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Bioorthogonal chemistry

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https://www.readbyqxmd.com/read/28640297/preparation-of-tetrazine-containing-2-1-complexes-of-99m-tc-and-in-vivo-targeting-using-bioorthogonal-inverse-electron-demand-diels-alder-chemistry
#1
Abdolreza Yazdani, Nancy Janzen, Shannon Czorny, Robert G Ungard, Tanya Miladinovic, Gurmit Singh, John F Valliant
The aim of this work was to synthesize and evaluate [2 + 1] (99m)Tc(i) polypyridine complexes containing tetrazines, which along with the corresponding Re(i) complexes, represent a new class of isostructural nuclear and turn-on luminescent probes that can be derivatized and targeted using bioorthogonal chemistry. To this end, [2 + 1] complexes of (99m)Tc(i) of the type [(99m)Tc(CO)3(N^N)(L)] (N^N = bathophenanthroline disulfonate (BPS) or 2,2'-bipyridine (bipy)), where the monodentate ligand (L) was a tetrazine linked to the metal through an imidazole derivative, were prepared...
June 22, 2017: Dalton Transactions: An International Journal of Inorganic Chemistry
https://www.readbyqxmd.com/read/28635265/metabolic-oligosaccharide-engineering-with-alkyne-sialic-acids-confers-neuraminidase-resistance-and-inhibits-influenza-reproduction
#2
Torben Heise, Christian Büll, Daniëlle M H Beurskens, Emiel Rossing, Marien de Jonge, Gosse J Adema, Thomas J Boltje, Jeroen Langereis
Metabolic incorporation of azide or alkyne modified sialic acids into the cellular glycosylation pathway enables the study of sialoglycan expression, localization and trafficking via bioorthogonal chemistry. Herein we report that such modifications of the sialic acid sugar can have a profound influence on their hydrolysis by neuraminidases (sialidase). Azidoacetyl modified sialic acids were prone to neuraminidase cleavage, whereas propargyloxycarbonyl (Poc) modified sialic acids were largely resistent to cleavage...
June 21, 2017: Bioconjugate Chemistry
https://www.readbyqxmd.com/read/28626570/riboflavin-as-a-bioorthogonal-photocatalyst-for-the-activation-of-a-pt-iv-prodrug
#3
Silvia Alonso-de Castro, Emmanuel Ruggiero, Ane Ruiz-de-Angulo, Elixabete Rezabal, Juan C Mareque-Rivas, Xabier Lopez, Fernando López-Gallego, Luca Salassa
Encouraging developments demonstrate that few transition metal and organometallic catalysts can operate in a bioorthogonal fashion and promote non-natural chemistry in living systems by minimizing undesired side reactions with cellular components. These catalytic processes have potential for applications in medicinal chemistry and chemical biology. However, the stringent conditions of the cell environment severely limit the number of accessible metal catalysts and exogenous reactions. Herein, we report an unorthodox approach and a new type of bioorthogonal catalytic reaction, in which a metal complex is an unconventional substrate and an exogenous biological molecule acts as a catalyst...
June 1, 2017: Chemical Science
https://www.readbyqxmd.com/read/28590752/optimization-of-an-enzymatic-antibody-drug-conjugation-approach-based-on-coenzyme-a-analogs
#4
Jan Grünewald, Yunho Jin, Julie Vance, Jessica Read, Xing Wang, Yongqin Wan, Huanfang Zhou, Weijia Ou, Heath E Klock, Eric C Peters, Tetsuo Uno, Ansgar Brock, Bernhard H Geierstanger
Phosphopantetheine transferases (PPTases) can be used to efficiently prepare site-specific antibody-drug conjugates (ADCs) by enzymatically coupling coenzyme A (CoA)-linker payloads to 11-12 amino acid peptide substrates inserted into antibodies. Here, a two-step strategy is established wherein in a first step, CoA analogs with various bioorthogonal reactivities are enzymatically installed on the antibody for chemical conjugation with a cytotoxic payload in a second step. Because of the high structural similarity of these CoA analogs to the natural PPTase substrate CoA-SH, the first step proceeds very efficiently and enables the use of peptide tags as short as 6 amino acids compared to the 11-12 amino acids required for efficient one-step coupling of the payload molecule...
