153086-78-3Relevant academic research and scientific papers
Shell cross-linked nanoparticles designed to target angiogenic blood vessels via αvβ3 receptor-ligand interactions
Pan, Dipanjan,Turner, Jeffrey L.,Wooley, Karen L.
, p. 7109 - 7115 (2004)
The design, synthesis, and characterization of a novel polymeric nanostructured material bearing surface-attached integrin antagonists are demonstrated. The covalent coupling of a complex and biologically active small molecule to a well-defined nanostructured material combines the elegance of synthetic organic chemistry with the state-of-the-art polymer chemistry. This unique material offers potential in targeting to tumor neovasculature and delivery of diagnostic and therapeutic agents.
Polyacrylamides bearing pendant α-sialoside groups strongly inhibit agglutination of erythrocytes by influenza virus: The strong inhibition reflects enhanced binding through cooperative polyvalent interactions
Sigal,Mammen,Dahmann,Whitesides
, p. 3789 - 3800 (1996)
An ELISA assay is described for measuring the binding of influenza virus A-X31 to α-sialoside groups that are linked to biotin-labeled polyacrylamides. The efficacy of these polymers in inhibiting the adhesion of influenza virus to erythrocytes (as measured by a hemagglutination assay) was shown to be directly related to the binding affinity of the polymers for the viral surface: the differences in inhibitory efficacy among the polymeric inhibitors and monomeric α-methyl sialoside, among fractions of a polymeric, polyvalent inhibitor with narrow molecular weight ranges, and among polymeric inhibitors prepared by copolymerization or modification of a preformed polymer chain, all correlated with differences in the affinity of the inhibitors for the surface of the virus. The polymeric inhibitors studied had affinities for the viral surface that ranged between 103 and >106 greater than α-methyl sialoside, on the basis of total sialic acid groups in solution. The role of steric stabilization in the mechanism by which these polymers inhibit hemagglutination was investigated. The ability of the polymeric, polyvalent inhibitors to inhibit the binding of a polyclonal antibody to the viral surface suggests that steric stabilization may also be an important effect in this system.
A cholesterol-based tether for creating photopatterned lipid membrane arrays on both a silica and gold surface
Han, Xiaojun,Achalkumar, Ammathnadu S.,Bushby, Richard J.,Evans, Stephen D.
, p. 6363 - 6370 (2009)
We report a new cholesterolbased self-assembled monolayer (SAM) for use in attaching lipid membranes to both gold and silica surfaces that can be patterned by deep UV (254 nm) photolysis. It allows essentially equivalent patterned supported bilayers to be created both on gold for impedance studies and on silica for fluorescence studies. On either surface an amine-functionalised SAM is reacted with an N-hydroxysuccinimidylcarbonyl-functionalised E03-cholesteryl derivative. The formation of the aminefunctionalised SAM and its reaction with the E03-cholesteryl derivative were followed by contact-angle measurements, ellipsometry and X-ray pho-toelectron spectroscopy. The resultant layer of cholesterol tethers was patterned by deep UV photolysis, which regenerates the original SiO2 surface in exposed regions on a silica substrate and oxidises thiol groups on a gold substrate. This patterned surface containing hydrophilic SiO2 (or -OH groups) and hydrophobic cholesterol tether regions can be converted to a surface patterned with supported lipid bi- and monolayers (respectively) by immersing in a solution of small unilamellar vesicles of egg yolk phosphatidycholine. The formation of the lipid bi- and monolayer regions on the silica surface was evidenced by fluorescence microscopy. Crucially the bilayer regions remain fully fluid yielding lipid mobilities comparable to those found in physisorbed bilayers. Furthermore charged fluorescent lipids are shown to migrate in an applied field thus providing a platform for the studying the electrophoresis (potentially) for a wide range of charged membrane components, such as membrane proteins. The formation of the patterned lipid membrane on the gold surface was confirmed by electrochemical impedance measurements.
