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Bioorthogonal chemistry

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https://www.readbyqxmd.com/read/28426149/click-chemistry-mediated-rapid-microbubble-catching-for-acute-thrombus-ultrasound-molecular-imaging
#1
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
#2
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
#3
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
#4
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 using bioorthogonal ligation chemistry. The labeling intensity not only depends on the rate of the ligation reaction but also on the extent to which the natural sialic acids are replaced by the modified ones, i...
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
#5
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...
March 17, 2017: Nature Reviews. Drug Discovery
https://www.readbyqxmd.com/read/28297599/coupling-of-immunostimulants-to-live-cells-through-metabolic-glycoengineering-and-bioorthogonal-click-chemistry
#6
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
#7
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
#8
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
#9
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...
February 20, 2017: Small
https://www.readbyqxmd.com/read/28215631/posttranscriptional-chemical-labeling-of-rna-by-using-bioorthogonal-chemistry
#10
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
#11
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
#12
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
#13
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
https://www.readbyqxmd.com/read/28139910/cell-selective-bioorthogonal-metabolic-labeling-of-rna
#14
Kim Nguyen, Michael Fazio, Miles Kubota, Sarah Nainar, Chao Feng, Xiang Li, Scott X Atwood, Timothy W Bredy, Robert C Spitale
Stringent chemical methods to profile RNA expression within discrete cellular populations remains a key challenge in biology. To address this issue, we developed a chemical-genetic strategy for metabolic labeling of RNA. Cell-specific labeling of RNA can be profiled and imaged using bioorthogonal chemistry. We anticipate that this platform will provide the community with a much-needed chemical toolset for cell-type specific profiling of cell-specific transcriptomes derived from complex biological systems.
February 7, 2017: Journal of the American Chemical Society
https://www.readbyqxmd.com/read/28137568/drug-target-identification-using-an-itraq-based-quantitative-chemical-proteomics-approach-based-on-a-target-profiling-study-of-andrographolide
#15
J Wang, Y K Wong, J Zhang, Y-M Lee, Z-C Hua, H-M Shen, Q Lin
Identifying the cellular binding targets of drugs and other bioactive small molecules is a crucial step for understanding their molecular mechanisms of action as well as potential off-target effects. The field of chemical proteomics is an emerging discipline in chemical biology using synthetic chemistry and high-throughput detection techniques to study small molecule-protein interactions. In this chapter, we describe a quantitative chemical proteomics protocol combining bioorthogonal click chemistry and quantitation by isobaric tags for relative and absolute quantification (iTRAQ) to identify the specific binding targets of drugs and bioactive small molecules such as natural products...
2017: Methods in Enzymology
https://www.readbyqxmd.com/read/28130882/direct-intracellular-delivery-of-cell-impermeable-probes-of-protein-glycosylation-by-using-nanostraws
#16
Alexander M Xu, Derek S Wang, Peyton Shieh, Yuhong Cao, Nicholas A Melosh
Bioorthogonal chemistry is an effective tool for elucidating metabolic pathways and measuring cellular activity, yet its use is currently limited by the difficulty of getting probes past the cell membrane and into the cytoplasm, especially if more complex probes are desired. Here we present a simple and minimally perturbative technique to deliver functional probes of glycosylation into cells by using a nanostructured "nanostraw" delivery system. Nanostraws provide direct intracellular access to cells through fluid conduits that remain small enough to minimize cell perturbation...
January 28, 2017: Chembiochem: a European Journal of Chemical Biology
https://www.readbyqxmd.com/read/28094987/crystal-engineering-of-self-assembled-porous-protein-materials-in-living-cells
#17
Satoshi Abe, Hiroyasu Tabe, Hiroshi Ijiri, Keitaro Yamashita, Kunio Hirata, Kohei Atsumi, Takuya Shimoi, Masaki Akai, Hajime Mori, Susumu Kitagawa, Takafumi Ueno
Crystalline porous materials have been investigated for development of important applications in molecular storage, separations, and catalysis. The potential of protein crystals is increasing as they become better understood. Protein crystals have been regarded as porous materials because they present highly ordered 3D arrangements of protein molecules with high porosity and wide range of pore sizes. However, it remains difficult to functionalize protein crystals in living cells. Here, we report that polyhedra, a natural crystalline protein assembly of polyhedrin monomer (PhM) produced in insect cells infected by cypovirus, can be engineered to extend porous networks by deleting selected amino acid residues located on the intermolecular contact region of PhM...
March 28, 2017: ACS Nano
https://www.readbyqxmd.com/read/28074503/bioorthogonal-diversification-of-peptides-through-selective-ruthenium-ii-catalyzed-c-h-activation
#18
Alexandra Schischko, Hongjun Ren, Nikolaos Kaplaneris, Lutz Ackermann
Methods for the chemoselective modification of amino acids and peptides are powerful techniques in biomolecular chemistry. Among other applications, they enable the total synthesis of artificial peptides. In recent years, significant momentum has been gained by exploiting palladium-catalyzed cross-coupling for peptide modification. Despite major advances, the prefunctionalization elements on the coupling partners translate into undesired byproduct formation and lengthy synthetic operations. In sharp contrast, we herein illustrate the unprecedented use of versatile ruthenium(II)carboxylate catalysis for the step-economical late-stage diversification of α- and β-amino acids, as well as peptides, through chemo-selective C-H arylation under racemization-free reaction conditions...
February 1, 2017: Angewandte Chemie
https://www.readbyqxmd.com/read/28034806/targeting-the-extracellular-matrix-of-ovarian-cancer-using-functionalized-drug-loaded-lyophilisomes
#19
Sophieke C H A van der Steen, René Raavé, Sjoerd Langerak, Laurens van Houdt, Sander M J van Duijnhoven, Sanne A M van Lith, Leon F A G Massuger, Willeke F Daamen, William P Leenders, Toin H van Kuppevelt
Epithelial ovarian cancer is characterized by a high mortality rate and is in need for novel therapeutic avenues to improve patient outcome. The tumor's extracellular matrix ("stroma") offers new possibilities for targeted drug-delivery. Recently we identified highly sulfated chondroitin sulfate (CS-E) as a component abundantly present in the ovarian cancer extracellular matrix, and as a novel target for anti-cancer therapy. Here, we report on the functionalization of drug-loaded lyophilisomes (albumin-based biocapsules) to specifically target the stroma of ovarian carcinomas with the potential to eliminate cancer cells...
April 2017: European Journal of Pharmaceutics and Biopharmaceutics
https://www.readbyqxmd.com/read/28027640/hydrogels-for-therapeutic-delivery-current-developments-and-future-directions
#20
Sytze J Buwalda, Tina Vermonden, Wim E Hennink
Hydrogels are attractive materials for the controlled release of therapeutics because of their capacity to embed biologically active agents in their water-swollen network. Recent advances in organic and polymer chemistry, bioengineering and nanotechnology have resulted in several new developments in the field of hydrogels for therapeutic delivery. In this Perspective, we present our view on the state-of-the-art in the field, thereby focusing on a number of exciting topics, including bioorthogonal cross-linking methods, multicomponent hydrogels, stimuli-responsive hydrogels, nanogels, and the release of therapeutics from 3D printed hydrogels...
January 10, 2017: Biomacromolecules
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