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Click chemistry

Michał Gładysz, Piotr Ruszkowski, Jan Milecki
We describe synthesis of novel acyclic nucleoside analogues which are building blocks for CuAAC reaction and their activity against two types of human cancer cell lines (HeLa, KB). Three of chosen compounds show promising cytotoxic activity. Synthesis pathway starting from simple and easily accessible substrates employing DMT or TBDPS protective groups is described. Adenosine and thymidine analogues containing alkyne moiety and adenosine analogue containing azido group were synthesized. The obtained units showed ability of forming triazole motif under the CuAAC reaction conditions...
January 16, 2018: Nucleosides, Nucleotides & Nucleic Acids
Emanuele Mauri, Edoardo Micotti, Arianna Rossetti, Lucio Melone, Simonetta Papa, Giulia Azzolini, Stefano Rimondo, Pietro Veglianese, Carlo Punta, Filippo Rossi, Alessandro Sacchetti
Polymer functionalization strategies have recently attracted considerable attention for several applications in biomaterials science. In particular, technological advancements in medical imaging have focused on the design of polymeric matrices to improve non-invasive approaches and diagnostic accuracy. In this scenario, the use of microwave irradiation of aqueous solutions containing appropriate combinations of polymers is gaining increasing interest in the synthesis of sterile hydrogels without using monomers, eliminating the need to remove unreacted species...
January 15, 2018: Soft Matter
Jie Su, Xiwen He, Langxing Chen, Yukui Zhang
An efficient glycoproteins enrichment platform is one of vital preprocessing steps in biomarker research and in particular glycoproteomics. In this work, a well-defined boronic acid functionalized magnetic graphene oxide nanocomposite (Fe3O4-GO@PAAPBA) was synthesized for the selective enrichment of glycoproteins from complex biological samples via a novel strategy based on the "thiol-ene" click chemistry and surface initiated atom transfer radical polymerization (SI-ATRP). The initiator of ATRP was anchored to the surface of substrate through "thiol-ene" click reaction...
April 1, 2018: Talanta
Ruilin Zhang, Hongfei Gao, Yanming Ren, Yulong Xiao, Jinliang Hu, Xiaohong Cheng
Novel discotic mesogens P/n-M (n = 12, 16, 18, M = 2H, Zn and Cu) bearing a porphyrin core, triazole linkages and peripheral 3,4,5-trialkoxybenzyl units have been synthesized by "click chemistry" approach. The thermal behavior, photophysical properties and morphologies of these compounds were investigated by polarizing optical microscopy (POM), differential scanning calorimetry (DSC), X-ray diffraction (XRD), UV and PL spectra, scanning electron microscopy (SEM) and transmission electron microscopy (TEM). These compounds can self-assemble into hexagonal columnar phases in their pure states and form organogels in 1,4-dioxane with unusually flower-like sphere morphology...
January 12, 2018: Chemistry, An Asian Journal
Geraldo Célio Brandão, Franciele C Rocha Missias, Lucas Miquéias Arantes, Luciana Ferreira Soares, Kuldeep K Roy, Robert J Doerksen, Alaide Braga de Oliveira, Guilherme Rocha Pereira
Lapachol is an abundant prenyl naphthoquinone occurring in Brazilian Bignoniaceae that was clinically used, in former times, as an antimalarial drug, despite its moderate effect. Aiming to search for potentially better antimalarials, a series of 1,2,3-triazole derivatives was synthesized by chemical modification of lapachol. Alkylation of the hydroxyl group gave its propargyl ether which, via copper-catalyzed cycloaddition (CuAAC) click chemistry with different organic azides, afforded 17 naphthoquinonolyl triazole derivatives...
December 24, 2017: European Journal of Medicinal Chemistry
Neeraj Kapoor, Ivana Vanjak, James Rozzelle, Aym Berges, Wei Chan, Gang Yin, Cuong Tran, Aaron K Sato, Alexander R Steiner, Thao P Pham, Ashley J Birkett, Carole Long, Jeff Fairman, Kazutoyo Miura
Malaria, one of the most common vector borne human diseas-es, is a major world health issue. In 2015 alone, more than 200 million people were infected with malaria, out of which, 429,000 died. Even though artemisinin-based combination therapies (ACT) are highly effective at treating malaria infections, novel efforts towards development of vaccines to prevent transmission are still needed. Pfs25, a post-fertilization stage parasite surface antigen, is a leading transmission-blocking vaccine (TBV) candidate. It is postulated that Pfs25 anchors to the cell membrane using a glycosylphosphatidyl-inositol (GPI) linker, which itself possesses proinflammatory properties...
January 11, 2018: Biochemistry
Bert T Lai, Jeré A Wilson, Jacquie Malette Loredo, Suresh M Pitram, Nicole A LaBerge, James R Heath, Heather Agnew
The IL-17 cytokine family is associated with multiple immune and autoimmune diseases and comprises important diagnostic and therapeutic targets. We developed epitope-targeted ligands designed for differential detection of human IL-17F and its closest homologue IL-17A. Non-overlapping and unique epitopes on IL-17F and IL-17A were identified by comparative sequence analysis of the two proteins. Synthetic variants of these epitopes were utilized as targets for in situ click screens against a comprehensive library of synthetic peptide macrocycles with 5-mer variable regions...
