74654-07-2Relevant academic research and scientific papers
Non-invasive, real-time reporting drug release in vitro and in vivo
Zhang, Yanfeng,Yin, Qian,Yen, Jonathan,Li, Joanne,Ying, Hanze,Wang, Hua,Hua, Yuyan,Chaney, Eric J.,Boppart, Stephen A.,Cheng, Jianjun
, p. 6948 - 6951 (2015)
We developed a real-time drug-reporting conjugate (CPT-SS-CyN) composed of a near-infrared (NIR) fluorescent cyanine-amine dye (CyN), a disulfide linker, and a model therapeutic drug (camptothecin, CPT). Treatment with dithiothreitol (DTT) induces cleavage of the disulfide bond, followed by two simultaneous intramolecular cyclization reactions with identical kinetics, one to cleave the urethane linkage to release the NIR dye and the other to cleave the carbonate linkage to release CPT. The released CyN has an emission wavelength (760 nm) that is significantly different from CPT-SS-CyN (820 nm), enabling easy detection and monitoring of drug release. A linear relationship between the NIR fluorescence intensity at 760 nm and the amount of CPT released was observed, substantiating the use of this drug-reporting conjugate to enable precise, real-time, and non-invasive quantitative monitoring of drug release in live cells and semi-quantitative monitoring in live animals. This journal is
Oligonucleotide arrays from aldehyde-bearing glass with coated background
Dombi, Kendra L.,Griesang, Niels,Richert, Clemens
, p. 816 - 824 (2002)
Presented here is a method for preparing small DNA arrays on aldehyde-bearing glass slides. Immobilization involves reductive amination and employs oligonucleotides with 3′-terminal lysine residues, obtained in high yield from solid phase syntheses. Spot patterns are produced by protecting selected areas of the aldehyde slides with wax, coating the free surface with a methyl triethylene glycol derivative, and removing the wax with dichloromethane. The DNA arrays give better signal to noise ratios in hybridization experiments than slides without passified background.
Targeting G Protein-Coupled Receptors with Magnetic Carbon Nanotubes: The Case of the A3 Adenosine Receptor
Pineux, Florent,Federico, Stephanie,Klotz, Karl-Norbert,Kachler, Sonja,Michiels, Carine,Sturlese, Mattia,Prato, Maurizio,Spalluto, Giampiero,Moro, Stefano,Bonifazi, Davide
supporting information, p. 1909 - 1920 (2020/09/11)
The A3 adenosine receptor (AR) is a G protein-coupled receptor (GPCR) overexpressed in the membrane of specific cancer cells. Thus, the development of nanosystems targeting this receptor could be a strategy to both treat and diagnose cancer. Iron-filled carbon nanotubes (CNTs) are an optimal platform for theranostic purposes, and the use of a magnetic field can be exploited for cancer magnetic cell sorting and thermal therapy. In this work, we have conjugated an A3AR ligand on the surface of iron-filled CNTs with the aim of targeting cells overexpressing A3ARs. In particular, two conjugates bearing PEG linkers of different length were designed. A docking analysis of A3AR showed that neither CNT nor linker interferes with ligand binding to the receptor; this was confirmed by in vitro preliminary radioligand competition assays on A3AR. Encouraged by this result, magnetic cell sorting was applied to a mixture of cells overexpressing or not the A3AR in which our compound displayed indiscriminate binding to all cells. Despite this, it is the first time that a GPCR ligand has been anchored to a magnetic nanosystem, thus it opens the door to new applications for cancer treatment.
MULTI-ELECTRON REDOX-ACTIVE ORGANIC MOLECULES FOR HIGH-ENERGY-DENSITY NONAQUEOUS REDOX FLOW BATTERIES
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Page/Page column 10-13, (2020/12/11)
The invention relates to 1,4-diaminoanthraquinones and an electrolyte, and their use in batteries.
Cell-Penetrating Dynamic-Covalent Benzopolysulfane Networks
Cheng, Yangyang,Zong, Lili,López-Andarias, Javier,Bartolami, Eline,Okamoto, Yasunori,Ward, Thomas R.,Sakai, Naomi,Matile, Stefan
supporting information, p. 9522 - 9526 (2019/06/24)
Cyclic oligochalcogenides (COCs) are emerging as promising systems to penetrate cells. Clearly better than and different to the reported diselenolanes and epidithiodiketopiperazines, we introduce the benzopolysulfanes (BPS), which show efficient delivery, insensitivity to inhibitors of endocytosis, and compatibility with substrates as large as proteins. This high activity coincides with high reactivity, selectively toward thiols, exceeding exchange rates of disulfides under tension. The result is a dynamic-covalent network of extreme sulfur species, including cyclic oligomers, from dimers to heptamers, with up to nineteen sulfurs in the ring. Selection from this unfolding adaptive network then yields the reactivities and selectivities needed to access new uptake pathways. Contrary to other COCs, BPS show high retention on thiol affinity columns. The identification of new modes of cell penetration is important because they promise new solutions to challenges in delivery and beyond.
