- Carrier-Free Delivery of Precise Drug–Chemogene Conjugates for Synergistic Treatment of Drug-Resistant Cancer
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Combinatorial antitumor therapies using different combinations of drugs and genes are emerging as promising ways to overcome drug resistance, which is a major cause for the failure of cancer treatment. However, dramatic pharmacokinetic differences of drug
- Guo, Yuanyuan,Li, Yuehua,Qian, Qiuhui,Yan, Deyue,Zhang, Chuan,Zhu, Lijuan,Zhu, Xinyuan
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- Pillar[5]arene-Based [2]Rotaxane: Synthesis, Characterization, and Application in a Coupling Reaction
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Mechanically interlocked molecules are a class of smart supramolecular species because of their interesting topological structure and application in various areas, such as biology and nanoscience. In this work, we used "multicomponent reaction"to fabricate a new [2]rotaxane based on pillar[5]arene from different small-sized molecules. The molecular structure of the obtained [2]rotaxane R was confirmed by 1H and 13C NMR, high-resolution electrospray ionization mass spectrometry, two-dimensional nuclear Overhauser effect spectroscopy, and density functional theory studies. Interestingly, the [2]rotaxane-based organometallic cross-linked catalyst (Pd?R) was easily constructed via the coordination between triazole groups and Pd(NO3)2. Pd?R proved to be a good catalyst for the Suzuki-Miyaura coupling reaction with excellent stability and repeatability.
- Ding, Yue,Guo, Hao,Ou, Changjin,Wang, Jin,Wang, Yang,Yan, Chaoguo,Yao, Yong,Ye, Junmei,Yuan, Xiaolei,Zhang, Zhecheng
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- Very contracted to extended co -conformations with or without oscillations in two- and three-station ['2]daisy chains
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The syntheses of various two- and three-station mannosyl [c2]daisy chains, based on a dibenzo-24-crown-8 macrocyclic moiety and an ammonium, a triazolium, and a mono- or disubstituted pyridinium amide station, are reported. The ability of these molecules to act as molecular machine based mimetics has been further studied by 1H NMR studies. In all the protonated ammonium states, the interwoven rotaxane dimers adopt an extended co-conformation. However, carbamoylation of the ammonium station led to many different other [c2]daisy chain co-conformations, depending on the other molecular stations belonging to the axle. In the two-station [c2]daisy chains containing an ammonium and a mono- or disubstituted pyridinium amide station, two large-amplitude relative movements of the interwoven components were noticed and afforded either an extended and a contracted or very contracted state with, in the latter case, an impressive chairlike conformational flipping of the mannopyranose from 1C4 to 4C1. In the case of the three-station-based [c2]daisy chains containing an ammonium, a triazolium, and disubstituted pyridinium amide, an extended and a half-contracted molecular state could be obtained because of the stronger affinity of the dibenzo-24-crown-8 part for, respectively, the ammonium, the triazolium, and the disubstituted pyridinium amide. Eventually, with axles comprising an ammonium, a triazolium, and a monosubstituted pyridinium amide, an extended conformation was noticed in the protonated state whereas a continuous oscillation between half-contracted and contracted states, in fast-exchange on the NMR time scale, was triggered by carbamoylation. Variations of the solvent or the temperature allow the modification of the population of each co-conformer. Thermodynamic data provided a small free Gibbs energy δG of 2.1 kJ·mol -1 between the two translational isomers at 298 K.
- Romuald, Camille,Busseron, Eric,Coutrot, Frederic
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- Crosslinked Internal Alkyne-Based Stereo Elastomers: Polymers with Tunable Mechanical Properties
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New methods to introduce and control polymer network crosslinking and improve mechanical properties of the resulting materials have been investigated extensively. Common methods to enhance the mechanical properties of elastomers include "vulcanization"by
- Hsu, Yen-Hao,Dove, Andrew P.,Becker, Matthew L.
