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[PMID]:28498845
[Au] Autor:Vodstrcil LA; Rupasinghe TWT; Kong FYS; Tull D; Worthington K; Chen MY; Huston WM; Timms P; McConville MJ; Fairley CK; Bradshaw CS; Tabrizi SN; Hocking JS
[Ad] Endereço:Centre for Epidemiology and Biostatistics, Melbourne School of Population and Global Health, University of Melbourne, Parkville, Australia.
[Ti] Título:Measurement of tissue azithromycin levels in self-collected vaginal swabs post treatment using liquid chromatography and tandem mass spectrometry (LC-MS/MS).
[So] Source:PLoS One;12(5):e0177615, 2017.
[Is] ISSN:1932-6203
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:BACKGROUND: Azithromycin is recommended for the treatment of uncomplicated urogenital chlamydia infection although the standard 1gram dose sometimes fails to eradicate the infection (treatment failure). One hypothesis proposed for treatment failure has been insufficient levels of the antibiotic at the site of infection. We developed an assay using liquid chromatography and tandem mass spectrometry (LC-MS/MS) to measure azithromycin concentration in high-vaginal swabs and monitor how concentration changes over time following routine azithromycin treatment. METHODS: Azithromycin concentrations were measured in two groups of women either within the first 24h of taking a 1g dose (N = 11) or over 9 days (N = 10). Azithromycin concentrations were normalised to an internal standard (leucine enkephalin), and the bulk lipid species phosphatidylcholine [PC(34:1)], using an Agilent 6490 triple quadrupole instrument in positive ionisation mode. The abundances of azithromycin, PC(34:1), and leu-enkephalin were determined by multiple reaction monitoring and absolute levels of azithromycin estimated using standard curves prepared on vaginal specimens. RESULTS: Vaginal azithromycin concentrations of women were rapidly obtained after 5h post-treatment (mean concentration = 1031mcg/mg of lipid, range = 173-2693mcg/mg). In women followed for 9 days, peak concentrations were highest after day 2 (mean concentration = 2206mcg/mg, range = 721-5791mcg/mg), and remained high for at least 9 days with a mean concentration of 384mcg/mg (range = 139-1024mcg/mg) on day 9. CONCLUSION: Our study confirmed that a single 1g dose of azithromycin is rapidly absorbed and remains in the vagina at relatively high levels for at least a week, suggesting that poor antibiotic absorption is unlikely to be an explanation for treatment failure.
[Mh] Termos MeSH primário: Azitromicina/metabolismo
Azitromicina/farmacocinética
Cromatografia Líquida/métodos
Espectrometria de Massas em Tandem/métodos
Vagina/metabolismo
[Mh] Termos MeSH secundário: Antibacterianos/sangue
Antibacterianos/metabolismo
Antibacterianos/farmacocinética
Azitromicina/sangue
Encefalina Leucina/sangue
Encefalina Leucina/metabolismo
Encefalina Leucina/farmacocinética
Feminino
Seres Humanos
[Pt] Tipo de publicação:CLINICAL TRIAL; JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Anti-Bacterial Agents); 58822-25-6 (Enkephalin, Leucine); 83905-01-5 (Azithromycin)
[Em] Mês de entrada:1709
[Cu] Atualização por classe:170907
[Lr] Data última revisão:
170907
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:170513
[St] Status:MEDLINE
[do] DOI:10.1371/journal.pone.0177615


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[PMID]:28296145
[Au] Autor:Karad SN; Pal M; Crowley RS; Prisinzano TE; Altman RA
[Ad] Endereço:Department of Medicinal Chemistry, The University of Kansas, 1251 Wescoe Hall Drive, Lawrence, Kansas, 66045, USA.
[Ti] Título:Synthesis and Opioid Activity of Tyr -ψ[(Z)CF=CH]-Gly and Tyr -ψ[(S)/(R)-CF CH-NH]-Gly Leu-enkephalin Fluorinated Peptidomimetics.
[So] Source:ChemMedChem;12(8):571-576, 2017 Apr 20.