January 10, 2018: Chemistry: a European Journal
Kuan Lu, Lude Cai, Xue Zhang, Guodong Wu, Congjun Xu, Yanfang Zhao, Ping Gong
A novel series of substituted benzamide derivatives bearing a 1,2,3-triazole moiety were designed and synthesized by click chemistry. Human dihydroorotate dehydrogenase inhibition assay was used to evaluate the synthesized compounds as potent hDHODH inhibitors. Most compounds showed moderate to significant potency, accompanied with a suitable clogD7.4 value and compounds 4d, 4o, and 5j effectively inhibited the activity of hDHODH with IC50 values of 2.1, 2.1 and 1.5 μM, respectively. Compound 4o also effectively suppressed proliferation of the activated PBMCs...
December 30, 2017: Bioorganic Chemistry
K Barry Sharpless, Bing Gao, Suhua Li, Peng Wu, John E Moses
Thionyl tetrafluoride (SOF4) is a valuable connective gas for sulfur fluoride exchange (SuFEx) click chemistry, that enables multidimensional linkages to be created via sulfur-oxygen (S-O) and sulfur-nitrogen (S-N) bonds. In this report, we expand the available SuFEx chemistry of SOF4 to include organolithium nucleophiles, and demonstrate, for the first time, the controlled projection of sulfur-carbon links at the sulfur center of SOF4-derived iminosulfur oxydifluorides (R1-N=SOF2). This protocol enables rapid and modular access to sulfonimidoyl fluorides [R1-N=SOFR2], another array of versatile SuFEx connectors with readily tunable reactivity of the S-F handle...
January 4, 2018: Angewandte Chemie
Patrícia Manuela Ribeiro Pereira, Waqar Rizvi, Naga Venkata Satya Dinesh Kumar Bhupathiraju, Naxhije Berisha, Rosa Fernandes, Joao P C Tome, Charles Michael Michael Drain
The use of glycosylated compounds is actively pursued as a therapeutic strategy for cancer due to the overexpression of various types of sugar receptors and transporters on most cancer cells. Conjugation of saccharides to photosensitizers such as porphyrins provides a promising strategy to improve the selectivity and cell uptake of the photosensitizers, enhancing the overall photosensitizing efficacy. Most porphyrin-carbohydrate conjugates are linked via the carbon-1 position of the carbohydrate because this is the most synthetically accessible approach...
January 9, 2018: Bioconjugate Chemistry
Javier Ramos-Soriano, Jose Juan Reina, Beatriz M Illescas, Javier Rojo, Nazario Martín
The synthesis of multivalent systems based on hexakis-adducts of [60]fullerene employing a biocompatible copper-free click chemistry strategy has been accomplished. A symmetric hexakis-adduct of fullerene bearing 12 maleimide units 3 is reported and it has been employed to carry out the thiol-maleimide Michael addition. To achieve orthogonal click addition, an asymmetric derivative bearing one maleimide and ten cyclooctynes has been synthesized. The sequential and one-pot transformations of the two clickable groups have been explored, finding the best results in the case of the one-pot experiment...
January 9, 2018: Journal of Organic Chemistry
Hamza Turhan, Ece Tukenmez, Bunyamin Karagoz, Niyazi Bicak
Crosslinked 2-bromoethyl methacrylate polymer (PBEMA) was prepared in micro-spherical form (2-5µm) by precipitation polymerization methodology. The bromide substituent was substituted with an azide group, which was then coupled with 1-[(2-Propynyloxy)methyl]pyrene] via alkyne-azide click chemistry. The pyrene-linked microspheres showed an intense green-blue excimer emission with a maximum at 480nm, implying π-π stacking between the pyrene moieties on the microsphere surfaces. This fluorescence emission is extremely sensitive to the aromatic nitro compounds...
March 1, 2018: Talanta
Young Kim, Zhe Zhang, Jae-Hyuck Shim, Tae Sup Lee, Ching-Hsuan Tung
Cell therapies are promising up-and-coming therapeutic strategies for many diseases. For maximal therapeutic benefits, injected cells have to navigate their way to a designated area, including organ and tissue; unfortunately, the majority of therapeutic cells are currently administered without a guide or homing device. To improve this serious shortcoming, a functionalization method was developed to equip cells with a homing signal. Its application was demonstrated by applying an Azadibenzocyclooctyne-bisphosphonate (ADIBO-BP) and azide paired bioorthogonal chemistry on cells for bone specific homing...
