- Straightforward synthesis of fluorinated amphiphilic thiols
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C8-perfluoroalkyl thiols bearing a polyoxyethylene chain of variable length were prepared in good yields following a straightforward synthetic strategy. These thiols are soluble in organic solvents of different polarities from chloroform to methanol. The thiol with a PEG550 chain shows very good solubility in water. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
- Gentilini, Cristina,Boccalon, Mariangela,Pasquato, Lucia
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Read Online
- Enzymatic synthesis of organic-polymer-grafted DNA
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To create bioorganic hybrid materials, interdisciplinary work in the fields of chemistry, biology and materials science is conducted. DNA block copolymers are promising hybrid materials due to the combination of properties intrinsic to both the polymer an
- Baccaro, Anna,Marx, Andreas
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Read Online
- Alkaline earth metal-sensing anthracene fluorophore-hosts
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Novel anthracene fluorophore-hosts 1-4, bonding through an ester or ether linkage to a crown ether or polyether side-arm, have been synthesized. Addition of an alkaline earth metal cation to a host solution causes a unique fluorescence intensity change. That is, the hosts bonding through an ester linkage, compounds 1 and 3, give fluorescence quenching, whereas the hosts bonding through an ether linkage, compounds 2 and 4, give fluorescence enhancement. The host having a crown ether side-arm, compound 2, recognises calcium cations more strongly than barium cations, in contrast to the host having a polyether side-arm, compound 4, which prefers barium cations to calcium cations.
- Iwata, Satoru,Matsuoka, Hideo,Tanaka, Kiyoshi
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Read Online
- Micelle/monomer control over the membrane-disrupting properties of an amphiphilic antibiotic
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A homologous series of amphotericin B-oligo(ethylene glycol) conjugates has been synthesized, via condensation of the carboxylic acid group of amphotericin B with oligo(ethylene glycol)-substituted amines [NH2(CH2-CH2O)(n)CH3, where n = 1, 6, 15], and examined with respect to their aggregation properties and their ability to disrupt the membrane integrity of Candida albicans and human red blood cells. Incremental increase in the size of the oligo(ethylene glycol) moiety leads to a significant increase in the critical micelle concentration of the macrolide and to a corresponding increase in the concentration that is required for hemolysis. In sharp contrast, the same increase in oligo(ethylene glycol) size affords only a modest reduction in antifungal activity; the net result is a separation of antifungal and hemolytic activity. These results clearly highlight the need for taking into account the aggregation properties of membrane-disrupting antibiotics with respect to target recognition and specificity and also with regard to rational molecular design.
- Yamashita, Keiji,Janout, Vaclav,Bernard, Edward M.,Armstrong, Donald,Regen, Steven L.
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Read Online
- Targeting G Protein-Coupled Receptors with Magnetic Carbon Nanotubes: The Case of the A3 Adenosine Receptor
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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.
- Pineux, Florent,Federico, Stephanie,Klotz, Karl-Norbert,Kachler, Sonja,Michiels, Carine,Sturlese, Mattia,Prato, Maurizio,Spalluto, Giampiero,Moro, Stefano,Bonifazi, Davide
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supporting information
p. 1909 - 1920
(2020/09/11)
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- Compound, preparation method thereof and application of compound as fluorescent probe for detecting near-infrared two-region of acetoaldehyde (by machine translation)
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The invention provides a compound, a preparation method thereof and application of the compound as an acetone aldehyde near-infrared two-zone fluorescent probe. The compound has the structure shown by general I and has good response to propionaldehyde. ,
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Paragraph 0094-0096
(2020/06/09)
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- Self-Assembly and Molecular Recognition in Water: Tubular Stacking and Guest-Templated Discrete Assembly of Water-Soluble, Shape-Persistent Macrocycles