[Is] ISSN:1860-7187
[Cp] País de publicação:Germany
[La] Idioma:eng
[Ab] Resumo:We describe the design, synthesis, and opioid activity of fluoroalkene (Tyr -ψ[(Z)CF=CH]-Gly ) and trifluoroethylamine (Tyr -ψ[(S)/(R)-CF CH-NH]-Gly ) analogues of the endogenous opioid neuropeptide, Leu-enkephalin. The fluoroalkene peptidomimetic exhibited low nanomolar functional activity (5.0±2 nm and 60±15 nm for δ- and µ-opioid receptors, respectively) with a µ/δ-selectivity ratio that mimics that of the natural peptide. However, the trifluoroethylamine peptidomimetics, irrespective of stereochemistry, did not activate the opioid receptors, which suggest that bulky CF substituents are not tolerated at this position.
[Mh] Termos MeSH primário: Analgésicos Opioides/farmacologia
Encefalina Leucina/análogos & derivados
Hidrocarbonetos Fluorados/farmacologia
Peptidomiméticos/farmacologia
[Mh] Termos MeSH secundário: Analgésicos Opioides/síntese química
Animais
Células CHO
Cricetulus
Encefalina Leucina/síntese química
Encefalina Leucina/farmacologia
Seres Humanos
Hidrocarbonetos Fluorados/síntese química
Peptidomiméticos/síntese química
Receptores Opioides/agonistas
Estereoisomerismo
Relação Estrutura-Atividade
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Analgesics, Opioid); 0 (Hydrocarbons, Fluorinated); 0 (Peptidomimetics); 0 (Receptors, Opioid); 58822-25-6 (Enkephalin, Leucine)
[Em] Mês de entrada:1709
[Cu] Atualização por classe:170926
[Lr] Data última revisão:
170926
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:170316
[St] Status:MEDLINE
[do] DOI:10.1002/cmdc.201700103


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[PMID]:28173925
[Au] Autor:Abbood A; Smadja C; Taverna M; Herrenknecht C
[Ad] Endereço:Institut Galien Paris-Sud, UMR CNRS 8612, Proteins and Nanotechnology in Analytical Science (PNAS), CNRS, Univ. Paris-Sud, Université Paris-Saclay, 5 rue Jean Baptiste Clément, 92290 Châtenay-Malabry, France; Faculty of Pharmacy, Tishreen University, Boulevard Aleppo, Latakia, Syria.
[Ti] Título:Hydrophilic interaction liquid chromatography for dalargin separation from its structural analogues and side products.
[So] Source:J Chromatogr A;1498:155-162, 2017 May 19.
[Is] ISSN:1873-3778
[Cp] País de publicação:Netherlands
[La] Idioma:eng
[Ab] Resumo:Retention behaviour of Dalargin and five peptide analogues of Leu-enkephalin, has been extensively studied by hydrophilic interaction liquid chromatography (HILIC) on a bare silica stationary phase (Atlantis HILIC silica). The influence of buffer pH, ionic strength, and organic modifier content on peptide retentions was examined. Variation of organic modifier content (70-90% ACN) shows that, as expected, the most polar peptide, Dalargin, is the most retained. Moreover, at acidic pH, the retention mechanism for all the peptides studied seems to rely, mainly, on adsorption phenomenon. By varying the pswH buffer (between 4.4-7.5), we observed that the retention of all the peptides was mainly governed by their total number of charges, whatever the variation (increase or decrease) of their retention factor. At pswH 7.5, an increase of the cationic counter-ion concentration (NH ) lead to a decrease of the retention factor of Dalargin, suggesting a weak cation exchange for this peptide. For the other peptides, the variation of the retention factors was negligible between 5-15mM. Above 15mM, the retention factors of all the peptides increased, probably due to an increase of the water layer thickness at the surface of the stationary phase. In the second part of the study, qualitative analysis of non-purified dalargin, resulting from solid-phase synthesis, was realized. Optimisation of the separation of the target peptide from its side products has been first performed with UV detection. Then, by coupling the HILIC column with ESI-MS, using the optimal separation conditions, it was possible to identify Dalargin and to propose the amino-acids sequence of its side-products.
