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Click chemistry

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https://www.readbyqxmd.com/read/28226245/subconjunctival-injectable-dendrimer-dexamethasone-gel-for-the-treatment-of-corneal-inflammation
#1
Uri Soiberman, Siva P Kambhampati, Tony Wu, Manoj K Mishra, Yumin Oh, Rishi Sharma, Jiangxia Wang, Abdul Elah Al Towerki, Samuel Yiu, Walter J Stark, Rangaramanujam M Kannan
Corneal inflammation is often encountered as a key pathological event in many corneal diseases. Current treatments involve topical corticosteroids which require frequent instillations due to rapid tear turnover, causing side-effects such as corneal toxicity and elevated intraocular pressure (IOP). Hence, new interventions that can reduce side effects, dosing frequency, and increase patient compliance can be highly beneficial. In this study, we explore a subconjunctival injectable gel based on G4-PAMAM dendrimer and hyaluronic acid, cross-linked using thiol-ene click chemistry, incorporated with dendrimer dexamethasone (D-Dex) conjugates as a potential strategy for sustained delivery and enhanced bioavailability of corticosteroids...
February 16, 2017: Biomaterials
https://www.readbyqxmd.com/read/28225818/heat-induced-radiolabeling-and-click-chemistry-a-powerful-combination-for-generating-multifunctional-nanomaterials
#2
Hushan Yuan, Moses Q Wilks, Georges El Fakhri, Marc D Normandin, Charalambos Kaittanis, Lee Josephson
A key advantage of nanomaterials for biomedical applications is their ability to feature multiple small reporter groups (multimodality), or combinations of reporter groups and therapeutic agents (multifunctionality), while being targeted to cell surface receptors. Here a facile combination of techniques for the syntheses of multimodal, targeted nanoparticles (NPs) is presented, whereby heat-induced-radiolabeling (HIR) labels NPs with radiometals and so-called click chemistry is used to attach bioactive groups to the NP surface...
2017: PloS One
https://www.readbyqxmd.com/read/28220919/phosphorescent-pt-ii-complexes-bearing-a-monoanionic-c-n-n-luminophore-and-tunable-ancillary-ligands
#3
Marian Hebenbrock, Linda Stegemann, Jutta Kösters, Nikos L Doltsinis, Jens Müller, Cristian A Strassert
A versatile design strategy is presented towards new monoanionic pincer luminophores, showing that cyclometallating C^N^N ligands can yield phosphorescent Pt(ii) complexes even if a neutral 1,2,3-triazole ring is inserted by click chemistry. The overall charge, intermolecular interactions and excited state properties can be manipulated and controlled by varying the nature of the ancillary ligand, and its effect on the structural and the triplet state characteristics can be thoroughly investigated and correlated by means of theory and spectroscopy...
February 21, 2017: Dalton Transactions: An International Journal of Inorganic Chemistry
https://www.readbyqxmd.com/read/28211065/the-synthesis-of-weak-acidic-type-hybrid-monolith-via-thiol-ene-click-chemistry-and-its-application-in-hydrophilic-interaction-chromatography
#4
Jiao Zeng, Shengquan Liu, Menglin Wang, Shouzhuo Yao, Yingzhuang Chen
In this work, a porous structure and good permeability monolithic column was polymerized in UV transparent fused-silica capillaries via photo-initiated thiol-ene click polymerization of 2, 4, 6, 8-tetravinyl-2, 4, 6, 8- tetramethylcyclotetrasiloxane (TMTVS), pentaerythritol tetra(3-mercaptopropionate) (PETMP), itaconic acid, respectively, in the presence of porogenic solvents (tetrahydrofuran and methanol) and a initiator (2, 2-dimethoxy-2-phenylacetophenone) (DMPA) within 30 min. The physical properties of this monolith were characterized by scanning electron microscopy (SEM), Fourier transform infrared (FT-IR) spectroscopy and nitrogen adsorption/desorption measurements...
February 17, 2017: Electrophoresis
https://www.readbyqxmd.com/read/28206741/polyketide-bioderivatization-using-the-promiscuous-acyltransferase-kircii
#5
Ewa M Musiol-Kroll, Florian Zubeil, Thomas Schafhauser, Thomas Härtner, Andreas Kulik, John McArthur, Irina Koryakina, Wolfgang Wohlleben, Stephanie Grond, Gavin J Williams, Sang Yup Lee, Tilmann Weber
During polyketide biosynthesis, acyltransferases (ATs) are the essential gatekeepers which provide the assembly lines with precursors and thus contribute greatly to structural diversity. Previously, we demonstrated that the discrete AT KirCII from the kirromycin antibiotic pathway accesses nonmalonate extender units. Here, we exploit the promiscuity of KirCII to generate new kirromycins with allyl- and propargyl-side chains in vivo, the latter were utilized as educts for further modification by "click" chemistry...