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- Controlling the chair conformation of a mannopyranose in a large-amplitude [2]rotaxane molecular machine
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Large-amplitude mannosyl [2]rotaxane molecular machines based on an anilinium and mono- or disubstituted pyridinium amide stations were synthesized. Dibenzo[24]crown-8 (DB24C8) initially resides around the anilinium station in both the cases. The mannosyl [2]rotaxane molecular machines 3a,b were successfully obtained from the initially prepared mannoside azide 1a,b containing a pyridinium amide moiety and the alkyne ammonium 2, by using the copper(I)-catalyzed Huisgen alkyne-azide 1,3-dipolar cycloaddition, also called CuAAC click chemistry. The interlocked architecture of glycorotaxanes 3a,b and 4a,b and the localization of the macrocycle at different pH were studied by 1H NMR spectroscopy. It was observed that the DB24C8 moved toward the pyridinium amide station upon deprotonation. However, with the disubstituted amide, DB24C8 forms hydrogen bonds with the pyridinium H7 atoms, which are located near the cationic nitrogen atom, and interacts by ion dipole contacts with the cationic charge.
- Coutrot, Frederic,Busseron, Eric
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- "Click" chemistry in a supramolecular environment: Stabilization of organogels by copper(I)-catalyzed azide-alkyne [3 + 2] cycloaddition
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Organogels are thermoreversible, viscoelastic (soft) materials consisting of low molecular weight compounds which self-assemble into fibers, often of micrometer lengths and nanometer diameters. The installation of terminal azide and alkyne functional grou
- Diaz, David D.,Rajagopal, Karthikan,Strable, Erica,Schneider, Joel,Finn
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- A glutathione-responsive photosensitizer with fluorescence resonance energy transfer characteristics for imaging-guided targeting photodynamic therapy
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Here, we have synthesized and characterized a novel activatable photosensitizer (PS) 8a in which two well-designed boron dipyrromethene (BODIPY) derivatives are utilized as the photosensitizing fluorophore and quencher respectively, which are connected by a disulfide linker via two successive Cu (?) catalyzed click reactions. The fluorescence emission and singlet oxygen production of 8a are suppressed via intramolecular fluorescence resonance energy transfer (FRET) from the excited BODIPY-based PS part to quencher unit, but both of them can be simultaneously switched on by cancer-related biothiol glutathione (GSH) in phosphate buffered saline (PBS) solution with 0.05% Tween 80 as a result of cleavage of disulfide. Also, 8a exhibits a bright fluorescence image and a substantial ROS production in A549 human lung adenocarcinoma, HeLa human cervical carcinoma and H22 mouse hepatoma cells having a relatively high concentration of GSH, thereby leading to a significant photocytotoxicity, with IC50 values as low as 0.44 μM, 0.67 μM and 0.48 μM, respectively. In addition, the photosensitizer can be effectively activated and imaged in H22 transplanted hepatoma tumors of mice and shows a strong inhibition on tumor growth. All these results suggest that such a GSH-responsive photosensitizer based on FRET mechanism may provide a new strategy for tumor-targeted and fluorescence imaging-guided cancer therapy.
- Cao, Jing-Jing,Li, Xiao-Qiang,Liu, Jian-Yong,Xu, Gan,Yang, De-Chao,Zhang, Ming-Shan
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- Synthesis and characterization of new H-shaped triphenylene discotic room-temperature liquid crystal tetramers by a copper-free click reaction
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Herein, four new H-shaped triphenylene discotic liquid crystal tetramers have been designed and synthesized using a copper-free [3+2] cycloaddition reaction between the triphenylene dimer and diazide compounds. To probe the molecular self-assembly and mesophase properties, the length and rigid spacers in diazide have been tailored. The tetramers 7 with a soft spacer display a room-temperature enantiotropic DLC mesophase, and X-ray diffraction confirms that they exhibit an unusual mesophase of a lamellar-hexagonal columnar phase (Colhl). The results of the photophysical tests show that all the new H-shaped DLC tetramers display relatively high intensity photoluminescence properties.
