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[PMID]:29216584
[Au] Autor:DeBoyace K; Zdaniewski C; Wildfong PLD
[Ad] Endereço:Duquesne University Graduate School of Pharmaceutical Sciences, 600 Forbes Ave, Pittsburgh, PA 15282, United States.
[Ti] Título:Differential scanning calorimetry isothermal hold times can impact interpretations of drug-polymer dispersability in amorphous solid dispersions.
[So] Source:J Pharm Biomed Anal;150:43-50, 2018 Feb 20.
[Is] ISSN:1873-264X
[Cp] País de publicação:England
[La] Idioma:eng
[Ab] Resumo:Differential scanning calorimetry (DSC) is a commonly employed analytical technique for the analysis and characterization of amorphous solid dispersions. However, steps typical of standard temperature programs can alter the material in situ. Data for two active pharmaceutical ingredients are detailed, wherein isothermal hold times, traditionally employed to remove thermal history and/or residual solvent, were observed to impact the observed dispersability of the compounds in polyvinylpyrrolidone vinyl-acetate copolymer (PVPva). Re-crystallized tolbutamide was observed to re-dissolve in PVPva, while terfenadine was observed to crystallize during the isothermal hold period. Exposing co-solidified drug-polymer mixtures to temperature changes and experimental hold times can potentially confound correct categorization of dispersability, particularly when DSC is used as the lone characterization technique. This work illustrates the importance of using a combination of techniques to improve the certainty of conclusions made with respect to the true, initial physical state of a co-solidified mixture.
[Mh] Termos MeSH primário: Varredura Diferencial de Calorimetria/métodos
Pirrolidinas/química
Terfenadina/química
Tolbutamida/química
Compostos de Vinila/química
[Mh] Termos MeSH secundário: Química Farmacêutica/métodos
Cristalização
Polímeros/química
Solubilidade
Solventes/química
Temperatura Ambiente
Fatores de Tempo
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Polymers); 0 (Pyrrolidines); 0 (Solvents); 0 (Vinyl Compounds); 0 (poly(vinylpyrrolidone-co-vinyl-acetate)); 7BA5G9Y06Q (Terfenadine); 982XCM1FOI (Tolbutamide)
[Em] Mês de entrada:1801
[Cu] Atualização por classe:180130
[Lr] Data última revisão:
180130
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:171208
[St] Status:MEDLINE


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[PMID]:28847583
[Au] Autor:Ortner F; Wiemeyer H; Mazzotti M
[Ad] Endereço:Institute of Process Engineering, ETH Zurich, 8092 Zurich, Switzerland.
[Ti] Título:Interconversion and chromatographic separation of carbohydrate stereoisomers on polystyrene-divinylbenzene resins.
[So] Source:J Chromatogr A;1517:54-65, 2017 Sep 29.
[Is] ISSN:1873-3778
[Cp] País de publicação:Netherlands
[La] Idioma:eng
[Ab] Resumo:Mutarotation of sugars causes distorted and splitted peaks in liquid chromatography. The shape of the elution profile is affected by the different anomeric and isomeric forms in solution. The rate of interconversion between the different forms relative to the propagation velocity in the column determines the extent of the distortion. This interplay of interconversion reaction and chromatographic separation was examined both experimentally and theoretically. Elution profiles resulting from pulse injections of glucose and fructose solutions at different flow rates and temperatures were analyzed both qualitatively and quantitatively. Adsorption equilibrium and reaction kinetic parameters were estimated by a simple fitting procedure, based on peak elution times and area ratios obtained from the analysis of the experimental profiles. To enhance the accuracy of the model parameters further, estimated reaction kinetic parameters were provided as an initial guess for inverse fitting to elution profiles, using a numeric mass balance model. Simulations with the numeric model, based on the enhanced parameters, allowed a very precise description of the experimental profiles. Accuracy of the fitted parameters was further confirmed through comparison with literature values. Reaction rate constants for the adsorbed phase were calculated and interpreted based on apparent rate constant values determined in this work, and on literature data for aqueous solutions.
