- Synthesis and antibacterial activity of pyridinium-tailored aromatic amphiphiles
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In this Letter, the antibacterial activities of pyridinium-tailored aromatic amphiphiles were evaluated by turbidimeter tests in vitro. The bioassays revealed that most of the target compounds exhibit appreciable inhibition activities against the plant pathogenic bacteria Xanthomonas oryzae pv. oryzae, Ralstonia solanacearum, and Xanthomonas axonopodis pv. citri. The half-maximal effective concentrations (EC50) of 2-NP-10, 9-AP-10, and 9-AP-7 against these three bacteria were relatively high, which may be ascribed to the favourable hydrophobicity/hydrophilicity balance in these compounds. Our results suggest that pyridinium-tailored aromatic amphiphiles are promising bactericide candidates against plant bacterial diseases.
- Wang, Peiyi,Gao, Manni,Zhou, Lei,Wu, Zhibing,Hu, Deyu,Yang, Song,Hu, Jun
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- Synthesis, Surface Activity, and Biological Activities of Phosphonium and Metronidazole Salts
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A series of phosphonium amphiphilic compounds was synthesized. Cationic parts of molecules contain triphenylphosphonium moieties. Lipophilic parts of compounds are represented by straight alkyl chain or the alkyl chains which are ornamented by benzyl or metronidazole. The physicochemical properties of phosphonium amphiphilic compounds were investigated by the measurements of surface tension and conductivity. The critical micelle concentration (cmc), the surface tension value at the cmc (γcmc), the surface area at the surface saturation per head group (Acmc) were determined. The lowest cmc value was determined for phosphonium salts with straight dodecyl alkyl chain. Its value was 1.5 × 10?3 mol dm?3. Surface tension at the cmc decreases with the addition of bulky moieties (benzyl, radical from metronidazol) at the end of alkyl chains. Biological activities of compounds were studied on human erythrocytes and strains of Acanthamoeba lugdunensis and Acanthamoeba quina. Dodecyltriphenylphosphonium bromide showed the highest activity against Acanthamoeba. To the best of our knowledge, it is the first compound of the group of phosphonium amphiphiles, which exhibited high activity against Acanthamoeba. The determined structure–activity relationship indicated nonspecific trophocidal and hemolytic activity that depends on physicochemical properties of the studied compounds.
- Luká?, Milo?,Pisár?ik, Martin,Garajová, Mária,Mrva, Martin,Du?eková, Aneta,Vrták, Andrej,Horáková, Renáta,Horváth, Branislav,Devínsky, Ferdinand
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p. 1025 - 1032
(2020/07/27)
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- Synthesis and biodistribution studies of 99mTc labeled fatty acid derivatives prepared via “Click approach” for potential use in cardiac imaging
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123I-Iodophenylpentadecanoic acid (IPPA) is a metabolic agent used in nuclear medicine for diagnosis of myocardial defects. Efforts are underway worldwide to develop a 99mTc substitute of the above radiopharmaceutical for the aforementioned application. Herein, we report synthesis and biodistribution studies of 99mTc labeled fatty acids (8, 11, and 15 carbons) obtained via “click chemistry” for its potential use in myocardial imaging. ω-Bromo fatty acids (8C/11C/15C) were synthetically modified at bromo terminal to introduce a heterocyclic triazole with glycine sidearm in a five step procedure. Modified fatty acids were subsequently radiolabeled with preformed [99mTc(CO)3]+ synthon to yield the desired fatty acid complexes which were evaluated in Swiss mice. All the radiolabeled complexes were obtained with radiochemical purities >80%, as characterized by HPLC. Biodistribution studies of all three complexes in Swiss mice showed myocardial uptake of ~6-9% ID/g at 2?minutes post-injection, close to*I-IPPA (~9% ID/g). Complexes exhibited significant retention in the myocardium up to 30?minutes (~1% ID/g) but were lower to the standard agent (~7% ID/g). Similar uptake of activity in myocardium for the newly synthesized complexes in comparison to 125I-IPPA along with favorable in vivo pharmacokinetics merits potential for the present “click” design of complexes for myocardial imaging.
- Das, Soumen,Mathur, Anupam,Sakhare, Navin,Mallia, Madhava B.,Sarma, Haladhar Dev,Sachdev, Satbir Singh,Dash, Ashutosh
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p. 1048 - 1057
(2018/10/09)
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- FATTY ACIDS AND THEIR USE IN CONJUGATION TO BIOMOLECULES
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The invention provides a conjugate comprising a biomolecule linked to a fatty acid via a linker wherein the fatty acid has the following Formulae A1, A2 or A3: wherein R1, R2, R3, R4, Ak, n, m and p are defined herein. The invention also relates to a method for manufacturing the conjugate of the invention such as GDF15 conjugate, and its therapeutic uses such as treatment or prevention of metabolic disorders or diseases, type 2 diabetes mellitus, obesity, pancreatitis, dyslipidemia, alcoholic and nonalcoholic fatty liver disease/steatohepatitis and other progressive liver diseases, insulin resistance, hyperinsulinemia, glucose intolerance, hyperglycemia, metabolic syndrome, hypertension, cardiovascular disease, atherosclerosis, peripheral arterial disease, stroke, heart failure, coronary heart disease, diabetic complications (including but not limited to chronic kidney disease), neuropathy, gastroparesis and other metabolic disorders. The present invention further provides a combination of pharmacologically active agents and a pharmaceutical composition.
