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Bioorthogonal chemistry

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https://www.readbyqxmd.com/read/28926550/bioorthogonal-chemistry-click-on-click-off
#1
Caitlin Deane
No abstract text is available yet for this article.
September 19, 2017: Nature Chemical Biology
https://www.readbyqxmd.com/read/28915034/affinity-guided-oxime-chemistry-for-selective-protein-acylation-in-live-tissue-systems
#2
Tomonori Tamura, Zhining Song, Kazuma Amaike, Shin Lee, Sifei Yin, Shigeki Kiyonaka, Itaru Hamachi
Catalyst-mediated protein modification is a powerful approach for the imaging and engineering of natural proteins. We have previously developed affinity-guided 4-dimethylaminopyridine (DMAP) (AGD) chemistry as an efficient protein modification method using a catalytic acyl transfer reaction. However, because of the high electrophilicity of the thioester acyl donor molecule, AGD chemistry suffers from nonspecific reactions to proteins other than the target protein in crude biological environments, such as cell lysates, live cells, and tissue samples...
September 15, 2017: Journal of the American Chemical Society
https://www.readbyqxmd.com/read/28898061/post-synthetic-modification-of-bacterial-peptidoglycan-using-bioorthogonal-n-acetylcysteamine-analogs-and-peptidoglycan-o-acetyltransferase-b
#3
Yiben Wang, Klare M Lazor, Kristen Elizabeth DeMeester, Hai Liang, Tyler K Heiss, Catherine Leimkuhler Grimes
Bacteria have the natural ability to install protective post-synthetic modifications onto its bacterial peptidoglycan (PG), the coat woven into bacterial cell wall. Peptidoglycan O-acetyltransferase B (PatB) catalyzes the O-acetylation of PG in Gram (-) bacteria, which aids in bacterial survival, as it prevents autolysins such as lysozyme from cleaving the PG. We explored the mechanistic details of PatB's acetylation function and determined that PatB has substrate specificity for bioorthgonal short N-acetyl cysteamine (SNAc) donors...
September 12, 2017: Journal of the American Chemical Society
https://www.readbyqxmd.com/read/28898047/transglutaminase-catalyzed-bioconjugation-using-one-pot-metal-free-bioorthogonal-chemistry
#4
Natalie M Rachel, Jacynthe L Toulouse, Joelle N Pelletier
General approaches for controlled protein modification are increasingly sought-after in the arena of chemical biology. Here, using bioorthogonal reactions, we present combinatorial chemoenzymatic strategies to effectuate protein labeling. Three metal-free conjugations were simultaneously or sequentially incorporated in a one-pot format with microbial transglutaminase (MTG) to effectuate protein labeling. MTG offers the particularity of conjugating residues with-in a protein sequence, rather than at its extremities, providing a route to labeling the native protein...
September 12, 2017: Bioconjugate Chemistry
https://www.readbyqxmd.com/read/28892360/in-vivo-imaging-guided-photothermal-photoacoustic-synergistic-therapy-with-bioorthogonal-metabolic-glycoengineering-activated-tumor-targeting-nanoparticles
#5
Lihua Du, Huan Qin, Teng Ma, Tao Zhang, Da Xing
Developing multifunctional phototheranostics with nanoplatforms offers promising potential for effective eradication of malignant solid tumors. In this study, we develop a multifunctional phototheranostic by combining photothermal therapy (PTT) and photoacoustic therapy (PAT) based on a tumor-targeting nanoagent (DBCO-ZnPc-LP). The nanoagent DBCO-ZnPc-LP was facilely prepared by self-assembling of a single lipophilic near-infrared (NIR) dye zinc(II)-phthalocyanine (ZnPc) with a lipid-poly(ethylene glycol) (LP) and following modified further with dibenzyl cyclootyne (DBCO) for introducing the two-step chemical tumor-targeting strategy based on metabolic glycoengineering and click chemistry...
September 13, 2017: ACS Nano
https://www.readbyqxmd.com/read/28884571/clickable-multifunctional-dumbbell-particles-for-in-situ-multiplex-single-cell-cytokine-detection
#6
Peng Zhao, Justin George, Bin Li, Nooshin Amini, Janet Paluh, Jun Wang
We report a novel strategy for fabrication of multifunctional dumbbell particles (DPs) through click chemistry for monitoring single-cell cytokine releasing. Two different types of DPs were prepared on a large scale through covalent bioorthogonal reaction between methyltetrazine and trans-cyclooctene on a microchip under a magnetic field. After collection of the DPs, the two sides of each particle were further functionalized with different antibodies for cell capturing and cytokine detection, respectively. These DPs labeled with different fluorescent dyes have been used for multiplex detection and analysis of cytokines secreted by single live cells...