[Mh] Termos MeSH primário: Carboidratos/química
Carboidratos/isolamento & purificação
Técnicas de Química Analítica/métodos
Cromatografia Líquida
Poliestirenos/química
Compostos de Vinila/química
[Mh] Termos MeSH secundário: Adsorção
Isomerismo
Cinética
Estereoisomerismo
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Carbohydrates); 0 (Polystyrenes); 0 (Vinyl Compounds); IZ715T4SBU (divinyl benzene)
[Em] Mês de entrada:1710
[Cu] Atualização por classe:171017
[Lr] Data última revisão:
171017
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:170830
[St] Status:MEDLINE


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[PMID]:28844300
[Au] Autor:Pei M; Huang X
[Ad] Endereço:State Key Laboratory of Marine Environmental Science, Key Laboratory of the Ministry of Education for Coastal and Wetland Ecosystem, College of the Environment and Ecology, Xiamen University, Xiamen 361005, China.
[Ti] Título:Preparation and evaluation of an adsorbent based on poly (muconic acid-co-divinylbenzene/ethylenedimethacrylate) for multiple monolithic fiber solid-phase microextraction of tetracycline antibiotics.
[So] Source:J Chromatogr A;1517:1-8, 2017 Sep 29.
[Is] ISSN:1873-3778
[Cp] País de publicação:Netherlands
[La] Idioma:eng
[Ab] Resumo:To extract tetracycline antibiotics (TAs) effectively, a new adsorbent based on poly (muconic acid-co-divinylbenzene/ethylenedimethacrylate) monolith was fabricated and used as the extraction medium of multiple monolithic fiber solid-phase microextraction (MD/MF-SPME). The effect of the fabrication parameters on extraction efficiency was studied thoroughly. Elemental analysis, infrared spectroscopy, scanning electron microscopy and mercury intrusion porosimetry were used to check the physicochemical properties of the adsorbent. Some key parameters that affect the extraction performance of MD/MF-SPME for TAs were investigated systematically. Under the optimized experimental conditions, the prepared adsorbent could effectively extract the TAs through multiple interactions. At the same time, a simple and sensitive method for monitoring trace TAs in honey samples was developed by coupling MD/MF-SPME with high-performance liquid chromatography tandem mass spectrometry detection (MD/MF-SPME-HPLC-MS/MS). The limits of detection (S/N=3) for target compounds were in the range of 7.3-17.1ng/kg. The intra-day and inter-day precision (relative standard deviations, n=4, %) at 0.5µg/kg and 20.0µg/kg spiking concentrations were 5.0-9.5% and 3.6-10.0%, respectively. The mean recoveries of the target TAs in the real honey samples were between 70.5-111.0%.
[Mh] Termos MeSH primário: Análise de Alimentos/métodos
Mel/análise
Metacrilatos/química
Microextração em Fase Sólida/instrumentação
Tetraciclinas/isolamento & purificação
Compostos de Vinila/química
[Mh] Termos MeSH secundário: Antibacterianos/isolamento & purificação
Cromatografia Líquida de Alta Pressão
Fibras na Dieta/análise
Limite de Detecção
Microscopia Eletrônica de Varredura
Ácido Sórbico/análogos & derivados
Ácido Sórbico/química
Espectrofotometria Infravermelho
Espectrometria de Massas em Tandem
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Anti-Bacterial Agents); 0 (Dietary Fiber); 0 (Methacrylates); 0 (Tetracyclines); 0 (Vinyl Compounds); 3KD92ZL2KH (muconic acid); 7BK5G69305 (ethylene dimethacrylate); IZ715T4SBU (divinyl benzene); X045WJ989B (Sorbic Acid)
[Em] Mês de entrada:1710
[Cu] Atualização por classe:171116
[Lr] Data última revisão:
171116
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:170829
[St] Status:MEDLINE


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[PMID]:28836855
[Au] Autor:Chamsai B; Limmatvapirat S; Sungthongjeen S; Sriamornsak P
[Ad] Endereço:a Department of Pharmaceutical Technology, Faculty of Pharmacy , Silpakorn University , Nakhon Pathom , Thailand.
[Ti] Título:Enhancement of solubility and oral bioavailability of manidipine by formation of ternary solid dispersion with d-α-tocopherol polyethylene glycol 1000 succinate and copovidone.
[So] Source:Drug Dev Ind Pharm;43(12):2064-2075, 2017 Dec.