- Zhang, Kan,Bai, Yuefeng,Feng, Chun,Ning, Guanghui,Ni, Hailiang,Yu, Wenhao,Zhao, Keqing,Wang, Biqin,Hu, Ping
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- Electron-Equivalent Valency through Molecularly Well-Defined Multivalent DNA
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Oligonucleotide-functionalized nanoparticles (NPs), also known as "programmable atom equivalents"(PAEs), have emerged as a class of versatile building blocks for generating colloidal crystals with tailorable structures and properties. Recent studies have shown that, at small size and low DNA grafting density, PAEs can also behave as "electron equivalents"(EEs), roaming through and stabilizing a complementary PAE sublattice. However, it has been challenging to obtain a detailed understanding of EE-PAE interactions and the underlying colloidal metallicity because there is inherent polydispersity in the number of DNA strands on the surfaces of these NPs; thus, the structural uniformity and tailorability of NP-based EEs are somewhat limited. Herein, we report a strategy for synthesizing colloidal crystals where the EEs are templated by small molecules, instead of NPs, and functionalized with a precise number of DNA strands. When these molecularly precise EEs are assembled with complementary NP-based PAEs, X-ray scattering and electron microscopy reveal the formation of three distinct "metallic"phases. Importantly, we show that the thermal stability of these crystals is dependent on the number of sticky ends per EE, while lattice symmetry is controlled by the number and orientation of EE sticky ends on the PAEs. Taken together, this work introduces the notion that, unlike conventional electrons, EEs that are molecular in origin can have a defined valency that can be used to influence and guide specific phase formation.
- Cheng, Ho Fung,Wang, Shunzhi,Mirkin, Chad A.
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supporting information
p. 1752 - 1757
(2021/02/06)
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- Design, synthesis, antimicrobial evaluation and in silico studies of symmetrical bis (urea-1,2,3-triazole) hybrids
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Abstract: In search of 1,2,3-triazole-based antimicrobials, some symmetrical bis(urea-1,2,3-triazole) hybrids were synthesized via clicked Huisgen cycloaddition. The structural characterization was done by different physical and spectral techniques like N
- Poonia, Nisha,Lal, Kashmiri,Kumar, Ashwani
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p. 1087 - 1103
(2020/11/10)
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- MONOMER AND MULTIMERIC ANTI-HBV AGENTS
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The present invention is directed to compounds, compositions and methods for preventing, treating or curing hepatitis B (HBV) infection in human subjects or other animal hosts. The compounds are as also pharmaceutically acceptable, salts, prodrugs, and other derivatives thereof as pharmaceutical compositions and methods for treatment, prevention or eradication of HBV infection.
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Page/Page column 143; 185-186
(2020/05/15)
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- Janus NLO dendrimers with different peripheral functional groups: Convenient synthesis and enhanced NLO performance with the aid of the Ar-ArF self-assembly
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In this work, three dendrimers with different peripheral functional groups were successfully prepared through a powerful "click chemistry" reaction. Thanks to their spherical topological structure, the NLO performance is superior to that of the corresponding conical dendrimers. Among them, Janus dendrimer J1 with phenyl and pentafluorophenyl groups at the periphery demonstrated the highest NLO effect of 118.0 pm V-1. Also, thanks to the Ar-ArF self-assembly effect, its optical transparency and thermal stability were also improved, with degradation temperatures higher than 260 °C.
- Liu, Guangchao,Liao, Qiuyan,Deng, Haiyu,Zhao, Wenjing,Chen, Pengyu,Tang, Runli,Li, Qianqian,Li, Zhen
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supporting information
p. 7344 - 7351
(2019/06/27)
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- Synthesis, Antioxidant, and Antimicrobial Activities of Novel Bis-Aroylbenzofuran Fused 1,2,3-Triazoles Bearing Alkane Spacers
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A series of novel fused bis-aroylbenzodifuran derivatives linked via bis-1,2,3-triazole moiety containing alkane spacers 15, 19a–19d are synthesized in 68–80% yields by the Huisgen cycloaddition (Click) reaction of alkane azides 4–8 with acetylene interme
- Kiran,Sarasija,Rao,Jeyanthi,Rao,Ashok
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p. 2410 - 2419
(2019/01/04)
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- Antioxidant Properties of Novel Dimers Derived from Natural β-Elemene through Inhibiting H2O2-Induced Apoptosis
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A series of novel β-elemene dimer derivatives were synthesized and evaluated for their antioxidant activities. The results indicated that most of the target compounds showed more potent cytoprotective effects than positive control vitamin E. In particular, dimer D5 exhibited the strongest antioxidant activity, which was significantly superior to the active compound D1 obtained in our previous study. Besides, D5 did not produce obvious cytotoxicity in normal human umbilical vein endothelial cells (HUVECs) and increased the viability of HUVECs injured by H2O2 in a concentration-dependent manner. Further studies suggested that the cytoprotective action of D5 might be mediated, at least in part, by increasing the intracellular superoxide dismutase activity and nitric oxide secretion as well as decreasing the intracellular malonyldialdehyde content and lactate dehydrogenase release. Furthermore, D5 observably inhibited ROS generation and prevented H2O2-induced apoptosis in HUVECs possibly via inhibiting the activation of the MAPK signaling pathway.