June 14, 2017: Bioconjugate Chemistry
https://www.readbyqxmd.com/read/28582715/in%C3%A2-vivo-stem-cell-tracking-with-imageable-nanoparticles-that-bind-bioorthogonal-chemical-receptors-on-the-stem-cell-surface
#5
Sangmin Lee, Hwa In Yoon, Jin Hee Na, Sangmin Jeon, Seungho Lim, Heebeom Koo, Sang-Soo Han, Sun-Woong Kang, Soon-Jung Park, Sung-Hwan Moon, Jae Hyung Park, Yong Woo Cho, Byung-Soo Kim, Sang Kyoon Kim, Taekwan Lee, Dongkyu Kim, Seulki Lee, Martin G Pomper, Ick Chan Kwon, Kwangmeyung Kim
It is urgently necessary to develop reliable non-invasive stem cell imaging technology for tracking the in vivo fate of transplanted stem cells in living subjects. Herein, we developed a simple and well controlled stem cell imaging method through a combination of metabolic glycoengineering and bioorthogonal copper-free click chemistry. Firstly, the exogenous chemical receptors containing azide (-N3) groups were generated on the surfaces of stem cells through metabolic glycoengineering using metabolic precursor, tetra-acetylated N-azidoacetyl-d-mannosamine(Ac4ManNAz)...
September 2017: Biomaterials
https://www.readbyqxmd.com/read/28572909/green-to-far-red-emitting-fluorogenic-tetrazine-probes-synthetic-access-and-no-wash-protein-imaging-inside-living-cells
#6
Achim Wieczorek, Philipp Werther, Jonas Euchner, Richard Wombacher
Fluorogenic probes for bioorthogonal labeling chemistry are highly beneficial to reduce background signal in fluorescence microscopy imaging. 1,2,4,5-Tetrazines are known substrates for the bioorthogonal inverse electron demand Diels-Alder reaction (DAinv) and tetrazine substituted fluorophores can exhibit fluorogenic properties. Herein, we report the synthesis of a palette of novel fluorogenic tetrazine dyes derived from widely-used fluorophores that cover the entire emission range from green to far-red. We demonstrate the power of the new fluorogenic probes in fixed and live cell labeling experiments and present the first example of intracellular live cell protein imaging using tetrazine-based probes under no-wash conditions...
February 1, 2017: Chemical Science
https://www.readbyqxmd.com/read/28525770/-expand-and-click-a-new-method-for-labeling-hiv-1-envelope-glycoproteins
#7
Melissa V Fernandez, Eric O Freed
In this issue of Cell Chemical Biology, Sakin et al. (2017) investigate the nanoscale behavior of the HIV-1 envelope (Env) glycoprotein complex by using genetic code expansion, bioorthogonal amino acids, synthetic dyes, and click chemistry. This minimally invasive approach allows the measurement of native Env cellular distribution and dynamics.
May 18, 2017: Cell Chemical Biology
https://www.readbyqxmd.com/read/28497539/inverse-electron-demand-diels-alder-reactions-principles-and-applications
#8
Jianwei Xu, Zhuang Mao Png Png, Huining Zeng Zeng, Qun Ye
Inverse electron-demand Diels-Alder reaction (iEDDA) represents an intriguing class of cycloaddition reaction that has attracted increasing attention for its applications in bioorthogonal chemistry, total synthesis of natural products, and materials science. In many cases, the application of iEDDA has been demonstrated as an innovative approach to achieve the target structures. The theoretical aspects of this class of reactions are of particular interest for scientists to understand various factors, such as steric strain and electron density of the attached groups, to govern the reaction and thus to elucidate the reaction mechanism...
May 12, 2017: Chemistry, An Asian Journal
https://www.readbyqxmd.com/read/28485436/silver-nanoparticle-plasmonic-enhanced-f%C3%A3-rster-resonance-energy-transfer-fret-imaging-of-protein-specific-sialylation-on-the-cell-surface
#9
Tingbi Zhao, Ting Li, Yang Liu
A large amount of proteins are post-translationally modified with a sialic acid terminal oligosaccharide, and sialylation directly affects the function of glycoproteins and adjusts relevant biological processes. Herein, we developed a method for imaging analysis of protein-specific sialylation on the cell surface via silver nanoparticle (AgNPs) plasmonic enhanced Förster resonance energy transfer (FRET). In this strategy, the target monosaccharide was labelled with the FRET acceptor of Cy5 via bioorthogonal chemistry...
May 9, 2017: Nanoscale
https://www.readbyqxmd.com/read/28478678/cyclopropenones-for-metabolic-targeting-and-sequential-bioorthogonal-labeling
#10
R David Row, Hui-Wen Shih, Austin T Alexander, Ryan A Mehl, Jennifer A Prescher
Cyclopropenones are attractive motifs for bioorthogonal chemistry, owing to their small size and unique modes of reactivity. Unfortunately, the fastest-reacting cyclopropenones are insufficiently stable for routine intracellular use. Here we report cyclopropenones with improved stability that maintain robust reactivity with bioorthogonal phosphines. Functionalized cyclopropenones were synthesized and their lifetimes in aqueous media and cellular environments were analyzed. The most robust cyclopropenones were further treated with a panel of phosphine probes, and reaction rates were measured...