[Is] ISSN:1520-5762
[Cp] País de publicação:England
[La] Idioma:eng
[Ab] Resumo:CONTEXT: Low bioavailability of oral manidipine (MDP) is due to its low water solubility. OBJECTIVE: The objective of this study was to increase the solubility and bioavailability of MDP by fabricating ternary solid dispersion (tSD) with d-α-tocopherol polyethyleneglycol-1000-succinate and copovidone. METHODS: In this study, solid ternary phase diagram was applied in order to check the homogeneity of tSD prepared by melting and solidifying with dry ice. The physicochemical properties of different formulations were determined by differential scanning calorimetry (DSC), powder X-ray diffraction (PXRD), Fourier transform infrared spectroscopy (FTIR) and hot stage microscopy. Their solubility, dissolution, stability and bioavailability were also investigated. RESULTS AND DISCUSSION: The results demonstrated that tSD obtained from ternary phase diagram divided into homogeneous and non-homogeneous regions. In the homogenous region, the transparent characteristics of tSD was observed and considered as a glass solution, which have a higher MDP solubility than that in non-homogenous region. The hot stage microscopy, DSC and PXRD confirmed that solid dispersion was formed in which MDP was molecularly dispersed in the carriers, especially in the homogenous region of phase diagram. FTIR analysis demonstrated strong hydrogen bonding between amine groups of MDP and carbonyl groups of copovidone, which supported a higher solubility and dissolution of tSD. The pharmacokinetic study in Wistar rats showed that the tSD had the greatest effect on oral bioavailability. Immediate hypotensive effect of tSD was also observed in vivo. CONCLUSIONS: The improvement of stability, dissolution and oral bioavailability of MDP could be achieved by using tSD technique.
[Mh] Termos MeSH primário: Di-Hidropiridinas/química
Di-Hidropiridinas/farmacocinética
Polietilenoglicóis/química
Pirrolidinas/química
Succinatos/química
Compostos de Vinila/química
alfa-Tocoferol/química
alfa-Tocoferol/farmacocinética
[Mh] Termos MeSH secundário: Animais
Disponibilidade Biológica
Varredura Diferencial de Calorimetria
Pós
Ratos
Ratos Wistar
Solubilidade
Espectroscopia de Infravermelho com Transformada de Fourier
Difração de Raios X
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Dihydropyridines); 0 (Powders); 0 (Pyrrolidines); 0 (Succinates); 0 (Vinyl Compounds); 0 (poly(vinylpyrrolidone-co-vinyl-acetate)); 30IQX730WE (Polyethylene Glycols); 6O4754US88 (manidipine); H4N855PNZ1 (alpha-Tocopherol); U076Q6Q621 (polyethylene glycol 1000)
[Em] Mês de entrada:1710
[Cu] Atualização por classe:171018
[Lr] Data última revisão:
171018
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:170825
[St] Status:MEDLINE
[do] DOI:10.1080/03639045.2017.1371731


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[PMID]:28662853
[Au] Autor:Chen S; Li XX; Shu L; Somsundaran P; Li JR
[Ad] Endereço:Key Laboratory of Beijing on Regional Air Pollution Control, College of Environmental and Energy Engineering, Beijing University of Technology, Beijing 100124, PR China. Electronic address: chensha@bjut.edu.cn.
[Ti] Título:The high efficient separation of divinylbenzene and ethylvinylbenzene isomers using high performance liquid chromatography with Fe-based MILs packed columns.
[So] Source:J Chromatogr A;1510:25-32, 2017 Aug 11.
[Is] ISSN:1873-3778
[Cp] País de publicação:Netherlands
[La] Idioma:eng
[Ab] Resumo:The baseline separation of divinylbenzene (DVB) and ethylvinylbenzene (EVB) isomers was achieved using HPLC with MIL-53(Fe) and MIL-100(Fe) packed columns respectively when hexane/dichloromethane (100:0) used as mobile phase, at flow rate of 0.5mLmin , room temperature, and monitored with a UV detector at 254nm. The two Fe-based MILs packed columns showed different separated performances, analytes had short retention time on MIL-100(Fe) compared to MIL-53(Fe), but selectivity of DVB isomers (m-DVB and p-DVB) was lower, which was mainly due to the differences of the pore size and structure of MILs. Moreover, the results of calculated thermodynamic parameters showed that the separation of DVB and EVB isomers was not only controlled by enthalpy change (ΔH), but also controlled by entropy change (ΔS). The head-to-tail stacking was the main reason for the separation according to the mechanism of the DVB and EVB isomers on Fe-based MILs packed columns.
