Review
Biochemistry & Molecular Biology
Gaoxiang Zhao, Zhutie Li, Renshuai Zhang, Liman Zhou, Haibo Zhao, Hongfei Jiang
Summary: Bioorthogonal chemistry represents highly efficient and biocompatible reactions that proceed selectively and rapidly in biological situations. Tetrazine bioorthogonal reactions play an important role in in vivo imaging applications, allowing for the easy tracking of real signals through controlled fluorescence or radiation off-on mechanism.
FRONTIERS IN MOLECULAR BIOSCIENCES
(2022)
Review
Biochemistry & Molecular Biology
Maryana Handula, Kuo-Ting Chen, Yann Seimbille
Summary: The pretargeting strategy using bioorthogonal reactions such as IEDDA has been developed to overcome the limitations of direct targeting in radioimmunotherapy. IEDDA is the fastest bioorthogonal reaction known so far and its biocompatibility and ideal kinetics make it appealing for pretargeting applications. Researchers have conducted in-depth studies on TCO and Tz for their sensitivity to conditions and the need to optimize reagents for the IEDDA reaction in biomedical applications.
Article
Chemistry, Multidisciplinary
Philipp Geng, Eileen List, Franziska Ronicke, Hans-Achim Wagenknecht
Summary: Two green fluorescent tetrazine-modified cyanine-styryl dyes were synthesized for bioorthogonal labelling of DNA. The fluorescence of these dyes can be released by their interaction with DNA and through the conjugated tetrazine as quencher moiety. The dyes can penetrate cells at low concentrations and undergo fluorogenic reactions with BCN-modified DNA in living cells. The two-factor fluorescence release significantly improves the signal-to-noise ratio, eliminating the need for washing procedures prior to cell imaging.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Martin Wilkovitsch, Dennis Svatunek, Hannes Mikula, Christoph Denk
Summary: In this study, we demonstrate a viable and transferable strategy of post-radiolabeling oxidation to synthesize highly reactive F-18-tetrazines, overcoming limited compound stability.
MONATSHEFTE FUR CHEMIE
(2023)
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
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
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
Biochemistry & Molecular Biology
Revathy Sahadevan, Anupama Binoy, Sai K. Vechalapu, Pandurangan Nanjan, Sushabhan Sadhukhan
Summary: We have developed a new cell-permeable and Click-able bioorthogonal probe, YnEGCG, for in situ detection and identification of EGCG's interacting proteins. This probe retains the biological activities of EGCG and identified 160 direct EGCG targets, including previously unknown proteins. The targets are distributed in various subcellular compartments and are mainly involved in regulating key metabolic processes. This study also suggests that EGCG is closely associated with apoptosis and has potential in inducing toxicity in cancer cells.
INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES
(2023)
Article
Biochemistry & Molecular Biology
Jana Brabcova, Alicia Andreu, David Aguilera, Zaida Cabrera, Blanca de las Rivas, Rosario Munoz, Jose M. Palomo
Summary: In this study, materials with carboxylic groups were functionalized with geranyl-amine molecules using an EDC/NHS strategy, and applied for site-selective immobilization of proteins. Different strategies were explored, including reversible hydrophobic immobilization and covalent attachment, resulting in significant increases in activity and successful selective immobilization under various conditions.
Article
Biochemical Research Methods
Thomas T. C. Yue, Ying Ge, Francesco A. Aprile, Michelle T. Ma, Truc T. Pham, Nicholas J. Long
Summary: Bioconjugates of antibodies and their derivatives labeled with beta(+)-emitting radionuclides can be used for diagnostic PET imaging. Site-specific attachment of radioactive cargo to antibody delivery vectors provides well-defined immunoconjugates. This study demonstrates the successful application of the oxaziridine chemistry for site-specific radiolabeling of trastuzumab-derived Fab immunoconjugates with Ga-68. The resulting radiotracers show higher affinity for HER2 receptors and better tumor delineation in PET imaging compared to non-modified conjugates.
