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Click chemistry

Samuel Nkrumah-Agyeefi, Carmen Scholz
A novel approach to the post-biosynthetic chemical modification of bromo and alkyne functionalized poly(3-hydroxyalkanoates), (PHAs), via copper-catalyzed azide-alkyne cycloaddition (CuAAC) and strain promoted azide alkyne cycloaddition (SPAAC) is reported. Optimum conditions for the biosynthesis of the PHA copolymers, poly(3-hydroxynonanoate-co-3-hydroxy-11-bromoundecanoate) (PHNUBr) and poly(3-hydroxynonanoate-co-3-hydroxy-10-undecynoate) (PHNUD), using Pseudomonas oleovorans as cell factories were 20h of fermentation time and a total carbon substrate concentration of 40mM...
December 2, 2016: International Journal of Biological Macromolecules
Elisa Romeo, Silvia Pontis, Stefano Ponzano, Fabiola Bonezzi, Marco Migliore, Simona Di Martino, Maria Summa, Daniele Piomelli
Activity-based protein profiling (ABPP) is a method for the identification of an enzyme of interest in a complex proteome through the use of a chemical probe that targets the enzyme's active sites. A reporter tag introduced into the probe allows for the detection of the labeled enzyme by in-gel fluorescence scanning, protein blot, fluorescence microscopy, or liquid chromatography-mass spectrometry. Here, we describe the preparation and use of the compound ARN14686, a click chemistry activity-based probe (CC-ABP) that selectively recognizes the enzyme N-acylethanolamine acid amidase (NAAA)...
November 23, 2016: Journal of Visualized Experiments: JoVE
Jianying Chen, Xiaohu Li, Mengyu Feng, Kun Luo, Juan Yang, Bo Zhang
Development of novel materials for enrichment of glycopeptides is the key to a comprehensive analysis of the glycoproteome, which is closely related to several major diseases and biomarker findings. We synthesized phenylboronic acid (PBA) bound to SiO2 microspheres by a thiol-ene click chemistry method (this material was denoted as click PBA) and used it to separate cis-diol-containing molecules and enrich glycopeptides in hydrophilic interaction chromatography mode. Successful preparation of click PBA was confirmed by elemental analysis, X-ray photoelectron spectroscopy, N2 adsorption-desorption isotherms, and high-resolution scanning electron microscopy...
November 29, 2016: Analytical and Bioanalytical Chemistry
Binh Cao Quan Nguyen, Hideaki Takahashi, Yoshihiro Uto, M D Shahinozzaman, Shinkichi Tawata, Hiroshi Maruta
An old anti-inflammatory/analgesic drug called Toradol is a racemic form of Ketorolac (50% R-form and 50% S-form) that blocks the oncogenic RAC-PAK1-COX-2 (cyclooxygenase-2) signaling, through the direct inhibition of RAC by the R-form and of COX-2 by the S-form, eventually down-regulating the production of prostaglandins. However, due to its COOH moiety which is clearly repulsive to negatively-charged phospholipid-based plasma membrane, its cell-permeability is rather poor (the IC50 against the growth of human cancer cells such as A549 is around 13 μM)...
November 20, 2016: European Journal of Medicinal Chemistry
Vlastimil Mazanek, Alena Libanska, Jiri Sturala, Daniel Bouša, David Sedmidubský, Martin Pumera, Zbynek Janousek, Jan Plutnar, Zdenek Sofer
Fluorographene is the youngest stoichiometric derivative of graphene, thus, its reactivity is just poorly explored. Compared to graphene, a significantly higher reactivity of C-F bonds makes this material a suitable platform for a large number of chemical modifications. Fluorographene is also the only member of halogengraphenes family, which can be prepared in stoichiometric composition C1F1. Here, we present the chemical modification of fluorographene with Grignard reagents which are well known in organic chemistry for the formation of new C-C bonds...
November 23, 2016: Chemistry: a European Journal
Pamela Thompson, Ebele Ezeadi, Ian Hutchinson, Ryan Fleming, Binyam Bezabeh, Jia Lin, Shenlan Mao, Cui Chen, Luke Masterson, Haihong Zhong, Dorin Toader, Philip Howard, Herren Wu, Changshou Gao, Nazzareno Dimasi
Antibody-drug conjugates (ADCs) have become a powerful platform to deliver cytotoxic agents selectively to cancer cells. ADCs have traditionally been prepared by stochastic conjugation of a cytotoxic drug using an antibody's native cysteine or lysine residues. Through strategic selection of the mammalian expression host, we were able to introduce azide-functionalized glycans onto a homogeneously glycosylated anti-EphA2 monoclonal antibody in one step. Conjugation with an alkyne-bearing pyrrolobenzodiazepine dimer payload (SG3364) using copper-catalyzed click chemistry yielded a site-specific ADC with a drug-to-antibody ratio (DAR) of four...
