- Dithio-phospholipids for oriented immobilization of proteins to gold surfaces
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We report the syntheses of phospholipids containing a dithio-group on their hydrophobic end and a choline or a biotin-group on their hydrophilic end. As demonstrated by surface plasmon resonance, a monolayer of these dithiolipids on gold affords specific binding of streptavidin and of biotinylated molecules in further steps.
- Kada, Gerald,Riener, Christian K.,Gruber, Hermann J.
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- A novel fluorescent long-chain fatty acid-substituted dye: labeling and biodegrading of Microthrix parvicella
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Microthrix parvicella (M. parvicella) is a filamentous bacterium that induces bulking in activated sludge. Here, we used the affinity of long-chain fatty acids (LCFA) for M. parvicella to create a novel fluorescent probe of carbazole modified by LCFA. The structure was characterized by 1H NMR spectroscopy and mass spectrometry. The spectral properties, photostability, and hydrophobic properties of the probe were also characterized. Fluorescent-labeling results showed that it can label M. parvicella in situ and could be biodegraded via metabolism. The stable docking mode of carbazole probes with different fatty acid chains and lipases was also docked by the density functional tight-binding (DFTB) method.
- Gu, Yingchun,Lin, Dayong,Fei, Xuening,Wang, Cuihong,Yang, Qi,Tang, Yalin,Ren, Xueling
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- Bond insertion, complexation, and penetration pathways of vapor-deposited aluminum atoms with HO- and CH3O-terminated organic monolayers
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The interaction of vapor-deposited Al atoms with self-assembled monolayers (SAMs) of HS-(CH2)16-X (X = -OH and -OCH3) chemisorbed at polycrystalline Au{111} surfaces was studied using time-of-flight secondary-ion mass spectrometry, X-ray photoelectron spectroscopy, and infrared reflectance spectroscopy. Whereas quantum chemical theory calculations show that Al insertion into the C-C, C-H, C-O, and O-H bonds is favorable energetically, it is observed that deposited Al inserts only with the OH SAM to form an -O-Al-H product. This reaction appears to cease prior to complete -OH consumption, and is followed by formation of a few overlayers of a nonmetallic type of phase and finally deposition of a metallic film. In contrast, for the OCH3 SAM, the deposited Al atoms partition along two parallel paths: nucleation and growth of an overlayer metal film, and penetration through the OCH3 SAM to the monolayer/Au interface region. By considering a previous observation that a CH3 terminal group favors penetration as the dominant initial process, and using theory calculations of Al-molecule interaction energies, we suggest that the competition between the penetration and overlayer film nucleation channels is regulated by small differences in the Al-SAM terminal group interaction energies. These results demonstrate the highly subtle effects of surface structure and composition on the nucleation and growth of metal films on organic surfaces and point to a new perspective on organometallic and metal-solvent interactions.
- Fisher, Gregory L.,Walker, Amy V.,Hooper, Andrew E.,Tighe, Timothy B.,Bahnck, Kevin B.,Skriba, Hope T.,Reinard, Michael D.,Haynie, Brendan C.,Opila, Robert L.,Winograd, Nicholas,Allara, David L.
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- NOVEL AMIDE DERIVATIVES OF LINAGLIPTIN AND PROCESS FOR THE PREPARATION THEREOF
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The present disclosure relates to novel hydroxyl or halogen or hydrogen substituted derivatives of Palmitic acid or Palmitoyl halide amide of Linagliptin compound of formula I and process for preparing the same. The said compounds used in pharmaceutical composition for the treatment of type 2 diabetes mellitus, wherein R1 = C2 to C16 alkyl substituted by halogen or hydroxyl or hydrogen.
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Page/Page column 19
(2021/04/17)
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- Discovery and Pharmacological Studies of 4-Hydroxyphenyl-Derived Phosphonium Salts Active in a Mouse Model of Visceral Leishmaniasis
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We report the discovery of new 4-hydroxyphenyl phosphonium salt derivatives active in the submicromolar range (EC50 from 0.04 to 0.28 μM, SI > 10) against the protozoan parasite Leishmania donovani. The pharmacokinetics and in vivo oral efficacy of compound 1 [(16-(2,4-dihydroxyphenyl)-16-oxohexadecyl)triphenylphosphonium bromide] in a mouse model of visceral leishmaniasis were established. Compound 1 reduced the parasite load in spleen (98.9%) and liver (95.3%) of infected mice after an oral dosage of four daily doses of 1.5 mg/kg. Mode of action studies showed that compound 1 diffuses across the plasma membrane, as designed, and targets the mitochondrion of Leishmania parasites. Disruption of the energetic metabolism, with a decrease of intracellular ATP levels as well as mitochondrial depolarization together with a significant reactive oxygen species production, contributes to the leishmanicidal effect of 1. Importantly, this compound was equally effective against antimonials and miltefosine-resistant clinical isolates of Leishmania infantum, indicating its potential as antileishmanial lead.