[Mh] Termos MeSH primário: Cromatografia Líquida de Alta Pressão
Leucina Encefalina-2-Alanina/análogos & derivados
Encefalina Leucina/análise
[Mh] Termos MeSH secundário: Compostos de Amônio/química
Encefalina Leucina/química
Encefalina Leucina/isolamento & purificação
Leucina Encefalina-2-Alanina/análise
Leucina Encefalina-2-Alanina/química
Leucina Encefalina-2-Alanina/isolamento & purificação
Concentração de Íons de Hidrogênio
Interações Hidrofóbicas e Hidrofílicas
Íons/química
Concentração Osmolar
Peptídeos/análise
Peptídeos/isolamento & purificação
Dióxido de Silício/química
Espectrometria de Massas por Ionização por Electrospray
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Ammonium Compounds); 0 (Ions); 0 (Peptides); 58822-25-6 (Enkephalin, Leucine); 63631-40-3 (Enkephalin, Leucine-2-Alanine); 7631-86-9 (Silicon Dioxide); V13505565P (enkephalin-Leu, Ala(2)-Arg(6)-)
[Em] Mês de entrada:1709
[Cu] Atualização por classe:170906
[Lr] Data última revisão:
170906
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:170209
[St] Status:MEDLINE


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[PMID]:28132733
[Au] Autor:Sarrut M; Rouvière F; Heinisch S
[Ad] Endereço:Université de Lyon, Institut des Sciences Analytiques, UMR 5280, CNRS, Université Lyon 1, ENS Lyon, 5 rue de la Doua, 69100 Villeurbanne, France.
[Ti] Título:Theoretical and experimental comparison of one dimensional versus on-line comprehensive two dimensional liquid chromatography for optimized sub-hour separations of complex peptide samples.
[So] Source:J Chromatogr A;1498:183-195, 2017 May 19.
[Is] ISSN:1873-3778
[Cp] País de publicação:Netherlands
[La] Idioma:eng
[Ab] Resumo:This study was devoted to the search for conditions leading to highly efficient sub-hour separations of complex peptide samples with the objective of coupling to mass spectrometry. In this context, conditions for one dimensional reversed phase liquid chromatography (1D-RPLC) were optimized on the basis of a kinetic approach while conditions for on-line comprehensive two-dimensional liquid chromatography using reversed phase in both dimensions (on-line RPLCxRPLC) were optimized on the basis of a Pareto-optimal approach. Maximizing the peak capacity while minimizing the dilution factor for different analysis times (down to 5min) were the two objectives under consideration. For gradient times between 5 and 60min, 15cm was found to be the best column length in RPLC with sub-2µm particles under 800bar as system pressure. In RPLCxRPLC, for less than one hour as first dimension gradient time, the sampling rate was found to be a key parameter in addition to conventional parameters including column dimension, particle size, flow-rate and gradient conditions in both dimensions. It was shown that the optimum sampling rate was as low as one fraction per peak for very short gradient times (i.e. below 10min). The quality descriptors obtained under optimized RPLCxRPLC conditions were compared to those obtained under optimized RPLC conditions. Our experimental results for peptides, obtained with state of the art instrumentation, showed that RPLCxRPLC could outperform 1D-RPLC for gradient times longer than 5min. In 60min, the same peak intensity (same dilution) was observed with both techniques but with a 3-fold lower injected amount in RPLCxRPLC. A significant increase of the signal-to-noise ratio mainly due to a strong noise reduction was observed in RPLCxRPLC-MS compared to the one in 1D-RPLC-MS making RPLCxRPLC-MS a promising technique for peptide identification in complex matrices.
