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https://www.readbyqxmd.com/read/29240290/bioorthogonal-cycloadditions-with-sub-millisecond-intermediates
#1
Yujia Qing, Gökçe Su Pulcu, Nicolas Bell, Hagan Bayley
Tetrazine- and sydnone-based click chemistries have emerged as important bioconjugation strategies with fast kinetics and N2 or CO2 as the only by-product. Mechanistic studies of these reactions have focused on the initial rate-determining cycloaddition steps. The subsequent N2 or CO2 release from the bicyclic intermediates has been approached mainly through computational studies, which have predicted lifetimes of femtoseconds. In the present study, bioorthogonal cycloadditions involving N2 or CO2 extrusion have been examined experimentally at the single-molecule level by using a protein nanoreactor...
December 14, 2017: Angewandte Chemie
https://www.readbyqxmd.com/read/29192289/caspase-3-7-specific-metabolic-precursor-for-bioorthogonal-tracking-of-tumor-apoptosis
#2
Man Kyu Shim, Hong Yeol Yoon, Sangmin Lee, Mun Kyeong Jo, Jooho Park, Jong-Ho Kim, Seo Young Jeong, Ick Chan Kwon, Kwangmeyung Kim
Apoptosis is one of the most important intracellular events in living cell, which is a programmed cell death interrelated with caspase enzyme activity for maintaining homeostasis in multicellular organisms. Therefore, direct apoptosis imaging of living cells can provide enormous advantages for diagnosis, drug discovery, and therapeutic monitoring in various diseases. However, a method of direct apoptosis imaging has not been fully validated, especially for live cells in in vitro and in vivo. Herein, we developed a new apoptosis imaging technology via a direct visualization of active caspase-3/-7 activity in living cells...
November 30, 2017: Scientific Reports
https://www.readbyqxmd.com/read/29130210/imaging-newly-transcribed-rna-in-cells-by-using-a-clickable-azide-modified-utp-analog
#3
Anupam A Sawant, Sanjeev Galande, Seergazhi G Srivatsan
Robust RNA labeling and imaging methods that enable the understanding of cellular RNA biogenesis and function are highly desired. In this context, we describe a practical chemical labeling method based on a bioorthogonal reaction, namely, azide-alkyne cycloaddition reaction, which facilitates the fluorescence imaging of newly transcribed RNA in both fixed and live cells. This strategy involves the transfection of an azide-modified UTP analog (AMUTP) into mammalian cells, which gets specifically incorporated into RNA transcripts by RNA polymerases present inside the cells...
2018: Methods in Molecular Biology
https://www.readbyqxmd.com/read/29109777/improved-tumor-targeting-and-longer-retention-time-of-nir-fluorescent-probes-using-bioorthogonal-chemistry
#4
Xianghan Zhang, Bo Wang, Na Zhao, Zuhong Tian, Yunpeng Dai, Yongzhan Nie, Jie Tian, Zhongliang Wang, Xiaoyuan Chen
The traditional labeling method for targeted NIR fluorescence probes requires directly covalent-bonded conjugation of targeting domains and fluorophores in vitro. Although this strategy works well, it is not sufficient for detecting or treating cancers in vivo, due to steric hindrance effects that relatively large fluorophore molecules exert on the configurations and physiological functions of specific targeting domains. The copper-free, "click-chemistry"-assisted assembly of small molecules in living systems may enhance tumor accumulation of fluorescence probes by improving the binding affinities of the targeting factors...
2017: Theranostics
https://www.readbyqxmd.com/read/29095606/ex-uno-plura-differential-labeling-of-phospholipid-biosynthetic-pathways-with-a-single-bioorthogonal-alcohol
#5
Timothy W Bumpus, Felice J Liang, Jeremy M Baskin
Imaging approaches that track biological molecules within cells are essential tools in modern biochemistry. Lipids are particularly challenging to visualize, as they are not directly genetically encoded. Phospholipids, the most abundant subgroup of lipids, are structurally diverse and accomplish many cellular functions, acting as major structural components of membranes and as signaling molecules that regulate cell growth, division, apoptosis, cytoskeletal dynamics, and numerous other physiological processes...
