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bioorthogonal click

Julian Fink, Jürgen Seibel
Sphingolipids and glycosphingolipids can regulate cell recognition and signalling. Ceramide and sphingosine-1-phosphate are major players in the sphingolipid pathways and are involved in the initiation and regulation of signalling, apoptosis, stress responses and infection. Specific chemically synthesized sphingolipid derivatives containing small functionalities like azide or alkyne can mimic the biological properties of natural lipid species, which turns them into useful tools for the investigation of the highly complex sphingolipid metabolism by rapid and selective "click chemistry" using sensitive tags like fluorophores...
June 1, 2018: Biological Chemistry
Koji Nagahama, Yuuka Kimura, Ayaka Takemoto
To date, many scientists have thoroughly investigated both cells and cellular functions, resulting in the identification of numerous molecular mechanisms underlying the cellular functions. Based on these findings, medical scientists and pharmacologists have developed many technological applications for cells and cellular functions in medicine. How can material scientists utilize cells and cellular functions? Here, we show a concept for utilizing cells and their functions from the viewpoint of materials science...
June 6, 2018: Nature Communications
Esmi L Zajaczkowski, Qiong-Yi Zhao, Zong Hong Zhang, Xiang Li, Wei Wei, Paul R Marshall, Laura J Leighton, Sarah Nainar, Chao Feng, Robert C Spitale, Timothy W Bredy
Transcriptome-wide expression profiling of neurons has provided important insights into the underlying molecular mechanisms and gene expression patterns that transpire during learning and memory formation. However, there is a paucity of tools for profiling stimulus-induced RNA within specific neuronal cell populations. A bioorthogonal method to chemically label nascent (i.e. newly transcribed) RNA in a cell-type-specific and temporally controlled manner, which is also amenable to bioconjugation via click chemistry, was recently developed and optimized within conventional immortalized cell lines...
June 6, 2018: ACS Chemical Neuroscience
Julia G Fraseur, Tamara L Kinzer-Ursem
As the proteomics field continues to expand, scientists are looking to integrate cross-disciplinary tools for studying protein structure, function, and interactions. Protein purification remains a key tool for many characterization studies. Calmodulin (CaM) is a calcium-binding messenger protein with over a hundred downstream binding partners, and is involved in a host of physiological processes, from learning and memory to immune and cardiac function. To facilitate biophysical studies of calmodulin, researchers have designed a site-specific labeling process for use in bioconjugation applications while maintaining high levels of protein activity...
2018: PloS One
Benjamin Spangler, Dustin Dovala, William S Sawyer, Katherine V Thompson, David A Six, Folkert Reck, Brian Y Feng
The Gram-negative cell envelope presents a formidable barrier to xenobiotics, and achieving sufficient compound exposure inside the cell is a key challenge for the discovery of new antibiotics. To provide insight on the molecular determinants governing compound exposure in Gram-negative bacteria, we developed a methodology leveraging a cyclooctyne-based bioorthogonal probe to assess compartment-specific compound exposure. This probe can be selectively localized to the periplasmic or cytoplasmic compartments of Gram-negative bacteria...
May 30, 2018: ACS Infectious Diseases
Amanda L Garner
Click chemistry has emerged as a powerful tool in our arsenal for unlocking new biology. This includes its utility in both chemical biology and drug discovery. An emerging application of click chemistry is in the development of biochemical assays for high-throughput screening to identify new chemical probes and drug leads. This Feature Article will discuss the advancements in click chemistry that were necessary for the development of a new class of biochemical assay, catalytic enzyme-linked click chemistry assay or cat-ELCCA...
May 21, 2018: Chemical Communications: Chem Comm
Yevgeny Brudno, Matthew J Pezone, Tracy K Snyder, Oktay Uzun, Christopher T Moody, Michael Aizenberg, David J Mooney
Local drug presentation made possible by drug-eluting depots has demonstrated benefits in a vast array of diseases, including in cancer, microbial infection and in wound healing. However, locally-eluting depots are single-use systems that cannot be refilled or reused after implantation at inaccessible sites, limiting their clinical utility. New strategies to noninvasively refill drug-eluting depots could dramatically enhance their clinical use. In this report we present a refillable hydrogel depot system based on bioorthogonal click chemistry...