[Mh] Termos MeSH primário: Cromatografia Líquida de Alta Pressão/métodos
Cromatografia de Fase Reversa/métodos
Modelos Teóricos
Peptídeos/análise
[Mh] Termos MeSH secundário: Bradicinina/análise
Bradicinina/isolamento & purificação
Encefalina Leucina/análise
Encefalina Leucina/isolamento & purificação
Espectrometria de Massas
Mapeamento de Peptídeos
Peptídeos/isolamento & purificação
Espectrofotometria Ultravioleta
Fatores de Tempo
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Peptides); 58822-25-6 (Enkephalin, Leucine); S8TIM42R2W (Bradykinin)
[Em] Mês de entrada:1709
[Cu] Atualização por classe:170906
[Lr] Data última revisão:
170906
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:170131
[St] Status:MEDLINE


  5 / 3309 MEDLINE  
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[PMID]:28091903
[Au] Autor:Solin AV; Lyashev AY; Lyashev YD
[Ad] Endereço:Kursk State Medical University, Ministry of Health of the Russian Federation, Kursk, Russia. medps@yandex.ru.
[Ti] Título:Effects of Opioid Peptides on Changes in Lipid Metabolism in Rats Subjected to Swimming Stress.
[So] Source:Bull Exp Biol Med;162(3):313-315, 2017 Jan.
[Is] ISSN:1573-8221
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:Blood levels of nonesterified fatty acids, total cholesterol, triglycerides, and LDL increased in rats subjected to forced swimming stress. Administration of opioid peptides dynorphin A(1-13), DSLET, or DAGO reduced stress-induced disturbances in lipid metabolism. Dynorphin A(1-13) and DAGO produced the most pronounced effects and prevented an increase in concentrations of nonesterified fatty acids, triglycerides, total cholesterol, and LDL as soon as 39 h after treatment. Only DSLET increased HDL content in the plasma of stressed rats. The observed effects can be explained by the stress-limiting effects of opioids, e.g. attenuation of the effect of catecholamines on the adipose tissue and inhibition of the generation LPO products suppressing activity of the cholesterol metabolizing enzyme.
[Mh] Termos MeSH primário: Analgésicos Opioides/farmacologia
Dinorfinas/farmacologia
Ala(2)-MePhe(4)-Gly(5)-Encefalina/farmacologia
Encefalina Leucina/análogos & derivados
Metabolismo dos Lipídeos/efeitos dos fármacos
Fragmentos de Peptídeos/farmacologia
Estresse Psicológico/sangue
[Mh] Termos MeSH secundário: Animais
Colesterol/sangue
HDL-Colesterol/sangue
LDL-Colesterol/sangue
Encefalina Leucina/farmacologia
Ácidos Graxos não Esterificados/sangue
Masculino
Ratos
Ratos Wistar
Estresse Psicológico/tratamento farmacológico
Estresse Psicológico/fisiopatologia
Natação
Triglicerídeos/sangue
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Analgesics, Opioid); 0 (Cholesterol, HDL); 0 (Cholesterol, LDL); 0 (Fatty Acids, Nonesterified); 0 (Peptide Fragments); 0 (Triglycerides); 100929-53-1 (Enkephalin, Ala(2)-MePhe(4)-Gly(5)-); 111846-43-6 (dynorphin amide (1-13), Ala(2)-(5-F-Phe)(4)-); 58822-25-6 (Enkephalin, Leucine); 74913-18-1 (Dynorphins); 75644-90-5 (enkephalin, Ser(2), Leu(5), Thr(6)-); 97C5T2UQ7J (Cholesterol)
[Em] Mês de entrada:1702
[Cu] Atualização por classe:170208
[Lr] Data última revisão:
170208
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:170117
[St] Status:MEDLINE
[do] DOI:10.1007/s10517-017-3603-7


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[PMID]:27762555
[Au] Autor:Nadon JF; Rochon K; Grastilleur S; Langlois G; Dao TT; Blais V; Guérin B; Gendron L; Dory YL
[Ad] Endereço:Laboratoire de synthèse supramoléculaire, Département de chimie, Faculté des sciences ‡Département de pharmacologie-physiologie, §Département d'anesthésiologie, and ∥Département de médecine nucléaire et radiobiologie, Faculté de médecine et des sciences de la santé, ⊥Centre de recherche du CHUS,
[Ti] Título:Synthesis of Gly-ψ[(Z)CF═CH]-Phe, a Fluoroalkene Dipeptide Isostere, and Its Incorporation into a Leu-enkephalin Peptidomimetic.
[So] Source:ACS Chem Neurosci;8(1):40-49, 2017 Jan 18.
