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Click chemistry

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https://www.readbyqxmd.com/read/28640526/development-and-characterisation-of-a-99m-tc-tricarbonyl-labelled-estradiol-derivative-obtained-by-click-chemistry-with-potential-application-in-estrogen-receptors-imaging
#1
María Emilia Tejería, Javier Giglio, Silvia Dematteis, Ana Rey
Assessment of the presence of estrogen receptors in breast cancer is crucial for treatment planning. With the objective to develop a potential agent for estrogen receptors imaging we present the development and characterization of a (99m) Tc tricarbonyl labelled estradiol derivative. Using ethinylestradiol as starting material, a estradiol derivative bearing a 1,4-disubstituted 1,2,3-triazole-containing tridentate ligand system was synthesized by "Click Chemistry" and fully characterized. Labelling with high yield and radiochemical purity was achieved through the formation of a (99m) Tc-tricarbonyl complex...
June 22, 2017: Journal of Labelled Compounds & Radiopharmaceuticals
https://www.readbyqxmd.com/read/28639641/incorporation-of-click-chemistry-glycomimetics-dramatically-alters-triple-helix-stability-in-an-adiponectin-model-peptide
#2
Katherine R Lutteroth, Paul W R Harris, Tom H Wright, Harveen Kaur, Kevin Sparrow, Sung-Hyun Yang, Garth J S Cooper, Margaret A Brimble
Adiponectin (Adpn) has been shown to be a possible therapeutic for Type II diabetes, however the production of a therapeutic version of Adpn has proved to be challenging. Biological studies have highlighted the importance of the glycosylated lysine residues for the formation of bioactive high molecular weight oligomers of Adpn. Through the use of 'click' glycopeptide mimetics, we investigated the role of glycosylated lysine and serine residues for the formation of triple helical structures of the collagenous domain of Adpn, in the context of a collagen model peptide scaffold...
June 22, 2017: Organic & Biomolecular Chemistry
https://www.readbyqxmd.com/read/28639363/in-situ-generated-and-premade-1-copper-i-alkynes-in-cycloadditions
#3
REVIEW
Xinyan Wang, Xingyong Wang, Xuesong Wang, Jianlan Zhang, Chulong Liu, Yuefei Hu
The copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) was discovered in 2002, which has become the most remarkable example for "click chemistry" to date. In CuAAC reaction, 1-copper(I) alkyne has been recognized to be a key intermediate. However, many contradictory experimental results for this intermediate were reported in literature. For example, only the in-situ generated 1-copper(I) alkyne was used, while the premade 1-copper(I) alkyne proved to be inefficient under the standard conditions. The kinetic studies indicated that CuAAC reaction had a strict second-order dependence on Cu(I) and the DFT studies demonstrated that 1-copper(I) alkyne intermediate should be a dinuclear copper(I) complex...
June 22, 2017: Chemical Record: An Official Publication of the Chemical Society of Japan ... [et Al.]
https://www.readbyqxmd.com/read/28638478/-177-lu-labeled-phosphoramidate-based-psma-inhibitors-the-effect-of-an-albumin-binder-on-biodistribution-and-therapeutic-efficacy-in-prostate-tumor-bearing-mice
#4
Cindy J Choy, Xiaoxi Ling, Jonathan J Geruntho, Sophia K Beyer, Joseph D Latoche, Beatrice Langton-Webster, Carolyn J Anderson, Clifford E Berkman
Prostate-specific membrane antigen (PSMA) continues to be an active biomarker for small-molecule PSMA-targeted imaging and therapeutic agents for prostate cancer and various non-prostatic tumors that are characterized by PSMA expression on their neovasculature. One of the challenges for small-molecule PSMA inhibitors with respect to delivering therapeutic payloads is their rapid renal clearance. In order to overcome this pharmacokinetic challenge, we outfitted a (177)Lu-labeled phosphoramidate-based PSMA inhibitor (CTT1298) with an albumin-binding motif (CTT1403) and compared its in vivo performance with that of an analogous compound lacking the albumin-binding motif (CTT1401)...