September 18, 2017: ACS Applied Materials & Interfaces
https://www.readbyqxmd.com/read/28876890/bioorthogonal-cycloadditions-computational-analysis-with-the-distortion-interaction-model-and-predictions-of-reactivities
#7
Fang Liu, Yong Liang, K N Houk
Bioorthogonal chemistry has had a major impact on the study of biological processes in vivo. Biomolecules of interest can be tracked by using probes and reporters that do not react with cellular components and do not interfere with metabolic processes in living cells. Much time and effort has been devoted to the screening of potential bioorthogonal reagents experimentally. This Account describes how our groups have performed computational screening of reactivity and mutual orthogonality. Our collaborations with experimentalists have led to the development of new and useful reactions...
September 6, 2017: Accounts of Chemical Research
https://www.readbyqxmd.com/read/28825822/copper-catalyzed-alkene-aminoazidation-as-a-rapid-entry-to-1-2-diamines-and-installation-of-an-azide-reporter-onto-azahetereocycles
#8
Kun Shen, Qiu Wang
A copper-catalyzed aminoazidation of unactivated alkenes is achieved for the synthesis of versatile unsymmetrical 1,2-diamine derivatives. This transformation offers an effective approach to installing an amide and an azide from two diffenent amino precursors onto both terminal and internal alkenes, with remarkable regio- and stereoselectivity. Mechanistic studies show that this diamination reaction proceeds via a nucleophilic amino cyclization followed by an intermolecular C-N bond formation using electrophilic azidoiodinane...
September 5, 2017: Journal of the American Chemical Society
https://www.readbyqxmd.com/read/28752889/computationally-guided-discovery-of-a-reactive-hydrophilic-trans-5-oxocene-dienophile-for-bioorthogonal-labeling
#9
William D Lambert, Samuel L Scinto, Olga Dmitrenko, Samantha J Boyd, Ronald Magboo, Ryan A Mehl, Jason W Chin, Joseph M Fox, Stephen Wallace
The use of organic chemistry principles and prediction techniques has enabled the development of new bioorthogonal reactions. As this "toolbox" expands to include new reaction manifolds and orthogonal reaction pairings, the continued development of existing reactions remains an important objective. This is particularly important in cellular imaging, where non-specific background fluorescence has been linked to the hydrophobicity of the bioorthogonal moiety. Here we report that trans-5-oxocene (oxoTCO) displays enhanced reactivity and hydrophilicity compared to trans-cyclooctene (TCO) in the tetrazine ligation reaction...
August 9, 2017: Organic & Biomolecular Chemistry
https://www.readbyqxmd.com/read/28729656/endolysosomal-targeting-of-a-clinical-chlorin-photosensitiser-for-light-triggered-delivery-of-nano-sized-medicines
#10
Elnaz Yaghini, Ruggero Dondi, Kunal M Tewari, Marilena Loizidou, Ian M Eggleston, Alexander J MacRobert
A major problem with many promising nano-sized biotherapeutics including macromolecules is that owing to their size they are subject to cellular uptake via endocytosis, and become entrapped and then degraded within endolysosomes, which can significantly impair their therapeutic efficacy. Photochemical internalisation (PCI) is a technique for inducing cytosolic release of the entrapped agents that harnesses sub-lethal photodynamic therapy (PDT) using a photosensitiser that localises in endolysosomal membranes...
July 20, 2017: Scientific Reports
https://www.readbyqxmd.com/read/28723577/enabling-tools-for-high-throughput-detection-of-metabolites-metabolic-engineering-and-directed-evolution-applications
#11
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
#12
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
#13
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
#14
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 20, 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
#15
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
#16
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
#17
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
#18
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...
July 19, 2017: Bioconjugate Chemistry
https://www.readbyqxmd.com/read/28626570/riboflavin-as-a-bioorthogonal-photocatalyst-for-the-activation-of-a-pt-iv-prodrug
#19
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
#20
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...
July 19, 2017: Bioconjugate Chemistry
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