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https://www.readbyqxmd.com/read/28687600/pretargeted-imaging-and-therapy
#1
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
#2
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
#3
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
#4
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/28582715/in%C3%A2-vivo-stem-cell-tracking-with-imageable-nanoparticles-that-bind-bioorthogonal-chemical-receptors-on-the-stem-cell-surface
#5
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/28525770/-expand-and-click-a-new-method-for-labeling-hiv-1-envelope-glycoproteins
#6
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/28504153/injectable-hyaluronic-acid-poly-ethylene-glycol-hydrogels-crosslinked-via-strain-promoted-azide-alkyne-cycloaddition-click-reaction
#7
Shuangli Fu, Hui Dong, Xueyi Deng, Renxi Zhuo, Zhenlin Zhong
This paper reports injectable hyaluronic acid (HA)-based hydrogels crosslinked with azide-modified poly(ethylene glycol) (PEG) via the strain-promoted azide-alkyne cycloaddition (SPAAC) between cyclooctyne and azide groups. Cyclooctyne-modified HA (Cyclooctyne-HA) is prepared by the reaction of HA with 2-(aminoethoxy)cyclooctyne. To crosslink the modified HA, quadruply azide-terminated poly(ethylene glycol) (Azide-PEG) is designed and prepared. The mixture of Cyclooctyne-HA and Azide-PEG gelates in a few minutes to form a strong HA-PEG hydrogel...
August 1, 2017: Carbohydrate Polymers
https://www.readbyqxmd.com/read/28470743/correlative-light-and-electron-microscopy-reveals-discrepancy-between-gold-and-fluorescence-labelling
#8
D M VAN Elsland, E Bos, J B Pawlak, H S Overkleeft, A J Koster, S I VAN Kasteren
Electron microscopy (EM) is traditionally employed as a follow-up to fluorescence microscopy (FM) to resolve the cellular ultrastructures wherein fluorescently labelled biomolecules reside. In order to translate the information derived from FM studies to EM analysis, biomolecules of interest must be identified in a manner compatible with EM. Although fluorescent signals can serve this purpose when FM is combined with EM in correlative light and electron microscopy (CLEM), the traditional immunogold labelling remains commonly used in this context...
May 4, 2017: Journal of Microscopy
https://www.readbyqxmd.com/read/28451223/imaging-specific-newly-synthesized-proteins-within-cells-by-fluorescence-resonance-energy-transfer
#9
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/28451106/molecular-basis-for-functional-switching-of-gfp-by-two-disparate-non-native-post-translational-modifications-of-a-phenyl-azide-reaction-handle
#10
Andrew M Hartley, Harley L Worthy, Samuel C Reddington, Pierre J Rizkallah, D Dafydd Jones
Through the genetic incorporation of a single phenyl azide group into superfolder GFP (sfGFP) at residue 148 we provide a molecular description of how this highly versatile chemical handle can be used to positively switch protein function in vitro and in vivo via either photochemistry or bioconjugation. Replacement of H148 with p-azido-l-phenylalanine (azF) blue shifts the major excitation peak ∼90 nm by disrupting the H-bond and proton transfer network that defines the chromophore charged state. Bioorthogonal click modification with a simple dibenzylcyclooctyne or UV irradiation shifts the neutral-anionic chromophore equilibrium, switching fluorescence to the optimal ∼490 nm excitation...
October 1, 2016: Chemical Science
https://www.readbyqxmd.com/read/28449575/visualization-of-endogenous-erk1-2-in-cells-with-a-bioorthogonal-covalent-probe
#11
James Sipthorp, Honorine Lebraud, Rebecca Gilley, Andrew M Kidger, Hanneke Okkenhaug, Marc Saba-El-Leil, Sylvain Meloche, Christopher J Caunt, Simon J Cook, Tom D Heightman
The RAS-RAF-MEK-ERK pathway has been intensively studied in oncology, with RAS known to be mutated in ∼30% of all human cancers. The recent emergence of ERK1/2 inhibitors and their ongoing clinical investigation demands a better understanding of ERK1/2 behavior following small-molecule inhibition. Although fluorescent fusion proteins and fluorescent antibodies are well-established methods of visualizing proteins, we show that ERK1/2 can be visualized via a less-invasive approach based on a two-step process using inverse electron demand Diels-Alder cycloaddition...
June 21, 2017: Bioconjugate Chemistry
https://www.readbyqxmd.com/read/28426149/click-chemistry-mediated-rapid-microbubble-capture-for-acute-thrombus-ultrasound-molecular-imaging
#12
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
https://www.readbyqxmd.com/read/28399460/molecular-imaging-based-on-metabolic-glycoengineering-and-bioorthogonal-click-chemistry
#13
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/28306499/a-double-click-for-illuminating-plant-cell-walls
#14
Yuki Tobimatsu
In this issue of Cell Chemical Biology, Lion et al. (2017) report a multiplexed labeling method to visualize plant cell wall lignification in vivo. This approach uses two different lignin precursor analogs tagged with azide and alkyne reporters that can be independently incorporated into cell walls, then differentially derivatized in vivo via two bioorthogonal click reactions: strain-promoted and copper-assisted azide-alkyne cycloadditions.
March 16, 2017: Cell Chemical Biology
https://www.readbyqxmd.com/read/28297599/coupling-of-immunostimulants-to-live-cells-through-metabolic-glycoengineering-and-bioorthogonal-click-chemistry
#15
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...
April 19, 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
#16
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/28237112/proteomic-profiling-of-de-novo-protein-synthesis-in-starvation-induced-autophagy-using-bioorthogonal-noncanonical-amino-acid-tagging
#17
J Zhang, J Wang, Y-M Lee, T-K Lim, Q Lin, H-M Shen
Autophagy is an intracellular degradation process activated by stress factors such as nutrient starvation to maintain cellular homeostasis. There is emerging evidence demonstrating that de novo protein synthesis is involved in the autophagic process. However, up-to-date characterizing of these de novo proteins is technically difficult. In this chapter, we describe a novel method to identify newly synthesized proteins during starvation-mediated autophagy by bioorthogonal noncanonical amino acid tagging (BONCAT), in conjunction with isobaric tagging for relative and absolute quantification (iTRAQ)-based quantitative proteomics...
2017: Methods in Enzymology
https://www.readbyqxmd.com/read/28191852/artificial-chemical-reporter-targeting-strategy-using-bioorthogonal-click-reaction-for-improving-active-targeting-efficiency-of-tumor
#18
Hong Yeol Yoon, Min Lee Shin, Man Kyu Shim, Sangmin Lee, Jin Hee Na, Heebeom Koo, Hyukjin Lee, Jong-Ho Kim, Kuen Yong Lee, Kwangmeyung Kim, Ick Chan Kwon
Biological ligands such as aptamer, antibody, glucose, and peptide have been widely used to bind specific surface molecules or receptors in tumor cells or subcellular structures to improve tumor-targeting efficiency of nanoparticles. However, this active-targeting strategy has limitations for tumor targeting due to inter- and intraheterogeneity of tumors. In this study, we demonstrated an alternative active-targeting strategy using metabolic engineering and bioorthogonal click reaction to improve tumor-targeting efficiency of nanoparticles...
May 1, 2017: Molecular Pharmaceutics
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/28137568/drug-target-identification-using-an-itraq-based-quantitative-chemical-proteomics-approach-based-on-a-target-profiling-study-of-andrographolide
#20
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
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