72320-38-8Relevant articles and documents
Preparation of amphiphilic copolymers for covalent loading of paclitaxel for drug delivery system
Chen, Wulian,Zhang, Jin Z.,Hu, Jianhua,Guo, Qisang,Yang, Dong
, p. 366 - 374 (2014)
A novel drug-polymer conjugate was prepared by the copper-catalyzed azide-alkyne cycloaddition reaction between an azide-functional diblock copolymer and an alkyne-functional paclitaxel (PTX). The well-defined azide-functional diblock copolymer, poly(ethylene glycol) (PEG)-b-P(OEGEEMA-co- AzPMA), was synthesized via the atom transfer radical polymerization of oligo(ethylene glycol) ethyl ether methacrylate (OEGEEMA) and 3-azidopropyl methacrylate (AzPMA), using PEG-Br as macroinitiator and CuBr/PMDETA as a catalytic system. The alkyne-functional PTX was covalently linked to the copolymer via a click reaction, and the loading content of PTX could be easily tuned by varying the feeding ratio. Transmission electron microscopy and dynamic light scattering results indicated that the drug loaded copolymers could self-assemble into micelles in aqueous solution. Moreover, the drug release behavior of PEG-b-P(OEGEEMA-co-AzPMA-PTX) was pH dependent, and the cumulative release amount of PTX were 50.0% at pH 5.5, which is about two times higher than that at pH 7.4. The in vitro cytotoxicity experimental results showed that the diblock copolymer was biocompatible, with no obvious cytotoxicity, whereas the PTX-polymer conjugate could efficiently deliver PTX into HeLa and SKOV-3 cells, leading to excellent antitumor activity. 2013 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2014, 52, 366-374 The azide-functional diblock copolymer PEG-b-P(OEGEEMA-co-AzPMA) is synthesized, and alkyne-functional paclitaxel is conjugated to it, using click chemistry. The novel paclitaxel-polymer conjugate self-assembles into micellar nanoparticles in aqueous solution, and the loading content of paclitaxel is easily tuned by the feeding ratio. Copyright
Expanding the genetic code for site-specific labelling of tobacco mosaic virus coat protein and building biotin-functionalized virus-like particles
Wu,Zhang,Zhou,Wu,Ballard,Tian,Wang,Niu,Huang
, p. 4007 - 4009 (2014)
A method for site-specific and high yield modification of tobacco mosaic virus coat protein (TMVCP) utilizing a genetic code expanding technology and copper free cycloaddition reaction has been established, and biotin-functionalized virus-like particles were built by the self-assembly of the protein monomers.
Synthesis of amphiphilic block copolymer consisting of glycopolymer and poly(l-lactide) and preparation of sugar-coated polymer aggregates
Obata, Makoto,Otobuchi, Ryota,Kuroyanagi, Tadao,Takahashi, Masaki,Hirohara, Shiho
, p. 395 - 403 (2017)
The block glycopolymer, poly(2-(α-d-mannopyranosyloxy)ethyl methacrylate)-b-poly(l-lactide) (PManEMA-b-PLLA), was synthesized via a coupling approach. PLLA having an ethynyl group was successfully synthesized via ring-opening polymerization using 2-propyn-1-ol as an initiator. The ethynyl functionality of the resulting polymer was confirmed by MALDI-TOF mass spectroscopy. In contrast, PManEMA having an azide group was prepared via AGET ATRP using 2-azidopropyl 2-bromo-2-methylpropanoate as an initiator. The azide functionality of the resulting polymer was confirmed by IR spectroscopy. The Cu(I)-catalyzed 1,3-dipolar cycloaddition between PLLA and PManEMA was performed to afford PManEMA-b-PLLA. The block structure was confirmed by 1H NMR spectroscopy and size exclusion chromatography. The aggregating properties of the block glycopolymer, PManEMA16k-b-PLLA6.4k (Mn,PManEMA = 16,000, Mn,PLLA = 6400) was examined by 1H NMR spectroscopy, fluorometry using pyrene, and dynamic light scattering. The block glycopolymer formed complicated aggregates at concentrations above 21 mg·L?1 in water. The d-mannose presenting property of the aggregates was also characterized by turbidimetric assay using concanavalin A.