[Is] ISSN:1948-7193
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:A new Leu-enkephalin peptidomimetic designed to explore the hydrogen bond acceptor ability of the third peptide bond has been prepared and studied. This new analog is produced by replacing the third amide of Leu-enkephalin with a fluoroalkene. An efficient and innovative synthesis of the corresponding dipeptide surrogate Fmoc-Gly-ψ[(Z)CF═CH]-Phe-OH is described. The key step involves the alkylation of a tin dienolate from the less hindered face of its chiral sulfonamide auxiliary derived from camphor. Once its synthesis was complete, its incorporation into the peptidomimetic sequence was achieved on a solid support with chlorotrityl resin following the Fmoc strategy. The peptidomimetic was characterized using competition binding with [ I]-deltorphin I on membrane extracts of HEK293 cells expressing the mouse delta opioid receptor (DOPr) and based on its abilities to inhibit the electrically induced contractions of the mouse vas deferens and to activate the ERK1/2 signaling pathway in DRGF11/DOPr-GFP cells. Together with our previous observations, our findings strongly suggest that the third amide bond of Leu-enkephalin primarily acts as a hydrogen bond acceptor in DOPr. Consequently, this amide bond can be successfully replaced by an ester, a thioamide, or a fluoroalkene without greatly impacting the binding or biological activity of the corresponding analogs. The lipophilicity (LogD ) of the active analog was also measured. It appears that fluoroalkenes are almost as efficient at increasing the lipophilicity as normal alkenes.
[Mh] Termos MeSH primário: Ligação Competitiva/efeitos dos fármacos
Encefalina Leucina/química
Hidrocarbonetos Fluorados/síntese química
Hidrocarbonetos Fluorados/farmacologia
Peptidomiméticos/síntese química
Receptores Opioides delta/metabolismo
[Mh] Termos MeSH secundário: Animais
Linhagem Celular Transformada
Linhagem Celular Tumoral
Dipeptídeos/química
Encefalina Leucina/análogos & derivados
Proteínas de Fluorescência Verde/genética
Proteínas de Fluorescência Verde/metabolismo
Seres Humanos
Masculino
Camundongos
Peptidomiméticos/farmacologia
Fosforilação/efeitos dos fármacos
Ratos
Receptores Opioides delta/genética
Transfecção
Ducto Deferente/efeitos dos fármacos
Ducto Deferente/metabolismo
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Dipeptides); 0 (Hydrocarbons, Fluorinated); 0 (Peptidomimetics); 0 (Receptors, Opioid, delta); 147336-22-9 (Green Fluorescent Proteins); 58822-25-6 (Enkephalin, Leucine)
[Em] Mês de entrada:1710
[Cu] Atualização por classe:171030
[Lr] Data última revisão:
171030
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:161105
[St] Status:MEDLINE
[do] DOI:10.1021/acschemneuro.6b00163


  7 / 3309 MEDLINE  
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[PMID]:27374757
[Au] Autor:Wen DC; Hu XY; Wang YY; Luo JX; Lin W; Jia LY; Gong XY
[Ad] Endereço:School of Clinical Medicine, Chengdu University of Traditional Chinese Medicine, Chengdu 610072, Sichuan Province, China; Department of Infectious Diseases, Teaching Hospital of Chengdu University of Traditional Chinese Medicine, 610072 Sichuan Province, China.
[Ti] Título:Effects of aqueous extracts from Panax ginseng and Hippophae rhamnoides on acute alcohol intoxication: An experimental study using mouse model.
[So] Source:J Ethnopharmacol;192:67-73, 2016 Nov 04.