November 10, 2016: ACS Medicinal Chemistry Letters
Xingyue Ji, Cheng Zhou, Kaili Ji, Robert E Aghoghovbia, Zhixiang Pan, Vayou Chittavong, Bowen Ke, Binghe Wang
Prodrug strategies have been proven to be a very effective way of addressing delivery problems. Much of the chemistry in prodrug development relies on the ability to mask an appropriate functional group, which can be removed under appropriate conditions. However, developing organic prodrugs of gasotransmitters represent unique challenges. This is especially true with carbon monoxide, which does not have an easy "handle" for bioreversible derivatization. By taking advantage of an intramolecular Diels-Alder reaction, we have developed a prodrug strategy for preparations of organic CO prodrugs that are stable during synthesis and storage, and yet readily release CO with tunable release rates under near physiological conditions...
November 23, 2016: Angewandte Chemie
Tomislav Gregorić, Mirela Sedić, Petra Grbčić, Andrea Tomljenović Paravić, Sandra Kraljević Pavelić, Mario Cetina, Robert Vianello, Silvana Raić-Malić
Regioselective 1,4-disubstituted 1,2,3-triazole tethered pyrimidine-2,4-dione derivatives (5-23) were successfully prepared by the copper(I)-catalyzed click chemistry. While known palladium/copper-cocatalyzed method based on Sonogashira cross-coupling followed by the intramolecular 5-endo-dig ring closure generated novel 6-alkylfuro[2,3-d]pyrimidine-2-one-1,2,3-triazole hybrids (24b-37b), a small library of their 5-alkylethynyl analogs (24a-37a) was synthesized and described for the first time by tandem terminal alkyne dimerization and subsequent 5-endo-trig cyclization, which was additionally corroborated with computational and X-ray crystal structure analyses...
November 14, 2016: European Journal of Medicinal Chemistry
Caterina Zilio, Laura Sola, Marina Cretich, Anna Bernardi, Marcella Chiari
The interaction of carbohydrates with a variety of biological targets, including antibodies, proteins, viruses, and cells are of utmost importance in many aspects of biology. Glycan microarrays are increasingly used to determine the binding specificity of glycan-binding proteins. In this study, a novel microarray support is reported for the fabrication of glycan arrays that combines the higher sensitivity of a layered Si-SiO2 surface with a novel polymeric coating easily modifiable by subsequent click reaction...
2017: Methods in Molecular Biology
Ming Gao, Jun Ren, Kaikai Tian, Lingyun Jia
As an efficient and facile reaction, click chemistry has been growingly used in the preparation of chromatography media for immobilizing varying types of ligands. For the widely used Cu (I)-catalyzed alkyne-azide click reaction, a 1, 2, 3-triazole group will be inevitably introduced in the molecular linkage, which could give rise to unexpected non-specific adsorption especially for the media employing small compound ligands or high ligand density. Triazole-induced non-specific protein adsorption on sepharose resins was evaluated systematically in this work, by considering the effects of triazole content, length of spacer arm, and solution conditions...
December 9, 2016: Journal of Chromatography. A
Antoine Petrelli, Eric Samain, Stéphanie Pradeau, Sami Halila, Sebastien Fort
Glycan-protein interactions play a crucial role in physiological and pathological events. Hence, improving the isolation of carbohydrate-binding proteins (i.e. lectins and anti-glycan antibodies) from complex media can not only lead to a better understanding of their function, but also provides solutions for public health issues, such as water contamination or the need for universal blood plasma. Herein, we report a rapid and efficient method to produce carbohydrate-based affinity adsorbents combining enzymatic synthesis and metal-free click chemistry...
November 15, 2016: Chembiochem: a European Journal of Chemical Biology
Peng Zhang, Haiguan Yang, Tao Chen, Yuemei Qin, Fanggui Ye
In this work, a novel imidazolium-based monolith was fabricated through a simple route. With 1-vinyl-3-octadecylimidazolium bromide and ethylene dimethacrylate as monomers, pentaerythritol tetra-(3-mercaptopropionate) as crosslinker, AIBN as thermal initiator, the monolith was facilely fabricated by one-pot thiol-ene click chemistry. The influences of both the content of monomer /crosslinker and porogenic systems on the morphology, and permeability of the monolith were studied. The optimal reaction conditions were used to prepare a homogeneous and permeable monolith...