- Manzano, José Ignacio,Cueto-Díaz, Eduardo J.,Olías-Molero, Ana Isabel,Perea, Ana,Herraiz, Tomás,Torrado, Juan J.,Alunda, José María,Gamarro, Francisco,Dardonville, Christophe
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p. 10664 - 10675
(2019/12/04)
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- Amantadine hapten and preparing method and application thereof
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The invention relates to the field of preparation of haptens, in particular to an amantadine hapten and a preparing method and application thereof. When the amantadine hapten is prepared, amantadine and bromine polyhydroxyalkanoate serve as raw materials, and through a nucleophilic substitution reaction, amidogen groups in amantadine molecules are connected with the bromine polyhydroxyalkanoate; then through a hydrolysis reaction, carboxyl groups are introduced to obtain a corresponding product. The amantadine hapten can be coupled with a carrier protein to prepare an artificial antigen, the artificial antigen is prepared into a monoclonal antibody or a polyclonal antibody through an immune animal, and then the monoclonal antibody or the polyclonal antibody can be used for quickly detecting residues of the amantadine in an animal product.
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Paragraph 0084; 0086; 0092
(2019/10/01)
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- PROCESS FOR TREATING KERATIN FIBRES WITH A CATIONIC DISULFIDE COMPOUND
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Process for treating keratin fibres with a cationic disulfide compound The invention relates to a process for treating keratin fibres, in particular human keratin fibres such as the hair, comprising: (i) a step of applying a compound (I) and also the acid or base salts thereof, the optical or geometrical isomers thereof, and the solvates thereof such as hydrates, in which compound of formula (I) R1, R2, R3, R4, x, m, n, X-, areas defined in the description; (ii) a step of heating the keratin fibres to a temperature of at least 100°C, preferably ranging from 100 to 250°C; it is understood that steps (i) and (ii) may be performed at the same time or separately. The process makes it possible to obtain good hair-conditioning cosmetic properties, with a long-lasting effect. The invention also relates to the novel compounds and to a cosmetic composition comprising such a compound.
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Page/Page column 23
(2017/06/09)
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- Incorporation studies of clickable ceramides in Jurkat cell plasma membranes
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The incorporation properties of ceramide analogues for click chemistry in Jurkat T cells were investigated. The analogues varied in the acyl chain length and the position of the functional group for click chemistry. Fluorescence microscopy studies including anisotropy and quenching experiments showed significant differences in the accessibility of the functional group indicating different incorporation properties into the plasma membrane.
- Walter,Schlegel,Burgert,Kurz,Seibel,Sauer
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supporting information
p. 6836 - 6839
(2017/07/10)
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- METHOD FOR PRODUCING CROSS-COUPLING COMPOUND
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To provide a method for performing a cross-coupling reaction of a Grignard compound with an alkyl halide simply, efficiently and in high yield, a method for obtaining a ω-bromo long chain carboxylic acid simply and efficiently using an easily obtainable raw material and a method for producing a useful branched fatty acid simply and efficiently. [R1: an alkyl group having 1 to 15 carbon atoms, R2: an alkyl group having 1 to 30 carbon atoms with a carboxyl group and X and X': a halogen atom] [n : an integer of 9 to 17] [n : an integer of 9 to 17, R1a : a branched alkyl group having 3 to 8 carbon atoms and X: a halogen atom]
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Page/Page column 20-21
(2010/01/29)
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- Self-assembled monolayers of nitrile-functionalized alkanethiols on gold and silver substrates
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Self-assembled monolayers (SAMs) formed from nitrile-functionalized alkanethiols (AT), NC(CH2)16SH (NC-Cl6), on (111) gold and silver substrates were characterized by X-ray photoelectron spectroscopy, near-edge X-ray absorption fine structure spectroscopy, and contact angle measurements. The average chain tilt angles in NC-C16/Ag and NC-C16/Au were estimated to be 29.5° ± 5° and 42.5° ± 5° from the surface normal, respectively, while the data suggest lower ordering for NC-C16/Au. The -C≡N bonds were found to be predominantly oriented in the surface plane with a tilt angle of 65° ± 7° for both NC-C16/Au and NC-C16/ Ag. Comparison with previous data on CH3-terminated SAMs reveals that substitution of weakly interacting CH3 groups by the CN entities results in an increase in the average tilt angles of the alkyl chains by ~7.5° and ~17.5° in AT/Au and AT/Ag, respectively. A strong electrostatic interaction between the polar nitrile groups is assumed to underlie the structural behavior by controlling a balance between the headgroupsubstrate and interchain interactions. The near-parallel orientation of the nitrile groups to the surface in both of these SAMs can be explained on the basis of minimization of the unfavorable CN - CN dipole - dipole interactions.
- Frey,Shaporenko,Zharnikov,Harder,Allara
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p. 7716 - 7725
(2007/10/03)
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- Analogues of glycosphingolipids and glycerolipids suitable for conjugation to gold- and amino-functionalised surfaces
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A general synthesis of analogues of natural lipids, (i.e. lactosylceramide, globotriasylceramide, and phosphatidylcholine) where one of the alkyl chains carries a terminal thiol- or carboxyl functionality, is described. The lipids were prepared by N- or O-acylation of sphingosine or monoacylglycerol derivatives. These lipids are suitable for anchoring to gold- or amino-functionalised surfaces, thus creating mimics of a cell membrane for use in the study of protein-carbohydrate interaction. (C) 2000 Elsevier Science Ltd.