[Is] ISSN:1872-7573
[Cp] País de publicação:Ireland
[La] Idioma:eng
[Ab] Resumo:ETHNOPHARMACOLOGICAL RELEVANCE: Acute alcohol intoxication (AAI) is a frequent emergency, but therapeutic drugs with superior efficacy and safety are lacking. Panax ginseng (PG) and Hippophae rhamnoides (HR) respectively has a wide application as a complementary therapeutic agent in China for the treatment of AAI and liver injury induced by alcohol. We investigated the effects of aqueous extracts from PG and HR (AEPH) on AAI mice and identified its underlying mechanisms. MATERIALS AND METHODS: Models of AAI were induced by intragastric administration of ethanol (8g/kg). Seventy-two Specific pathogen-free (SPF) male Kunming mice were randomly divided into six groups: normal group, positive control group, AEPH of low dosage (100mg/kg) group, AEPH of medium dose (200mg/kg) group, AEPH of high dosage (400mg/kg) group and model group. The mice were treated with metadoxine (MTD, 500mg/kg) and AEPH. Thirty minutes later, the normal group was given normal saline, while the other groups were given ethanol (i.g., 8g/kg). The impact of AEPH was observed. In the same way, another seventy-two Kunming mice were randomly divided into six groups equally. The blood ethanol concentration at 0.5, 1, 1.5, 2, 3 and 6h after ethanol intake was determined by way of gas chromatography. The activity of alcohol dehydrogenase (ADH), aldehyde dehydrogenase (ALDH) and microsomal ethanol oxidase (EO) in liver, and the concentration of ß-endorphin (ß-EP), leucine-enkephalin (LENK) in the brain were determined by enzyme-linked-immunosorbent serologic assay (ELISA). RESULTS: AEPH markedly prolonged alcohol tolerance time and shortened sober-up time after acute ethanol administration. AEPH decreased blood ethanol levels in six tests after ethanol intake. The 7-day survival rate of AEPH group was obviously superior to model group. AEPH increased the activities of ADH, ALDH, and decreased EO activity in liver. The crucial find was that AEPH markedly decreased ß-EP and LENK concentration in the brain. CONCLUSIONS: AEPH can markedly increase the levels of ADH, ALDH, decrease EO activity in liver and decrease the concentration of ß-EP and LENK in the brain to against acute alcohol intoxication in mice.
[Mh] Termos MeSH primário: Intoxicação Alcoólica/tratamento farmacológico
Etanol
Hippophae/química
Fígado/efeitos dos fármacos
Panax/química
Extratos Vegetais/farmacologia
Solventes/química
Água/química
[Mh] Termos MeSH secundário: Álcool Desidrogenase/metabolismo
Oxirredutases do Álcool/metabolismo
Intoxicação Alcoólica/sangue
Aldeído Desidrogenase/metabolismo
Animais
Concentração Alcoólica no Sangue
Encéfalo/efeitos dos fármacos
Encéfalo/metabolismo
Sistema Enzimático do Citocromo P-450/metabolismo
Modelos Animais de Doenças
Relação Dose-Resposta a Droga
Encefalina Leucina/metabolismo
Cromatografia Gasosa-Espectrometria de Massas
Fígado/enzimologia
Masculino
Camundongos
Fitoterapia
Extratos Vegetais/isolamento & purificação
Plantas Medicinais
Fatores de Tempo
beta-Endorfina/metabolismo
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Blood Alcohol Content); 0 (Plant Extracts); 0 (Solvents); 059QF0KO0R (Water); 3K9958V90M (Ethanol); 58822-25-6 (Enkephalin, Leucine); 60617-12-1 (beta-Endorphin); 9035-51-2 (Cytochrome P-450 Enzyme System); EC 1.1.- (Alcohol Oxidoreductases); EC 1.1.1.- (microsomal ethanol-oxidizing system); EC 1.1.1.1 (Alcohol Dehydrogenase); EC 1.2.1.3 (Aldehyde Dehydrogenase)
[Em] Mês de entrada:1704
[Cu] Atualização por classe:170912
[Lr] Data última revisão:
170912
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:160705
[St] Status:MEDLINE


  8 / 3309 MEDLINE  
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[PMID]:27372839
[Au] Autor:Bag SS; Jana S; Pradhan MK
[Ad] Endereço:Bioorganic Chemistry Laboratory, Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati 781039, India. Electronic address: ssbag75@iitg.ernet.in.
[Ti] Título:Synthesis, photophysical properties of triazolyl-donor/acceptor chromophores decorated unnatural amino acids: Incorporation of a pair into Leu-enkephalin peptide and application of triazolylperylene amino acid in sensing BSA.