[Mh] Termos MeSH primário: Técnicas de Química Analítica/métodos
Cromatografia Líquida de Alta Pressão
Compostos Organometálicos/isolamento & purificação
Estirenos/isolamento & purificação
Compostos de Vinila/isolamento & purificação
[Mh] Termos MeSH secundário: Técnicas de Química Analítica/instrumentação
Hexanos/química
Ferro/química
Isomerismo
Cloreto de Metileno/química
Compostos Organometálicos/química
Estirenos/química
Termodinâmica
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Hexanes); 0 (Organometallic Compounds); 0 (Styrenes); 0 (Vinyl Compounds); 588X2YUY0A (Methylene Chloride); E1UOL152H7 (Iron); IZ715T4SBU (divinyl benzene)
[Em] Mês de entrada:1710
[Cu] Atualização por classe:171017
[Lr] Data última revisão:
171017
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:170701
[St] Status:MEDLINE


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[PMID]:28591791
[Au] Autor:Haraszti RA; Roux L; Coles AH; Turanov AA; Alterman JF; Echeverria D; Godinho BMDC; Aronin N; Khvorova A
[Ad] Endereço:RNA Therapeutics Institute, University of Massachusetts Medical School, 01605 Worcester, MA, USA.
[Ti] Título:5΄-Vinylphosphonate improves tissue accumulation and efficacy of conjugated siRNAs in vivo.
[So] Source:Nucleic Acids Res;45(13):7581-7592, 2017 Jul 27.
[Is] ISSN:1362-4962
[Cp] País de publicação:England
[La] Idioma:eng
[Ab] Resumo:5΄-Vinylphosphonate modification of siRNAs protects them from phosphatases, and improves silencing activity. Here, we show that 5΄-vinylphosphonate confers novel properties to siRNAs. Specifically, 5΄-vinylphosphonate (i) increases siRNA accumulation in tissues, (ii) extends duration of silencing in multiple organs and (iii) protects siRNAs from 5΄-to-3΄ exonucleases. Delivery of conjugated siRNAs requires extensive chemical modifications to achieve stability in vivo. Because chemically modified siRNAs are poor substrates for phosphorylation by kinases, and 5΄-phosphate is required for loading into RNA-induced silencing complex, the synthetic addition of a 5΄-phosphate on a fully modified siRNA guide strand is expected to be beneficial. Here, we show that synthetic phosphorylation of fully modified cholesterol-conjugated siRNAs increases their potency and efficacy in vitro, but when delivered systemically to mice, the 5΄-phosphate is removed within 2 hours. The 5΄-phosphate mimic 5΄-(E)-vinylphosphonate stabilizes the 5΄ end of the guide strand by protecting it from phosphatases and 5΄-to-3΄ exonucleases. The improved stability increases guide strand accumulation and retention in tissues, which significantly enhances the efficacy of cholesterol-conjugated siRNAs and the duration of silencing in vivo. Moreover, we show that 5΄-(E)-vinylphosphonate stabilizes 5΄ phosphate, thereby enabling systemic delivery to and silencing in kidney and heart.
[Mh] Termos MeSH primário: Organofosfonatos/farmacologia
RNA Interferente Pequeno/metabolismo
Compostos de Vinila/farmacologia
[Mh] Termos MeSH secundário: Animais
Exorribonucleases/metabolismo
Feminino
Inativação Gênica
Células HeLa
Seres Humanos
Interações Hidrofóbicas e Hidrofílicas
Rim/metabolismo
Fígado/metabolismo
Camundongos
Modelos Moleculares
Conformação de Ácido Nucleico
Fosforilação
Estabilidade de RNA/efeitos dos fármacos
RNA Guia/química
RNA Guia/genética
RNA Guia/metabolismo
RNA Interferente Pequeno/química
RNA Interferente Pequeno/genética
Complexo de Inativação Induzido por RNA/química
Complexo de Inativação Induzido por RNA/genética
Complexo de Inativação Induzido por RNA/metabolismo
Distribuição Tecidual
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Organophosphonates); 0 (RNA, Guide); 0 (RNA, Small Interfering); 0 (RNA-Induced Silencing Complex); 0 (Vinyl Compounds); 1746-03-8 (vinylphosphonic acid); EC 3.1.- (Exoribonucleases)
[Em] Mês de entrada:1710
[Cu] Atualização por classe:171011
[Lr] Data última revisão:
171011
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:170608
[St] Status:MEDLINE
[do] DOI:10.1093/nar/gkx507


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[PMID]:28583799
[Au] Autor:Hasegawa Y; Takada T; Nakamura M; Yamana K
[Ad] Endereço:Department of Materials Science and Chemistry, University of Hyogo, 2167 Shosha, Himeji 671-2280, Japan.