November 9, 2016: Electrophoresis
Maria Vittoria Spanedda, Marcella De Giorgi, Fatouma Saïd Hassane, Francis Schuber, Line Bourel-Bonnet, Benoît Frisch
Click chemistry represents a new bioconjugation strategy that can be used to conveniently attach various ligands to the surface of preformed liposomes. This efficient and chemoselective reaction involves a Cu(I)-catalyzed azide-alkyne cycloaddition which can be performed under mild experimental conditions in aqueous media. Here we describe the application of a model click reaction to the conjugation, in a single step, of unprotected α-1-thiomannosyl ligands, functionalized with an azide group, to liposomes containing a terminal alkyne-functionalized lipid anchor...
2017: Methods in Molecular Biology
Herbert W Kavunja, Brent F Piligian, Taylor J Fiolek, Hannah N Foley, Temitope O Nathan, Benjamin M Swarts
Protein O-mycoloylation is a unique post-translational lipidation that was recently discovered in Corynebacterium. We describe an alkyne-modified trehalose monomycolate chemical reporter that can metabolically tag O-mycoloylated proteins in C. glutamicum, enabling their detection and identification through click chemistry.
November 10, 2016: Chemical Communications: Chem Comm
S H Lone, Shakeel U Rehman, K A Bhat
Using a click chemistry approach, a series of gallic-acid-1-phenyl-1H-[1,2,3]triazol-4-ylmethyl esters was synthesized to develop more effective antioxidants. The results of DPPH screening indicate that few of the synthesized analogs display better antioxidant effect compared to the standards. Among all, compounds, 9 and 20 displayed highest DPPH radical scavenging effect with IC50 values as low as 6.4±0.2 and 7.9±0.4 µM respectively, compared to the standard ascorbic acid (IC50=12±0.8 µM) and gallic acid (IC50=9...
November 7, 2016: Drug Research
Lisa Suntrup, Stephan Hohloch, Biprajit Sarkar
Chelating 1,2,3-triazolylidenes have been established as privileged ligands in homogeneous catalysis. We present herein a new approach towards chelating 1,2,3-triazolylidene ligands based on the 1,5-regioisomer of the corresponding triazole, which can be obtained through simple click chemistry. The new ligands are compared to their 1,4-regioisomeric counterparts through coordination to the ruthenium p-cymene fragment. The complexes are characterized structurally and spectroscopically and are employed as (pre)catalysts in the reductive condensation of nitroarenes and primary alcohols to yield secondary amines...
November 4, 2016: Chemistry: a European Journal
Bo Qiao, Yun Liu, Semin Lee, Maren Pink, Amar H Flood
Anion-templated rotaxanes are a rare class of functional organic molecules capable of novel switching and mechanical behaviors. Yet, investigations of these properties are limited by existing synthetic strategies. We show a high-yielding synthesis (80%) of [3]rotaxanes using shape-persistent macrocycles, cyanostars, and anionic organo-phosphate templates catalyzed by low steric-demand click chemistry. The reaction yields correlate with the template's binding affinities. Use of longer linkers relieves steric congestion to enable a reversible acid-base response, opening the way to molecular switching...
November 17, 2016: Chemical Communications: Chem Comm
Guangcheng Wang, Zhiyun Peng, Jing Wang, Juan Li, Xin Li
A novel series of 2,4,5-triarylimidazole-1,2,3-triazole derivatives were synthesized via copper(I)-catalyzed azide-alkyne click chemistry, and evaluated for their α-glucosidase inhibitory activity. All tested compounds showed potent α-glucosidase inhibitory activity with IC50 ranging from 15.16±0.18 to 48.15±0.37μM, in comparison to the standard drug, acarbose (IC50=817.38±6.27μM). Among all the tested compounds, 5j was found to be the most active compound with IC50 value of 15.16±0.18μM and behaved as a noncompetitive inhibitor with a Ki of 14...
October 21, 2016: Bioorganic & Medicinal Chemistry Letters
John E Moses, Adam D Moorhouse
Correction for 'The growing applications of click chemistry' by John E. Moses et al., Chem. Soc. Rev., 2007, 36, 1249-1262.
November 3, 2016: Chemical Society Reviews
Violet Stoichevska, Yong Y Peng, Aditya V Vashi, Jerome A Werkmeister, Geoff J Dumsday, John A M Ramshaw
Recombinant bacterial collagens provide a new opportunity for safe biomedical materials. They are readily expressed in E. coli in good yield and can be readily purified by simple approaches. However, recombinant proteins are limited in that direct secondary modification during expression is generally not easily achieved. Thus, inclusion of unusual amino acids, cyclic peptides, sugars, lipids and other complex functions generally needs to be achieved chemically after synthesis and extraction. In the present study we have illustrated that bacterial collagens that have had their sequences modified to include cysteine residue(s), which are not normally present in bacterial collagen-like sequences, enable a range of specific chemical modification reactions to be produced...
November 2, 2016: Journal of Biomedical Materials Research. Part A
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