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Bioorthogonal chemistry

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https://www.readbyqxmd.com/read/28525770/-expand-and-click-a-new-method-for-labeling-hiv-1-envelope-glycoproteins
#1
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
#2
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
#3
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
#4
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
#5
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
#6
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
#7
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-catching-for-acute-thrombus-ultrasound-molecular-imaging
#8
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 one significant advantage for molecular imaging as it offers rapid, efficient, and strong binding, which may also benefit in stability, production, and chemical conjugation. The inverse-electron-demand Diels-Alder reaction between s-tetrazine and trans-cyclooctene (TCO) is an example of a highly selective and rapid bioorthogonal coupling reaction to be used successfully to prepare targeted molecular imaging probes. Herein, based on a two-step pretargeting bioorthogonal chemistry, we report a fast and reliable highly sensitive approach to achieve 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
#9
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
#10
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
#11
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
#12
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
#13
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...
March 28, 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
#14
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
https://www.readbyqxmd.com/read/28262560/bliss-a-bioorthogonal-dual-labeling-strategy-to-unravel-lignification-dynamics-in-plants
#15
Cedric Lion, Clémence Simon, Brigitte Huss, Anne-Sophie Blervacq, Louis Tirot, Djadidi Toybou, Corentin Spriet, Christian Slomianny, Yann Guerardel, Simon Hawkins, Christophe Biot
A better in vivo understanding of lignin formation within plant cell walls will contribute to improving the valorization of plant-derived biomass. Although bioorthogonal chemistry provides a promising platform to study the lignification process, methodologies that simultaneously detect multiple chemical reporters in living organisms are still scarce. Here, we have developed an original bioorthogonal labeling imaging sequential strategy (BLISS) to visualize and analyze the incorporation of both p-hydroxyphenyl (H) and guaiacyl (G) units into lignin in vivo with a combination of strain-promoted and copper-catalyzed azide-alkyne cycloadditions...
March 16, 2017: Cell Chemical Biology
https://www.readbyqxmd.com/read/28218446/in-situ-bioorthogonal-metabolic-labeling-for-fluorescence-imaging-of-virus-infection-in-vivo
#16
Hong Pan, Wen-Jun Li, Xiang-Jie Yao, Ya-Yun Wu, Lan-Lan Liu, Hua-Mei He, Ren-Li Zhang, Yi-Fan Ma, Lin-Tao Cai
Optical fluorescence imaging is an important strategy to explore the mechanism of virus-host interaction. However, current fluorescent tag labeling strategies often dampen viral infectivity. The present study explores an in situ fluorescent labeling strategy in order to preserve viral infectivity and precisely monitor viral infection in vivo. In contrast to pre-labeling strategy, mice are first intranasally infected with azide-modified H5N1 pseudotype virus (N3 -H5N1p), followed by injection of dibenzocyclooctyl (DBCO)-functionalized fluorescence 6 h later...
May 2017: Small
https://www.readbyqxmd.com/read/28215631/posttranscriptional-chemical-labeling-of-rna-by-using-bioorthogonal-chemistry
#17
REVIEW
Jerrin Thomas George, Seergazhi G Srivatsan
Recent developments in RNA labeling technology have provided viable tools to analyze RNA synthesis, processing and function in cell-free and cellular environments. Notably, emerging methodologies based on posttranscriptional chemical labeling by using bioorthogonal chemistry have enabled the visualization and profiling of exogenous and endogenous RNA transcripts. In this review, we first give an overview of different RNA labeling strategies based on chemical as well as genetically encoded systems. Subsequently, we provided a detailed discussion on methodologies that have been developed to introduce various bioorthogonal reactive groups into RNA transcripts, which are compatible for posttranscriptional functionalization...
February 16, 2017: Methods: a Companion to Methods in Enzymology
https://www.readbyqxmd.com/read/28194834/steering-siglec-sialic-acid-interactions-on-living-cells-using-bioorthogonal-chemistry
#18
Christian Büll, Torben Heise, Niek van Hilten, Johan F A Pijnenborg, Victor R L J Bloemendal, Lotte Gerrits, Esther D Kers-Rebel, Tina Ritschel, Martijn H den Brok, Gosse J Adema, Thomas J Boltje
Sialic acid sugars that terminate cell-surface glycans form the ligands for the sialic acid binding immunoglobulin-like lectin (Siglec) family, which are immunomodulatory receptors expressed by immune cells. Interactions between sialic acid and Siglecs regulate the immune system, and aberrations contribute to pathologies like autoimmunity and cancer. Sialic acid/Siglec interactions between living cells are difficult to study owing to a lack of specific tools. Here, we report a glycoengineering approach to remodel the sialic acids of living cells and their binding to Siglecs...
March 13, 2017: Angewandte Chemie
https://www.readbyqxmd.com/read/28183600/injectable-dextran-hydrogels-fabricated-by-metal-free-click-chemistry-for-cartilage-tissue-engineering
#19
Xiaoyu Wang, Zihan Li, Ting Shi, Peng Zhao, Kangkang An, Chao Lin, Hongwei Liu
Injectable dextran-based hydrogels were prepared for the first time by bioorthogonal click chemistry for cartilage tissue engineering. Click-crosslinked injectable hydrogels based on cyto-compatible dextran (Mw=10kDa) were successfully fabricated under physiological conditions by metal-free alkyne-azide cycloaddition (click) reaction between azadibenzocyclooctyne-modified dextran (Dex-ADIBO) and azide-modified dextran (Dex-N3). Gelation time of these dextran hydrogels could be regulated in the range of approximately 1...
April 1, 2017: Materials Science & Engineering. C, Materials for Biological Applications
https://www.readbyqxmd.com/read/28166295/correction-a-99mtc-labelled-tetrazine-for-bioorthogonal-chemistry-synthesis-and-biodistribution-studies-with-small-molecule-trans-cyclooctene-derivatives
#20
Alyssa Vito, Hussain Alarabi, Shannon Czorny, Omid Beiraghi, Jeff Kent, Nancy Janzen, Afaf R Genady, Salma A Al-Karmi, Stephanie Rathmann, Zoya Naperstkow, Megan Blacker, Lisset Llano, Paul J Berti, John F Valliant
[This corrects the article DOI: 10.1371/journal.pone.0167425.].
2017: PloS One
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