May 6, 2018: Biomaterials
Maomao He, Zhen Han, Jing Qiao, Liza Ngo, May P Xiong, Y George Zheng
Lysine acetylation plays vital roles in the regulation of fundamental cellular processes, which is mediated by lysine acetyltransferases (KATs). Developing chemical biology probes for KAT activity detection is of important value in providing improved understanding of their biological functions. We reported a panel of "turn-on" fluorescent probes for sensitive and selective detection of KAT enzymatic activity through a simple mix-and-read format. Combined with bioorthogonal substrate labelling and click chemistry, these probes produced strong "turn-on" fluorescent signals in response to KAT-mediated acylation process...
May 16, 2018: Chemical Communications: Chem Comm
Yueqin Zheng, Xingyue Ji, Bingchen Yu, Kaili Ji, David Gallo, Eva Csizmadia, Mengyuan Zhu, Manjusha Roy Choudhury, Ladie Kimberly C De La Cruz, Vayou Chittavong, Zhixiang Pan, Zhengnan Yuan, Leo E Otterbein, Binghe Wang
Controlled activation is a critical component in prodrug development. Here we report a concentration-sensitive platform approach for bioorthogonal prodrug activation by taking advantage of reaction kinetics. Using two 'click and release' systems, we demonstrate enrichment and prodrug activation specifically in mitochondria to demonstrate the principle of the approach. In both cases, the payload (doxorubicin or carbon monoxide) was released inside the mitochondrial matrix following the enrichment-initiated click reaction...
May 14, 2018: Nature Chemistry
Ron M Versteegen, Wolter Ten, Raffaella Rossin, Mark Ar de Geus, Henk M Janssen, Marc Stefan Robillard
The bioorthogonal cleavage of allylic carbamates from trans-cyclooctene (TCO) upon reaction with tetrazine is widely used to release amines. We disclose here that this reaction can also cleave TCO esters, carbonates, and, surprisingly, ethers. Mechanistic studies demonstrated that the elimination is mainly governed by the formation of the rapidly eliminating 1,4-dihydropyridazine tautomer, and less by the nature of the leaving group. In contrast to the widely used p-aminobenzyloxy linker, which affords a slow cleavage of aromatic but not of aliphatic ethers, the aromatic, benzylic and aliphatic TCO ethers cleaved as efficiently as the carbamate, carbonate and esters...
May 10, 2018: Angewandte Chemie
Fang Hu, Youyong Yuan, Wenbo Wu, Duo Mao, Bin Liu
Metabolic glycoengineering of unnatural glycans with bio-orthogonal chemical groups and a subsequent click reaction with fluorescent probes have been widely used in monitoring various bioprocesses. Herein, we developed a dual-responsive metabolic precursor that could specifically generate unnatural glycans with azide groups on the membrane of targeted cancer cells with high selectivity. Moreover, a water-soluble fluorescent light-up probe with aggregation-induced emission (AIE) was synthesized, which turned its fluorescence on upon a click reaction with azide groups on the cancer cell surface, enabling special cancer cell imaging with low background signal...
June 5, 2018: Analytical Chemistry
Nilesh M Meghani, Hardik H Amin, Chulhun Park, Jun-Bom Park, Jing-Hao Cui, Qing-Ri Cao, Beom-Jin Lee
The principles of bioorthogonal click chemistry and metabolic glycoengineering were applied to produce targeted anti-cancer drug delivery via fattigation-platform-based gelatin-oleic nanoparticles. A sialic acid precursor (Ac4 ManNAz) was introduced to the cell surface. Gelatin and oleic acid were conjugated by 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride/N-hydroxysuccinimide (EDC/NHS) chemistry with the subsequent covalent attachment of dibenzocyclooctyne (DBCO) in a click reaction on the cell surface...
July 10, 2018: International Journal of Pharmaceutics
Janet M Paper, Thiya Mukherjee, Kathrin Schrick
Background: Phospholipids are important structural and signaling molecules in plant membranes. Some fluorescent dyes can stain general lipids of membranes, but labeling and visualization of specific lipid classes have yet to be developed for most components of the membrane. New techniques for visualizing membrane lipids are needed to further delineate their dynamic structural and signaling roles in plant cells. In this study we examined whether propargylcholine, a bioortholog of choline, can be used to label the major membrane lipid, phosphatidylcholine, and other choline phospholipids in plants...