Host–Guest Complexes of Cyclodextrins and Nanodiamonds as a Strong Non-Covalent Binding Motif for Self-Assembled Nanomaterials
Schibilla, Frauke,Voskuhl, Jens,Fokina, Natalie A.,Dahl, Jeremy E. P.,Schreiner, Peter R.,Ravoo, Bart Jan
, p. 16059 - 16065 (2017)
We report the inclusion of carboxy- and amine-substituted molecular nanodiamonds (NDs) adamantane, diamantane, and triamantane by β-cyclodextrin and γ-cyclodextrin (β-CD and γ-CD), which have particularly well-suited hydrophobicity and symmetry for an optimal fit of the host and guest molecules. We studied the host–guest interactions in detail and generally observed 1:1 association of the NDs with the larger γ-CD cavity, but observed 1:2 association for the largest ND in the series (triamantane) with β-CD. We found higher binding affinities for carboxy-substituted NDs than for amine-substituted NDs. Additionally, cyclodextrin vesicles (CDVs) were decorated with d-mannose by using adamantane, diamantane, and triamantane as non-covalent anchors, and the resulting vesicles were compared with the lectin concanavalin A in agglutination experiments. Agglutination was directly correlated to the host–guest association: adamantane showed lower agglutination than di- or triamantane with β-CDV and almost no agglutination with γ-CDV, whereas high agglutination was observed for di- and triamantane with γ-CDV.
Evaluation of the synthesis of sialic Acid-PAMAM glycodendrimers without the use of sugar protecting Groups, and the Anti-HIV-1 properties of these compounds
Clayton, Russell,Hardman, Janee,Labranche, Celia C.,McReynolds, Katherine D.
, p. 2186 - 2197 (2011)
A study was undertaken to evaluate the feasibility of synthesizing six sialic acid-PAMAM glycodendrimers using unprotected sialic acid in as few as 1-4 steps using two different reaction pathways, and to assess the sulfated derivatives for anti-HIV activity. The syntheses were accomplished through either the direct attachment of the sialic acid carboxyl group to amine-terminated PAMAM (a divergent-like approach) using BOP coupling, or by first reacting sialic acid with a polar bifunctional spacer molecule, attaching the sugar-linker to carboxy-terminated PAMAM (a convergent-like approach), and again using BOP-mediated coupling reactions. It was hypothesized that the latter approach would be the most successful method, as any steric congestion between the sialic acid and the PAMAM would be minimized using an intervening polar linker. However, the divergent-like synthesis proved to be the superior method, resulting in 11.4%, 14%, and 28% of the fully substituted generations 0, 1, and 2 sialic acid-PAMAM conjugates, respectively, as compared to 6.4% of only the generation ?0.5 sialic acid-linker-PAMAM conjugate for the convergent-like method. Upon sulfation of the four glycodendrimers, binding capabilities to the recombinant HIV protein, gp120, were assessed using an ELISA assay. Compounds that showed promising binding characteristics were then further assessed for inhibition of HIV-1 infection using a well-characterized luciferase reporter gene neutralization assay. The generation 2 sulfated sialic acid-PAMAM glycodendrimer, sulfo-6, bearing 16 sialic acids with 11 sulfate groups incorporated at 4.03% sulfur content by weight, was found to inhibit all four HIV-1 strains tested in the low micromolar range.
Strong positive cooperativity in binding to the A3T3 repeat by Hoechst 33258 derivatives attaching the quinoline units at the end of a branched linker
Koda, Hironori,Brazier, John Alan,Onishi, Ippei,Sasaki, Shigeki
, p. 4583 - 4590 (2015)
Hoechst 33258 derivatives with additional interacting moieties attached at the ends of branched linkers were synthesized, and their DNA binding properties were investigated with regard to the A3T3 repeat by measuring fluorescence spectra. The binding prop
A Specific and Covalent JNK-1 Ligand Selected from an Encoded Self-Assembling Chemical Library
Zimmermann, Gunther,Rieder, Ulrike,Bajic, Davor,Vanetti, Sara,Chaikuad, Apirat,Knapp, Stefan,Scheuermann, J?rg,Mattarella, Martin,Neri, Dario
, p. 8152 - 8155 (2017)
We describe the construction of a DNA-encoded chemical library comprising 148 135 members, generated through the self-assembly of two sub-libraries, containing 265 and 559 members, respectively. The library was designed to contain building blocks potentially capable of forming covalent interactions with target proteins. Selections performed with JNK1, a kinase containing a conserved cysteine residue close to the ATP binding site, revealed the preferential enrichment of a 2-phenoxynicotinic acid moiety (building block A82) and a 4-(3,4-difluorophenyl)-4-oxobut-2-enoic acid moiety (building block B272). When the two compounds were joined by a short PEG linker, the resulting bidentate binder (A82-L-B272) was able to covalently modify JNK1 in the presence of a large molar excess of glutathione (0.5 mm), used to simulate intracellular reducing conditions. By contrast, derivatives of the individual building blocks were not able to covalently modify JNK1 in the same experimental conditions. The A82-L-B272 ligand was selective over related kinases (BTK and GAK), which also contain targetable cysteine residues in the vicinity of the active site.