Labeling of Phosphatidylinositol Lipid Products in Cells through Metabolic Engineering by Using a Clickable myo-Inositol Probe
Ricks, Tanei J.,Cassilly, Chelsi D.,Carr, Adam J.,Alves, Daiane S.,Alam, Shahrina,Tscherch, Kathrin,Yokley, Timothy W.,Workman, Cameron E.,Morrell-Falvey, Jennifer L.,Barrera, Francisco N.,Reynolds, Todd B.,Best, Michael D.
, p. 172 - 180 (2019)
Phosphatidylinositol (PI) lipids control critical biological processes, so aberrant biosynthesis often leads to disease. As a result, the capability to track the production and localization of these compounds in cells is vital for elucidating their complex roles. Herein, we report the design, synthesis, and application of clickable myo-inositol probe 1 a for bioorthogonal labeling of PI products. To validate this platform, we initially conducted PI synthase assays to show that 1 a inhibits PI production in vitro. Fluorescence microscopy experiments next showed probe-dependent imaging in T-24 human bladder cancer and Candida albicans cells. Growth studies in the latter showed that replacement of myo-inositol with probe 1 a led to an enhancement in cell growth. Finally, fluorescence-based TLC analysis and mass spectrometry experiments support the labeling of PI lipids. This approach provides a promising means for tracking the complex biosynthesis and trafficking of these lipids in cells.
Biodegradable microcapsules designed via 'click' chemistry
De Geest, Bruno G.,Van Camp, Wim,Du Prez, Filip E.,De Smedt, Stefaan C.,Demeester, Jo,Hennink, Wim E.
, p. 190 - 192 (2008)
Dextrans modified with alkyne and azide groups through hydrolysable carbonate esters form degradable microcapsules after CuI catalysed 'click' reaction between azides and alkynes yielding triazole cross-links. The Royal Society of Chemistry.
Boronic acid shell-crosslinked dextran-b-PLA micelles for acid-responsive drug delivery
Zhao, Ziwei,Yao, Xuemei,Zhang, Zhe,Chen, Li,He, Chaoliang,Chen, Xuesi
, p. 1609 - 1618 (2014)
Herein, 3-carboxy-5-nitrophenylboronic acid (CNPBA) shell-crosslinked micelles based on amphiphilic dextran-block-polylactide (Dex-b-PLA) are prepared and used for efficient intracellular drug deliveries. Due to the reversible pH-dependent binding with diols to form boronate esters, CNPBA modified Dex-b-PLA shows excellent pH-sensitivity. In neutral aqueous conditions, CNPBA-Dex-b-PLA forms shell-crosslinked micelles to enable DOX loading, while in acid conditions, the boronate esters hydrolyze and the micelles de-crosslink to release loaded DOX. In vitro release studies indicate that the release of the DOX cargo is minimized at physiological conditions, while there is a burst release in response to low pHs. The cell viability of CNPBA-Dex-b-PLA investigated by MTT assay was more than 90%, indicating that, as a drug delivery system, CNPBA-Dex-b-PLA has good cytocompatibility. These features suggest that the pH-responsive biodegradable CNPBA-Dex-b-PLA can efficiently load and deliver DOX into tumor cells and enhance the inhibition of cellular proliferation in vitro, providing a favorable platform as a drug delivery system for cancer therapy.
The Synthesis of Triazole Analogues of Antitumor Dehydropyrrolizidine Alkaloids
Pearson, William H.,Bergmeier, Stephen C.,Chytra, Jayne A.
