Article
Chemistry, Multidisciplinary
Veronika Slachtova, Simona Bellova, Agustina La-Venia, Juraj Galeta, Martin Dracinsky, Karel Chalupsky, Alexandra Dvorakova, Helena Mertlikova-Kaiserova, Peter Rukovansky, Rastislav Dzijak, Milan Vrabel
Summary: The development of reagents selective in complex biological media is a significant challenge. We demonstrate that N1-alkylation of 1,2,4-triazines produces more reactive triazinium salts when reacting with strained alkynes compared to the parent 1,2,4-triazines. These salts facilitate efficient modification of peptides and proteins through a powerful bioorthogonal ligation. The positively charged N1-alkyl triazinium salts possess favorable cell permeability and outperform analogous 1,2,4,5-tetrazines for intracellular fluorescent labeling applications. These new ionic heterodienes exhibit high reactivity, stability, synthetic accessibility, and improved water solubility, making them valuable additions to the repertoire of modern bioorthogonal reagents.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Review
Biochemistry & Molecular Biology
Karine Porte, Maxime Riberaud, Remi Chatre, Davide Audisio, Sebastien Papot, Frederic Taran
Summary: The advent of bioorthogonal chemistry has enabled ambitious applications of unnatural chemical reactions within living organisms, a long-sought goal in chemical biology. This review highlights the progress in understanding fundamental biological processes and the development of novel imaging and therapeutic strategies using bioorthogonal chemistry in animal models.
Review
Cell Biology
Monika Singha, Leslie Spitalny, Kim Nguyen, Abigail Vandewalle, Robert C. Spitale
Summary: This article outlines the current state of employing chemical approaches for cell-specific RNA expression studies, including the utility of metabolic labels, approaches for characterizing metabolic incorporation and enrichment of labeled RNAs, and how these approaches have been used to study biological systems by providing mechanistic insights into transcriptional dynamics. Further efforts in this area will focus on developing novel chemical handles for RNA enrichment and profiling, as well as innovative approaches to control cell-specific incorporation of chemically modified metabolic probes. These advancements in RNA metabolic labeling techniques enable sensitive detection of RNA expression dynamics within relatively small subsets of cells in living tissues and organisms, crucial for understanding complex developmental and pathological processes.
WILEY INTERDISCIPLINARY REVIEWS-RNA
(2021)
Article
Chemistry, Multidisciplinary
Chun Liu, Jingsheng Niu, Tingting Cui, Jinsong Ren, Xiaogang Qu
Summary: In this study, a near-infrared light-controllable carbonaceous nanocalabash motor catalyst was developed for active targeted synthesis of drugs inside biofilms. The catalyst exhibited good biocompatibility and rapid autonomous motion, enabling the generation of active molecules in deep biofilm layers to remove biofilms and eradicate bacteria.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Engineering, Biomedical
Xianzhi Zhang, Ryan F. Landis, Puspam Keshri, Roberto Cao-Milan, David C. Luther, Sanjana Gopalakrishnan, Yuanchang Liu, Rui Huang, Gengtan Li, Morgane Malassine, Imad Uddin, Brayan Rondon, Vincent M. Rotello
Summary: Bioorthogonal catalysis is a promising strategy for imaging and therapeutic applications, with the use of a polymeric scaffold to encapsulate transition metal catalysts resulting in bioorthogonal polyzymes that enhance stability and demonstrate therapeutic potential by transforming a nontoxic prodrug into an anticancer drug.