Mono-acylation of symmetric diamines in the presence of water
Tang, Wei,Fang, Shiyue
, p. 6003 - 6006 (2008)
Simply reacting equal equivalents of symmetric diamines with esters or carbonates in the presence of a suitable amount of water gave mono-acylated products in good to quantitative yields.
Anion interaction with ferrocene-functionalised cyclic and open-chain polyaza and aza-oxa cycloalkanes
Beer, Paul D.,Cadman, James,Lloris, Jose Manuel,Martinez-Manez, Ramoen,Soto, Juan,Pardo, Teresa,Dolores Marcos
, p. 1805 - 1812 (2000)
A family of ferrocene-functionalised receptors of different topologies have been used as receptors for anions. The compounds have been designed to contain both amine nitrogen and ether oxygen atoms and comprises from monoaza to pentaaza derivatives both open-chain (L1, L2, L3) or cyclic (L4, L5) and having from one to five ferrocenyl groups. Solution studies directed to determine the protonation constants of L1, L2 and L3 have been carried out in water (0.1 mol dm3 KNO3, 25 °C) and those of L4 and L5 in 1,4-dioxane-water (70:30 v/v, 0.1 mol dm-3 KNO3, 25 °C). The protonation behaviour of the receptors can be explained taking into account electrostatic considerations. Speciation studies in the presence of phosphate have been carried out in water for L', L2 and L3 and in dioxane-water for L4 and L5. Speciation studies have also been performed in the presence of ATP with L1, L2 and L3 in water. Selectivity of a mixture of receptors against a certain anion is discussed in terms of ternary diagrams. The shift of the redox potential of the ferrocenyl groups as a function of the pH has been studied. The difference between the oxidation potentials at basic and acidic pH has been determined experimentally and is compared with that theoretically predicted using an electrostatic model previously reported. The electrochemical shift in the presence of ATP and phosphate has been measured in water for L1, L2 and L3 and in the presence of phosphate and sulfate in 1,4-dioxane-water for L4 and L5 as a function of the pH. The electrochemical response found against those anions is quite poor with maximum cathodic shifts off. 30tO mV. The electrochemical response induced by HSO4 and H2PO4- has also been studied in acetonitrile solutions where a large cathodic shift for H2PO4- up to ca. 200 mV was found. The Royal Society of Chemistry 2000.
Amphiphilic [5:1]- and [3:3]-hexakisadducts of C60
Braun, Martin,Hartnagel, Uwe,Ravanelli, Elena,Schade, Boris,Boettcher, Christoph,Vostrowsky, Otto,Hirsch, Andreas
, p. 1983 - 2001 (2004)
We have synthesized and characterized a variety of new amphiphilic hexakisadducts of C60 involving mixed octahedral [5:1]- and [3:3]-addition patterns. The [5:1]-adducts 3 and 13 contain five pairs of didodecyl or diethyl malonates as non-polar addends and, as their polar part, an extended bis(malonate) involving C14 and ethylene glycol chains and two biotin termini. For the first time, amphiphilic [3:3]-hexakisadducts have been prepared using the e,e,e-trisadduct 18, which contains a cyclo-[3]-octyl malonate addend, as the precursor. As polar groups, we used malonates featuring carboxy, amino, or peptide termini. The charge on the termini, which can range from zero up to sixfold positive or sixfold negative, can be built up by protonation or deprotonation. All the amphiphilic [3:3]-hexakisadducts are very soluble in water in their completely charged forms. Initial investigations on the aggregation properties of the amphiphilic [3:3]-hexakisadducts, conducted using transmission electron microscopy (TEM) and pulse-gradient spin echo (PGSE) NMR spectroscopy, reveal the pH-dependent formation of aggregates. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
