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Bioorthogonal chemistry

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
Aurélien Godinat, Arkadiy A Bazhin, Elena A Goun
Bioorthogonal chemistry has developed significant over the past few decades, to the particular benefit of molecular imaging. Bioluminescence imaging (BLI) along with other imaging modalities have significantly benefitted from this chemistry. Here, we review bioorthogonal reactions that have been used to signific antly broaden the application range of BLI.
May 17, 2018: Drug Discovery Today
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
Tomonori Tamura, Tsuyoshi Ueda, Taiki Goto, Taku Tsukidate, Yonatan Shapira, Yuki Nishikawa, Alma Fujisawa, Itaru Hamachi
Selective modification of native proteins in live cells is one of the central challenges in recent chemical biology. As a unique bioorthogonal approach, ligand-directed chemistry recently emerged, but the slow kinetics limits its scope. Here we successfully overcome this obstacle using N-acyl-N-alkyl sulfonamide as a reactive group. Quantitative kinetic analyses reveal that ligand-directed N-acyl-N-alkyl sulfonamide chemistry allows for rapid modification of a lysine residue proximal to the ligand binding site of a target protein, with a rate constant of ~104  M-1  s-1 , comparable to the fastest bioorthogonal chemistry...
May 14, 2018: Nature Communications
Frederick M Tomlin, Chelsea G Gordon, Yisu Han, Taia S Wu, Ellen M Sletten, Carolyn R Bertozzi
The quadricyclane (QC) ligation is a bioorthogonal reaction between a quadricyclane moiety and a nickel bis(dithiolene) derivative. Here we show that a QC amino acid can be incorporated into a protein site-specifically using the pyrrolysine-based genetic code expansion platform, and subsequently used for ligation chemistry. Additionally, we exploited the photolability of the QC ligation product to render the adduct cleavable with a handheld UV lamp. We further developed a protein purification method that involves QC ligation of biotin to a protein of interest, capture on streptavidin resin, and finally release using only UV light...
April 4, 2018: Bioorganic & Medicinal Chemistry
R David Row, Jennifer A Prescher
Chemical tools are transforming our understanding of biomolecules and living systems. Included in this group are bioorthogonal reagents-functional groups that are inert to most biological species, but can be selectively ligated with complementary probes, even in live cells and whole organisms. Applications of these tools have revealed fundamental new insights into biomolecule structure and function-information often beyond the reach of genetic approaches. In many cases, the knowledge gained from bioorthogonal probes has enabled new questions to be asked and innovative research to be pursued...
May 4, 2018: Accounts of Chemical Research
Dennis G Hall, Burcin Akgun
In the last two decades, bioorthogonal chemistry has been one of the most preferred tools to achieve site-selective protein modifications. However, the most commonly applied bioorthogonal reactions are a handful quantity and may display some limitations, such as slow rates, use of unstable/cytotoxic reagents or side reactions. There is significant interest to expand the bioorthogonal chemistry toolbox. In this regard, boronic acids have recently been introduced in bioorthogonal chemistry and are exploited in three different strategies: 1) iminoboronate formation between 2-acetyl/formylarylboronic acids and hydrazine/hydroxylamine/semicarbazide derivatives; 2) boronic ester formation between a boronic acid and a 1,2-cis diol; 3) use of boronic acids as transient groups in a Suzuki-Miyaura cross-coupling reaction or via an oxidation of boronic acid with an oxidizing reagent...
May 3, 2018: Angewandte Chemie
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...
April 23, 2018: International Journal of Pharmaceutics
Thomas Bakkum, Tyrza van Leeuwen, Alexi J C Sarris, Daphne M van Elsland, Dimitrios Poulcharidis, Herman S Overkleeft, Sander I van Kasteren
One of the areas in which bioorthogonal chemistry - chemistry performed inside a cell or organism - has become of pivotal im-portance is in the study of host-pathogen interactions. The incorporation of bioorthogonal groups into the cell wall or proteome of intracellular pathogens has allowed the study within the endo-lysosomal system. However, for the approach to be successful, the incorporated bioorthogonal groups must be stable to chemical conditions found within these organelles, which are some of the harshest found in metazoans: the groups are exposed to oxidizing species, acidic conditions, and reactive thiols...
April 25, 2018: ACS Chemical Biology
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
Robert Serfling, Lisa Seidel, Thore Böttke, Irene Coin
The genetic incorporation of non-canonical amino acids (ncAAs) via amber stop codon suppression is a powerful technique to install artificial probes and reactive moieties onto proteins directly in the live cell. Each ncAA is incorporated by a dedicated orthogonal suppressor-tRNA/amino-acyl-tRNA-synthetase (AARS) pair that is imported into the host organism. The incorporation efficiency of different ncAAs can greatly differ, and be unsatisfactory in some cases. Orthogonal pairs can be improved by manipulating either the AARS or the tRNA...
