidisciplinary
Alexander S. Mikherdov, Roman A. Popov, Andrey S. Smirnov, Anastasiya A. Eliseeva, Alexander S. Novikov, Vadim P. Boyarskiy, Rosa M. Gomila, Antonio Frontera, Vadim Yu. Kukushkin, Nadezhda A. Bokach
Summary: In this study, two isostructural cocrystals were synthesized, revealing the similarity of halogen bond donors in their accepting role. The similarity and unique bonding features of the halogen bonds were further verified by theoretical calculations. Additionally, the study observed for the first time a tetrafurcated halogen bond involving four disunited acceptors.
CRYSTAL GROWTH & DESIGN
(2022)
Article
Chemistry, Inorganic & Nuclear
Artem V. Semenov, Sergey V. Baykov, Natalia S. Soldatova, Kirill K. Geyl, Daniil M. Ivanov, Antonio Frontera, Vadim P. Boyarskiy, Pavel S. Postnikov, Vadim Yu. Kukushkin
Summary: Five new copper(I) complexes were generated and isolated as a solid via a three-component reaction. These complexes consist of dibenzohalolium cation and 1,2,4-oxadiazolate anion, with simultaneous linkage between the O,O atoms of the anion and the halogen atom. The strong three-center halogen bonding between the oxadiazolate moieties and the dibenzohalolium cation was identified as the main force in stabilizing the copper(I) complexes.
INORGANIC CHEMISTRY
(2023)
Review
Biochemistry & Molecular Biology
Sergey V. V. Baykov, Anton A. A. Shetnev, Artem V. V. Semenov, Svetlana O. O. Baykova, Vadim P. P. Boyarskiy
Summary: This review discusses synthetic methods for obtaining 1,2,4-oxadiazole and their application in pharmaceutical preparation. The methods are divided into three groups, including two-stage protocols, one-pot synthesis, and oxidative cyclization. These methods have significant potential in drug design, allowing for the preparation of thermosensitive 1,2,4-oxadiazole and expanding the use of oxadiazole core as a linker in bioactive compound design.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2023)
Article
Biochemistry & Molecular Biology
Svetlana O. Baykova, Kirill K. Geyl, Sergey V. Baykov, Vadim P. Boyarskiy
Summary: A new synthetic route for quinazolin-2,4(1H,3H)-diones and thieno[2,3-d]pyrimidine-2,4(1H,3H)-diones substituted by pyridyl/quinolinyl moiety in position 3 has been developed. The method involves the annulation of substituted anthranilic esters or 2-aminothiophene-3-carboxylates with 1,1-dimethyl-3-(pyridin-2-yl) ureas, forming N-aryl-N'-pyridyl ureas and subsequent cyclocondensation into the desired heterocycles. The reaction exhibits moderate to good yields (up to 89%) and can be easily scaled to gram quantities.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2023)
Article
Chemistry, Inorganic & Nuclear
Roman A. Popov, Alexander S. Novikov, Vitalii V. Suslonov, Vadim P. Boyarskiy
Summary: Binuclear diaminocarbene complexes can replace the anionic chloride ligand with other halides, such as Br or I, and form mixtures of kinetically and thermodynamically controlled regioisomers. The interconversion of these regioisomers was observed in CDCl3 solutions. DFT calculations and X-ray crystallography study confirmed the presence of chalcogen bonding in the solid state and showed that the thermodynamic favorability for the formation of thermodynamically controlled regioisomers increases in the Cl < Br < I row.
Article
Chemistry, Inorganic & Nuclear
Konstantin V. Deriabin, Ekaterina A. Golovenko, Nikita S. Antonov, Sergey V. Baykov, Vadim P. Boyarskiy, Regina M. Islamova
Summary: A platinum polymer catalyst (Pt-PDMS) was synthesized by immobilizing a platinum catalytic complex in a polysiloxane chain using an azide-alkyne CuAAC cycloaddition. Insoluble Pt-PDMS can be used as an effective heterogeneous macrocatalyst for Si-O dehydrocoupling. Pt-PDMS is easy to recover, purify, and reuse again for heterogeneous catalysis.
DALTON TRANSACTIONS
(2023)
Article
Chemistry, Multidisciplinary
Reza Kia, Hadis Shojaei, Vadim P. P. Boyarskiy, Alexander S. S. Mikherdov
Summary: The complex [Re(CO)(3)(Ph(4)TAP)(OCOCF3)] was synthesized, characterized, and studied using computational approaches. The structure of the complex was compared with similar structures in the Cambridge Structural Database. The intra- and intermolecular interactions were determined using QTAIM, NCI-IGM, and NBO approaches and compared with similar structures. The complex exhibited interesting intermolecular n -> pi* and C-HMIDLINE HORIZONTAL ELLIPSIS pi interactions, which were supported by non-classic C-HMIDLINE HORIZONTAL ELLIPSISO hydrogen bonding, resulting in the supramolecular assembly of molecules into two concurrent chains.