February 22, 2017: ACS Synthetic Biology
https://www.readbyqxmd.com/read/28205404/macrocyclic-triamine-derived-glucose-analogues-for-99m-tc-co-3-labeling-synthesis-and-biological-evaluation-as-potential-tumor-imaging-agents
#6
Teli Liu, Qianqian Gan, Junbo Zhang
[(99m) Tc(CO)3 (H2 O)3 ](+) has attracted great attention among (99m) Tc-labeling techniques, due to its ease of preparation, readily substituted water molecules of the precursor fac-[(99m) Tc(CO)3 (H2 O)3 ](+) by a variety of functional groups, small size and inertness. Bifunctional chelator based on a macrocyclic polyamine framework shows easy complexation with [(99m) Tc(CO)3 (H2 O)3 ](+) to produce stable complex. In this study, two novel 1, 5, 9-triazacyclododecane derivatives containing a glucose group (6 and 7) were successfully synthesized by reacting different glucose-azides with alkyne-[12]aneN3 via the so-called click chemistry and radiolabeled with [(99m) Tc(CO)3 (H2 O)3 ](+) to form (99m) Tc(CO)3 -6 (C-1-substituted complex) and (99m) Tc(CO)3 -7 (C-2-substituted complex) in high yields...
February 2017: Chemical Biology & Drug Design
https://www.readbyqxmd.com/read/28199759/bioinspired-design-of-a-robust-elastomer-with-adaptive-recovery-via-triazolinedione-click-chemistry
#7
Jing Huang, Lijie Zhang, Zhenghai Tang, Siwu Wu, Nanying Ning, Haibin Sun, Baochun Guo
It is a significant but challenging task to simultaneously reinforce and functionalize diene rubbers. Inspired by "sacrificial bonds", the authors engineer sacrificial hydrogen bonds formed by pendent urazole groups in crosslinked solution-polymerized styrene butadiene rubber (SSBR) via triazolinedione click chemistry. This post-crosslinking modification reveals the effects of the sacrificial bonds based on a consistent covalent network. The "cage effect" of the pre-crosslinked network facilitates the heterogeneous distribution of urazole groups, leading to the formation of hydrogen-bonded multiplets...
February 15, 2017: Macromolecular Rapid Communications
https://www.readbyqxmd.com/read/28199365/click-chemistry-approach-to-study-mycoloylated-proteins-evidence-for-porb-and-porc-porins-mycoloylation-in-corynebacterium-glutamicum
#8
Hanane Issa, Emilie Huc-Claustre, Thamila Reddad, Nolwenn Bonadé Bottino, Maryelle Tropis, Christine Houssin, Mamadou Daffé, Nicolas Bayan, Nathalie Dautin
Protein mycoloylation is a recently identified, new form of protein acylation. This post-translational modification consists in the covalent attachment of mycolic acids residues to serine. Mycolic acids are long chain, α-branched, β-hydroxylated fatty acids that are exclusively found in the cell envelope of Corynebacteriales, a bacterial order that includes important genera such as Mycobacterium, Nocardia or Corynebacterium. So far, only 3 mycoloylated proteins have been identified: PorA, PorH and ProtX from C...
2017: PloS One
https://www.readbyqxmd.com/read/28199055/photo-induced-click-chemistry-for-dna-surface-structuring-via-direct-laser-writing
#9
Ljiljana Fruk, Antonina Kerbs, Patrick Mueller, Michael Kaupp, Ishtiaq Ahmed, Alexander S Quick, Doris Abt, Martin Wegener, Christof M Niemeyer, Christopher Barner-Kowollik
Oligonucleotides containing photo-caged dienes were prepared and shown to react quantitatively in a light-induced Diels-Alder cycloaddition with functional maleimides in aqueous solution within minutes. Due to its high yield and fast rate, the reaction was exploited for DNA surface patterning with sub-micrometer resolution employing direct laser writing (DLW). Functional DNA arrays were written via direct laser writing (DLW) in variable patterns, which were further encoded with fluorophores and proteins through DNA directed immobilisation...
February 15, 2017: Chemistry: a European Journal
https://www.readbyqxmd.com/read/28198057/c18-cooh-silica-preparation-characterisation-and-its-application-in-purification-of-quaternary-ammonium-alkaloids-from-coptis-chinensis
#10
Qing Wang, Yao Long, Lin Yao, Mao Ye, Li Xu
INTRODUCTION: Traditional methods for isolating and purifying quaternary ammonium alkaloids from Coptis chinensis do not discriminate the target alkaloids from co-extractives. Mixed-mode analytical chromatography has the potential to improve the separation of analytes in more complex extracts and, when used in a solid-phase extraction mode, improve the purity of isolated compounds. OBJECTIVE: To examine the high-performance liquid chromatographic separation capabilities of a mixed-mode, silica-based adsorbent and its application to the purification of quaternary ammonium alkaloids from Coptis chinensis based on solid-phase extraction...