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Supramolecular chemistry in aqueous media is an area with great fundamental and practical significance. To examine the role of multiple noncovalent interactions in controlled assembling and binding behavior in water, the self-association of five water-soluble hexakis(m-phenylene ethynylene) (m-PE) macrocycles, along with the molecular recognition behavior of the resultant assemblies, is investigated with UV-vis, fluorescence, CD, and NMR spectroscopy, mass spectrometry, and computational studies. In contrast to their different extents of self-aggregation in organic solvents, all five macrocycles remain aggregated in water at concentrations down to the micromolar (μM) range. CD spectroscopy reveals that 1-F6 and 1-H6, two macrocycles carrying chiral side chains and capable of H-bonded self-association, assemble into tubular stacks. The tubular stacks serve as supramolecular hosts in water, as exemplified by the interaction of macrocycles 1-H6 and 2-H6 and guests G1 through G4, each having a rod-like oligo(p-phenylene ethynylene) (p-PE) segment flanked by two hydrophilic chains. Fluorescence and 1H NMR spectroscopy revealed the formation of kinetically stable, discrete assemblies upon mixing 2-H6 and a guest. The binding stoichiometry, determined with fluorescence, 1H NMR, and ESI-MS, reveals that the discrete assemblies are novel pseudorotaxanes, each containing a pair of identical guest molecules encased by a tubular stack. The two guest molecules define the number of macrocyclic molecules that comprise the host, which curbs the "infinite" stack growth, resulting in a tubular stack with a cylindrical pore tailoring the length of the p-PE segment of the bound guests. Each complex is stabilized by the action of multiple noncovalent forces including aromatic stacking, side-chain H-bonding, and van der Waals interactions. Thus, the interplay of multiple noncovalent forces aligns the molecules of macrocycles 1 and 2 into tubular stacks with cylindrical inner pores that, upon binding rod-like guests, lead to tight, discrete, and well-ordered tubular assemblies that are unprecedented in water.
- Wang, Qiuhua,Zhong, Yulong,Miller, Daniel P.,Lu, Xiaoxing,Tang, Quan,Lu, Zhong-Lin,Zurek, Eva,Liu, Rui,Gong, Bing
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supporting information
p. 2915 - 2924
(2020/02/04)
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- Hydrophilic metal-organic polyhedra, preparation method thereof and gas separation membrane comprising the same
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The present invention relates to a hydrophilic metal-organic polyhedron, a production method thereof, and a gas separator including the same. More specifically, by producing the hydrophilic metal-organic polyhedron containing a polyethylene oxide-based organic ligand and mixing the same with a crosslinked polyethylene oxide polymer, the hydrophilic metal-organic polyhedron can be applied as a gas separator which exhibits a high CO_2/N_2 permeation selectivity.COPYRIGHT KIPO 2018
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Paragraph 0120-0121
(2018/05/29)
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- CARBON MONOXIDE-RELEASING MOLECULES AND THERAPEUTIC APPLICATIONS THEREOF
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Carbon monoxide-releasing organic molecules are described herein. The molecules can be synthesized prior to administration (e.g., ex vivo) or formed in vivo. In those embodiments where the molecules are formed in vivo, reactants are administered under physiological conditions and undergo a cycloaddition reaction to form a product which releases carbon monoxide. In applying such reactions for therapeutic applications in vivo, the cycloaddition and CO release typically occur only under near-physiological or physiological conditions. For example, in some embodiments, the cycloaddition reaction and/or release of carbon monoxide occur at a temperature of about 37° C and pH of about 7.4. Pharmaceutical compositions and methods for release carbon monoxide are also described.
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Paragraph 0439
(2018/06/06)
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- AMYLOID TARGETING AGENTS AND METHODS OF USING THE SAME
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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.
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Paragraph 0841; 0842
(2018/12/04)
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- Facially Amphipathic Glycopolymers Inhibit Ice Recrystallization
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Antifreeze glycoproteins (AFGPs) from polar fish are the most potent ice recrystallization (growth) inhibitors known, and synthetic mimics are required for low-temperature applications such as cell cryopreservation. Here we introduce facially amphipathic glycopolymers that mimic the three-dimensional structure of AFGPs. Glycopolymers featuring segregated hydrophilic and hydrophobic faces were prepared by ring-opening metathesis polymerization, and their rigid conformation was confirmed by small-angle neutron scattering. Ice recrystallization inhibition (IRI) activity was reduced when a hydrophilic oxo-ether was installed on the glycan-opposing face, but significant activity was restored by incorporating a hydrophobic dimethylfulvene residue. This biomimetic strategy demonstrates that segregated domains of distinct hydrophilicity/hydrophobicity are a crucial motif to introduce IRI activity, which increases our understanding of the complex ice crystal inhibition processes.