A halogen-bonding foldamer molecular film for selective reagentless anion sensing in water
Hein, Robert,Borissov, Arseni,Smith, Martin D.,Beer, Paul D.,Davis, Jason J.
supporting information, p. 4849 - 4852 (2019/05/02)
We describe self-assembled monolayers of novel halogen-bonding and hydrogen-bonding foldamer receptors capable of selectively recruiting perrhenate, iodide and thiocyanate in water. Unprecedented anion sensing via impedance-derived capacitance spectroscopy enables subsequent sensitive and selective anion detection without the need for a redox probe. Importantly, the sensing of any anion should be possible using this novel electrochemical approach.
Anion Recognition in Water by Charge-Neutral Halogen and Chalcogen Bonding Foldamer Receptors
Borissov, Arseni,Marques, Igor,Lim, Jason Y.C.,Félix, Vítor,Smith, Martin D.,Beer, Paul D.
supporting information, p. 4119 - 4129 (2019/03/07)
A novel strategy for the recognition of anions in water using charge-neutral σ-hole halogen and chalcogen bonding acyclic hosts is demonstrated for the first time. Exploiting the intrinsic hydrophobicity of halogen and chalcogen bond donor atoms integrated into a foldamer structural molecular framework containing hydrophilic functionalities, a series of water-soluble receptors was constructed for an anion recognition investigation. Isothermal titration calorimetry (ITC) binding studies with a range of anions revealed the receptors to display very strong and selective binding of large, weakly hydrated anions such as I- and ReO4-. This is achieved through the formation of 2:1 host-guest stoichiometric complex assemblies, resulting in an encapsulated anion stabilized by cooperative, multidentate, convergent σ-hole donors, as shown by molecular dynamics simulations carried out in water. Importantly, the combination of multiple σ-hole-anion interactions and hydrophobic collapse results in I- affinities in water that exceed all known σ-hole receptors, including cationic systems (β2 up to 1.68 × 1011 M-2). Furthermore, the anion binding affinities and selectivity trends of the first example of an all-chalcogen bonding anion receptor in pure water are compared with halogen bonding and hydrogen bonding receptor analogues. These results further advance and establish halogen and chalcogen bond donor functions as new tools for overcoming the challenging goal of anion recognition in pure water.
Thermodynamics of Halide Binding to a Neutral Bambusuril in Water and Organic Solvents
Fiala, Tomas,Sleziakova, Kristina,Marsalek, Kamil,Salvadori, Karolina,Sindelar, Vladimir
, p. 1903 - 1912 (2018/02/23)
Driving forces of anion binding in water in contrast to nonpolar environments are of high interest because of their relevance to biology and medicine. Here we report a neutral bambusuril macrocycle (1), soluble in both water and nonpolar solvents due to decoration with 12 polyethylene glycol-based substituents. The new bambusuril has the highest affinity for I- in pure water ever reported for a synthetic macrocycle relying on hydrogen bonding interactions rather than metal coordination or Coulombic forces. Isothermal titration calorimetry (ITC) experiments in nine different solvents, ranging from polar water to nonpolar carbon tetrachloride, provided insight into the forces responsible for halide binding by bambusurils. The different importance of anion solvation and solvent expulsion from the cavity of the macrocycle in various solvents is illustrated by the fact that halide binding in water and chloroform is exclusively driven by favorable enthalpy with an entropic penalty, while in alcohols and nonpolar solvents, both favorable enthalpy and entropy contribute to anion encapsulation. DFT calculations and correlation of thermodynamic data with the solvent Swain acity parameter further underscore the importance of solvent effects on anion binding by bambusurils.
AMYLOID TARGETING AGENTS AND METHODS OF USING THE SAME
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Paragraph 0820 - 0822, (2018/12/04)
Provided herein is the design and synthesis of novel molecular rotor fluorophores useful for detection of amyloid or amyloid like proteins. The fluorophores are designed to exhibit enhanced fluorescence emission upon associating with amyloid or amyloid like proteins as compared to unbound compound. Also disclosed herein are methods for treating diseases associated with amyloid or amyloid like proteins.
Tuneable Transient Thermogels Mediated by a pH- and Redox-Regulated Supramolecular Polymerization
Spitzer, Daniel,Rodrigues, Leona Lucas,Stra?burger, David,Mezger, Markus,Besenius, Pol
supporting information, p. 15461 - 15465 (2017/11/13)
A multistimuli-responsive transient supramolecular polymerization of β-sheet-encoded dendritic peptide monomers in water is presented. The amphiphiles, which contain glutamic acid and methionine, undergo a glucose oxidase catalyzed, glucose-fueled transient hydrogelation in response to an interplay of pH and oxidation stimuli, promoted by the production of reactive oxygen species (ROS). Adjusting the enzyme and glucose concentration allows tuning of the assembly and the disassembly rates of the supramolecular polymers, which dictate the stiffness and transient stability of the hydrogels. The incorporation of triethylene glycol chains introduces thermoresponsive properties to the materials. We further show that repair enzymes are able to reverse the oxidative damage in the methionine-based thioether side chains. Since ROS play an important role in signal transduction cascades, our strategy offers great potential for applications of these dynamic biomaterials in redox microenvironments.