February 15, 2017: Phytochemical Analysis: PCA
https://www.readbyqxmd.com/read/28195700/discovery-and-characterization-of-a-potent-and-specific-peptide-ligand-targeting-endothelial-progenitor-cells-and-endothelial-cells-for-tissue-regeneration
#11
Dake Hao, Wenwu Xiao, Ruiwu Liu, Priyadarsini Kumar, YuanPei Li, Ping Zhou, Fuzheng Guo, Diana L Farmer, Kit S Lam, Fengshan Wang, Aijun Wang
Endothelial progenitor cells (EPCs) and endothelial cells (ECs) play a vital role in endothelialization and vascularization for tissue regeneration. Various EPC/EC targeting biomolecules have been investigated to improve tissue regeneration with limited success often due to their limited functional specificity and structural stability. One-Bead-One-Compound (OBOC) combinatorial technology is an ultra-high throughput chemical library synthesis and screening method suitable for ligand discovery against a wide range of biological targets, such as integrins...
February 14, 2017: ACS Chemical Biology
https://www.readbyqxmd.com/read/28194957/highly-selective-and-large-scale-mass-spectrometric-analysis-of-4-hydroxynonenal-modification-via-fluorous-derivatization-and-fluorous-solid-phase-extraction
#12
Wenjuan Yuan, Ying Zhang, Yun Xiong, Tao Tao, Yi Wang, Jun Yao, Lei Zhang, Guoquan Yan, Huimin Bao, Haojie Lu
Modification of proteins with 4-hydroxynonenal (HNE) is known to alter the function of proteins and regulate the associated biological processes in eukaryotic cells. The development of mass spectrometry (MS) makes high-throughput analysis of HNE modification accessible. However, the identification of HNE modification is still hampered by the low frequency of this modification. Therefore, only a limited number of HNE modification sites have been identified. The enrichment of HNE-modified peptides is critical for the MS analysis of this modification because of its low abundance...
February 13, 2017: Analytical Chemistry
https://www.readbyqxmd.com/read/28194953/click-chemistry-reagent-for-identification-of-sites-of-covalent-ligand-incorporation-in-integral-membrane-proteins
#13
Melissa M Budelier, Wayland W L Cheng, Lucie Bergdoll, Zi-Wei Chen, Jeff Abramson, Kathiresan Krishnan, Mingxing Qian, Douglas F Covey, James W Janetka, Alex S Evers
Identifying sites of protein-ligand interaction is important for structure-based drug discovery and understanding protein structure-function relationships. Mass spectrometry (MS) has emerged as a useful tool for identifying residues covalently modified by ligands. Current methods use database searches that are dependent on acquiring interpretable fragmentation spectra (MS2) of peptide-ligand adducts. This is problematic for identifying sites of hydrophobic ligand incorporation in integral membrane proteins (IMPs), where poor aqueous solubility and ionization of peptide-ligand adducts and collision-induced adduct loss hinder the acquisition of quality MS2 spectra...
February 9, 2017: Analytical Chemistry
https://www.readbyqxmd.com/read/28192414/selective-in-vivo-metabolic-cell-labeling-mediated-cancer-targeting
#14
Hua Wang, Ruibo Wang, Kaimin Cai, Hua He, Yang Liu, Jonathan Yen, Zhiyu Wang, Ming Xu, Yiwen Sun, Xin Zhou, Qian Yin, Li Tang, Iwona T Dobrucki, Lawrence W Dobrucki, Eric J Chaney, Stephen A Boppart, Timothy M Fan, Stéphane Lezmi, Xuesi Chen, Lichen Yin, Jianjun Cheng
Distinguishing cancer cells from normal cells through surface receptors is vital for cancer diagnosis and targeted therapy. Metabolic glycoengineering of unnatural sugars provides a powerful tool to manually introduce chemical receptors onto the cell surface; however, cancer-selective labeling still remains a great challenge. Herein we report the design of sugars that can selectively label cancer cells both in vitro and in vivo. Specifically, we inhibit the cell-labeling activity of tetraacetyl-N-azidoacetylmannosamine (Ac4ManAz) by converting its anomeric acetyl group to a caged ether bond that can be selectively cleaved by cancer-overexpressed enzymes and thus enables the overexpression of azido groups on the surface of cancer cells...