- Graham, Ben,Fayter, Alice E. R.,Houston, Judith E.,Evans, Rachel C.,Gibson, Matthew I.
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supporting information
p. 5682 - 5685
(2018/05/09)
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- Phenothiazine derivatives and methods of use thereof
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The present disclosure relates to phenothiazine derivatives such as conjugates of phenothiazine compounds, as well as pharmaceutical compositions thereof. The present disclosure also relates to a method of making and the use of such compounds for treating cancer, e.g., a lung cancer, a colon cancer, breast cancer or pancreatic cancer.
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Page/Page column 44
(2017/08/01)
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- IN VITRO COMPOSITIONS COMPRISING HUMAN SAMPLE AND AMYLOID TARGETING AGENT
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Provided herein are compositions and methods useful for detection of amyloid related disorders in samples, such as human tissue, cell or body fluid. Use of the compositions and methods herein allows for the rapid, in vitro detection of amyloid accumulation, often before amyloid disorder symptoms are manifest or without introduction of foreign fluorophore molecules into a subject.
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Paragraph 00316
(2016/06/01)
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- Complex compound
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PROBLEM TO BE SOLVED: To provide a new complex compound that can be used as a catalyst for an organic synthesis reaction and in particular a surfactant type catalyst having both functions of catalytic ability and surface active ability. SOLUTION: A complex compound comprises a nitrogen-containing heterocyclic carbene ligand represented by formula (A) and including at least one metal atom selected from palladium, silver, rhodium, iridium, and ruthenium as a central metal. (R1 represents a divalent hydrocarbon group that has 2-20 carbon atoms and may include at least one atom selected from N, O, S and halogen atoms; R2 represents a hydrocarbon group having 6-70 carbon atoms and including a polyoxyalkylene group and/or a polyglyceryl group having a polymerization number of 2-20 or a hydrocarbon group having 2-20 carbon atoms and including at least one ionic functional group selected from a sulfonic acid group, a carboxyl group, an ammonium group, or their salts; and R3 represents a hydrocarbon group having 2-20 carbon atoms) SELECTED DRAWING: None COPYRIGHT: (C)2016,JPO&INPIT
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Paragraph 0039; 0040
(2016/10/10)
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- N-monosubstituted methoxy-oligo(ethylene glycol) carbamate ester prodrugs of resveratrol
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Resveratrol is a natural polyphenol with many interesting biological activities. Its pharmacological exploitation in vivo is, however, hindered by its rapid elimination via phase II conjugative metabolism at the intestinal and, most importantly, hepatic levels. One approach to bypass this problem relies on prodrugs. We report here the synthesis, characterization, hydrolysis, and in vivo pharmacokinetic behavior of resveratrol prodrugs in which the OH groups are engaged in an N-monosubstituted carbamate ester linkage. As promoiety, methoxy-oligo(ethylene glycol) groups (m-OEG) (CH3-[OCH2CH2]n-) of defined chain length (n = 3, 4, 6) were used. These are expected to modulate the chemico-physical properties of the resulting derivatives, much like longer poly(ethylene glycol) (PEG) chains, while retaining a relatively low MW and, thus, a favorable drug loading capacity. Intragastric administration to rats resulted in the appearance in the bloodstream of the prodrug and of the products of its partial hydrolysis, confirming protection from first-pass metabolism during absorption.
- Mattarei, Andrea,Azzolini, Michele,Zoratti, Mario,Biasutto, Lucia,Paradisi, Cristina
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p. 16085 - 16102
(2015/12/01)
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- AMYLOID TARGETING AGENTS AND METHODS OF USING THE SAME
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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 the methods for treating of diseases associated with an amyloid or amyloid like proteins.
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Paragraph 00820
(2015/11/10)
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- New derivatives of resveratrol
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A novel class of derivatives of resveratrol is provided which have favourable physico-chemical properties when compared with resveratrol itself. It is characterized by the presence of three carbamate functions, in which resveratrol is the oxygen-linked moiety, while the nitrogen atom carries a substituent conferring desirable characteristics to the molecule. These new compounds are especially suitable as precursors (prodrugs) and vehicles of resveratrol in preparations used as dietary integrators or in pharmaceutical compositions: they are stable towards oxidative degradation allowing for long shelf lifetimes and have suitable reactivity to regenerate and deliver resveratrol under physiological conditions.