, p. 156 - 159 (1990)
Several mono- and disubstituted 5,6-dihydro-4H-pyrrolotriazoles have been prepared via intramolecular 1,3-dipolar cycloadditions of azides with alkynes.These triazoles are analogues of the antitumor dehydropyrrolizidine alkaloids.
A coumarin derivative as a fluorogenic glycoproteomic probe for biological imaging
Rong, Lei,Liu, Li-Han,Chen, Si,Cheng, Han,Chen, Chang-Sheng,Li, Ze-Yong,Qin, Si-Yong,Zhang, Xian-Zheng
, p. 667 - 669 (2014)
Fluorescence imaging in living cells is typically carried out using a functionalized fluorescent dye. But it often causes strong background noise under many conditions where washing is not applicable. Here, we report on a coumarin based fluorogenic probe, which can be used as a bioorthogonal-labeling tool for glycoproteins. The results indicated that the probe was able to image glycoproteins in living cells and it may also be suitable for intracellular imaging.
Novel multi-sensitive pseudo-poly(amino acid) for effective intracellular drug delivery
Wu, Yanjuan,Zhou, Dongfang,Qi, Yanxin,Xie, Zhigang,Chen, Xuesi,Jing, Xiabin,Huang, Yubin
, p. 31972 - 31983 (2015)
Novel intracellular pH, glutathione (GSH) and reactive oxygen species (ROS)-responsive nanoparticles were obtained using mPEG2k-block-redox dual sensitive chain-block-mPEG2k (PRDSP) which was prepared by Cu(i)-catalyzed azide-alkyne cycloaddition (CuAAC) click polymerization. The disulfide bond, peroxalate ester and triazole units were regularly and repeatedly arranged in the hydrophobic blocks. The disulfide bond was GSH-sensitive and the peroxalate ester structure could be disrupted by acid and hydrogen peroxide. In addition, the triazole units are capable of forming pH-responsive hydrogen bonds. Dynamic Light Scattering (DLS) and transmission electron microscopy (TEM) were used to investigate the pH, GSH and ROS sensitivity of the PRDSP nanoparticles (NPs). The results indicated that the average diameter, size distribution and morphology greatly changed upon adding GSH/H2O2 or modulating the pH. As the preloaded model anticancer drug, doxorubicin (DOX) was quickly released from DOX-loaded PRDSP (PRDSP@DOX) NPs by addition of 10 mM glutathione (GSH), or 10 mM H2O2 or under acidic conditions rather than under physiological conditions. Confocal laser scanning microscopy (CLSM) and flow cytometric analyses revealed that PRDSP@DOX could effectively deliver DOX into the cytoplasm and nucleus of cells. Therefore, PRDSP NPs may be a promising redox heterogeneity-sensitive carrier for efficient and controlled anticancer drug release.
Hydrophilic Clicked 2,6-Bis-Triazolyl-pyridines Endowed with High Actinide Selectivity and Radiochemical Stability: Toward a Closed Nuclear Fuel Cycle
Macerata, Elena,Mossini, Eros,Scaravaggi, Stefano,Mariani, Mario,Mele, Andrea,Panzeri, Walter,Boubals, Nathalie,Berthon, Laurence,Charbonnel, Marie-Christine,Sansone, Francesco,Arduini, Arturo,Casnati, Alessandro
, p. 7232 - 7235 (2016)
There is still an evident need for selective and stable ligands able to separate actinide(III) from lanthanide(III) metal ions in view of the treatment of the accumulated radioactive waste and of the recycling of minor actinides. We have herein demonstrated that hydrophilic 2,6-bis-Triazolyl-pyridines are able to strip all actinides in all the different oxidation states from a diglycolamide-containing kerosene solution into an acidic aqueous phase. The ascertained high actinide selectivity, efficiency, extraction kinetics, and chemical/radiolytic stability spotlight this hydrophilic class of ligands as exceptional candidates for advanced separation processes fundamental for closing the nuclear fuel cycle and solving the environmental issues related to the management of existing nuclear waste.
