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Click chemistry

Mona Sharar, Essa M Saied, Mario C Rodriguez, Christoph Arenz, Maria Montes-Bayón, Michael W Linscheid
Oxidative transformation of cysteine thiol groups into different functional groups is considered a significant posttranslational modification of great importance in pathological and physiological processes. A cysteine sulfenic acid (SA) residue is the transient state for thiol group oxidation and it can react with free thiols to form disulfide bonds or can be further oxidized with reactive oxygen/reactive nitrogen species (ROS/RNS) to form sulfinic and sulfonic acids. The increase in ROS/RNS concentrations is correlated to age-related diseases such as cancer and Alzheimer's disease...
January 17, 2017: Analytical and Bioanalytical Chemistry
Shoujun Zhu, Qinglai Yang, Alexander L Antaris, Jingying Yue, Zhuoran Ma, Huasen Wang, Wei Huang, Hao Wan, Joy Wang, Shuo Diao, Bo Zhang, Xiaoyang Li, Yeteng Zhong, Kuai Yu, Guosong Hong, Jian Luo, Yongye Liang, Hongjie Dai
Fluorescence imaging multiplicity of biological systems is an area of intense focus, currently limited to fluorescence channels in the visible and first near-infrared (NIR-I; ∼700-900 nm) spectral regions. The development of conjugatable fluorophores with longer wavelength emission is highly desired to afford more targeting channels, reduce background autofluorescence, and achieve deeper tissue imaging depths. We have developed NIR-II (1,000-1,700 nm) molecular imaging agents with a bright NIR-II fluorophore through high-efficiency click chemistry to specific molecular antibodies...
January 17, 2017: Proceedings of the National Academy of Sciences of the United States of America
Yulong Wang, Limin Wang, Juanjuan Xue, Jinbo Dong, Jia Cai, Xiude Hua, Minghua Wang, Cunzheng Zhang, Fengquan Liu
A signal-amplified lateral flow test strip (SA-LFTS) for the detection of Cu2+ in aqueous solution was constructed based on Cu+-catalyzed click chemistry and hybridization of single-stranded DNA (ssDNA). Alkyne and azide modified ssDNA acted as specific elements for Cu2+ recognition, and a chemical ligation product formed through Cu+-catalyzed alkyne-azide cycloaddition. Hybridization of ssDNA-labeled gold nanoparticles resulted in high sensitivity, and the output signal could be observed directly by the naked eye...
2017: PloS One
Yiping Chen, Yunlei Xianyu, Xingyu Jiang
As one of the major tools for and by chemical science, biochemical analysis is becoming increasingly important in fields like clinical diagnosis, food safety, environmental monitoring, and the development of chemistry and biochemistry. The advancement of nanotechnology boosts the development of analytical chemistry, particularly the nanoparticle (NP)-based approaches for biochemical assays. Functional NPs can greatly improve the performance of biochemical analysis because they can accelerate signal transduction, enhance the signal intensity, and enable convenient signal readout due to their unique physical and chemical properties...
January 9, 2017: Accounts of Chemical Research
Amol M Vibhute, Poornenth Pushpanandan, Maria Varghese, Vera Koniecnzy, Colin W Taylor, Kana M Sureshan
Inositol 1,4,5-trisphosphate receptors (IP3Rs) are tetrameric intracellular channels through which many extracellular stimuli initiate the Ca(2+) signals that regulate diverse cellular responses. There is considerable interest in developing novel ligands of IP3R. Adenophostin A (AdA) is a potent agonist of IP3R and since some dimeric analogs of IP3R ligands are more potent than the corresponding monomer; we considered whether dimeric AdA analogs might provide agonists with increased potency. We previously synthesized traizolophostin, in which a simple triazole replaced the adenine of AdA, and showed it to be equipotent to AdA...
November 3, 2016: RSC Advances
Marie L Malone, Valerie J Cavett, Brian M Paegel
Combinatorial bead libraries figure prominently in next-generation sequencing and are also important tools for in vitro evolution. The most common methodology for generating such bead libraries, emulsion PCR (emPCR), enzymatically extends bead-immobilized oligonucleotide PCR primers in emulsion droplets containing a single progenitor library member. Primers are almost always immobilized on beads via noncovalent biotin-streptavidin binding. Here, we describe covalent bead functionalization with primers (∼10(6) primers/2...