April 9, 2018: Journal of Visualized Experiments: JoVE
Yinzhi Fang, Han Zhang, Zhen Huang, Samuel L Scinto, Jeffrey C Yang, Christopher W Am Ende, Olga Dmitrenko, Douglas S Johnson, Joseph M Fox
A photochemical synthesis of AgNO3 complexes of trans -cycloheptene (TCH) and trans -1-sila-4-cycloheptene (Si-TCH) derivatives is described. A low temperature flow photoreactor was designed to enable the synthesis of carbocyclic TCH derivatives due to their thermal sensitivity in the absence of metal coordination. Unlike the free carbocycles, TCH·AgNO3 complexes can be handled at rt and stored for weeks in the freezer (-18 °C). Si-TCH·AgNO3 complexes are especially robust, and are bench stable for days at rt, and for months in the freezer...
February 21, 2018: Chemical Science
Réka Petrovics, Bianka Söveges, Alexandra Egyed, Gergely Knorr, Attila Kormos, Tímea Imre, György Török, András Zeke, Éva Kocsmár, Gábor Lotz, Péter Kele, Krisztina Németh
One of the most popular means to follow interactions between bio(macro)molecules is Förster resonance energy transfer (FRET). There is large interest in widening the selection of fluorescent FRET pairs especially in the region of the red/far red range, where minimal autofluorescence is encountered. A set of bioorthogonally applicable fluorescent dyes, synthesized recently in our lab, were paired (Cy3T/Cy5T; Cy1A/Cy3T and Cy1A/CBRD1A) based on their spectral characteristics in order to test their potential in FRET applications...
April 9, 2018: Organic & Biomolecular Chemistry
Dilini N Kekulandara, Kusal T G Samarasinghe, Dhanushka N P Munkanatta Godage, Young-Hoon Ahn
Correction for 'Clickable glutathione using tetrazine-alkene bioorthogonal chemistry for detecting protein glutathionylation' by Dilini N. Kekulandara et al., Org. Biomol. Chem., 2016, 14, 10886-10893.
April 4, 2018: Organic & Biomolecular Chemistry
Tian Lv, Jianbing Wu, Fenghua Kang, Tingting Wang, Boheng Wan, Jin-Jian Lu, Yihua Zhang, Zhangjian Huang
A class of O2 -alkyl derived diazeniumdiolates 3a-f and 4a-c were designed and synthesized as new bioorthogonal NO precursors, which can be effectively uncaged in the presence of a palladium catalyst via bioorthogonal bond cleavage reactions to generate NO in living cancer cells, eliciting potent antiproliferative activity.
March 29, 2018: Organic Letters
Tobias Krüger, Stefanie Weiland, Georg Falck, Marcus Gerlach, Mareile Boschanski, Sarfaraz Alam, Kristian M Müller, Thomas Dierks, Norbert Sewald
Formylglycine generating enzymes are of increasing interest in the field of bioconjugation chemistry. They catalyze the site-specific oxidation of a cysteine residue to the aldehyde containing amino acid Cα-formylglycine (FGly). This non-canonical residue can be generated within any desired target protein and subsequently be used for bioorthogonal conjugation reactions. The prototypic formylglycine generating enzyme (FGE) and the iron-sulfur protein AtsB display slight variations in their recognition sequences...
March 26, 2018: Angewandte Chemie
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.
March 26, 2018: Chemical Communications: Chem Comm
Faming Wang, Yan Zhang, Zhi Du, Jinsong Ren, Xiaogang Qu
As a powerful tool for chemical biology, bioorthogonal chemistry broadens the ways to explore the mystery of life. In this field, transition metal catalysts (TMCs) have received much attention because TMCs can rapidly catalyze chemical transformations that cannot be accomplished by bio-enzymes. However, fine controlling chemical reactions in living systems like bio-enzymes is still a great challenge. Herein, we construct a versatile light-controlled bioorthogonal catalyst by modifying macroporous silica-Pd0 with supramolecular complex of azobenzene (Azo) and β-cyclodextrin (CD)...
March 23, 2018: Nature Communications
Junu Bae, Zijian Zhou, Thomas Theis, Warren S Warren, Qiu Wang
Hyperpolarized magnetic resonance (HP-MR) is a powerful, sensitive, and noninvasive approach to visualize molecular structure, function, and dynamics in vitro and in vivo. Current applications of HP-MR mostly rely on hyperpolarization of target compounds in dedicated hyperpolarizers because biomolecules can typically not be hyperpolarized directly in vivo. The injected hyperpolarized probes often undergo multiple metabolic pathways in living systems, and it remains challenging to localize and identify specific targets with high chemical selectivity...
March 2018: Science Advances
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