- Modular Toolkit of Multifunctional Block Copoly(2-oxazoline)s for the Synthesis of Nanoparticles
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Post-polymerization modification provides an elegant way to introduce chemical functionalities onto macromolecules to produce tailor-made materials with superior properties. This concept was adapted to well-defined block copolymers of the poly(2-oxazoline) family and demonstrated the large potential of these macromolecules as universal toolkit for numerous applications. Triblock copolymers with separated water-soluble, alkyne- and alkene-containing segments were synthesized and orthogonally modified with various low-molecular weight functional molecules by copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) and thiol-ene (TE) click reactions, respectively. Representative toolkit polymers were used for the synthesis of gold, iron oxide and silica nanoparticles.
- Keckeis, Philipp,Zeller, Enriko,Jung, Carina,Besirske, Patricia,Kirner, Felizitas,Ruiz-Agudo, Cristina,Schlaad, Helmut,C?lfen, Helmut
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supporting information
p. 8283 - 8287
(2021/05/07)
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- Clickable gold-nanoparticles as generic probe precursors for facile photoaffinity labeling application
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Rapid access to appropriately functionalized probes is crucial in chemical labeling approaches to target identification studies. We designed and synthesized clickable gold-nanoparticles as generic probe precursors that enable (1) one-step ligand derivatization by click chemistry, and (2) facile photoaffinity labeling application. Using cholesterol as a model ligand, we successfully demonstrated the utility of the ligand-clicked probe in photoaffinity labeling of endogenously expressed oxysterol-binding protein (OSBP) in cell lysate.
- Mori, Kanna,Sakurai, Kaori
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supporting information
p. 1268 - 1273
(2021/02/26)
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- PHOTOPROXIMITY PROFILING OF PROTEIN-PROTEIN INTERACTIONS IN CELLS
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Photoactive probes and probe systems for detecting biological interactions are described. The photoactive probes include probes that combine both photocleavable and photoreactive moieties. The photoactive probe systems can include a first probe comprising a photocatalytic group and a second probe comprising a group that can act as a substrate for the reaction catalyzed by the photocatalytic group. The probes and probe systems can also include groups that can specifically bind to a binding partner on a biological entity of interest and a detectable group or a precursor thereof. The probes and probe systems can detect spatiotemporal interactions of proteins or cells. In some embodiments, the interactions can be detected in live cells. Also described are methods of detecting the biological interactions.
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Page/Page column 114; 119
(2021/04/01)
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- Taxol-DHA-dextran coupling polymer, synthetic method thereof and application of polymer
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The invention provides a taxol-DHA-dextran coupling polymer, a synthetic method thereof and an application of the polymer, and belongs to the technical field of biological medicines. According to thepolymer, polysaccharides serve as polymer drug-loaded frameworks, so that an anti-tumor drug-polysaccharide passive targeted coupling polymer is prepared, taxol can be passively targeted into a tumortissue by the aid of an EPR effect, and an anti-tumor function is played. Water solubility and biocompatibility of taxol medicines can be increased, accumulation of anti-tumor medicines in the tumor tissue can be increased under the passive targeted action, general side effect and nervous side effect of the taxol medicines are reduced, and the polymer has good practical application values.
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Paragraph 0054; 0139; 0140; 0141; 0142; 0143
(2019/10/01)
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- Regulating miRNA-21 Biogenesis by Bifunctional Small Molecules
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We report a new strategy to regulate microRNAs (miRNAs) biogenesis by using bifunctional small molecules that consist of a pre-miRNA binding unit connected by a linker to a Dicer inhibiting unit. In this effort, fluorescence polarization-based screening was used to identify neomycin as a pre-miR-21 binding ligand. Although neomycin cannot inhibit miR-21 maturation, linking it to the RNase inhibitor 1 forms the bifunctional conjugate 7A, which inhibits the production of miR-21. We expect that this strategy will be applicable to design other molecules for miRNA regulation.
- Yan, Hao,Bhattarai, Umesh,Guo, Zhi-Fo,Liang, Fu-Sen
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supporting information
p. 4987 - 4990
(2017/05/04)
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- RNA targeting compounds and methods for making and using same
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Disclosed are RNA targeting compounds, methods for using the subject RNA targeting compounds to treat myotonic dystrophy and other diseases are also disclosed.