February 13, 2017: Nature Chemical Biology
https://www.readbyqxmd.com/read/28190897/synthesis-of-multivalent-glycopeptide-conjugates-that-mimic-an-hiv-epitope
#15
Jennifer K Bailey, Dung N Nguyen, Satoru Horiya, Isaac J Krauss
Recently, we reported a directed evolution method which enabled us to discover sequences of glycopeptides that bind with picomolar affinity to HIV antibody 2G12 and are of interest as HIV vaccine candidates. In this manuscript, we describe the syntheses of several of these large (~11-12 kDa) glycopeptides by a combination of fast flow peptide synthesis and click chemistry. We also discuss the optimization of their attachment to carrier protein CRM197, affording antigenic and immunogenic conjugates ready for animal vaccination...
October 6, 2016: Tetrahedron
https://www.readbyqxmd.com/read/28183645/synthesis-of-e7-peptide-modified-biodegradable-polyester-with-the-improving-affinity-to-mesenchymal-stem-cells
#16
Qian Li, Dongming Xing, Lie Ma, Changyou Gao
As the most promising stem cell, bone marrow-derived mesenchymal stem cells (BMSCs) has attracted many attentions and applied widely in regenerative medicine. A biodegradable polyester with tunable affinity to BMSCs plays critical role in determining the properties of the BMSCs-based constructs. In this study, maleimide functionalized biodegradable polyester (P(MTMC-LA)) was synthesized through ring-opening copolymerization between l-lactide (LA) and furan-maleimide functionalized trimethylene carbonate (FMTMC) and a subsequent retro Diels-Alder reaction...
April 1, 2017: Materials Science & Engineering. C, Materials for Biological Applications
https://www.readbyqxmd.com/read/28183600/injectable-dextran-hydrogels-fabricated-by-metal-free-click-chemistry-for-cartilage-tissue-engineering
#17
Xiaoyu Wang, Zihan Li, Ting Shi, Peng Zhao, Kangkang An, Chao Lin, Hongwei Liu
Injectable dextran-based hydrogels were prepared for the first time by bioorthogonal click chemistry for cartilage tissue engineering. Click-crosslinked injectable hydrogels based on cyto-compatible dextran (Mw=10kDa) were successfully fabricated under physiological conditions by metal-free alkyne-azide cycloaddition (click) reaction between azadibenzocyclooctyne-modified dextran (Dex-ADIBO) and azide-modified dextran (Dex-N3). Gelation time of these dextran hydrogels could be regulated in the range of approximately 1...
April 1, 2017: Materials Science & Engineering. C, Materials for Biological Applications
https://www.readbyqxmd.com/read/28181828/synthesis-of-sericin-based-conjugates-by-click-chemistry-enhancement-of-sunitinib-bioavailability-and-cell-membrane-permeation
#18
Luca Scrivano, Domenico Iacopetta, Maria Stefania Sinicropi, Carmela Saturnino, Pasquale Longo, Ortensia Ilaria Parisi, Francesco Puoci
Sericin is a natural protein that has been used in biomedical and pharmaceutical fields as raw material for polypeptide-based drug delivery systems (DDSs). In this paper, it has been employed as pharmaceutical biopolymer for the production of sunitinib-polypeptide conjugate. The synthesis has been carried out by simple click reaction in water, using the redox couple l-ascorbic acid/hydrogen peroxide as a free radical grafting initiator. The bioconjugate molecular weight (50 kDa < Mw < 75 kDa) was obtained by SDS-PAGE, while the spectroscopic characteristics have been studied in order to reveal the presence of grafted sunitinib...
November 2017: Drug Delivery
https://www.readbyqxmd.com/read/28173134/non-reducing-end-labeling-of-heparan-sulfate-via-click-chemistry-and-a-high-throughput-elisa-assay-for-heparanase
#19
Zhengliang L Wu, Xinyi Huang, Cheryl M Ethen, Timothy Tatge, Marta Pasek, Joseph Zaia
No abstract text is available yet for this article.
February 6, 2017: Glycobiology
https://www.readbyqxmd.com/read/28169081/conjugates-of-phosphorylated-zalcitabine-and-lamivudine-with-sio2-nanoparticles-synthesis-by-cuaac-click-chemistry-and-preliminary-assessment-of-anti-hiv-and-antiproliferative-activity
#20
Svetlana V Vasilyeva, Alexander A Shtil, Albina S Petrova, Sergei M Balakhnin, Polina Y Achigecheva, Dmitry A Stetsenko, Vladimir N Silnikov
Conjugates of phosphorylated dideoxynucleoside antiviral drugs dideoxycytidine (zalcitabine) and lamivudine with SiO2 nanoparticles were obtained via the copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) click chemistry between a nucleoside triphosphate containing an alkynyl group at the γ-phosphate or azidothymidine triphosphate and SiO2 nanoparticles containing alkyl azide or alkynyl groups, respectively. 4-(Prop-2-yn-1-yloxy)butylamino group has been attached to the γ-phosphate group of dideoxycytidine (zalcitabine) and lamivudine 5'-triphosphates via the phosphoramidate linkage...
January 25, 2017: Bioorganic & Medicinal Chemistry
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