ADVANCED HEALTHCARE MATERIALS
(2021)
Review
Chemistry, Multidisciplinary
Madonna M. A. Mitry, Francesca Greco, Helen M. I. Osborn
Summary: Bioorthogonal chemistry involves selective biocompatible reactions between functional groups that are not normally present in biology. It has been used to probe biomolecules in living systems, and has advanced biomedical strategies such as diagnostics and therapeutics. This review discusses challenges and opportunities in translating in vitro bioorthogonal approaches to in vivo settings, focusing on methods to deliver the bioorthogonal reaction components, and critically appraises the suitability of these reactions for in vivo applications.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Alejandro Gutierrez-Gonzalez, Paolo Destito, Jose R. Couceiro, Cibran Perez-Gonzalez, Fernando Lopez, Jose L. Mascarenas
Summary: Tailored ruthenium sandwich complexes with photoresponsive arene ligands efficiently catalyze azide-thioalkyne cycloaddition under UV light. These reactions are bioorthogonal in aqueous mixtures with biological components and can selectively modify biopolymers like DNA or peptides. This ruthenium-based technology is compatible and mutually orthogonal with the standard copper-catalyzed azide-alkyne cycloaddition.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Multidisciplinary Sciences
Yawen You, Qingqing Deng, Yibo Wang, Yanjuan Sang, Guangming Li, Fang Pu, Jinsong Ren, Xiaogang Qu
Summary: This study reports on a DNA-based biocompatible, highly efficient, and precisely targeted copper nanocatalyst, which exhibits excellent catalytic activity and achieves efficient prodrug activation and antitumor effects in cancer cells.
NATURE COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Maxime Riberaud, Karine Porte, Arnaud Chevalier, Lea Madegard, Aurelie Rachet, Agnes Delaunay-Moisan, Florian Vinchon, Pierre Thuery, Giovanni Chiappetta, Pier Alexandre Champagne, Gregory Pieters, Davide Audisio, Frederic Taran
Summary: Bioorthogonal click-and-release reactions have been developed for the selective release of drugs in biological media. This study presents the synthesis and reactivities of two new families of iminosydnone mesoionic reactants, allowing a bioorthogonal release of electrophilic species under physiological conditions. The reactions demonstrated high reactivity and the release of isocyanate electrophiles inside living cells, offering new perspectives in chemical biology.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Analytical
Sang-Kee Choi, Youngjun Lee, Sang Eun Yoon, Hongseo Choi, Jonghoon Kim, Jong H. Kim, Sanghee Lee, Wook Kim, Eunha Kim
Summary: This study introduces tetrazine-modified aggregation-induced emission luminogens for bioorthogonal fluorogenic imaging, demonstrating successful development of three different colorful fluorogenic tetrazine-fluorophores with unique fluorescent properties. Tetrazine modification induces fluorescence quenching and a synergistic effect between intramolecular charge transfer and tetrazine-mediated non-radiative decay was revealed through aggregate formation study and computational calculations. Additionally, the simple conjugation between triphenylphosphonium and tetrazine-fluorophore enabled the development of fluorogenic probes for spatiotemporally controlled bioorthogonal bioimaging of mitochondria in live cells without the need for washing the labels.
SENSORS AND ACTUATORS B-CHEMICAL
(2021)
Review
Biochemistry & Molecular Biology
Sang-Kee Choi, Jonghoon Kim, Eunha Kim
Summary: This review highlights the use of bioorthogonal chemistry in fluorescent imaging, with a focus on the inverse electron demand Diels-Alder (iEDDA) reactions. Tetrazine-functionalized dyes as fluorogenic probes are a key feature discussed, along with synthesis methods, quenching mechanisms, and applications in bioimaging. Traditional Pinner reactions, metal-catalyzed bond formations, and the fabrication of tetrazine-conjugated fluorophores are also covered in this review.
Article
Biochemistry & Molecular Biology
Mathivanan Chinnaraj, David A. Barrios, Carl Frieden, Tomasz Heyduk, Robert Flaumenhaft, Nicola Pozzi
Summary: Protein folding in the endoplasmic reticulum is assisted by various families of enzymes, including protein disulfide isomerases (PDIs) which can form or break disulfide bonds. Obtaining structural information on PDIs is challenging due to their size and flexibility, but single-molecule FRET has been shown as a feasible tool for studying their structure and dynamics. Proof-of-concept smFRET measurements of catalytically active PDI have expanded the toolkit for structural studies of PDIs.