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Page/Page column 52; 53
(2016/03/13)
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- Finding a human telomere DNA-RNA hybrid G-quadruplex formed by human telomeric 6-mer RNA and 16-mer DNA using click chemistry: A protective structure for telomere end
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Telomeric repeat-containing RNA is a non-coding RNA molecule newly found in mammalian cells. The telomere RNA has been found to localize to the telomere DNA, but how the newly discovered RNA molecule interacts with telomere DNA is less known. In this study, using the click chemistry we successfully found that a 6-mer human telomere RNA and 16-mer human telomere DNA sequence can form a DNA-RNA hybrid type G-quadruplex structure. Detection of the click-reaction products directly probes DNA-RNA G-quadruplex structures in a complicated solution, whereas traditional methods such as NMR and crystallography may not be suitable. Importantly, we found that formation of DNA-RNA G-quadruplex induced an exonuclease resistance for telomere DNA, indicating that such structures might be important for protecting telomeric DNA from enzyme digestion to avoid telomere DNA shortening. These results provide the direct evidence for formation of DNA-RNA hybrid G-quadruplex structure by human telomere DNA and RNA sequence, suggesting DNA-RNA hybrid G-quadruplex structure associated between telomere DNA and RNA may respond to chromosome end protection and/or present a valuable target for drug design.
- Xu, Yan,Suzuki, Yuta,Ishizuka, Takumi,Xiao, Chao-Da,Liu, Xiao,Hayashi, Tetsuya,Komiyama, Makoto
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supporting information
p. 4419 - 4421
(2014/12/10)
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- Multimerization of an apoptogenic TRAIL-mimicking peptide by using adamantane-based dendrons
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We have developed a straightforward strategy to multimerize an apoptogenic peptide that mimics the natural tumor necrosis factor-related apoptosis-inducing ligand (TRAIL) by using adamantane-based dendrons as multivalent scaffolds. The selective binding a
- Lamanna, Giuseppe,Smulski, Cristian R.,Chekkat, Neila,Estieu-Gionnet, Karine,Guichard, Gilles,Fournel, Sylvie,Bianco, Alberto
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p. 1762 - 1768
(2013/02/25)
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- Discovery of chemoselective and biocompatible reactions using a high-throughput immunoassay screening
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An immunoassay-based method was used to screen numerous combinations of dipoles and dipolarophiles for their ability to undergo chemoselective and biocompatible [3+2] cycloaddition reactions. The approach fulfills most of the requirements of the click concept and led to the discovery of a copper-catalyzed reaction that generates pyrazoles from sydnone and alkyne reagents. Copyright
- Kolodych, Sergii,Rasolofonjatovo, Evelia,Chaumontet, Manon,Nevers, Marie-Claire,Creminon, Christophe,Taran, Frederic
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supporting information
p. 12056 - 12060
(2013/12/04)
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- Reaction discovery by using a sandwich immunoassay
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Mmm, a reaction sandwich Using an immunoassay-based technique able to monitor any kind of cross-coupling reaction, a systematic and rapid evaluation of a large panel of random reactions was carried out. This approach led to the discovery of two new copper-promoted reactions: a desulfurization reaction of thioureas leading to isoureas and a cyclization reaction leading to thiazole derivatives from alkynes and N-hydroxy thioureas. Copyright
- Quinton, Julia,Kolodych, Sergii,Chaumonet, Manon,Bevilacqua, Valentina,Nevers, Marie-Claire,Volland, Herve,Gabillet, Sandra,Thuery, Pierre,Creminon, Christophe,Taran, Frederic
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supporting information; experimental part
p. 6144 - 6148
(2012/07/17)
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- Unraveling the protein targets of vancomycin in living S. aureus and E. faecalis cells
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Vancomycin is a potent glycopeptide antibiotic that has evolved to specifically bind to the d-Ala-d-Ala dipeptide termini of nascent peptidoglycans. Although this mode of action is well established, several studies indicate that vancomycin and analogues e
- Eirich, Juergen,Orth, Ronald,Sieber, Stephan A.