- Ohlsson, J?rgen,Magnusson, G?ran
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p. 9975 - 9984
(2007/10/03)
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- ω-Mercapto analogs of naturally occurring lipids
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Analogs of natural lipids, where one of the alkyl chains carries a terminal thiol functionality, were prepared by N- or O-acylation of sphingosine or monoacylglycerol derivatives, respectively, thus creating lipid mimics suitable for anchoring to e.g. gold surfaces.
- Ohlsson, Joergen,Magnusson, Goeran
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p. 2011 - 2014
(2007/10/03)
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- Process of preparing ω-hydroxy acids
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A new synthesis of ω-hydroxy acids, which employs commercially available starting materials and lowers the cost of production. The process involves coupling a fatty acyl group by enamine chemistry, followed by a ring expansion and selective reduction of ketoacid.
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- Multiple Electron Tunneling Paths across Self-Assembled Monolayers of Alkanethiols with Attached Ruthenium(II/III) Redox Centers
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Alkanethiol monolayers with pendant redox centers are deposited on gold electrodes by selfassembly.The monolayers are composed of both an electroactive thiol, HS(CH2)nC(O)NHCH2pyRu(NH3)5(2+/3+), with 10-15 methylene groups, and a diluent thiol, HS(CH2)mCOOH, also with 10-15 methylene groups.The monolayers are classified as "matched" (n = m), "exposed" ( n = 15, m = 10-14), and "buried" (n = 10, m = 11-15) according to the relative position of the redox center.Cyclic voltammograms in aqueous Na2SO4 indicate that the monolayers are close-packed with the redox centers residing in the aqueous phase in all but the most buried cases.Measurements of electron transfer kinetics by several methods (cyclic voltammetry, ac impedance spectroscopy, chronoamperometry) yield an internally consistent set of kinetic parameters, the standard rate constant ko, and the reorganization energy λ of the redox centers.The reorganization energies are in good agreement with the theoretically predicted value of 1.0 eV for the pyRu(NH3)5 redox centers.Plots of ln(ko) vs m are linear in all three cases.The slopes of the linear regression fit provide tunneling parameters (β, where ko ca. e-βm) of 0.97 +/- 0.03 (matched cases), 0,83 +/- 0.03 (exposed cases) and 0.16 +/- 0.02 (buried cases) per methylene.This pattern of β's is interpreted in terms of electronic coupling between the redox center and the electrode via both the redox thiol and the proximate diluent thiols, with the coupling via the diluent thiols dominating in the exposed cases.
- Finklea, Harry O.,Liu, Luna,Ravenscroft Melissa S.,Punturi, Sesto
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p. 18852 - 18858
(2007/10/03)
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- Spicamycin derivatives and their use as anticancer agents
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Spicamycin derivative represented by the formula (I) or a salt thereof: STR1 wherein R represents specific diverse substituents, for example, a linear alkadienyl having from 11 to 13 carbon atoms, and R1 and R2 respectively represent H or OH. Examples of specific compounds are 6-[4'-N-(N'-trans,trans 2,4-tridecadienoylglycyl)spicaminyl-amino]purine, and 6-[4'-N-(N'-trans,trans-2,4 dodecadienyoly glycyl) spicaminyl-amino]purine. Comopunds according to this invention are useful as a pharmaceutical for inhibition of a tumor, for example, human colon cancer.
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- Synthesis of Very Long Fatty Acid Methyl Esters
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Phosphoranes, produced by treating alkyltriphenylphosphonium bromides with lithium hexamethyldisilazide, reacted with ω-oxo esters to give modest yields of the corresponding methyl cis-alkenoates.By an alternative method, treatment of ω-iodo esters with the complexes formed from reactions of alkylcopper(I) and Grignard reagents gave methyl alkanoates, cis-alkenoates, and methylene-interrupted cis,cis-alka-dienoates and cis,cis,cis-trienoates.The stereochemical integrity of the esters was determined by 13C NMR spectroscopy.
- Kling, Marcel R.,Easton, Christopher J.,Poulos, Alf
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p. 1183 - 1190
(2007/10/02)
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- Macrocyclic complexes of technetium-99m for use as diagnostic radionuclides
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Stable neutral-lipophilic complexes of technetium-99m (Tc-99m) useful as diagnostic radionuclidic imaging agents are formed by complexing technetium-99m pertechnetate with alkylene amine oximes (viz. propylene amine oxime) in aqueous solutions under reducing conditions. The complexes have a zero charge, contain an O--H--O ring closure bond, and are sufficiently stable for parental administration in imaging by scintillation scanning. Substituents can be attached to the C2 to C4 alkylene carbon backbone of the tetradentate amine oxime ligands to structurally modify them and produce a variety of Tc-99m-radiopharmaceuticals with specific body imaging applications.
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- Hypolipidemic and antiatherosclerotic 4-(polyfluoroalkylamino)phenyl compounds
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This disclosure describes novel 4-(polyfluoroalkylamino)phenyl compounds useful as hypolipidemic and antiatherosclerotic agents.
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