May 17, 2017: Journal of the American Chemical Society
https://www.readbyqxmd.com/read/28472168/development-of-prostate-specific-membrane-antigen-targeted-ultrasound-microbubbles-using-bioorthogonal-chemistry
#11
Aimen Zlitni, Melissa Yin, Nancy Janzen, Samit Chatterjee, Ala Lisok, Kathleen L Gabrielson, Sridhar Nimmagadda, Martin G Pomper, F Stuart Foster, John F Valliant
Prostate specific membrane antigen (PSMA) targeted microbubbles (MBs) were developed using bioorthogonal chemistry. Streptavidin-labeled MBs were treated with a biotinylated tetrazine (MBTz) and targeted to PSMA expressing cells using trans-cyclooctene (TCO)-functionalized anti-PSMA antibodies (TCO-anti-PSMA). The extent of MB binding to PSMA positive cells for two different targeting strategies was determined using an in vitro flow chamber. The initial approach involved pretargeting, where TCO-anti-PSMA was first incubated with PSMA expressing cells and followed by MBTz, which subsequently showed a 2...
2017: PloS One
https://www.readbyqxmd.com/read/28451223/imaging-specific-newly-synthesized-proteins-within-cells-by-fluorescence-resonance-energy-transfer
#12
Linfeng Sheng, Lesi Cai, Jie Liu, Sichun Zhang, Jing-Juan Xu, Xinrong Zhang, Hong-Yuan Chen
Metabolic azide amino acid labelling followed by the use of bioorthogonal chemistry is an efficient technique for imaging newly synthesized proteins. Recently, AHA-labelling together with the proximity-ligation assay was used to identify newly synthesized proteins of interest (POI) (Tom Dieck et al., Nat. Meth. 2015, 12, 411). Here we build on this study replacing the proximity-ligation assay with FRET to improve the spatial resolution. Herein, we develop a FRET-based strategy for imaging the newly synthesized endogenous POI within cells: a FRET acceptor is installed onto the newly synthesized proteins via click chemistry, and a FRET donor onto the POI via immunocytochemistry...
January 1, 2017: Chemical Science
https://www.readbyqxmd.com/read/28449250/self-assembly-of-peptide-boroxoles-on-cis-dihydroxylated-oligoamide-templates-in-water
#13
André Wuttke, Armin Geyer
We develop templates that can be used to stabilize consistent oligomers of a bioactive peptide. In the present study, we synthesize oligomers of an antibody epitope from the amyloidogenic prion protein. Dynamic covalent chemistry is the basis for the spontaneous condensation of 2, 3, 4 or 6 peptides with qualified polyol templates presenting the required number of bioorthogonal ligation sites. To study this process in aqueous solution, the N-terminal amino acid of a 13-mer peptide is first acylated with 4-carboxy-benzoboroxole (1-hydroxy-1,3-dihydrobenzo[c][1,2] oxaborole-5-carboxylic acid) and then mixed with the template to obtain self-assembled miniamyloids of specified degree of oligomerization...
April 27, 2017: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/28426149/click-chemistry-mediated-rapid-microbubble-capture-for-acute-thrombus-ultrasound-molecular-imaging
#14
Tuantuan Wang, Chuxiao Yuan, Bingyang Dai, Yang Liu, Mingxi Li, Zhenqiang Feng, Qing Jiang, Zhihong Xu, Ningwei Zhao, Ning Gu, Fang Yang
Bioorthogonal coupling chemistry has been studied as a potentially advantageous approach for molecular imaging because it offers rapid, efficient, and strong binding, which might also benefit stability, production, and chemical conjugation. The inverse-electron-demand Diels-Alder reaction between a 1,2,4,5-tetrazine and trans-cyclooctene (TCO) is an example of a highly selective and rapid bioorthogonal coupling reaction that has been used successfully to prepare targeted molecular imaging probes. Here we report a fast, reliable, and highly sensitive approach, based on a two-step pretargeting bioorthogonal approach, to achieving activated-platelet-specific CD62p-targeted thrombus ultrasound molecular imaging...