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experimental part
p. 12144 - 12153
(2011/10/04)
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- Mixed phosphane η5-CpRuCl(PR3)2 complexes as ambifunctional catalysts for anti-markovnikov hydration of terminal alkynes
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The catalytic activity of [CpRu(L)2(MeCN)]PF6 (L = 2-diphenylphosphinopyridine with bulky groups at C-6) for anti-Markovnikov hydration of terminal alkynes to aldehydes is retained when one heterocyclic ligand L is replaced by L′ = PPh3. Equal amounts of CpRuCl(PPh3)2 (1) and phosphane L in acetone solution equilibrate to a mixture of 1, CpRuCl(L)(PPh3) (2), and CpRuCl(L)2 (3), which acts as highly active in situ catalyst for preparative anti-Markovnikov hydration of alkynes in water-rich media (2 mol % [Ru], 60 °C, 3-18 h in 4:1 (v/v) acetone/water). Reactions were completed in 15 min at 160 °C.
- Boeck, Florian,Kribber, Thomas,Xiao, Li,Hintermann, Lukas
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supporting information; experimental part
p. 8138 - 8141
(2011/07/08)
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- Optimization of the azobenzene scaffold for reductive cleavage by dithionite; development of an azobenzene cleavable linker for proteomic applications
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In this paper we conducted an extensive reactivity study to determine the key structural features that favour the dithionite-triggered reductive cleavage of the azo-arene group. Our stepwise investigation allowed identification of a highly reactive azo-arene structure 25 bearing a carboxylic acid, at the ortho position of the electron-poor arene and an ortho-Oalkyl-resorcinol as the electron-rich arene. Based on this 2(2′-alkoxy-4′-hydroxyphenylazo) benzoic acid (HAZA) scaffold, the orthogonally protected difunctional azo-arene cleavable linker 26 was designed and synthesized. Selective linker deprotection and derivatization was performed by introducing an alkyne reactive group and a biotin affinity tag. This optimized azo-arene cleavable linker led to a total cleavage in less than 10 s with only 1 mM dithionite. Similar results were obtained in biological media.
- Leriche, Geoffray,Budin, Ghyslain,Brino, Laurent,Wagner, Alain
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supporting information; experimental part
p. 4360 - 4364
(2010/09/20)
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- Bioorthogonal chemical reporters for monitoring protein acetylation
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"Chemical equation presented" Protein acetylation is a key post-translational modification that regulates diverse biological activities in eukaryotes. Here we report bioorthogonal chemical reporters that enable direct in-gel fluorescent visualization and
- Yang, Yu-Ying,Ascano, Janice M.,Hang, Howard C.
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supporting information; experimental part
p. 3640 - 3641
(2010/05/15)
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- A photolabile linker for the mild and selective cleavage of enriched biomolecules from solid support
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(Chemical Equation Presented) Selective release of enriched biomolecules from solid support is a desirable goal in proteomic and metabolomic studies. Here we demonstrate that photocleavage of a light-sensitive phenacyl ester bond is a suitable alternative
- Orth, Ronald,Sieber, Stephan A.
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supporting information; experimental part
p. 8476 - 8479
(2010/02/28)
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- Squalene-derived flexible linkers for bioactive peptides
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A regiochemical and stereochemical mixture of flexible linkers bearing terminal azide functionality was synthesized in two steps from squalene and was used to connect two high affinity NDP-α-MSH ligands or two low affinity MSH(4) ligands. The ligands were N-terminally acylated using N-hydroxysuccinimidoyl 5-hexynoate and were subsequently attached to the linker via copper-catalyzed 'click' 3 + 2 cyclization of the azide and alkyne moieties. In vitro biological evaluations showed that the binding affinity to the human melanocortin 4 receptor was not diminished for most linker-ligand combinations relative to the corresponding parental ligand. Statistical and cooperative binding effects were observed for dimeric constructs containing the low affinity ligand MSH(4), but not for dimeric NDP-α-MSH constructs, presumably due to slow off rates for this high affinity ligand.
- Jagadish, Bhumasamudram,Sankaranarayanan, Rajesh,Xu, Liping,Richards, Reyniak,Vagner, Josef,Hruby, Victor J.,Gillies, Robert J.,Mash, Eugene A.
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p. 3310 - 3313
(2008/02/08)
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- Sandwich immunoassay as a high-throughput screening method for cross-coupling reactions
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Catalyst sandwich: An efficient and sensitive high-throughput-screening method that uses sandwich immunoassays was developed and applied to the Sonogashira reaction. This new method is amenable to coupling reactions and allows the screening of more than 1
- Vicennati, Paola,Bensel, Nicolas,Wagner, Alain,Creminon, Christophe,Taran, Frederic
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p. 6863 - 6866
(2007/10/03)
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