[Ti] Título:Ferrocene conjugated oligonucleotide for electrochemical detection of DNA base mismatch.
[So] Source:Bioorg Med Chem Lett;27(15):3555-3557, 2017 08 01.
[Is] ISSN:1464-3405
[Cp] País de publicação:England
[La] Idioma:eng
[Ab] Resumo:We describe the synthesis, binding, and electrochemical properties of ferrocene-conjugated oligonucleotides (Fc-oligos). The key step for the preparation of Fc-oligos contains the coupling of vinylferrocene to 5-iododeoxyuridine via Heck reaction. The Fc-conjugated deoxyuridine phosphoramidite was used in the Fc-oligonucleotide synthesis. We show that thiol-modified Fc-oligos deposited onto gold electrodes possess potential ability in electrochemical detection of DNA base mismatch.
[Mh] Termos MeSH primário: Pareamento Incorreto de Bases
DNA/genética
Desoxiuridina/análogos & derivados
Técnicas Eletroquímicas/métodos
Compostos Ferrosos/química
Oligonucleotídeos/química
[Mh] Termos MeSH secundário: Sequência de Bases
DNA/química
Eletrodos
Ouro/química
Idoxuridina/química
Metalocenos
Compostos de Vinila/química
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (Ferrous Compounds); 0 (Metallocenes); 0 (Oligonucleotides); 0 (Vinyl Compounds); 1271-51-8 (vinylferrocene); 7440-57-5 (Gold); 9007-49-2 (DNA); LGP81V5245 (Idoxuridine); U96PKG90JQ (ferrocene); W78I7AY22C (Deoxyuridine)
[Em] Mês de entrada:1708
[Cu] Atualização por classe:171125
[Lr] Data última revisão:
171125
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:170607
[St] Status:MEDLINE


  8 / 3756 MEDLINE  
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[PMID]:28415456
[Au] Autor:Bolbasov EN; Popkov AV; Popkov DA; Gorbach EN; Khlusov IA; Golovkin AS; Sinev A; Bouznik VM; Tverdokhlebov SI; Anissimov YG
[Ad] Endereço:Tomsk Polytechnic University, 30 Lenin Av., Tomsk 634050, Russian Federation.
[Ti] Título:Osteoinductive composite coatings for flexible intramedullary nails.
[So] Source:Mater Sci Eng C Mater Biol Appl;75:207-220, 2017 Jun 01.
[Is] ISSN:1873-0191
[Cp] País de publicação:Netherlands
[La] Idioma:eng
[Ab] Resumo:This work presents composite coatings based on a copolymer of vinylidene fluoride with tetrafluoroethylene (VDF-TeFE) and hydroxyapatite (HA) for flexible intramedullary nails (FIN). The effect of the proportion of VDF-TeFE (100-25% wt.) on physicochemical and biological properties of the composite coatings was investigated. It was shown that a decrease of VDF-TeFE in the coating hinders its crystallization in ß and γ forms which have piezoelectric properties. The decrease also reduces an adhesive strength to 9.9±2.4MPa and a relative elongation to 5.9±1.2%, but results in increased osteogenesis. It was demonstrated that the composite coatings with 35% VDF-TeFE has the required combination of physicochemical properties and osteogenic activity. Comparative studies of composite coatings (35% VDF-TeFE) and calcium phosphate coatings produced using micro-arc oxidation, demonstrated comparable results for strength of bonding of these FINs with trabecular bones (~530MPa). It was hypothesized that the high osteoinductive properties of the composite coatings are due to their piezoelectric properties.