[So] Source:Bioorg Med Chem;24(16):3579-95, 2016 Aug 15.
[Is] ISSN:1464-3391
[Cp] País de publicação:England
[La] Idioma:eng
[Ab] Resumo:The research in the field of design and synthesis of unnatural amino acids is growing at a fast space for the increasing demand of proteins of potential therapeutics and many other diversified novel functional applications. Thus, we report herein the design and synthesis of microenvironment sensitive fluorescent triazolyl unnatural amino acids (UNAA) decorated with donor and/or acceptor aromatic chromophores via click chemistry. The synthesized fluorescent amino acids show interesting solvatochromic characteristic and/or intramolecular charge transfer (ICT) feature as is revealed from the UV-visible, fluorescence photophysical properties and DFT/TDDFT calculation. HOMO-LUMO distribution shows that the emissive states of some of the amino acids are characterized with more significant electron redistribution between the triazolyl moiety and the aromatic chromophores linked to it leading to modulated emission property. A pair of donor-acceptor amino acid shows interesting photophysical interaction property indicating a FRET quenching event. Furthermore, one of the amino acid, triazolyl-perylene amino acid, has been exploited for studying interaction with BSA and found that it is able to sense BSA with an enhancement of fluorescence intensity. Finally, we incorporated a pair of donor/acceptor amino acids into a Leu-enkephalin analogue pentapeptide which was found to adopt predominantly type II ß-turn conformation. We envisage that our investigation is of importance for the development of new fluorescent donor-acceptor unnatural amino acids a pair of which can be exploited for generating fluorescent peptidomimetic probe of interesting photophysical property for applications in studying peptide-protein interaction.
[Mh] Termos MeSH primário: Aminoácidos/química
Encefalina Leucina/química
Perileno/química
Soroalbumina Bovina/química
Triazóis/síntese química
[Mh] Termos MeSH secundário: Espectroscopia de Ressonância Magnética Nuclear de Carbono-13
Espectrometria de Massas
Espectroscopia de Prótons por Ressonância Magnética
Espectrometria de Fluorescência
Espectrofotometria Ultravioleta
Triazóis/química
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Amino Acids); 0 (Triazoles); 27432CM55Q (Serum Albumin, Bovine); 58822-25-6 (Enkephalin, Leucine); 5QD5427UN7 (Perylene)
[Em] Mês de entrada:1708
[Cu] Atualização por classe:171116
[Lr] Data última revisão:
171116
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:160704
[St] Status:MEDLINE


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[PMID]:27089914
[Au] Autor:Torres-Reverón A; Palermo K; Hernández-López A; Hernández S; Cruz ML; Thompson KJ; Flores I; Appleyard CB
[Ad] Endereço:Department of Basic Sciences: Physiology and Pharmacology, Ponce Health Sciences University, Ponce, PR, USA Department of Clinical Psychology, Ponce Health Sciences University/Ponce Research Institute, Ponce, PR, USA anntorres@psm.edu.
[Ti] Título:Endometriosis Is Associated With a Shift in MU Opioid and NMDA Receptor Expression in the Brain Periaqueductal Gray.
[So] Source:Reprod Sci;23(9):1158-67, 2016 Sep.
[Is] ISSN:1933-7205
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:Studies have examined how endometriosis interacts with the nervous system, but little attention has been paid to opioidergic systems, which are relevant to pain signaling. We used the autotransplantation rat model of endometriosis and allowed to progress for 60 days. The brain was collected and examined for changes in endogenous opioid peptides, mu opioid receptors (MORs), and the N-methyl-d-aspartate subunit receptor (NR1) in the periaqueductal gray (PAG), since both of these receptors can regulate PAG activity. No changes in endogenous opioid peptides in met- and leu-enkephalin or ß-endorphin levels were observed within the PAG. However, MOR immunoreactivity was significantly decreased in the ventral PAG in the endometriosis group. Endometriosis reduced by 20% the number of neuronal profiles expressing MOR and reduced by 40% the NR1 profiles. Our results suggest that endometriosis is associated with subtle variations in opioidergic and glutamatergic activity within the PAG, which may have implications for pain processing.