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Paragraph 0057-0059
(2014/09/29)
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- Site-specifically phosphorylated lysine peptides
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Protein phosphorylation controls major processes in cells. Although phosphorylation of serine, threonine, and tyrosine and also recently histidine and arginine are well-established, the extent and biological significance of lysine phosphorylation has remained elusive. Research in this area has been particularly limited by the inaccessibility of peptides and proteins that are phosphorylated at specific lysine residues, which are incompatible with solid-phase peptide synthesis (SPPS) due to the intrinsic acid lability of the P(=O)-N phosphoramidate bond. To address this issue, we have developed a new synthetic route for the synthesis of site-specifically phospholysine (pLys)-containing peptides by employing the chemoselectivity of the Staudinger-phosphite reaction. Our synthetic approach relies on the SPPS of unprotected ε-azido lysine-containing peptides and their subsequent reaction to phosphoramidates with phosphite esters before they are converted into the natural modification via UV irradiation or basic deprotection. With these peptides in hand, we demonstrate that electron-transfer dissociation tandem mass spectrometry can be used for unambiguous assignment of phosphorylated-lysine residues within histone peptides and that these peptides can be detected in cell lysates using a bottom-up proteomic approach. This new tagging method is expected to be an essential tool for evaluating the biological relevance of lysine phosphorylation.
- Bertran-Vicente, Jordi,Serwa, Remigiusz A.,Schümann, Michael,Schmieder, Peter,Krause, Eberhard,Hackenberger, Christian P. R.
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supporting information
p. 13622 - 13628
(2015/02/05)
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- Two-dimensional self-assembly of amphiphilic porphyrins on a dynamically shrinking droplet surface
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Developing a new field of molecular self-assembly in the sub-micrometer regime - with precision as high as that used to make discrete nano-sized molecular architectures through molecular design - is a major challenge for supramolecular chemistry. At present, however, there is no effective strategy for controlling the assembling molecules when their quantity is greater than one thousand. Herein, we propose a potential solution by exploiting a novel supramolecular system in conjunction with dynamically shrinking oil droplets, enabling more than a thousand component molecules to organize simultaneously into the form of sub-micrometer-scale ring structures. In our developed system, amphiphilic porphyrins, having potential two-dimensional assembling ability, were compartmentalized into droplets with narrow distributions and molecular numbers. These droplets were subsequently transformed into discrete ring-like structures during the process of solvent removal from the inner organic layer, i.e., shrinking the droplets. Unique self-assembled structures, which are not accessible through conventional supramolecular strategies, can be selectively created depending on the initial stage of the droplet. This journal is The Royal Society of Chemistry 2014.
- Numata, Munenori,Takigami, Yusuke,Hirose, Naoya,Sakai, Ryoichiro
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supporting information
p. 1627 - 1632
(2014/03/21)
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- Alkyne phosphonites for sequential azide-azide couplings
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When Staudinger meets Huisgen! A combination of the copper-catalyzed variant of the Huisgen azide-alkyne cycloaddition (CuAAC) and the Staudinger reaction, the two most successful chemoselective reactions for the transformation of azides, leads to a chemi
- Vallée, M. Robert J.,Artner, Lukas M.,Dernedde, Jens,Hackenberger, Christian P. R.
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supporting information
p. 9504 - 9508
(2013/09/23)
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- Traceless Staudinger acetylation of azides in aqueous buffers
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In this paper, we demonstrate the applicability of water-soluble p-dimethylaminoethyl substituted phosphinomethanethiol in acetyl transfer reactions by the traceless Staudinger ligation with unprotected *-azido lysine containing peptides in aqueous buffer systems. Additionally, we present an improved synthesis pathway for the water-soluble phosphinothiol linkers requiring less steps in a comparable overall yield in comparison to previously published protocols.
- Sowa, Sylwia,Mühlberg, Michaela,Pietrusiewicz, K. Michal,Hackenberger, Christian P.R.