2017: Theranostics
https://www.readbyqxmd.com/read/28636400/click-biotinylation-of-plga-template-for-biotin-receptor-oriented-delivery-of-doxorubicin-hydrochloride-in-4t1-cell-induced-breast-cancer
#5
Yuvraj Singh, K K Durga Rao Viswanadham, Arun Kumar Jajoriya, Jayagopal Meher, Kavit Raval, Swati Jaiswal, Jayant Dewangan, H K Bora, Srikanta Kumar Rath, Jawahar Lal, Durga Prasad Mishra, Manish Kumar Chourasia
PLGA was functionalized with PEG and biotin using click chemistry to generate a biotin receptor targeted copolymer (Biotinylated-PEG-PLGA) which in turn was used to fabricate ultrafine nanoparticles (BPNP) of doxorubicin hydrochloride (DOX) for effective delivery in 4T1 cell induced breast cancer. However adequate entrapment of a hydrophilic bioactive like DOX in a hydrophobic polymer system made of PLGA is not usually possible. We therefore modified a conventional W/O/W emulsion method by utilizing ammonium chloride in the external phase to constrain DOX in dissolved polymer phase by supressing its inherent aqueous solubility as per common ion effect...
June 21, 2017: Molecular Pharmaceutics
https://www.readbyqxmd.com/read/28632960/snap-tag-based-subcellular-proteins-labeling-and-fluorescent-imaging-with-naphthalimides
#6
Chao Wang, Xinbo Song, Yi Xiao
Genetically encoded technologies provide methods for specific labeling and imaging of proteins, which is essential for the understanding of their subcellular localization and function. Herein, we employ naphthalimide, an efficient two-photon fluorophore, to develop O6-benzylguanine (BG) derivatives for specific labeling of subcellular proteins and fluorescent imaging through the SNAP-tag. The three naphthalimide-BG derivatives, TNI-BG, QNI-BG and ONI-BG are conveniently synthesized through modular "click chemistry" with high yields...
June 20, 2017: Chembiochem: a European Journal of Chemical Biology
https://www.readbyqxmd.com/read/28632300/chemo-bacterial-synthesis-of-a-sialyl-tn-cyclopeptide-vaccine-candidate
#7
Emeline Richard, C Pifferi, M Fiore, Eric Samain, Audrey Le Gouellec, Sébastien Fort, Olivier Renaudet, Bernard Priem
A conjugatable form of the tumour-associated carbohydrate antigen sialyl-Tn (Neu5Ac-alfa-2,6-GalNAc) was efficiently produced in Escherichia coli. Metabolically engineered E. coli strains overexpressing the 6-sialyl-transferase gene of Photobacterium sp. and CMP-Neu5Ac synthetase genes of Neisseria meningitidis were cultivated at high density in presence of GalNAc-alfa-propargyl as the exogeneous acceptor. The target disaccharides, which were produced on the scale of several hundred milligrams, were then conjugated using CuAAC click chemistry to a fully synthetic and immunogenic scaffold with the aim to create a candidate anticancer vaccine...
June 20, 2017: Chembiochem: a European Journal of Chemical Biology
https://www.readbyqxmd.com/read/28628303/folate-and-heptamethine-cyanine-modified-chitosan-based-nanotheranostics-for-tumor-targeted-near-infrared-fluorescence-imaging-and-photodynamic-therapy
#8
Yingying Zhang, Tingting Lv, Huijuan Zhang, Xiaodong Xie, Ziying Li, Haijun Chen, Yu Gao
Folate (FA) and heptamethine cyanine (Cy7)-modified chitosan (CF7) was synthesized by click chemistry and its self-assembled nanoparticles (CF7Ns) were developed for tumor-specific imaging and photodynamic therapy. The characterization spectrum confirmed CF7 had a good FA and Cy7 conjugation efficacy. The diameter of CF7Ns measured by DLS was about 291.6 nm and the morphology observed with AFM showed filamentous clusters of particles. The results of targeting ability of CF7Ns demonstrated enhanced targeting behaviors of CF7Ns compared with non-FA-modified nanoparticles C7Ns in FA receptor-positive HeLa cells...