January 9, 2017: ACS Combinatorial Science
Jacob L Houghton, Rosemery Membreno, Dalya Abdel-Atti, Kristen M Cunanan, Sean Carlin, Wolfgang W Scholz, Pat B Zanzonico, Jason S Lewis, Brian M Zeglis
The pretargeting system based on the inverse electron demand Diels-Alder reaction (IEDDA) between trans-cyclooctene (TCO) and tetrazine (Tz) combines the favorable pharmacokinetic properties of radiolabeled small molecules with the affinity and specificity of antibodies. This strategy has proven to be an efficient method for the molecularly targeted delivery of pharmaceuticals, including isotopes for radiological imaging. Despite encouraging results from in vivo PET imaging studies, this promising system has yet to be thoroughly evaluated for pretargeted radioimmunotherapy (PRIT)...
January 2017: Molecular Cancer Therapeutics
Songzi Kou, Zhongguang Yang, Fei Sun
Practical methods for oceanic uranium extraction have yet to be developed in order to tap into the vast uranium reserve in the ocean as an alternative energy. Here we present a protein hydrogel system containing a network of recently engineered super uranyl binding proteins (SUPs) that is assembled through thiol-maleimide click chemistry under mild conditions. Monodisperse SUP hydrogel microbeads fabricated by a microfluidic device further enable uranyl (UO22+) enrichment from seawater with great efficiency (Enrichment index, K = 2...
January 6, 2017: ACS Applied Materials & Interfaces
Anatoly Mayburd, Ancha Baranova
PURPOSE: Novel, "outside of the box" approaches are needed for evaluating candidate molecules, especially in oncology. Throughout the years of 2000-2010, the efficiency of drug development fell to barely acceptable levels, and in the second decade of this century, levels have improved only marginally. This dismal condition continues despite unprecedented progress in the development of a variety of high-throughput tools, computational methods, aggregated databases, drug repurposing programs and innovative chemistries...
October 2016: Journal of Pharmacy & Pharmaceutical Sciences: a Publication of the Canadian Society for Pharmaceutical Sciences
Clancy C Slack, Joel A Finbloom, Keunhong Jeong, Carson J Bruns, David E Wemmer, Alexander Pines, Matthew B Francis
We report a CB6 rotaxane for the (129)Xe hyperCEST NMR detection of matrix metalloprotease 2 (MMP-2) activity. MMP-2 is overexpressed in cancer tissue, and hence is a cancer marker. A peptide containing an MMP-2 recognition sequence was incorporated into the rotaxane, synthesized via CB6-promoted click chemistry. Upon cleavage of the rotaxane by MMP-2, CB6 became accessible for (129)Xe@CB6 interactions, leading to protease-responsive hyperCEST activation.
January 3, 2017: Chemical Communications: Chem Comm
Ligang Lin, Hui Sun, Kaiyu Zhang, Yonghui Zhong, Qi Cheng, Xihui Bian, Qingping Xin, Bowen Cheng, Xianshe Feng, Yuzhong Zhang
Affinity membrane has great potential for applications in bioseparation and purification. Disclosed herein is the design of a novel affinity membrane with macrocyclic spacer arms for lysozyme binding. The clickable azide-cyclodextrin (CD) arms and clickable alkyne ethylene-vinyl alcohol (EVAL) chains are designed and prepared. By the azide-alkyne click reaction, the EVAL-CD-ligands affinity membranes with CD spacer arms in three-dimensional micro channels have been successfully fabricated. The FT-IR, XPS, NMR, SEM and SEM-EDS results give detailed information of structure evolution...
December 26, 2016: Journal of Hazardous Materials
Maria-Jose Bañuls, Pilar Jiménez-Meneses, Albert Meyer, Jean-Jacques Vasseur, François Morvan, Jorge Escorihuela, Rosa Puchades, Angel Maquieira
Nucleic acid microarray-based assay technology has recognized lacks in reproducibility, reliability and analytical sensitivity. Here, a new strategy of probe attachment modes for silicon-based materials is built up. Thus, hybridization ability is enhanced combining thiol-ene or thiol-yne click chemistry reactions, with a multi-point attachment of polythiolated probes. The viability and performance of this approach were demonstrated determining specifically Salmonella PCR products up to 20 pM sensitivity level...
January 2, 2017: Bioconjugate Chemistry
Marianneza Chatzipetrou, Maria Massaouti, Georgios Tsekenis, Anke Kristin Trilling, Esther van Andel, Luc M W Scheres, Maarten Marinus Johannes Smulders, Han Zuilhof, Ioanna Zergioti
In this paper we present the immobilization of thiol-modified aptamers on alkyne- or alkene-terminated silicon nitride surfaces, by laser-initiated "click chemistry" reactions. The aptamers are printed onto the surface by Laser Induced Forward Transfer (LIFT), which initiates the covalent bonding of the aptamers by thiol-ene or thiol-yne reactions that occur upon UV irradiation of the thiol-modified aptamers with ns laser pulses. This combination of LIFT and laser-initiated click chemistry allows the creation of high-resolution patterns without the need of masks...
