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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/28306499/a-double-click-for-illuminating-plant-cell-walls
#3
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
#4
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
#5
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
#6
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
#7
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 intra-heterogeneity 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...
February 13, 2017: Molecular Pharmaceutics
https://www.readbyqxmd.com/read/28183600/injectable-dextran-hydrogels-fabricated-by-metal-free-click-chemistry-for-cartilage-tissue-engineering
#8
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
#9
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/28070577/sulfur-dioxide-prodrugs-triggered-release-of-so2via-a-click-reaction
#10
Wenyi Wang, Xingyue Ji, Zhenming Du, Binghe Wang
Sulfur dioxide (SO2) is being recognized as a possible endogenous gasotransmitter with importance on par with that of NO, CO, and H2S. Herein we describe a series of SO2 prodrugs that are activated for SO2 release via a bioorthogonal click reaction. The release rate can be tuned by adjusting the substituents on the prodrug.
January 24, 2017: Chemical Communications: Chem Comm
https://www.readbyqxmd.com/read/28067514/click-and-fluoresce-a-bioorthogonally-activated-smart-probe-for-wash-free-fluorescent-labeling-of-biomolecules
#11
Xingyue Ji, Kaili Ji, Vayou Chittavong, Robert E Aghoghovbia, Mengyuan Zhu, Binghe Wang
Bioorthogonally activated smart probes greatly facilitate the selective labeling of biomolecules in living system. Herein, we described a novel type of smart probes with tunable reaction rates, high fluorescence turn-on ratio, and easy access. The practicality of such probes was demonstrated by selective labeling of lipid and hCAII in Hela cells.
January 23, 2017: Journal of Organic Chemistry
https://www.readbyqxmd.com/read/28045502/legomedicine-a-versatile-chemo-enzymatic-approach-for-the-preparation-of-targeted-dual-labeled-llama-antibody-nanoparticle-conjugates
#12
Sanne A M van Lith, Sander M J van Duijnhoven, Anna C Navis, William P J Leenders, Edward Dolk, Jos W H Wennink, Cornelus F van Nostrum, Jan C M van Hest
Conjugation of llama single domain antibody fragments (Variable Heavy chain domains of Heavy chain antibodies, VHHs) to diagnostic or therapeutic nanoparticles, peptides, proteins, or drugs offers many opportunities for optimized targeted cancer treatment. Currently, mostly nonspecific conjugation strategies or genetic fusions are used that may compromise VHH functionality. In this paper we present a versatile modular approach for bioorthogonal VHH modification and conjugation. First, sortase A mediated transPEGylation is used for introduction of a chemical click moiety...
February 15, 2017: Bioconjugate Chemistry
https://www.readbyqxmd.com/read/28034806/targeting-the-extracellular-matrix-of-ovarian-cancer-using-functionalized-drug-loaded-lyophilisomes
#13
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/27998071/characterization-of-the-artemisinin-binding-site-for-translationally-controlled-tumor-protein-tctp-by-bioorthogonal-click-chemistry
#14
Weichao Li, Yiqing Zhou, Guanghui Tang, Youli Xiao
Despite the fact that multiple artemisinin-alkylated proteins in Plasmodium falciparum have been identified in recent studies, the alkylation mechanism and accurate binding site of artemisinin-protein interaction have remained elusive. Here, we report the chemical-probe-based enrichment of the artemisinin-binding peptide and characterization of the artemisinin-binding site of P. falciparum translationally controlled tumor protein (TCTP). A peptide fragment within the N-terminal region of TCTP was enriched and found to be alkylated by an artemisinin-derived probe...
December 21, 2016: Bioconjugate Chemistry
https://www.readbyqxmd.com/read/27965173/clickecm-development-of-a-cell-derived-extracellular-matrix-with-azide-functionalities
#15
S M Ruff, S Keller, D E Wieland, V Wittmann, G E M Tovar, M Bach, P J Kluger
In vitro cultured cells produce a complex extracellular matrix (ECM) that remains intact after decellularization. The biological complexity derived from the variety of distinct ECM molecules makes these matrices ideal candidates for biomaterials. Biomaterials with the ability to guide cell function are a topic of high interest in biomaterial development. However, these matrices lack specific addressable functional groups, which are often required for their use as a biomaterial. Due to the biological complexity of the cell-derived ECM, it is a challenge to incorporate such functional groups without affecting the integrity of the biomolecules within the ECM...