December 26, 2017: Bioorganic & Medicinal Chemistry
Kira Astakova, Roslyn Ray, Maria Taskova, Jesper Uhd, Annika Carstens, Kevin Morris
The use of nucleic acid, DNA and RNA, based strategies to disrupt gene expression as a therapeutic is quickly emerging. Indeed, synthetic oligonucleotides represent a major component of emerging gene therapeutics. However, the efficiency and specificity of intracellular uptake for non-modified oligonucleotides is rather poor. Utilizing RNA based oligonucleotides as therapeutics is even more challenging to deliver, due to extremely fast enzymatic degradation of the RNAs. Similar to unmodified oligonucleotides, RNAs also get rapidly degraded in vivo and show large off-target binding even when they are able to reach and enter the desired target cells...
January 4, 2018: Molecular Pharmaceutics
Jiawang Guo, Xia Zhao, Jun Hu, Yuan Lin, Qian Wang
Cell-based ELISA (CELLISA) has been widely used in disease diagnoses due to its simplicity and low cost. Recently, peroxidase-like nanomaterials have emerged as promising systems for CELLISA applications. In this work, Tobacco mosaic virus (TMV) was simultaneously tailored with peroxidase-like inorganic nanoparticles (platinum nanoparticles) and cancer cell target groups (folic acid) to obtain TMV-FA-Pt nanoparticles for cancer cell detection. Induced by the uniformly distributed reactive groups and well-defined structure of the TMV particle, platinum nanoparticles could be grown in situ on the exterior surface of TMV with excellent monodispersity and uniform spatial distribution...
January 4, 2018: Molecular Pharmaceutics
Aashiq Hussain, Mushtaq A Qurishi, Abid Hamid, S Koul
Cancer is regarded as second leading cause of death worldwide. Therefore, there is a high demand for the discovery, development and improvement of novel anti-cancer agents which could efficiently prevent proliferative pathways and clonal expansion of cells. In view of this, a new series of bioactive scaffolds viz triazoles linked 7-hydroxycoumarin (1) were synthesized using click chemistry approach. All the synthesized compounds were screened for cytotoxicity against a panel of seven different human cancer cell lines viz...
December 29, 2017: Anti-cancer Agents in Medicinal Chemistry
Xinxin Gao, Rami N Hannoush
Protein palmitoylation plays diverse roles in regulating the trafficking, stability, and activity of cellular proteins. The advent of click chemistry has propelled the field of protein palmitoylation forward by providing specific, sensitive, rapid, and easy-to-handle methods for studying protein palmitoylation. This year marks the 10th anniversary since the first click chemistry-based fatty acid probes for detecting protein lipid modifications were reported. The goal of this review is to highlight key biological advancements in the field of protein palmitoylation during the past 10 years...
December 18, 2017: Cell Chemical Biology
Ghandoura Moussa, Rana Alaaeddine, Lynn M Alaeddine, Rasha Nassra, Ahmed S F Belal, Azza Ismail, Ahmed F El-Yazbi, Yasser S Abdel-Ghany, Aly Hazzaa
Click chemistry was used to synthesize a new series of thioquinazolinone molecules equipped with propargyl moiety,1,2,3-triazolyl and isoxazolyl rings. Our design was based on merging pharmacophores previously reported to exhibit COX-2 inhibitory activities to a thioquinazolinone-privileged scaffold. The synthesized compounds were subjected to in vitro cyclooxygenase COX-1/COX-2 and 15-LOX inhibition assays. Compounds 2c, 3b, 3h, 3j, and 3k showed COX-2 inhibition with IC50 (μM) 0.18, 0.19, 0.11, 0.16 and 0...
December 18, 2017: European Journal of Medicinal Chemistry
V Ganga Reddy, Srinivasa Reddy Bonam, T Srinivasa Reddy, Ravikumar Akunuri, V G M Naidu, V Lakshma Nayak, Suresh K Bhargava, H M Sampath Kumar, P Srihari, Ahmed Kamal
Topoisomerases (topo-I and topo-II) have occupied a significant role in DNA replication, transcription, and are a promising set of antitumor targets. In the present approach, a series of new 4β-amidotriazole linked podophyllotoxin derivatives (10a-i and 11a-k) were designed, synthesized by employing the click chemistry and their biological activities were evaluated. The majority of derivatives showed promising antiproliferative activity with IC50 values ranging from 1 to 10 μM on the six human cancer cell lines; cervical (HeLa), breast (MCF-7), prostate (DU-145), lung (A549), liver (HepG2) and colon (HT-29)...
December 14, 2017: European Journal of Medicinal Chemistry
Chad J Pickens, Stephanie N Johnson, Melissa M Pressnall, Martin Leon, Cory Berkland
Interrogating biological systems is often limited by access to biological probes. The emergence of "click chemistry" has revolutionized bioconjugate chemistry by providing facile reaction conditions amenable to both biologic molecules and small molecule probes such as fluorophores, toxins, or therapeutics. One particularly popular version is the copper-catalyzed azide-alkyne cycloaddition (AAC) reaction, which has spawned new alternatives such as the strain-promoted azide-alkyne cycloaddition reaction, among others...
December 29, 2017: Bioconjugate Chemistry
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