November 8, 2017: Biochemistry
https://www.readbyqxmd.com/read/29048718/azido-functionalized-5-cap-analogs-for-preparation-of-translationally-active-mrnas-suitable-for-fluorescent-labeling-in-living-cells
#6
Adam Mamot, Pawel Sikorski, Marcin Warminski, Joanna Kowalska, Jacek Jemielity
The 7-methylguanosine (m7G) cap structure is a unique feature present at the 5' ends of messenger RNAs (mRNAs) that can be subjected to extensive modifications, resulting in alterations to mRNA properties (e.g. translability, susceptibility to degradation). It also can provide molecular tools to study mRNA metabolism. Here, we developed new mRNA 5' cap-based tools that enable the site-specific labeling of RNA at the 5' end using strain-promoted azide-alkyne cycloaddition (SPAAC), i.e. bioorthogonal, copper-free click chemistry, and support the mRNA's basic function in protein biosynthesis...
October 19, 2017: Angewandte Chemie
https://www.readbyqxmd.com/read/29044843/discovery-of-new-click-and-release-reactions-by-screening-of-mesoionics-and-cycloalkynes-combinations
#7
Frédéric Taran, Sabrina Bernard, Davide Audisio, Riomet Margaux, Sarah Bregant, Antoine Sallustrau, Lucie Plougastel, Elodie Decuypere, Sandra Gabillet, Ramar Arun Kumar, Jijy Elyian, Minh Nguyet Trinh, Oleksandr Koniev, Alain Wagner, Sergii Kolodych
We report the discovery of a new bioorthogonal click and release reaction involving imino-sydnones and strained alkynes. This transformation leads to two products resulting from both ligation and fragmentation of imino-sydnones under physiological conditions. Optimized imino-sydnones were successfully used to design innovative cleavable linkers for protein modifications opening new areas in the fields of drug release and target fishing applications. This click and release technology offers for the first time the possibility to exchange tags on proteins with functionalized cyclooctynes under mild and bioorthogonal conditions...
October 17, 2017: Angewandte Chemie
https://www.readbyqxmd.com/read/29035405/visible-light-mediated-cleavage-of-polymer-chains-under-physiological-conditions-via-quinone-photoreduction-and-trimethyl-lock
#8
Vinh X Truong, Fanyi Li, Francesca Ercole, John S Forsythe
We introduce a click and visible-light triggered unclick approach via thio-bromo reaction and hydroquinone photoreduction/trimethyl lock cleavage for polymer modifications. Both reactions can be carried out in water and at ambient temperature, enabling preparation of bioorthogonal hydrogels for encapsulation and controlled release of various cells.
November 7, 2017: Chemical Communications: Chem Comm
https://www.readbyqxmd.com/read/28985740/nanoscale-click-reactive-scaffolds-from-peptide-self-assembly
#9
Alexander P M Guttenplan, Laurence J Young, Dijana Matak-Vinkovic, Clemens F Kaminski, Tuomas P J Knowles, Laura S Itzhaki
BACKGROUND: Due to their natural tendency to self-assemble, proteins and peptides are important components for organic nanotechnology. One particular class of peptides of recent interest is those that form amyloid fibrils, as this self-assembly results in extremely strong, stable quasi-one-dimensional structures which can be used to organise a wide range of cargo species including proteins and oligonucleotides. However, assembly of peptides already conjugated to proteins is limited to cargo species that do not interfere sterically with the assembly process or misfold under the harsh conditions often used for assembly...
October 6, 2017: Journal of Nanobiotechnology
https://www.readbyqxmd.com/read/28971673/integrating-two-efficient-and-specific-bioorthogonal-ligation-reactions-with-natural-metabolic-incorporation-in-one-cell-for-virus-dual-labeling
#10
Li-Li Huang, Kejiang Liu, Qianmei Zhang, Jin Xu, Dongxu Zhao, Houshun Zhu, Hai-Yan Xie
Though techniques in bioorthogonal chemistry and metabolic incorporation have been developed over the past decade, it remains difficult to integrate different bioorthogonal reactions or metabolic incorporations into one system. In this report, the protein and DNA metabolic incorporations were combined with two bioorthogonal reactions in one cell to develop a facile and universal method for virus dual labeling. Azide and vinyl groups were introduced into the proteins or genomes of viruses, respectively, through the intrinsic biosynthesis of biomolecules, which were subsequently fluorescently labeled via copper-free click chemistry or alkene-tetrazine ligation reactions during natural propagation process in host cells...
