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https://www.readbyqxmd.com/read/28070577/sulfur-dioxide-prodrugs-triggered-release-of-so2via-a-click-reaction
#1
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 10, 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
#2
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 9, 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
#3
Sanne A M van Lith, Sander M J van Duijnhoven, Anna C Navis, Edward Dolk, Jos W H Wennink, Cornelus F van Nostrum, Jan C M van Hest, William P J Leenders, 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...
January 18, 2017: Bioconjugate Chemistry
https://www.readbyqxmd.com/read/28034806/targeting-the-extracellular-matrix-of-ovarian-cancer-using-functionalized-drug-loaded-lyophilisomes
#4
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 an 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...
December 26, 2016: 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
#5
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
#6
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...
December 10, 2016: Acta Biomaterialia
https://www.readbyqxmd.com/read/27935295/metabolism-based-click-mediated-platform-for-specific-imaging-and-quantification-of-cell-surface-sialic-acids
#7
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
#8
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
#9
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
#10
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
#11
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
https://www.readbyqxmd.com/read/27738680/a-photorelease-catch-and-photorelease-strategy-for-bioconjugation-utilizing-a-p-hydroxyphenacyl-group
#12
D Madea, T Slanina, P Klán
A bioorthogonal 'catch and photorelease' strategy, which combines alkyne-azide cycloaddition between p-hydroxyphenacyl azide and alkyne derivatives to form a 1,2,3-triazole adduct and subsequent photochemical release of the triazole moiety via a photo-Favorskii rearrangement, is introduced. The first step can also involve photorelease of a strained alkyne and its Cu-free click reaction with azide.
October 14, 2016: Chemical Communications: Chem Comm
https://www.readbyqxmd.com/read/27724898/direct-imaging-of-glycans-in-arabidopsis-roots-via-click-labeling-of-metabolically-incorporated-azido-monosaccharides
#13
Jorin Hoogenboom, Nathalja Berghuis, Dario Cramer, Rene Geurts, Han Zuilhof, Tom Wennekes
BACKGROUND: Carbohydrates, also called glycans, play a crucial but not fully understood role in plant health and development. The non-template driven formation of glycans makes it impossible to image them in vivo with genetically encoded fluorescent tags and related molecular biology approaches. A solution to this problem is the use of tailor-made glycan analogs that are metabolically incorporated by the plant into its glycans. These metabolically incorporated probes can be visualized, but techniques documented so far use toxic copper-catalyzed labeling...
October 10, 2016: BMC Plant Biology
https://www.readbyqxmd.com/read/27706239/spatial-and-temporal-resolution-of-global-protein-synthesis-during-hsv-infection-using-bioorthogonal-precursors-and-click-chemistry
#14
Catherine Su Hui Teo, Remigiusz A Serwa, Peter O'Hare
We used pulse-labeling with the methionine analogue homopropargylglycine (HPG) to investigate spatiotemporal aspects of protein synthesis during herpes simplex virus (HSV) infection. In vivo incorporation of HPG enables subsequent selective coupling of fluorochrome-capture reagents to newly synthesised proteins. We demonstrate that HPG labeling had no effect on cell viability, on accumulation of test early or late viral proteins, or on overall virus yields. HPG pulse-labeling followed by SDS-PAGE analysis confirmed incorporation into newly synthesised proteins, while parallel processing by in situ cycloaddition revealed new insight into spatiotemporal aspects of protein localisation during infection...
October 2016: PLoS Pathogens
https://www.readbyqxmd.com/read/27696881/quantitative-secretome-analysis-of-activated-jurkat-cells-using-click-chemistry-based-enrichment-of-secreted-glycoproteins
#15
Kathrin Elisabeth Witzke, Kristin Rosowski, Christian Müller, Maike Ahrens, Martin Eisenacher, Dominik A Megger, Jürgen Knobloch, Andrea R Koch, Thilo Bracht, Barbara Sitek
Quantitative secretome analyses are a high-performance tool for the discovery of physiological and pathophysiological changes in cellular processes. However, serum supplements in cell culture media limit secretome analyses, but serum depletion often leads to cell starvation and consequently biased results. To overcome these limiting factors, we investigated a model of T cell activation (Jurkat cells) and performed an approach for the selective enrichment of secreted proteins from conditioned medium utilizing metabolic marking of newly synthesized glycoproteins...