- Chen, Jichao,Wang, Ruifan,Wang, Tianyu,Ding, Qilong,Khalil, Aliahmad,Xu, Shengtao,Lin, Aijun,Yao, Hequan,Xie, Weijia,Zhu, Zheying,Xu, Jinyi
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supporting information
p. 443 - 448
(2017/04/21)
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- Tetracarboxylic dianhydride containing triazole, polymer, liquid crystal aligning agent, liquid crystal aligning membrane, and display element
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The invention provides tetracarboxylic dianhydride containing triazole, a polymer, a liquid crystal aligning agent, a liquid crystal aligning membrane, and a display element. The tetracarboxylic dianhydride is represented by the formula (1); wherein in the formula (1), the X represents a divalent organic group containing at least one triazole ring, the R1 and R2 individually represent one of trivalent groups, which are represented in the description; and at least one hydrogen atom of these groups can be replaced by a methyl group, an ethyl group, or a phenyl group. The liquid crystal aligning agent can form a liquid crystal aligning membrane that is hard to peel off or eliminate.
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Paragraph 0796; 0797
(2016/10/08)
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- TRIAZOLE-CONTAINING TETRACABOXYLIC ACID DIANHYDRIDES, LIQUID CRYSTAL ALIGNING AGENTS, LIQUID CRYSTAL ALIGNMENT LAYERS, AND LIQUID CRYSTAL DISPLAY DEVICES USING THE SAME
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The purpose of the present invention is to provide a liquid crystal aligning agent allowing formation of a liquid crystal aligning layer which can hardly be exfoliated or cut. In the present invention, provided is tetracarboxylic acid dianhydride represented by chemical formula 177. In chemical formula 177, X is a divalent organic group comprising at least one triazole ring; R1 and R2 are each independently one radical selected from the group consisting of the following trivalent radicals represented by chemical formula 178; and at least one hydrogen among the trivalent radicals may be substituted with methyl, ethyl or phenyl.COPYRIGHT KIPO 2016
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Paragraph 0778; 0779
(2017/01/05)
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- FTC-containing molecules: large second-order nonlinear optical performance and excellent thermal stability, and the key development of the “Isolation Chromophore” concept
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A series of second-order nonlinear optical (NLO) molecules, M1-M5, were designed and successfully synthesized through the convenient ‘‘click chemistry’’ reaction, which contain two different types of chromophore moieties, the FTC chromophore and nitro-based azo ones, according to the concept of “Isolation Chromophore”. All these five molecules possess excellent thermal stability and very large NLO performance, with an ultrahigh d33 value of 384 pm V?1 at the wavelength of 1950 nm achieved for M1, furthering the rational design of excellent NLO materials.
- Chen, Pengyu,Yin, Xiuyang,Xie, Yujun,Li, Shufang,Luo, Shiyu,Zeng, Huiyi,Guo, Guocong,Li, Qianqian,Li, Zhen
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supporting information
p. 11474 - 11481
(2016/12/18)
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- Antimicrobial Properties of Mono-and Di-fac-rhenium Tricarbonyl 2-Pyridyl-1,2,3-triazole Complexes
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A family of mono-and di-fac-rhenium tricarbonyl 2-pyridyl-1,2,3-triazole complexes with different aliphatic and aromatic substituents was synthesized in good-to-excellent yields (46-99%). The complexes were characterized by 1H and 13
- Kumar, Sreedhar V.,Lo, Warrick K. C.,Brooks, Heather J. L.,Hanton, Lyall R.,Crowley, James D.