June 19, 2017: Biomacromolecules
https://www.readbyqxmd.com/read/28628182/prodigiosenes-conjugated-to-tamoxifen-and-estradiol
#9
Estelle Marchal, Carlotta Figliola, Alison Thompson
We report the synthesis of the first click-appended prodigiosene conjugates. Four prodigiosene conjugates of estradiol functionalised at the 7α-position were prepared, as were three prodigiosene conjugates of tamoxifen. The coupling between a prodigiosene and an 11-hydroxy estradiol derivative via an ether linkage was investigated, as was the 11- and 7-functionalisation of the estradiol core. The robustness of estradiol protecting groups was severely challenged by reactions typically used to equip such frameworks for 11- and 7-functionalisation...
June 19, 2017: Organic & Biomolecular Chemistry
https://www.readbyqxmd.com/read/28627581/controlled-self-assembly-of-alginate-microgels-by-rapidly-binding-molecule-pairs
#10
Yuebi Hu, Angelo S Mao, Rajiv M Desai, Huanan Wang, David A Weitz, David J Mooney
Controlled self-assembly of cell-encapsulating microscale polymeric hydrogels (microgels) could be advantageous in a variety of tissue engineering and regenerative medicine applications. Here, a method of assembly by chemical modification of alginate polymer with binding pair molecules (BPM) was explored. Alginate was modified with several types of BPM, specifically biotin and streptavidin and click chemistry compounds, and fabricated into 25-30 μm microgels using a microfluidic platform. These microgels were demonstrated to self-assemble under physiological conditions...
June 19, 2017: Lab on a Chip
https://www.readbyqxmd.com/read/28622565/a-shear-induced-network-of-aligned-wormlike-micelles-in-a-sugar-based-molecular-gel-from-gelation-to-biocompatibility-assays
#11
Juliette Fitremann, Barbara Lonetti, Emiliano Fratini, Isabelle Fabing, Bruno Payré, Christelle Boulé, Isabelle Loubinoux, Laurence Vaysse, Luis Oriol
A new low molecular weight hydrogelator with a saccharide (lactobionic) polar head linked by azide-alkyne click chemistry was prepared in three steps. It was obtained in high purity without chromatography, by phase separation and ultrafiltration of the aqueous gel. Gelation was not obtained reproducibly by conventional heating-cooling cycles and instead was obtained by shearing the aqueous solutions, from 2 wt% to 0.25 wt%. This method of preparation favored the formation of a quite unusual network of interconnected large but thin 2D-sheets (7nm-thick) formed by the association side-by-side of long and aligned 7nm diameter wormlike micelles...
June 9, 2017: Journal of Colloid and Interface Science
https://www.readbyqxmd.com/read/28619718/click-chemistry-enables-preclinical-evaluation-of-targeted-epigenetic-therapies
#12
Dean S Tyler, Johanna Vappiani, Tatiana Cañeque, Enid Y N Lam, Aoife Ward, Omer Gilan, Yih-Chih Chan, Antje Hienzsch, Anna Rutkowska, Thilo Werner, Anne J Wagner, Dave Lugo, Richard Gregory, Cesar Ramirez Molina, Neil Garton, Christopher R Wellaway, Susan Jackson, Laura MacPherson, Margarida Figueiredo, Sabine Stolzenburg, Charles C Bell, Colin House, Sarah-Jane Dawson, Edwin D Hawkins, Gerard Drewes, Rab K Prinjha, Raphaël Rodriguez, Paola Grandi, Mark A Dawson
The success of new therapies hinges on our ability to understand their molecular and cellular mechanisms of action. Here we modify BET bromodomain inhibitors, an epigenetic-based therapy, to create functionally conserved compounds that are amenable to click-chemistry and can be used as molecular probes in vitro and in vivo. Using click-proteomics and click-sequencing we explore the gene regulatory function of bromodomain containing 4 protein (BRD4) and the transcriptional changes induced by BET inhibitors. Studying mouse models of acute leukemia, we use high-resolution microscopy and flow cytometry to highlight the heterogeneity of drug activity within tumor cells located in different tissue compartments...