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p. 3465 - 3472
(2013/07/11)
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- CONJUGATE OF A PHOTOSENSITISER AND CHITOSAN AND USES THEREOF
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The present invention relates to novel chitosan-based conjugates, e.g. nanocarriers, comprising a derivative of the biocompatible polymer chitosan conjugated to a photosensitising agent, and uses thereof in photochemical internalisation (PCI) and photodynamic therapy (PDT). The invention also relates to the use of the novel conjugates of the invention in treatment or prevention of diseases, particularly cancer, and for vaccination purposes.
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Page/Page column 83; 84
(2014/01/09)
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- Synthesis, self-assembly, and catalytic activity of 1H-imidazole amphiphiles
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We prepared polycatenar 1H-imidazole amphiphiles having a structure in which a 1H-imidazole head was connected through a benzene ring to a pheny group having two or three oligo(ethylene glycol) chains and studied their supramolecular assembly by fluorescence spectroscopy, transmission electron microscopy (TEM) and atomic force microscopy (AFM). When the aqueous solutions of the amphiphiles (5 × 10-5 M ~ 10-3 M) were deposited onto a carbon-coated copper grid and dried, twisted structures with diameters of ~200-300 nm were imaged by TEM and AFM. We presume that the structures comprised a chain of the amphiphile dimers formed via successive hydrogen bonding between the 1H of the imidazole group and 3N of the neighboring one. In a solution of pH 4, entangled fibers with diameters of several nanometers were observed by TEM. In a pH 10 solution, film-like aggregates formed exclusively. The 1H-imidazole amphiphiles hydrolyzed tetraethoxysilane to induce gelation to form fibrous and spherical silica structures at neutral pH in aqueous solutions. No silica was formed when imidazole was used instead of the amphiphiles, suggesting that the selfassembled aggregates of the amphiphiles were responsible for the gelation.
- Park, Jun Ha,Kim, Min Soo,Seo, Sang Hyuk,Chang, Ji Young
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experimental part
p. 2193 - 2198
(2012/06/04)
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- A modular approach for the construction and modification of glyco-SAMs utilizing 1,3-dipolar cycloaddition
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We report the synthesis of a broad variety of functionalized molecules for assembly on gold, allowing the formation of biologically relevant SAMs by a modular approach: either utilizing 1,3-dipolar cycloaddition of alkynes and azides in solution or by 'cl
- Kleinert, Mike,Winkler, Tobias,Terfort, Andreas,Lindhorst, Thisbe K.
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experimental part
p. 2118 - 2132
(2009/02/01)
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- Self-assembly of photochromic diarylethenes with amphiphilic side chains: Reversible thermal and photochemical control
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(Graph Presented) Diarylethene derivatives with hexaethylene glycol side chains were synthesized and their self-assembling and photochromic reactivity were investigated. The diarylethenes showed photochromism in organic solvents and even in water. The aqueous solution of the compounds turned turbid quickly upon heating. The clouding behavior was investigated using 1H NMR spectroscopy, dynamic light scattering, and absorption spectroscopy. It was revealed that, in the aqueous solution, the compounds self-assembled into aggregates, and the aggregates were loosened by raising the temperature. The cloud-point temperature of the closed-ring isomer was 5-7°C lower than that of the open-ring isomer. When asymmetric methyl groups were introduced in the amphiphilic side chains, induced circular dichroism (ICD) was observed upon irradiation with UV light in water. This ICD was explained by the difference in the self-assembling behavior between the open- and the closed-ring isomers. It was suggested that the closed-ring isomers assembled into a chiral nanostructure.
- Hirose, Takashi,Matsuda, Kenji,Irie, Masahiro
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p. 7499 - 7508
(2007/10/03)
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- Nonionic Amphiphilic Compounds from Lysine as Molecular Mimics of Lecithins
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New monodisperse nonionic surfactant molecules, based on lysine with two fatty acid chains in the hydrophobic part and one or two polyoxoethylene methoxycapped chains (EOn-Me) in the hydrophilic headgroup, are synthesized as mimics of natural lecithins.Their surface-activity properties indicate that these compounds have surfactant behavior whose global hydrophobic contribution is comparable to that of one fatty chain. - Key Words: Amphiphilic compounds; critical micelle concentration; mimics of lecithins; surface tension
- Seguer, J.,Selve, C.,Allouch, M.,Infante, M. R.
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