January 1, 2017: Langmuir: the ACS Journal of Surfaces and Colloids
Beijun Liu, Haifeng Huang, Zhibin Yang, Beiyin Liu, Sanhu Gou, Chao Zhong, Xiufeng Han, Yun Zhang, Jingman Ni, Rui Wang
Currently, antimicrobial peptides have attracted considerable attention because of their broad-sprectum activity and low prognostic to induce antibiotic resistance. In our study, for the first time, a series of side-chain hybrid dimer peptides J-AA (Anoplin-Anoplin), J-RR (RW-RW), and J-AR (Anoplin-RW) based on the wasp peptide Anoplin and the arginine- and tryptophan-rich hexapeptide RW were designed and synthesized by click chemistry, with the intent to improve the antimicrobial efficacy of peptides against bacterial pathogens...
December 28, 2016: Peptides
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
Yue Wang, Jingjing Zhu, Lianwen Zhang
O-GlcNAc transferase (OGT) is a key enzyme involved in dynamic O-GlcNAcylation of nuclear and cytoplasmic proteins similar to phosphorylation. Discovery of cell-permeable OGT inhibitors is significant to clarify the function and regulatory mechanism of O-GlcNAcylation. This will establish the foundation for the development of therapeutic drugs for relevant diseases. Here, we report two cell-permeable OGT inhibitors (APNT and APBT), developed from low-activity precursors (IC50 > 1 mM) via "tethering in situ click chemistry (TISCC)"...
December 29, 2016: Journal of Medicinal Chemistry
David Harvey, Philip Bardelang, Sara L Goodacre, Alan Cockayne, Neil R Thomas
In a new, versatile approach to fun-ction-alizing recombinant spider silk, L-azidohomoalanine is introduced residue-specifically in the minispidroin protein 4RepCT through expression in an E. coli methionine auxotroph. Both fluorophores and the antibiotic levofloxacin are attached to this bio-orthogonal amino acid using copper-catalyzed click chemistry, either before or after the silk fibers are self-assembled.
December 28, 2016: Advanced Materials
Panita Maturavongsadit, Xiangdong Bi, Kamolrat Metavarayuth, Jittima Amie Luckanagul, Qian Wang
This study aims to investigate the effect of the structures of crosslinkers on the in vitro chondrogenic differentiation of bone mesenchymal stem cells (BMSCs) in hyaluronic acid (HA)-based hydrogels. The hydrogels were prepared by the covalent crosslinking of methacrylated HA with different types of thiol-tailored molecules, including dithiothreitol (DTT), 4-arm polyethylene glycol (PEG), and multi-arm polyamidoamine (PAMAM) dendrimer using thiol-ene "click" chemistry. The microstructure, mechanical properties, diffusivity and degradation rates of the resultant hydrogels were controlled by the structural feature of different crosslinkers...
December 27, 2016: ACS Applied Materials & Interfaces
Zhengliang L Wu, Xinyi Huang, Cheryl Ethen, Timothy Tatge, Marta Pasek, Joseph Zaia
Heparan sulfate (HS) is a linear polysaccharide found in the extracellular matrix (ECM) and on the cell membrane. It plays numerous roles in cellular events, including cell growth, migration and differentiation through binding to various growth factors, cytokines and other ECM proteins. Heparanase (HPSE) is an endoglycosidase that cleaves HS in the ECM and cell membrane. By degrading HS, HPSE not only alters the integrity of the ECM but also releases growth factors and angiogenic factors bound to HS chains, therefore, changes various cellular activities, including cell mobility that is critical for cancer metastasis...
December 26, 2016: Glycobiology
Gopi Nath Vemuri, Meng Chu, Han Dong, Brian J Spinello, C Scott Hartley
ortho-Phenylene oligomers fold into compact helical conformations in solution, and have therefore recently emerged as a class of foldamers. Previous work has shown that their folding is controlled by arene-arene stacking interactions parallel to the helical axis. Such interactions might reasonably be expected to be sensitive to solvent, but little is known of solvent effects in this system. Here, we report on the behavior of a representative set of o-phenylene oligomers in solvents ranging from non-polar (benzene) to polar and protic (methanol and water)...
December 23, 2016: Organic & Biomolecular Chemistry
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