June 15, 2017: Science
https://www.readbyqxmd.com/read/28613820/protein-modification-by-endogenously-generated-lipid-electrophiles-mitochondria-as-the-source-and-target
#13
William N Beavers, Kristie L Rose, James J Galligan, Michelle M Mitchener, Carol A Rouzer, Keri A Tallman, Connor R Lamberson, Xiaojing Wang, Salisha Hill, Pavlina T Ivanova, H Alex Brown, Bing Zhang, Ned A Porter, Lawrence J Marnett
Determining the impact of lipid electrophile-mediated protein damage that occurs during oxidative stress requires a comprehensive analysis of electrophile targets adducted under pathophysiological conditions. Incorporation of ω-alkynyl linoleic acid into the phospholipids of macrophages prior to activation by Kdo2-lipid A, followed by protein extraction, click chemistry and streptavidin affinity capture, enabled a systems-level survey of proteins adducted by lipid electrophiles generated endogenously during the inflammatory response...
June 14, 2017: ACS Chemical Biology
https://www.readbyqxmd.com/read/28612408/sufex-mediated-synthesis-of-sterically-hindered-and-electron-deficient-secondary-and-tertiary-amides-via-acyl-fluoride-intermediates
#14
John Edward Moses, Pallavi Sharma, Andrew Barrow, Christian Spiteri, Christopher Smedley, Marie-Claire Giel
Amide bond formation is one of the most executed reactions in chemistry and biology. This is largely due to the ubiquity of the amide functional group in biological molecules, natural products and pharmaceutically important drugs. We report here the development of "SuFExAmide": a new Sulfur Fluoride Exchange (SuFEx) click chemistry based protocol for the efficient amidation of carboxylic acids via acyl fluoride intermediates. We have developed benzene-1,3-disulfonyl fluoride as a cost effective, powerful and versatile coupling agent, which delivers challenging secondary and tertiary amides in excellent yield from sterically hindered and electron-deficient amines...
June 14, 2017: Chemistry: a European Journal
https://www.readbyqxmd.com/read/28608961/high-affinity-click-rgd-peptidomimetics-as-radiolabeled-probes-for-imaging-%C3%AE-v%C3%AE-3-integrin
#15
Monica Piras, Andrea Testa, Ian N Fleming, Sergio Dall'Angelo, Alexandra Andriu, Sergio Menta, Mattia Mori, Gavin D Brown, Duncan Forster, Kaye J Williams, Matteo Zanda
Non-peptidic RGD-mimic ligands were designed and synthesized by click chemistry between an arginine-azide mimic and an aspartic acid-alkyne mimic. Some of these molecules combine excellent in vitro properties (high αvβ3 affinity, selectivity, drug-like logD, high metabolic stability) with a variety of radiolabeling options (e.g. tritium and [18F]fluorine, plus compatibility with radio-iodination), not requiring the use of chelators or prosthetic groups. The binding mode of the resulting triazole RGD-mimics to αvβ3 or αIIbβ3 receptors was investigated by molecular modeling simulations...