October 3, 2016: Journal of Proteome Research
https://www.readbyqxmd.com/read/27668214/super-resolution-imaging-of-plasma-membrane-proteins-with-click-chemistry
#16
Pablo Mateos-Gil, Sebastian Letschert, Sören Doose, Markus Sauer
Besides its function as a passive cell wall, the plasma membrane (PM) serves as a platform for different physiological processes such as signal transduction and cell adhesion, determining the ability of cells to communicate with the exterior, and form tissues. Therefore, the spatial distribution of PM components, and the molecular mechanisms underlying it, have important implications in various biological fields including cell development, neurobiology, and immunology. The existence of confined compartments in the plasma membrane that vary on many length scales from protein multimers to micrometer-size domains with different protein and lipid composition is today beyond all questions...
2016: Frontiers in Cell and Developmental Biology
https://www.readbyqxmd.com/read/27643597/click-ms-tagless-protein-enrichment-using-bioorthogonal-chemistry-for-quantitative-proteomics
#17
Arne H Smits, Annika Borrmann, Mark Roosjen, Jan C M van Hest, Michiel Vermeulen
Epitope-tagging is an effective tool to facilitate protein enrichment from crude cell extracts. Traditionally, N- or C-terminal fused tags are employed, which, however, can perturb protein function. Unnatural amino acids (UAAs) harboring small reactive handles can be site-specifically incorporated into proteins, thus serving as a potential alternative for conventional protein tags. Here, we introduce Click-MS, which combines the power of site-specific UAA incorporation, bioorthogonal chemistry, and quantitative mass spectrometry-based proteomics to specifically enrich a single protein of interest from crude mammalian cell extracts...
December 16, 2016: ACS Chemical Biology
https://www.readbyqxmd.com/read/27622469/an-oga-resistant-probe-allows-specific-visualization-and-accurate-identification-of-o-glcnac-modified-proteins-in-cells
#18
Jing Li, Jiajia Wang, Liuqing Wen, He Zhu, Shanshan Li, Kenneth Huang, Kuan Jiang, Xu Li, Cheng Ma, Jingyao Qu, Aishwarya Parameswaran, Jing Song, Wei Zhao, Peng George Wang
O-linked β-N-acetyl-glucosamine (O-GlcNAc) is an essential and ubiquitous post-translational modification present in nucleic and cytoplasmic proteins of multicellular eukaryotes. The metabolic chemical probes such as GlcNAc or GalNAc analogues bearing ketone or azide handles, in conjunction with bioorthogonal reactions, provide a powerful approach for detecting and identifying this modification. However, these chemical probes either enter multiple glycosylation pathways or have low labeling efficiency. Therefore, selective and potent probes are needed to assess this modification...
November 18, 2016: ACS Chemical Biology
https://www.readbyqxmd.com/read/27613050/quantitation-of-protein-translation-rate-in-vivo-with-bioorthogonal-click-chemistry
#19
Borja Belda-Palazón, Alejandro Ferrando, Rosa Farràs
The development of novel bioorthogonal reactives that can be used to tag biomolecules in vivo has revolutionized the studies of cellular and molecular biology. Among those novel reactive substances, amino acid analogs can be used to label nascent proteins, thus opening new avenues for measuring protein translation rates in vivo with a limited manipulation of the sample. Here, we describe the use of Click-chemistry to tag and separate newly synthesized proteins in mammalian cells that can be used, coupled with western analysis, to estimate the translation rate of any protein of interest...
2016: Methods in Molecular Biology
https://www.readbyqxmd.com/read/27573264/recent-advances-in-inverse-electron-demand-hetero-diels-alder-reactions-of-1-oxa-1-3-butadienes
#20
REVIEW
Aleksandra Pałasz
This review is an endeavor to highlight the progress in the inverse-electron-demand hetero-Diels-Alder reactions of 1-oxa-1,3-butadienes in recent years. The huge number of examples of 1-oxadienes cycloadditions found in the literature clearly demonstrates the incessant importance of this transformation in pyran ring synthesis. This type of reaction is today one of the most important methods for the synthesis of dihydropyrans which are the key building blocks in structuring of carbohydrate and other natural products...
June 2016: Topics in Current Chemistry (Journal)
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