Article
Chemistry, Multidisciplinary
Athanasios Markos, Maurice Biedermann, Johannes Heimgartner, Adeline Schmitt, Kathrin Lang, Helma Wennemers
Summary: In this study, C,N-cyclic-N'-acyl azomethine imines (AMIs) were introduced to bioorthogonal reactions in an aqueous environment, showing stability under physiological conditions and selective reactivity with isonitriles. The AMI-isonitrile ligation demonstrated biocompatibility and orthogonality to commonly used bioorthogonal reactions.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
Fayang Xie, Xiangqian Jia, Zhu Zhu, Yunfei Wu, Haolin Jiang, Hongzhi Yang, Yu Cao, Rui Zhu, Bing Zhou, Juanjuan Du, Yefeng Tang
Summary: The article introduces a novel bioconjugation reaction using a chemical trigger to release highly strained TCH species, with the reactivity-stability balance of BNU derivatives being adjustable by manipulating their N-1 substituents. This method has been successfully applied to protein labeling and cell imaging, opening a new avenue for research in bioconjugate chemistry.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Review
Chemistry, Multidisciplinary
Frederik Mueggenburg, Sabine Mueller
Summary: This review summarizes the synthetic methods of azide-modified nucleosides and their applications in RNA and DNA functionalization.
Article
Plant Sciences
Oriane Morel, Cedric Lion, Godfrey Neutelings, Jonathan Stefanov, Fabien Baldacci-Cresp, Clemence Simon, Christophe Biot, Simon Hawkins, Corentin Spriet
Summary: This article introduces a methodology called REPRISAL for mapping the lignification capacity of plant cell walls in detail. REPRISAL combines three separate approaches, including chemical reporters labeling, automatic segmentation algorithm, and ratiometric analysis, to analyze the distribution and proportions of monolignol reporters in different cell wall zones. The methodology is applied to study the lignification capacity in Arabidopsis, Populus, flax, and maize, as well as the incorporation of a fucose reporter into noncellulosic cell wall polymers.
Article
Biochemistry & Molecular Biology
Di Wu, Pierre-Andre Gilormini, Sakura Toda, Christophe Biot, Cedric Lion, Yann Guerardel, Chihiro Sato, Ken Kitajima
Summary: This study investigated the role of the C-domain in the CMP-Kdn-dependent inhibition in rainbow trout and mice. The results showed that the C-domain affects the catalytic activity of rtCSS when using Kdn as a substrate, and the inhibition is C-domain-dependent.
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS
(2022)
Article
Biochemistry & Molecular Biology
Vincent Rigolot, Yannick Rossez, Christophe Biot, Cedric Lion
Summary: Most Escherichia coli strains associated with neonatal meningitis express the K1 capsule, a sialic acid polysaccharide that is directly related to their pathogenicity. However, bacterial capsules are seldom targeted despite their important role as virulence factors, and the K1 polysialic acid (PSA) antigen that shields bacteria from the immune system still remains untackled. In this study, we develop a fluorescence microplate assay that combines metabolic oligosaccharide engineering (MOE) and bioorthogonal chemistry to detect K1 capsules. The assay is optimized, validated, and can be used for screening approaches to identify novel capsule-targeted antibiotics.
RSC CHEMICAL BIOLOGY
(2023)
Editorial Material
Biochemistry & Molecular Biology
Marie Lopez, Yung-Sing Wong, Christophe Biot, Boris Vauzeilles
Summary: Chemical biology is a growing field that uses chemical and physicochemical tools to address biological questions at the molecular level. Chemical biologists design and develop molecular tools to understand and modify biological processes, and observe their effects in complex biological environments. This field finds applications in areas such as healthcare and the environment.
Article
Chemistry, Multidisciplinary
Clemence Simon, Cedric Lion, Hania Ahouari, Herve Vezin, Simon Hawkins, Christophe Biot
Summary: This study demonstrates the ligation of TEMPO-based probes with monolignol reporters in plant cell walls through Diels-Alder chemistry, enabling the study of lignification using EPR spectroscopy and imaging.
CHEMICAL COMMUNICATIONS
(2021)
Correction
Chemistry, Multidisciplinary
Clemence Simon, Cedric Lion, Hania Ahouari, Herve Vezin, Simon Hawkins, Christophe Biot
Summary: The study corrected EPR imaging of sinapyl alcohol and its application to the study of plant cell wall lignification by Clemence Simon et al. in Chem. Commun., 2021.
CHEMICAL COMMUNICATIONS
(2021)