June 13, 2017: ChemMedChem
https://www.readbyqxmd.com/read/28606535/durable-flame-retardant-finishing-of-cotton-fabrics-with-halogen-free-organophosphonate-by-uv-photoinitiated-thiol-ene-click-chemistry
#16
Lijin Xu, Wei Wang, Dan Yu
Cotton fabrics are treated with a synthetic non-halogenated organophosphorus flame retardant by UV photoinitiated thiol-ene click chemistry. Thiol reactive precursors on cotton surface were prepared by 3-Mercaptopropyltriethoxysilane. The flame retardant property has been tested with different concentrations of flame retardant treatment (i.e., wt 2%, 5%, and 8%) by limited oxygen index (LOI) and vertical burning tests and maintained after 30 washing cycles, which was improved with concentration increases. Thermogravimetric analysis showed that the treatment greatly enhanced the char forming ability of cellulose and the highest residue was left as much as 48...
September 15, 2017: Carbohydrate Polymers
https://www.readbyqxmd.com/read/28605154/addition-of-a-cyclophosphine-to-nitriles-an-inorganic-click-reaction-featuring-protio-organo-and-main-group-catalysis
#17
Saurabh Sunil Chitnis, Hazel A Sparkes, Vincent T Annibale, Natalie E Pridmore, Alex M Oliver, Ian Manners
We report the addition of a cyclotriphosphine to a broad range of nitriles giving access to the first examples of free 1-aza-2,3,4-triphospholenes in a rapid, ambient temperature, one-pot, high-yield protocol. The reaction produces electron-rich heterocycles (four lone pairs) and features homoatomic σ-bond heterolysis, thereby combining the key features of the 1,3-dipolar cycloaddition chemistry of azides and cyclopropanes. We also report the first catalytic addition of P-P bonds to the CN triple bond. The coordination chemistry of the new heterocycles is explored...
June 12, 2017: Angewandte Chemie
https://www.readbyqxmd.com/read/28600889/a-novel-versatile-precursor-suitable-for-18-f-radiolabelling-via-click-chemistry
#18
B Lugato, S Stucchi, S Ciceri, M N Iannone, E A Turolla, L Giuliano, C Chinello, S Todde, P Ferraboschi
As an effort to improve (18) F radiolabelling of biomolecules in terms of method robustness and versatility, we report the synthesis and radiolabelling of a new azido precursor potentially useful for the so called "click-reaction", in particular the ligand-free version of the copper(I)-catalyzed alkyne-azide cycloaddition (CuAAC). The new azido precursor may help to overcome problems sometimes exhibited by most of the currently used analogues, as it is safe to handle and it displays long term chemical stability, thus facilitating the development of new radiolabelling procedures...
June 10, 2017: Journal of Labelled Compounds & Radiopharmaceuticals
https://www.readbyqxmd.com/read/28598594/tethering-growth-factors-to-collagen-surfaces-using-copper-free-click-chemistry-surface-characterization-and-in-vitro-biological-response
#19
Hyun Jong Lee, Gabriella Fernandes-Cunha, Ilham Putra, Won-Gun Koh, David Myung
Surface modifications with tethered growth factors have mainly been applied to synthetic polymeric biomaterials in well-controlled, acellular settings, followed by seeding with cells. The known bio-orthogonality of copper-free click chemistry provides an opportunity to not only use it in vitro to create scaffolds or pro-migratory tracks in the presence of living cells, but also potentially apply it to living tissues directly as a coupling modality in situ. In this study, we studied the chemical coupling of growth factors to collagen using biocompatible copper-free click chemistry and its effect on the enhancement of growth factor activity in vitro...
June 9, 2017: ACS Applied Materials & Interfaces
https://www.readbyqxmd.com/read/28597878/incorporation-studies-of-clickable-ceramides-in-jurkat-cell-plasma-membranes
#20
T Walter, J Schlegel, A Burgert, A Kurz, J Seibel, M Sauer
The incorporation properties of ceramide analogues for click chemistry in Jurkat T cells were investigated. The analogues varied in the acyl chain length and the position of the functional group for click chemistry. Fluorescence microscopy studies including anisotropy and quenching experiments showed significant differences in the accessibility of the functional group indicating different incorporation properties into the plasma membrane.
June 9, 2017: Chemical Communications: Chem Comm
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