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Page/Page column 124
(2016/01/25)
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- COMPOUNDS
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The invention relates to new derivatives of 5-aminolevulinic acid (5-ALA) and their use as photosensitizing agents. In particular, it relates to compounds of general formula I and their pharmaceutically acceptable salts, to methods for preparing such compounds and their medical and cosmetic use, for example in methods of photodynamic therapy and diagnosis: wherein R1 represents a hydrogen atom or an optionally substituted alkyl or cycloalkyl group; R2, each of which may be the same or different, represents a hydrogen atom or an optionally substituted alkyl group; and X is a linking group.
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Page/Page column 58
(2014/02/16)
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- Self-assembly of pyridinium-functionalized anthracenes: Molecular-skeleton-directed formation of microsheets and microtubes
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Two amphiphilic regioisomers, 9-AP (1-[11-(9-anthracenylmethoxy)-11- oxoundecyl]pyridinium bromide), and 2-AP (1-[11-(2-anthracenyl methoxy)-11-oxoundecyl]pyridinium bromide), were synthesized and their assembly behaviors were studied. Due to the anisotropic features of the anthracene structure, different substituted positions on the anthracene ring lead 9-AP and 2-AP to adapt "shaver" and "spatula"-like molecular shapes, respectively, which consequently dictate the structure of their final assemblies. While "shaver"-shaped 9-AP assembled into microsheets, driven by π-π interactions, "spatula"-shaped 2-AP assembled into microtubular structures, promoted primarily by charge-transfer interactions. Self-assembly: Two anthracene-based amphiphilic regioisomers, 9-AP and 2-AP, were synthesized. Due to the anisotropy of the anthracene structure, different substitutions on anthracene rings led 9-AP and 2-AP to adapt different molecular structures and self-assembled morphologies (see figure). While "shaver"-shaped 9-AP assembled into microsheets through π-π interactions, "spatula"-shaped 2-AP transformed into microtubes due to charge-transfer interactions.
- Hu, Jun,Wang, Peiyi,Lin, Yuan,Zhang, Jidong,Smith, Mark,Pellechia, Perry J.,Yang, Song,Song, Baoan,Wang, Qian
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supporting information
p. 7603 - 7607
(2014/07/07)
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- Supramolecular architectures from bent-core dendritic molecules
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Control of the self-assembly of small molecules to generate architectures with diverse shapes and dimensions is a challenging research field. We report unprecedented results on the ability of ionic, bent dendritic molecules to aggregate in water. A range of analytical techniques (TEM, SEM, SAED, and XRD) provide evidence of the formation of rods, spheres, fibers, helical ribbons, or tubules from achiral molecules. The compact packing of the bent-core structures, which promotes the bent-core mesophases, also occurs in the presence of a poor solvent to provide products ranging from single objects to supramolecular gels. The subtle balance of molecule/solvent interactions and appropriate molecular designs also allows the transfer of molecular conformational chirality to morphological chirality in the overall superstructure. Functional motifs and controlled morphologies can be combined, thereby opening up new prospects for the generation of nanostructured materials through a bottom-up strategy.
- Cano, Miguel,Snchez-Ferrer, Antoni,Serrano, Jos Luis,Gimeno, Nlida,Ros, M. Blanca
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supporting information
p. 13449 - 13453
(2015/02/19)
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- Liquid crystalline 4-(2,3 Dihydroxypropoxy) diphenyl 4-n-alcoxy acids
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4-(2,3 Dihydroxypropoxy) diphenyl 4-oxy-hexanoic acid and 4-(2,3 dihydroxypropoxy) diphenyl 4-oxy-undecanoic acid have been synthesized and analyzed by IR and NMR experiments. The liquid crystalline character and the phase transitions of these two acids have been studied by differential scanning calorimetry (DSC) and variable temperature X-ray diffraction (VTXRD). These two liquid crystalline monomers are designed to be flexible, rigid and polyfunctional, so that they can be used in the synthesis of new macromolecules with side chain liquid crystals.
- Lopez-Velazquez, Delia,Hernandez-Sosa, Armando R.,Perez, Ernesto,Castillo-Rojas, Susana
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experimental part
p. 175 - 184
(2012/04/05)
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- Synthesis of bifunctional hydroxamic acids as novel ligands for the hydrophilic stabilization of iron oxide nanoparticles
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A general method for synthesizing bifunctional hydroxamic acids containing carboxylic acid or amino functionalities is reported. Various products from simple alkyl to complex dendrimer-like structures are described. Such molecules have recently been used in ligand-exchange reactions for the hydrophilic stabilization of originally oleic acid protected iron oxide nanoparticles. Georg Thieme Verlag Stuttgart · New York.