[Mh] Termos MeSH primário: Endometriose/metabolismo
Substância Cinzenta Periaquedutal/metabolismo
Receptores de N-Metil-D-Aspartato/metabolismo
Receptores Opioides mu/metabolismo
[Mh] Termos MeSH secundário: Animais
Encefalina Leucina/metabolismo
Encefalina Metionina/metabolismo
Feminino
Ratos
Ratos Sprague-Dawley
beta-Endorfina/metabolismo
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (NR1 NMDA receptor); 0 (Receptors, N-Methyl-D-Aspartate); 0 (Receptors, Opioid, mu); 58569-55-4 (Enkephalin, Methionine); 58822-25-6 (Enkephalin, Leucine); 60617-12-1 (beta-Endorphin)
[Em] Mês de entrada:1710
[Cu] Atualização por classe:171026
[Lr] Data última revisão:
171026
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:160420
[St] Status:MEDLINE
[do] DOI:10.1177/1933719116630410


  10 / 3309 MEDLINE  
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[PMID]:27012427
[Au] Autor:Rogers SA; Kempen TA; Pickel VM; Milner TA
[Ad] Endereço:Feil Family Brain and Mind Research Institute, Weill Cornell Medicine, 407 East 61st Street, New York, NY 10065, United States. Electronic address: sarogers9@gmail.com.
[Ti] Título:Enkephalin levels and the number of neuropeptide Y-containing interneurons in the hippocampus are decreased in female cannabinoid-receptor 1 knock-out mice.
[So] Source:Neurosci Lett;620:97-103, 2016 May 04.
[Is] ISSN:1872-7972
[Cp] País de publicação:Ireland
[La] Idioma:eng
[Ab] Resumo:Drug addiction requires learning and memory processes that are facilitated by activation of cannabinoid-1 (CB1) and opioid receptors in the hippocampus. This involves activity-dependent synaptic plasticity that is partially regulated by endogenous opioid (enkephalin and dynorphin) and non-opioid peptides, specifically cholecystokinin, parvalbumin and neuropeptide Y, the neuropeptides present in inhibitory interneurons that co-express CB1 or selective opioid receptors. We tested the hypothesis that CB1 receptor expression is a determinant of the availability of one or more of these peptide modulators in the hippocampus. This was achieved by quantitatively analyzing the immunoperoxidase labeling for each of these neuropeptide in the dorsal hippocampus of female wild-type (CB1+/+) and cannabinoid receptor 1 knockout (CB1-/-) C57/BL6 mice. The levels of Leu(5)-enkephalin-immunoreactivity were significantly reduced in the hilus of the dentate gyrus and in stratum lucidum of CA3 in CB1-/- mice. Moreover, the numbers of neuropeptide Y-immunoreactive interneurons in the dentate hilus were significantly lower in the CB1-/- compared to wild-type mice. However, CB1+/+ and CB1-/- mice did not significantly differ in expression levels of either dynorphin or cholecystokinin, and showed no differences in numbers of parvalbumin-containing interneurons. These findings suggest that the cannabinoid and opioid systems have a nuanced, regulatory relationship that could affect the balance of excitation and inhibition in the hippocampus and thus processes such as learning that rely on this balance.
[Mh] Termos MeSH primário: Encefalina Leucina/metabolismo
Hipocampo/metabolismo
Interneurônios/metabolismo
Neuropeptídeo Y/metabolismo
Receptor CB1 de Canabinoide/genética
[Mh] Termos MeSH secundário: Animais
Contagem de Células
Colecistocinina/metabolismo
Dinorfinas/metabolismo
Feminino
Hipocampo/citologia
Interneurônios/citologia
Camundongos
Camundongos Endogâmicos C57BL
Camundongos Knockout
Fibras Musgosas Hipocampais/metabolismo
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Neuropeptide Y); 0 (Receptor, Cannabinoid, CB1); 58822-25-6 (Enkephalin, Leucine); 74913-18-1 (Dynorphins); 9011-97-6 (Cholecystokinin)
[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:160326
[St] Status:MEDLINE



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