November 7, 2017: Analytical Chemistry
https://www.readbyqxmd.com/read/28957709/nano-sized-metabolic-precursors-for-heterogeneous-tumor-targeting-strategy-using-bioorthogonal-click-chemistry-in%C3%A2-vivo
#11
Sangmin Lee, Seulhee Jung, Heebeom Koo, Jin Hee Na, Hong Yeol Yoon, Man Kyu Shim, Jooho Park, Jong-Ho Kim, Seulki Lee, Martin G Pomper, Ick Chan Kwon, Cheol-Hee Ahn, Kwangmeyung Kim
Herein, we developed nano-sized metabolic precursors (Nano-MPs) for new tumor-targeting strategy to overcome the intrinsic limitations of biological ligands such as the limited number of biological receptors and the heterogeneity in tumor tissues. We conjugated the azide group-containing metabolic precursors, triacetylated N-azidoacetyl-d-mannosamine to generation 4 poly(amidoamine) dendrimer backbone. The nano-sized dendrimer of Nano-MPs could generate azide groups on the surface of tumor cells homogeneously regardless of cell types via metabolic glycoengineering...
December 2017: Biomaterials
https://www.readbyqxmd.com/read/28926550/bioorthogonal-chemistry-click-on-click-off
#12
Caitlin Deane
No abstract text is available yet for this article.
September 19, 2017: Nature Chemical Biology
https://www.readbyqxmd.com/read/28898061/postsynthetic-modification-of-bacterial-peptidoglycan-using-bioorthogonal-n-acetylcysteamine-analogs-and-peptidoglycan-o-acetyltransferase-b
#13
Yiben Wang, Klare M Lazor, Kristen E DeMeester, Hai Liang, Tyler K Heiss, Catherine L Grimes
Bacteria have the natural ability to install protective postsynthetic 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 26, 2017: Journal of the American Chemical Society
https://www.readbyqxmd.com/read/28892360/in-vivo-imaging-guided-photothermal-photoacoustic-synergistic-therapy-with-bioorthogonal-metabolic-glycoengineering-activated-tumor-targeting-nanoparticles
#14
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 26, 2017: ACS Nano
https://www.readbyqxmd.com/read/28891646/synergic-click-boronate-thiosemicarbazone-system-for-fast-and-irreversible-bioorthogonal-conjugation-in-live-cells
#15
Burcin Akgun, Caishun Li, Yubin Hao, Gareth Lambkin, Ratmir Derda, Dennis G Hall
Fast, high-yielding, and selective bioorthogonal "click" reactions employing nontoxic reagents are in high demand for their great utility in the conjugation of biomolecules in live cells. Although a number of click reactions were developed for this purpose, many are associated with drawbacks and limitations that justify the development of alternative systems for both single- or dual-labeling applications. Recent reports have highlighted the potential of boronic ester formation as a bioorthogonal click reaction between abiotic boronic acids and diols...
October 11, 2017: Journal of the American Chemical Society
https://www.readbyqxmd.com/read/28884571/clickable-multifunctional-dumbbell-particles-for-in-situ-multiplex-single-cell-cytokine-detection
#16
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 27, 2017: ACS Applied Materials & Interfaces
https://www.readbyqxmd.com/read/28687600/pretargeted-imaging-and-therapy
#17
REVIEW
Mohamed Altai, Rosemery Membreno, Brendon Cook, Vladimir Tolmachev, Brian M 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 2 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 nontarget tissues, and facilitate the use of short-lived radionuclides that would otherwise be incompatible with antibody-based vectors...
October 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
#18
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
#19
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
#20
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
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