2018: Plant Methods
Attila Kormos, Christine Koehler, Eszter A Fodor, Zsófia R Rutkai, Madison E Martin, Gábor Mező, Edward A Lemke, Péter Kele
Fluorogenic probes can be used to minimize the background fluorescence of unreacted and nonspecifically adsorbed reagents. The preceding years have brought substantial developments in the design and synthesis of bioorthogonally applicable fluorogenic systems mainly based on the quenching effects of azide and tetrazine moieties. The modulation power exerted by these bioorthogonal motifs typically becomes less efficient on more conjugated systems; that is, on probes with redshifted emission wavelength. To reach efficient quenching, that is, fluorogenicity, even in the red range of the spectrum, we present the synthesis, fluorogenic, and conjugation characterization of bistetrazine-cyanine probes with emission maxima between 600 and 620 nm...
April 20, 2018: Chemistry: a European Journal
Margaux Riomet, Elodie Decuypere, Karine Porte, Sabrina Bernard, Lucie Plougastel, Sergii Kolodych, Davide Audisio, Frédéric Taran
Emerging applications in the field of chemical biology are currently limited by the lack of bioorthogonal reactions allowing both removal and linkage of chemical entities on complex biomolecules. We recently discovered a novel reaction between iminosydnones and strained alkynes leading to two products resulting from ligation and fragmentation of iminosydnones under physiological conditions. We now report the synthesis of a panel of substituted iminosydnones and the structure reactivity relationship between these compounds and strained alkyne partners...
April 17, 2018: Chemistry: a European Journal
Anaëlle Doerflinger, Nam Nguyen Quang, Edmond Gravel, Guillaume Pinna, Marie Vandamme, Frédéric Ducongé, Eric Doris
Polydiacetylene micelles were functionalized with controlled amounts of biotin using bioorthogonal click chemistry. The biotinylated micelles were evaluated in the selective targeting of the MCF-7 cancerous cell line and were shown to be readily internalized. The efficiency of the cellular uptake was correlated to the density of grafted biotin.
April 5, 2018: Chemical Communications: Chem Comm
Kuo-Ting Chen, Christian Ieritano, Yann Seimbille
Herein, we describe a synthetic strategy for the regioselective labeling of peptides by using a bioorthogonal click reaction between 2-cyanobenzothiazole (CBT) and a 1,2-aminothiol moiety. This methodology allows for the facile and site-specific modification of peptides with various imaging agents, including fluorophores and radioisotope-containing prosthetic groups. We investigated the feasibility of an early-stage incorporation of dipeptide 1 into targeting vectors, such as c[RGDyK(C)] and HER2 pep , during solid-phase peptide synthesis...
March 2018: ChemistryOpen
Kuo-Ting Chen, Christian Ieritano, Yann Seimbille
Invited for this month's cover picture is the group of Dr. Yann Seimbille at the Life Sciences Division at TRIUMF (Canada). The cover picture shows how a simple and innovative methodology based on the bioorthogonal click reaction between 2-cyanobenzothiazole and 1,2-aminothiol has been elaborated to facilitate the labeling of peptide biovectors. Read the full text of their Communication at 10.1002/open.201700191.
March 2018: ChemistryOpen
Wenshu Zheng, Huiling Li, Wenwen Chen, Jiangjiang Zhang, Nuoxin Wang, Xuefeng Guo, Xingyu Jiang
A fast (1 min), straightforward but efficient, click chemistry-based system that enables the rapid detection of free copper (Cu) ions in either biological fluids or living cells without tedious pretreatment is provided. Cu can quickly induce the conjugation between graphene oxide (GO) and a fluorescent dye via click reaction. On the basis of the high specificity of bioorthogonal reaction and the effective quenching ability of GO, the assay studied in this paper can respond to Cu ions in less than 1 min with excellent selectivity and sensitivity, which is the fastest sensor for Cu as far as it is known...
April 2018: Small
Katja Hartstock, Benedikt S Nilges, Anna Ovcharenko, Nicolas V Cornelissen, Nikolai Püllen, Ann-Marie Lawrence-Dörner, Sebastian A Leidel, Andrea Rentmeister
m6 A is the most abundant internal modification in eukaryotic mRNA. It is introduced by METTL3-METTL14 and tunes mRNA metabolism, impacting cell differentiation and development. Precise transcriptome-wide assignment of m6 A sites is of utmost importance. However, m6 A does not interfere with Watson-Crick base pairing, making polymerase-based detection challenging. We developed a chemical biology approach for the precise mapping of methyltransferase (MTase) target sites based on the introduction of a bioorthogonal propargyl group in vitro and in cells...
February 20, 2018: Angewandte Chemie
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