April 1, 2017: Acta Biomaterialia
https://www.readbyqxmd.com/read/27935295/metabolism-based-click-mediated-platform-for-specific-imaging-and-quantification-of-cell-surface-sialic-acids
#16
Yong Liang, Xin Jiang, Rong Yuan, Yang Zhou, Caixia Ji, Limin Yang, Haifeng Chen, Qiuquan Wang
Although we believe that the cell surface sialic acids (Sias) are playing an important role in cell-cell interactions and related tumor metastasis processes, acquisition of their quantitative information has yet been a challenge to date. Here, we reported the construction of a new analytical platform for Sias-specific imaging and quantification. We used N-azidoacetyl-mannosamine tetraacylated as a metabolic sugar substrate to bioassemble azido-Sias on the surface of cells via the metabolic pathway of Sias de novo synthesis...
December 12, 2016: Analytical Chemistry
https://www.readbyqxmd.com/read/27869340/dual-5-cap-labeling-based-on-regioselective-rna-methyltransferases-and-bioorthogonal-reactions
#17
Josephin M Holstein, Fabian Muttach, Stephan H H Schiefelbein, Andrea Rentmeister
The ability to detect and localize defined RNA strands inside living cells requires probes with high specificity, sensitivity, and signal-to-background ratio. To track low-abundant biomolecules, such as strands of regular mRNA, and distinguish fluorescence signal from the background after bioorthogonal reactions in cells, it is imperative to employ turn-on concepts. Here, we have presented a straightforward enzymatic approach to allow site-specific modification of two different positions on the 5' cap of eukaryotic mRNA with either identical or different small functional groups...
November 21, 2016: Chemistry: a European Journal
https://www.readbyqxmd.com/read/27779857/controlled-detachment-of-chemically-glued-cells
#18
Heebeom Koo, Sei Kwang Hahn, Seok Hyun Yun
We demonstrate a chemically detachable cell-glue system based on linkers containing disulfide bonds as well as functional groups for metabolic glycoengineering and bioorthogonal click chemistry. Azide groups are generated on the cell surface by metabolic glycoengineering, and they are further modified into tetrazine (Tz) or trans-cyclooctene (TCO) using rationally designed cross-linkers. When the Tz-modified and TCO-modified cells are mixed together, cell gluing between these two cell groups is established by Tz-TCO click chemistry...
November 16, 2016: Bioconjugate Chemistry
https://www.readbyqxmd.com/read/27775882/application-of-noncanonical-amino-acids-for-protein-labeling-in-a-genomically-recoded-escherichia-coli
#19
Kalle Kipper, Ebba Gregorsson Lundius, Vladimir Curic, Ivana Nikic, Edward A Lemke, Manfred Wiessler, Johan Elf
Small synthetic fluorophores are in many ways superior to fluorescent proteins as labels for imaging. A major challenge is to use them for a protein-specific labeling in living cells. Here, we report on our use of noncanonical amino acids that are genetically encoded via the pyrrolysyl-tRNA/pyrrolysyl-RNA synthetase pair at artificially introduced TAG codons in a recoded E. coli strain. The strain is lacking endogenous TAG codons and the TAG-specific release factor RF1. The amino acids contain bioorthogonal groups that can be clicked to externally supplied dyes, thus enabling protein-specific labeling in live cells...
October 24, 2016: ACS Synthetic Biology
https://www.readbyqxmd.com/read/27762044/cathepsin%C3%A2-b-specific-metabolic-precursor-for-in%C3%A2-vivo-tumor-specific-fluorescence-imaging
#20
Man Kyu Shim, Hong Yeol Yoon, Ju Hee Ryu, Heebeom Koo, Sangmin Lee, Jae Hyung Park, Jong-Ho Kim, Seulki Lee, Martin G Pomper, Ick Chan Kwon, Kwangmeyung Kim
Recently, metabolic glycoengineering with bioorthogonal click reactions has focused on improving the tumor targeting efficiency of nanoparticles as delivery vehicles for anticancer drugs or imaging agents. It is the key technique for developing tumor-specific metabolic precursors that can generate unnatural glycans on the tumor-cell surface. A cathepsin B-specific cleavable substrate (KGRR) conjugated with triacetylated N-azidoacetyl-d-mannosamine (RR-S-Ac3 ManNAz) was developed to enable tumor cells to generate unnatural glycans that contain azide groups...
November 14, 2016: Angewandte Chemie
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