BIOCONJUGATE CHEMISTRY
(2023)
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
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)
Article
Chemistry, Medicinal
Ru Si, Ping Hai, Yongbiao Zheng, Jin Wang, Qingqing Zhang, Yanchen Li, Xiaoyan Pan, Jie Zhang
Summary: Proteolysis Targeting Chimera (PROTAC) is a bifunctional molecule that degrades binding proteins through the ubiquitin-proteasome pathway. Despite its potential in overcoming drug resistance and targeting undruggable targets, PROTAC faces challenges such as poor membrane permeability and bioavailability due to its large molecular weight. In this study, we used intracellular self-assembly to construct tumor-specific PROTACs using small molecular precursors. These precursors, incorporated with azide and alkyne as bioorthogonal groups, reacted with each other under the catalysis of copper ions in tumor tissues, resulting in novel PROTACs. These intracellular self-assembled PROTACs effectively induced degradation of VEGFR-2 and EphB4 in U87 cells, as well as promoting apoptosis and blocking cells in S phase. The high selectivity of these tumor-specific intracellular self-assembled PROTACs was attributed to the high concentration of copper ions in tumor tissue. Additionally, this strategy reduced the molecular weight of PROTACs and improved membrane permeability. These findings greatly expand the application of bioorthogonal reactions in the discovery of novel PROTACs.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2023)
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, Medicinal
Ha Eun Shim, Sajid Mushtaq, Lee Song, Chang Heon Lee, Hyosun Lee, Jongho Jeon
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2018)
Article
Environmental Sciences
Ha Eun Shim, Jae Young Lee, Chang Heon Lee, Sajid Mushtaq, Ha Yeon Song, Lee Song, Seong-Jin Choi, Kyuhong Lee, Jongho Jeon
Article
Chemistry, Analytical
Sajid Mushtaq, Mi Hee Choi, Jung Eun Yang, Ha Eun Shim, Lee Song, Ha Yeon Song, Yong Jun Choi, Jongho Jeon
JOURNAL OF RADIOANALYTICAL AND NUCLEAR CHEMISTRY
(2018)
Review
Biochemistry & Molecular Biology
Jongho Jeon
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2019)
Article
Chemistry, Multidisciplinary
Sang Yeob Lee, Ha Eun Shim, Jung Eun Yang, Yong Jun Choi, Jongho Jeon
Review
Biochemistry & Molecular Biology
Jae Young Lee, Sajid Mushtaq, Jung Eun Park, Hee Soon Shin, So-Young Lee, Jongho Jeon
Article
Chemistry, Multidisciplinary
Mah Rukh Zia, Muhammad Asim Raza, Sang Hyun Park, Naseem Irfan, Rizwan Ahmed, Jung Eun Park, Jongho Jeon, Sajid Mushtaq
Summary: The study presented silver/iron oxide nanocomposites as an efficient method for removing radioactive iodine from contaminated water. The material demonstrated high adsorption capacity and removal efficiencies, and could be easily removed after the adsorption process.
Review
Chemistry, Multidisciplinary
Sajid Mushtaq, Asia Bibi, Jung Eun Park, Jongho Jeon
Summary: Nanotechnology has made significant contributions to molecular imaging and cancer therapy, but there is still a gap between preclinical products and clinically approved drugs. Effective translation of preclinical results to clinical settings requires critical studies such as detailed pharmacokinetics and biodistribution research and efficient drug delivery to target organs.
Article
Engineering, Environmental
Sajid Mushtaq, Jung Eun Park, Ha Eun Shim, Chang Heon Lee, Hee Soon Shin, So-Young Lee, Jongho Jeon
Summary: This study investigates the biodistribution of PHMG in rats using radioanalytical techniques. The results show that PHMG is mainly distributed in the liver and lungs, and has a slow clearance rate from internal organs. The study also compares the biodistribution of PHMG exposed through different routes and finds that it causes damage to both pulmonary and extrapulmonary organs.
ENVIRONMENTAL ENGINEERING RESEARCH
(2022)
Article
Environmental Sciences
Jung Eun Park, Jun-Ho Shin, Wonzin Oh, Sang-June Choi, Jeongju Kim, Chorong Kim, Jongho Jeon
Summary: A chitosan-coated iron oxide nanoparticle immobilized hydrophilic poly(vinylidene) fluoride membrane has been developed for efficient removal of hexavalent chromium from aqueous solutions. The nanocomposite membrane showed high adsorption capacity and maintained its removal efficiency in the presence of competing ions. This filtration process holds promise as a practical method for wastewater treatment.
Article
Chemistry, Multidisciplinary
Jun-Ho Shin, Jung Eun Yang, Jung Eun Park, Sun-Wook Jeong, Sang-June Choi, Yong Jun Choi, Jongho Jeon
Summary: In this study, functionalized polyvinylidene fluoride membranes modified with chitosan-coated iron oxide nanomaterials were developed for efficient treatment of anionic dye-contaminated water. The composite membrane showed high removal capacity for anionic dyes, especially under acidic conditions. It could be reused multiple times without significant decrease in adsorption performance and demonstrated high efficiency in removing various anionic dyes. The easy preparation and rapid decolorization procedures make this composite membrane suitable for efficient water treatment.
Article
Environmental Sciences
Jung Eun Park, Jun Young Lee, Jungho Chae, Chang Ho Min, Hee Soon Shin, So Young Lee, Jae Young Lee, Jeong Hoon Park, Jongho Jeon
Summary: Exposure to diesel particulate matter (DPM) can cause severe respiratory diseases and toxic effects on extrapulmonary organs, as shown by molecular imaging and radiolabeling techniques in animal models. DPM was primarily distributed in the lungs, but also translocated to other organs such as the heart, spleen, and liver.
Article
Biochemical Research Methods
Yong Dae Park, Jam-Eon Park, Hyeon Sik Kim, Seung-Hyeon Choi, Jung Eun Park, Jongho Jeon, Seung-Hwan Park
BIOCONJUGATE CHEMISTRY
(2020)
Article
Chemistry, Multidisciplinary
Chang Heon Lee, Ha Eun Shim, Lee Song, Hi Gyu Moon, Kyuhong Lee, Jung Eun Yang, Ha Yeon Song, Yong Jun Choi, Dae Seong Choi, Jongho Jeon
CHEMICAL COMMUNICATIONS
(2019)