- Hofmann, Andreas,Graf, Christina,Kung, Shih-Hao,Kim, Myeongseob,Peng, Xiaogang,El-Aama, Randa,Ruehl, Eckart
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experimental part
p. 1150 - 1158
(2010/06/13)
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- Synthesis and preliminary biological studies of hemifluorinated bifunctional bolaamphiphiles designed for gene delivery
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The multistep synthesis of a new series of dissymmetric hemifluorocarbon bolaamphiphiles designed for gene transport is described. The dissymmetric functionalization of diiodoperfluoroctane leads to bolaamphiphile molecules composed of a partially fluorocarbon core end-capped with a glycoside and an ammonium salt derived from histidine or lysine. Initial biological results indicate that one of the bolaamphiphile - end-capped with a lysine and a lactobionamide residue - induces a remarkably low cytotoxicity on COS-7 cells and, when self-assembled with DNA plasmid, generates a significant in vitro transfection efficiency without the addition of any fusogenic lipid. the Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2006.
- Denoyelle, Severine,Polidori, Ange,Brunelle, Melanie,Vuillaume, Pascal Y.,Laurent, Sylvette,ElAzhary, Yousef,Pucci, Bernard
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p. 629 - 646
(2007/10/03)
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- Discotic liquid crystalline poly(propylene imine) dendrimers based on triphenylene
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The design, synthesis, and mesomorphic properties of a new series of homodendrimers consisting of the commercially available poly(propylene imine) (PPI) dendrimers (G = 1-5), PPI-(NH2)n (n = 4, 8, 16, 32, 64), functionalized with a discotic triphenylene moiety are reported. The liquid crystalline behavior was investigated by means of differential scanning calorimetry (DSC), polarizing-light optical microscopy (POM), and X-ray diffractometry (XRD). All of the homodendrimers showed mesomorphic properties, with the second to fifth generations giving a hexagonal columnar mesophase (Colh) and the first generation a rectangular columnar mesophase (Colr). The X-ray study reveals that these mesophases show a highly ordered structure with segregation of triphenylenes and dendrimers into separate columns and a regular stacking distance inside the triphenylene columns. GPC analysis showed that the dendrimers had good monodispersity and MALDI-TOF studies of the first three generations gave good evidence that all of the terminal amino groups of the dendrimers were functionalized with a discotic unit.
- McKenna, Mark D.,Barbera, Joaquin,Marcos, Mercedes,Serrano, Jose Luis
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p. 619 - 625
(2007/10/03)
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- End-on and side-on nematic liquid crystal dendrimers
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A group of nematic materials based on poly(propyleneimine) dendrimers (PPI) containing two types of mesogenic subunits were synthesized. The presence of different types of mesogenic group, the topology of the attachment to the core (end-on and side-on), and the chemical nature of the linking connection to the PPI scaffold (imine or amide) were used to tailor the mesomorphic properties. The materials were characterized by a variety of techniques including 1H, 13C NMR spectroscopy, GPC, MALDI-TOF MS, DSC, POM, and X-ray diffraction. The crystalline state, when it exists, was found to be suppressed for most of the materials once they had undergone the first transition to the Isotropic phase. The majority of the compounds exhibited glass transitions near to or lower than room temperature and an accompanying wide temperature range mesophaae. All of the side-on dendrimers synthesized exhibit a nematic mesophase whereas end-on dendrimers exhibit different mesophases depending on the length of the terminal chain of the mesogenic unit (nematic for n = 2, 4, 5). The 2H NMR technique was used to investigate the symmetry of the nematic phase formed by the side-on dendrimers (G = 3). These studies revealed that the symmetry of the nematic phase is uniaxial. They also allow the investigation of the orientational order of the phase and the rate of field-induced director alignment.
- Pastor, Laura,Barbera, Joaquin,McKenna, Mark,Marcos, Mercedes,Martin-Rapun, Rafael,Serrano, Jose Luis,Luckhurst, Geoffrey R.,Mainal, Azizah
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p. 9386 - 9394
(2007/10/03)
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- Contrast media for infarction and necrosis imaging
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The invention relates to new compounds that are suitable as contrast media especially for infarction and necrosis imaging, process for their production and pharmaceutical agents that contain these compounds.
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- Channel-Type Molecular Structures Part 2 Synthesis of Bouquet-Shaped Molecules Based on a β-Cyclodextrin Core
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A new series of channel-type molecules presenting the features of potential transmembrane structures is described.They result from the grafting of amphiphilic side chains on a β-cyclodextrin derivative 3 that constitutes the organizing core.They belong to the 'bouquet' family (B).Compounds bearing poly(oxyethylene) side chains, BOCD 16 and 17, and their polymethylene analogues BCCD 18 and 19, were synthesized.The properties investigated emphasize the suitability of such molecules to be incorporated into lipid bilayer membranes.
- Canceill, Josette,Jullien, Ludovic,Lacombe, Liliane,Lehn, Jean-Marie
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p. 791 - 812
(2007/10/02)
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