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p. 489 - 498
(2016/06/01)
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- Cucurbit[6]uril as a potential catalyst for the acidic decomposition of azidoaminoalkanes
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Five azidoalkyl-1-amines and p-azidoaniline have been synthesized and complexed with cucurbit[6]uril in acidic solutions. Isothermal titration calorimetry has been employed to determine the association constant K and the enthalpy of complex formation ΔH of the azidoalkyl- and azidoarylamines. 4-Azidobutyl-1-amine forms by far the most stable complex. Cucurbit[6]uril significantly catalyzes the decomposition of the azidoalkyl- and azidoarylamines studied.
- Wieland, Marcel,Mieusset, Jean-Luc,Brinker, Udo H.
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experimental part
p. 4351 - 4353
(2012/10/08)
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- Reduction-degradable linear cationic polymers as gene carriers prepared by Cu(I)-catalyzed azide-alkyne cycloaddition
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Linear reduction-degradable cationic polymers with different secondary amine densities (S2 and S3) and their nonreducible counterparts (C2 and C3) were synthesized by Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC) step-growth polymerization of the dia
- Wang, Yang,Zhang, Rui,Xu, Ning,Du, Fu-Sheng,Wang, Ying-Li,Tan, Ying-Xia,Ji, Shou-Ping,Liang, De-Hai,Li, Zi-Chen
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scheme or table
p. 66 - 74
(2012/01/06)
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- Universal cyclic polymer templates
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Two unique molecular templates for generating polymeric materials with a cyclic molecular architecture were developed by combining ring-expansion metathesis polymerization and click chemistry. These two universal cyclic polymers were used in three examples to demonstrate the wide range of potential materials enabled. They include functional cyclic polymers, cyclic polymer brushes, and cyclic gels.
- Zhang, Ke,Lackey, Melissa A.,Wu, Ying,Tew, Gregory N.
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supporting information; experimental part
p. 6906 - 6909
(2011/06/19)
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- Stabilization of Cu(0)-nanoparticles into the nanopores of modified montmorillonite: An implication on the catalytic approach for "click" reaction between azides and terminal alkynes
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In situ generation of Cu(0)-nanoparticles in the nanopores of modified montmorillonite and their catalytic activity in 1,3-dipolar cycloaddition reactions between azides and terminal alkynes to synthesise 1,2,3-triazoles have been carried out. The modific
- Borah, Bibek Jyoti,Dutta, Dipanka,Saikia, Partha Pratim,Barua, Nabin Chandra,Dutta, Dipak Kumar
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experimental part
p. 3453 - 3460
(2012/01/15)
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- Solid-phase synthesis of (ω-Aminoalkyl)peptoids using azide chemistry
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Functionalized (ω-aminoalkyl)peptoids - useful molecular transporters for drugs and probes into cells - have been synthesized by a combined microwave-assisted sub-monomer peptoid synthesis with 1-amino ω- azidoalkanes and a subsequent reduction of the azide moiety on solid supports. This method enables the preparation of unprecedented chiral amino-functionalized and PEG-type peptoids. Both the scope and limitations of this process are presented herein. Georg Thieme Verlag Stuttgart New York.
- Fritz, Daniel,Br?se, Stefan
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scheme or table
p. 1544 - 1548
(2010/08/22)
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- Structure-activity relationship for thiohydantoin androgen receptor antagonists for castration-resistant prostate cancer (CRPC)
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A structure-activity relationship study was carried out on a series of thiohydantoins and their analogues 14 which led to the discovery of 92 (MDV3100) as the clinical candidate for the treatment of hormone refractory prostate cancer.
- Jung, Michael E.,Ouk, Samedy,Yoo, Dongwon,Sawyers, Charles L.,Chen, Charlie,Tran, Chris,Wongvipat, John
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experimental part
p. 2779 - 2796
(2010/09/05)
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- "Click polyester": Synthesis of polyesters containing triazole units in the main chain via safe and rapid "click" chemistry and their properties
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Click Cu(I)-catalyzed polymerizations of diynes that contained ester linkages and diazides were performed to produce polyesters (click polyesters) of large molecular weights [(~1.0-7.0) × 104], that contained main-chain 1,4-disubstitued triazol
- Nagao, Yu,Takasu, Akinori
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experimental part
p. 4207 - 4218
(2011/11/14)
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- Hydrogen-bonded deugdan heterocomplex: Structure and stability and a scalable synthesis of DeUG with reactive functionality
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A convenient, scalable synthesis of the supramolecular building block 7-deazaguanine-based urea (DeUG) is reported. Incorporation of reactive moieties (DeUG azide 10 and alkyne 11 for copper-catalyzed azide-alkyne cycloadditions, "click chemistry") and a demonstration of transesterification (DeUG glycol, 12) highlights the versatility. X-ray structures of DeUG and a DeUG-DAN heterocomplex were obtained. Kassoc for the 1.2 heterocomplex was estimated to be 2 x 108 M-1 in chloroform.