April 20, 2017: Chembiochem: a European Journal of Chemical Biology
https://www.readbyqxmd.com/read/28399460/molecular-imaging-based-on-metabolic-glycoengineering-and-bioorthogonal-click-chemistry
#15
REVIEW
Hong Yeol Yoon, Heebeom Koo, Kwangmeyung Kim, Ick Chan Kwon
Metabolic glycoengineering is a powerful technique that can introduce various chemical groups to cellular glycan by treatment of unnatural monosaccharide. Particularly, this technique has enabled many challenging trials for molecular imaging in combination with click chemistry, which provides fast and specific chemical conjugation reaction of imaging probes to metabolically-modified live cells. This review introduces recent progress in molecular imaging based on the combination of these two cutting-edge techniques...
July 2017: Biomaterials
https://www.readbyqxmd.com/read/28399446/enzyme-mediated-tagging-of-rna
#16
REVIEW
Lea Anhäuser, Andrea Rentmeister
RNA molecules can play diverse roles in the cell owing to their secondary structure dynamics and various binding modes. Studying localization and dynamics of RNA in vitro or in cells requires tagging with suitable reporter molecules-fluorophores being the most prominent ones. Enzymatic RNA labeling approaches are currently emerging as valuable alternatives to purely chemical synthesis and to binding- or hybridization-based RNA-imaging approaches. Different classes of enzymes allow for cotranscriptional or posttranscriptional installation of small functional groups in RNA...
April 8, 2017: Current Opinion in Biotechnology
https://www.readbyqxmd.com/read/28318083/dienophile-modified-mannosamine-derivatives-for-metabolic-labeling-of-sialic-acids-a-comparative-study
#17
Jeremias E G A Dold, Jessica Pfotzer, Anne-Katrin Späte, Valentin Wittmann
Sialic acids play an important role in numerous cell adhesion processes, and sialylation levels are known to be altered under certain pathogenic conditions, such as cancer. Metabolic glycoengineering with mannosamine derivatives is a convenient way to introduce non-natural chemical reporter groups into sialylated glycoconjugates, offering the opportunity to label sialic acids by using bioorthogonal ligation chemistry. The labeling intensity depends not only on the rate of the ligation reaction but also on the extent to which the natural sialic acids are replaced by the modified ones; that is, the incorporation efficiency...
March 20, 2017: Chembiochem: a European Journal of Chemical Biology
https://www.readbyqxmd.com/read/28303026/strategies-and-challenges-for-the-next-generation-of-antibody-drug-conjugates
#18
REVIEW
Alain Beck, Liliane Goetsch, Charles Dumontet, Nathalie Corvaïa
Antibody-drug conjugates (ADCs) are one of the fastest growing classes of oncology therapeutics. After half a century of research, the approvals of brentuximab vedotin (in 2011) and trastuzumab emtansine (in 2013) have paved the way for ongoing clinical trials that are evaluating more than 60 further ADC candidates. The limited success of first-generation ADCs (developed in the early 2000s) informed strategies to bring second-generation ADCs to the market, which have higher levels of cytotoxic drug conjugation, lower levels of naked antibodies and more-stable linkers between the drug and the antibody...
May 2017: Nature Reviews. Drug Discovery
https://www.readbyqxmd.com/read/28297599/coupling-of-immunostimulants-to-live-cells-through-metabolic-glycoengineering-and-bioorthogonal-click-chemistry
#19
Aline Mongis, Friedrich Piller, Véronique Piller
The present study investigated the potential of metabolic glycoengineering followed by bioorthogonal click chemistry for introducing into cell-surface glycans different immunomodulating molecules. Mouse tumor models EG7 and MC38-OVA were treated with Ac4GalNAz and Ac4ManNAz followed by ligation of immunostimulants to modified cell-surface glycans of the living cells through bioorthogonal click chemistry. The presence of covalently bound oligosaccharide and oligonucleotide immunostimulants could be clearly established...
April 19, 2017: Bioconjugate Chemistry
https://www.readbyqxmd.com/read/28264159/streamlined-synthesis-and-assembly-of-a-hybrid-sensing-architecture-with-solid-binding-proteins-and-click-chemistry
#20
Brian J F Swift, Jared A Shadish, Cole A DeForest, François Baneyx
Combining bioorthogonal chemistry with the use of proteins engineered with adhesive and morphogenetic solid-binding peptides is a promising route for synthesizing hybrid materials with the economy and efficiency of living systems. Using optical sensing of chloramphenicol as a proof of concept, we show here that a GFP variant engineered with zinc sulfide and silica-binding peptides on opposite sides of its β-barrel supports the fabrication of protein-capped ZnS:Mn nanocrystals that exhibit the combined emission signatures of organic and inorganic fluorophores...
March 13, 2017: Journal of the American Chemical Society
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