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Bioorthogonal chemistry

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https://www.readbyqxmd.com/read/28723577/enabling-tools-for-high-throughput-detection-of-metabolites-metabolic-engineering-and-directed-evolution-applications
#1
REVIEW
Jyun-Liang Lin, James M Wagner, Hal S Alper
Within the Design-Build-Test Cycle for strain engineering, rapid product detection and selection strategies remain challenging and limit overall throughput. Here we summarize a wide variety of modalities that transduce chemical concentrations into easily measured absorbance, luminescence, and fluorescence signals. Specifically, we cover protein-based biosensors (including transcription factors), nucleic acid-based biosensors, coupled enzyme reactions, bioorthogonal chemistry, and fluorescent and chromogenic dyes and substrates as modalities for detection...
July 16, 2017: Biotechnology Advances
https://www.readbyqxmd.com/read/28699691/gold-triggered-uncaging-chemistry-in-living-systems
#2
Ana M Pérez-López, Belén Rubio-Ruiz, Víctor Sebastián, Lloyd Hamilton, Catherine Adam, Thomas L Bray, Silvia Irusta, Paul M Brennan, Guy Lloyd-Jones, Dirk Sieger, Jesús Santamaría, Asier Unciti-Broceta
Recent advances in bioorthogonal catalysis are increasing our capacity to manipulate the fate of molecules in complex biological systems. Herein we report a novel bioorthogonal uncaging strategy that is triggered by heterogeneous gold catalysis and facilitates the activation of a structurally-diverse range of therapeutics in cancer cell culture. Furthermore, this solid supported catalytic system enabled -for the first time- the locally-controlled release of a fluorescent dye in the brain of a zebrafish, offering a novel way to modulate the activity of bioorthogonal reagents in the most fragile and complex organs...
July 12, 2017: Angewandte Chemie
https://www.readbyqxmd.com/read/28687600/pretargeted-imaging-and-therapy
#3
Mohamed Altai, Rosemery Membreno, Brendon Cook, Vladimir Tolmachev, Brian Zeglis
In vivo pretargeting stands as a promising approach to harnessing the exquisite tumor-targeting properties of antibodies for nuclear imaging and therapy while simultaneously skirting their pharmacokinetic limitations. The core premise of pretargeting lies in administering the targeting vector and radioisotope separately and having the two components combine within the body. In this manner, pretargeting strategies decrease the circulation time of the radioactivity, reduce the uptake of the radionuclide in healthy non-target tissues, and facilitate the use of short-lived radionuclides that would otherwise be incompatible with antibody-based vectors...
July 7, 2017: Journal of Nuclear Medicine: Official Publication, Society of Nuclear Medicine
https://www.readbyqxmd.com/read/28682403/single-trigger-dual-responsive-nanoparticles-for-controllable-and-sequential-prodrug-activation
#4
Neil M Robertson, Yang Yang, Irfan Khan, Vincent E LaMantia, Maksim Royzen, Mehmet V Yigit
Here we have developed a novel approach where two synergistically acting drugs were completely inactivated upon chemical immobilization on a nanoparticle template and activated in response to a chemical stimulus. The activation rate of each drug payload is controlled using a biologically inert bioorthogonal chemistry approach. By exploiting the subtle differences in the 'click-to-release' bioorthogonal reaction, we engineered a single delivery platform capable of releasing the payloads in a time-staggered manner in response to a single dose of a highly specific, yet reactive, small molecule...
July 6, 2017: Nanoscale
https://www.readbyqxmd.com/read/28678258/-18-f-fluoroalkyl-azides-for-rapid-radiolabeling-and-re-investigation-of-their-potential-towards-in-vivo-click-chemistry
#5
Christoph Denk, Martin Wilkovitsch, Philipp Skrinjar, Dennis Svatunek, Severin Mairinger, Claudia Kuntner, Thomas Filip, Johannes Fröhlich, Thomas Wanek, Hannes Mikula
In recent years, radiofluorinated alkyl azides have been reported for click radiolabeling and pretargeted PET imaging, but only little is known about the biodistribution and metabolism of these compounds. In this work, we present a significantly improved procedure for the synthesis of [(18)F]fluoroethyl azide and reinvestigated this radiolabeled probe in detail showing poor stability and very restricted suitability for in vivo application. Therefore, modified low-molecular-weight [(18)F]fluoroalkyl azides were developed...
July 19, 2017: Organic & Biomolecular Chemistry
https://www.readbyqxmd.com/read/28650431/illuminating-vital-surface-molecules-of-symbionts-in-health-and-disease
#6
Jason E Hudak, David Alvarez, Ashwin Skelly, Ulrich H von Andrian, Dennis L Kasper
The immunomodulatory surface molecules of commensal and pathogenic bacteria are critical to microorganisms' survival and the host's response(1,2). Recent studies have highlighted the unique and important responses elicited by commensal-derived surface macromolecules(3-5). However, the technology available to track these molecules in host cells and tissues remains primitive. We report, here, an interdisciplinary approach that uses metabolic labelling combined with bioorthogonal click chemistry (that is, reactions performed in living organisms)(6) to specifically tag up to three prominent surface immunomodulatory macromolecules-peptidoglycan, lipopolysaccharide and capsular polysaccharide-either simultaneously or individually in live anaerobic commensal bacteria...
June 26, 2017: Nature Microbiology
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
#7
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
#8
Torben Heise, Christian Büll, Daniëlle M Beurskens, Emiel Rossing, Marien I de Jonge, Gosse J Adema, Thomas J Boltje, Jeroen D 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 (Az)-modified sialic acids were prone to neuraminidase cleavage, whereas propargyloxycarbonyl (Poc)-modified sialic acids were largely resistant to cleavage...
June 27, 2017: Bioconjugate Chemistry
https://www.readbyqxmd.com/read/28626570/riboflavin-as-a-bioorthogonal-photocatalyst-for-the-activation-of-a-pt-iv-prodrug
#9
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
#10
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
#11
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
#12
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
#13
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
#14
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
#15
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
#16
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
#17
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
#18
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
#19
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
#20
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
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