[Mh] Termos MeSH primário: Pinos Ortopédicos
Regeneração Óssea
Materiais Revestidos Biocompatíveis/química
Durapatita/química
Fluorcarbonetos/química
Teste de Materiais
Compostos de Vinila/química
[Mh] Termos MeSH secundário: Animais
Cães
Feminino
Seres Humanos
Masculino
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Coated Materials, Biocompatible); 0 (Fluorocarbons); 0 (Vinyl Compounds); 3C1IX2905B (1,1-difluoroethylene); 91D9GV0Z28 (Durapatite); OMW63Z518S (tetrafluoroethylene)
[Em] Mês de entrada:1707
[Cu] Atualização por classe:170724
[Lr] Data última revisão:
170724
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:170419
[St] Status:MEDLINE


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[PMID]:28409451
[Au] Autor:Honsho M; Fujiki Y
[Ad] Endereço:Medical Institute of Bioregulation, Kyushu University, 3-1-1 Maidashi, Higashi-ku, Fukuoka, 812-8582, Japan.
[Ti] Título:Analysis of Plasmalogen Synthesis in Cultured Cells.
[So] Source:Methods Mol Biol;1595:55-61, 2017.
[Is] ISSN:1940-6029
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:Plasmalogen synthesis can be analyzed by metabolic labeling, followed by the separation of ethanolamine plasmalogens from glycerophospholipids on one-dimensional thin-layer chromatography. The vinyl-ether bond of plasmalogens is acid-labile, which allows separating plasmalogens as 2-acyl-glycerophospholipids from diacyl-glycerophospholipids.
[Mh] Termos MeSH primário: Plasmalogênios/biossíntese
[Mh] Termos MeSH secundário: Radioisótopos de Carbono
Linhagem Celular
Células Cultivadas
Etanolamina/química
Etanolamina/metabolismo
Marcação por Isótopo
Ácido Palmítico/química
Compostos de Vinila/química
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Carbon Radioisotopes); 0 (Plasmalogens); 0 (Vinyl Compounds); 2H2T044E11 (vinyl ether); 2V16EO95H1 (Palmitic Acid); 5KV86114PT (Ethanolamine)
[Em] Mês de entrada:1705
[Cu] Atualização por classe:170518
[Lr] Data última revisão:
170518
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:170415
[St] Status:MEDLINE
[do] DOI:10.1007/978-1-4939-6937-1_6


  10 / 3756 MEDLINE  
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[PMID]:28406614
[Au] Autor:George JT; Srivatsan SG
[Ad] Endereço:Department of Chemistry, Indian Institute of Science Education and Research (IISER) Pune , Dr. Homi Bhabha Road, Pashan, Pune 411008, India.
[Ti] Título:Vinyluridine as a Versatile Chemoselective Handle for the Post-transcriptional Chemical Functionalization of RNA.
[So] Source:Bioconjug Chem;28(5):1529-1536, 2017 May 17.
[Is] ISSN:1520-4812
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:The development of modular and efficient methods to functionalize RNA with biophysical probes is very important in advancing the understanding of the structural and functional relevance of RNA in various cellular events. Herein, we demonstrate a two-step bioorthogonal chemical functionalization approach for the conjugation of multiple probes onto RNA transcripts using a 5-vinyl-modified uridine nucleotide analog (VUTP). VUTP, containing a structurally noninvasive and versatile chemoselective handle, was efficiently incorporated into RNA transcripts by in vitro transcription reactions. Furthermore, we show for the first time the use of a palladium-mediated oxidative Heck reaction in functionalizing RNA with fluorogenic probes by reacting vinyl-labeled RNA transcripts with appropriate boronic acid substrates. The vinyl label also permitted the post-transcriptional functionalization of RNA by a reagent-free inverse electron demand Diels-Alder (IEDDA) reaction in the presence of tetrazine substrates. Collectively, our results demonstrate that the incorporation of VUTP provides newer possibilities for the modular functionalization of RNA with variety of reporters.
[Mh] Termos MeSH primário: Processamento Pós-Transcricional do RNA
RNA/química
Uridina Trifosfato/química
Compostos de Vinila/química
[Mh] Termos MeSH secundário: Animais
Reação de Cicloadição
Elétrons
Seres Humanos
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Vinyl Compounds); 63231-63-0 (RNA); UT0S826Z60 (Uridine Triphosphate)
[Em] Mês de entrada:1708
[Cu] Atualização por classe:170817
[Lr] Data última revisão:
170817
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:170414
[St] Status:MEDLINE
[do] DOI:10.1021/acs.bioconjchem.7b00169



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