- Kuykendall, Darrell W.,Anderson, Cyrus A.,Zimmerman, Steven C.
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supporting information; experimental part
p. 61 - 64
(2009/07/04)
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- High-throughput synthesis of azide libraries suitable for direct "click" chemistry and in situ screening
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A key challenge in current drug discovery is the development of high-throughput (HT) amenable chemical reactions that allow rapid synthesis of diverse chemical libraries of enzyme inhibitors. The Cu(I)-catalyzed, 1,3-dipolar cycloaddition between an azide and an alkyne, better known as "click chemistry", is one such method that has received the most attention in recent years. Despite its popularity, there is still a lack of robust and efficient chemical strategies that give access to diverse libraries of azide-containing building blocks (key components in click chemistry). We report herein a highly robust and efficient strategy for high-throughput synthesis of a 325-member azide library. The method is highlighted by its simplicity and product purity. The utility of the library is demonstrated with the subsequent "click" synthesis of the corresponding bidentate inhibitors against PTP1B.
- Srinivasan, Rajavel,Tan, Lay Pheng,Wu, Hao,Yang, Peng-Yu,Kalesh, Karunakaran A.,Yao, Shao Q.
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supporting information; experimental part
p. 1821 - 1828
(2009/06/28)
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- Dual-mode recognition of transition metal ions by bis-triazoles chained pyrenes
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Fluorescent chemosensors 7-10, with variable methylene chain length as spacers between the two triazole methyl ether units, have been synthesized under 'Click' condition, where the bistriazoles are used as the metal ion binding sites and the pyrenes as th
- Hung, Hao-Chih,Cheng, Chi-Wen,Ho, I-Ting,Chung, Wen-Sheng
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scheme or table
p. 302 - 305
(2009/04/14)
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- Size-specific ligands for RNA hairpin loops
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The targeting of one mRNA in the transcriptome requires small molecules that bind with substantial affinity and specificity. As such, compounds with specificity for individual RNA secondary structural motifs could be useful for targeting RNA. Described herein is the synthesis of a combinatorial library of 105 dimers of deoxystreptamine and the subsequent identification of compounds with specificity for specific RNA hairpin loop sizes, including tetraloops and octaloops. Such compounds will be useful for the perturbation of RNA function in vivo. Copyright
- Thomas, Jason R.,Liu, Xianjun,Hergenrother, Paul J.
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p. 12434 - 12435
(2007/10/03)
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- An efficient and practical method for the synthesis of mono-N-protected α,ω-diaminoalkanes
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The large-scale synthesis of mono-N-protected (Cbz, Boc, Ts, and Ns) α,ω-diaminoalkanes (the number of carbon atoms=3, 4, 5 and 6) are accomplished in 81-94% yield by the protection of amine and subsequent reduction of an azido group from α,ω-azido alkyl amines. α,ω-Azido alkyl amines are prepared efficiently by the partial reduction of α,ω-diazidoalkanes which are obtained from the corresponding dibromoalkanes.
- Lee, Jae Wook,Jun, Sung Im,Kim, Kimoon
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p. 2709 - 2711
(2007/10/03)
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- Bistriazenes: Multifunctional alkylating agents
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The synthesis of bis(methyltriazeno)alkanes is readily accomplished by reaction of methyllithium with the appropriate diazidoalkane. These compounds possess interesting properties in solution, suggestive of an array of intermolecular hydrogen bonding.
- Blumenstein, Jeffrey J.,Michejda, Christopher J.
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p. 183 - 186
(2007/10/02)
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