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  1 / 157 MEDLINE  
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[PMID]:27558352
[Au] Autor:Saatchi K; Tod SE; Leung D; Nicholson KE; Andreu I; Buchwalder C; Schmitt V; Häfeli UO; Gray SL
[Ad] Endereço:Faculty of Pharmaceutical Sciences, University of British Columbia, Vancouver, BC, Canada.
[Ti] Título:Characterization of alendronic- and undecylenic acid coated magnetic nanoparticles for the targeted delivery of rosiglitazone to subcutaneous adipose tissue.
[So] Source:Nanomedicine;13(2):559-568, 2017 Feb.
[Is] ISSN:1549-9642
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:Obesity is a state of positive energy balance where excess white adipose tissue accumulates to the detriment of metabolic health. Improving adipocyte function with systemic administration of thiazolidinediones (TZDs) improves metabolic outcomes in obesity, however TZD use is limited clinically due to undesirable side effects. Here we evaluate magnetic nanoparticles (MNPs) as a tool to target rosiglitazone (Rosi) specifically to adipose tissue. Results show Rosi can be adsorbed to MNPs (Rosi-MNPs) with hydrophobic coatings for which we present binding and release kinetics. Rosi adsorbed to MNPs retained the ability to induce PPARγ target gene expression in cells. Biodistribution analysis of radiolabeled Rosi-MNPs revealed a fat-implanted magnet significantly enhanced localization of Rosi to the targeted adipose tissue when administered by subcutaneous injection to obese mice. We propose MNPs for targeted delivery of anti-diabetic agents to superficially located subcutaneous adipose tissue.
[Mh] Termos MeSH primário: Hipoglicemiantes/administração & dosagem
Nanopartículas de Magnetita
Tiazolidinedionas/administração & dosagem
Ácidos Undecilênicos
[Mh] Termos MeSH secundário: Tecido Adiposo
Animais
Camundongos
Camundongos Endogâmicos C57BL
Obesidade/tratamento farmacológico
Gordura Subcutânea
Distribuição Tecidual
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Hypoglycemic Agents); 0 (Magnetite Nanoparticles); 0 (Thiazolidinediones); 0 (Undecylenic Acids); 05V02F2KDG (rosiglitazone)
[Em] Mês de entrada:1710
[Cu] Atualização por classe:171002
[Lr] Data última revisão:
171002
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:160826
[St] Status:MEDLINE


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[PMID]:26902505
[Au] Autor:Shi D; Zhao Y; Yan H; Fu H; Shen Y; Lu G; Mei H; Qiu Y; Li D; Liu W
[Ti] Título:Antifungal effects of undecylenic acid on the biofilm formation of Candida albicans.
[So] Source:Int J Clin Pharmacol Ther;54(5):343-53, 2016 May.
[Is] ISSN:0946-1965
[Cp] País de publicação:Germany
[La] Idioma:eng
[Ab] Resumo:Undecylenic acid can effectively control skin fungal infection, but the mechanism of its fungal inhibition is unclear. Hyphal growth of Candida albicans (C. albicans) and biofilm formation have been well recognized as important virulence factors for the initiation of skin infection and late development of disseminated infection. In this study, we seek to investigate antifungal mechanisms of undecylenic acid by evaluating the virulence factors of C. albicans during biofilm formation. We found that undecylenic acid inhibits biofilm formation of C. albicans effectively with optimal concentration above 3 mM. In the presence of this compound, the morphological transition from yeast to filamentous phase is abolished ultimately when the concentration of undecylenic acid is above 4 mM. Meanwhile, the cell surface is crumpled, and cells display an atrophic appearance under scanning electron microscopy even with low concentration of drug treatment. On the other hand, the drug treatment decreases the transcriptions of hydrolytic enzymes such as secreted aspartic protease, lipase, and phospholipase. Hyphal formation related genes, like HWP1, are significantly reduced in transcriptional level in drug-treated biofilm condition as well. The down-regulated profile of these genes leads to a poorly organized biofilm in undecylenic acid treated environment.
[Mh] Termos MeSH primário: Antifúngicos/farmacologia
Biofilmes/efeitos dos fármacos
Candida albicans/efeitos dos fármacos
Ácidos Undecilênicos/farmacologia
[Mh] Termos MeSH secundário: Biofilmes/crescimento & desenvolvimento
Candida albicans/genética
Candida albicans/crescimento & desenvolvimento
Candida albicans/metabolismo
Candida albicans/patogenicidade
Relação Dose-Resposta a Droga
Regulação Fúngica da Expressão Gênica/efeitos dos fármacos
Viabilidade Microbiana/efeitos dos fármacos
Fatores de Virulência/metabolismo
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (Antifungal Agents); 0 (Undecylenic Acids); 0 (Virulence Factors); K3D86KJ24N (undecylenic acid)
[Em] Mês de entrada:1606
[Cu] Atualização por classe:160420
[Lr] Data última revisão:
160420
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:160224
[St] Status:MEDLINE
[do] DOI:10.5414/CP202460


  3 / 157 MEDLINE  
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[PMID]:26231861
[Au] Autor:Piotrowski M; Jantas D; Szczepanowicz K; Lukasiewicz S; Lason W; Warszynski P
[Ad] Endereço:Jerzy Haber Institute of Catalysis and Surface Chemistry, Polish Academy of Sciences, Niezapominajek 8, 30-239 Kraków, Poland.
[Ti] Título:Polyelectrolyte-coated nanocapsules containing undecylenic acid: Synthesis, biocompatibility and neuroprotective properties.
[So] Source:Colloids Surf B Biointerfaces;135:8-17, 2015 Nov 01.
[Is] ISSN:1873-4367
[Cp] País de publicação:Netherlands
[La] Idioma:eng
[Ab] Resumo:The main objectives of the present study were to investigate the biocompatibility of polyelectrolyte-coated nanocapsules and to evaluate the neuroprotective action of the nanoencapsulated water-insoluble neuroprotective drug-undecylenic acid (UDA), in vitro. Core-shell nanocapsules were synthesized using nanoemulsification and the layer-by-layer (LbL) technique (by saturation method). The average size of synthesized nanocapsules was around 80 nm and the concentration was 2.5 × 10(10) particles/ml. Their zeta potential values ranged from less than -30 mV for the ones with external polyanion layers through -4 mV for the PEG-ylated layers to more than 30 mV for the polycation layers. Biocompatibility of synthesized nanocarriers was evaluated in the SH-SY5Y human neuroblastoma cell line using cell viability/toxicity assays (MTT reduction, LDH release). The results obtained showed that synthesized nanocapsules coated with PLL and PGA (also PEG-ylated) were non-toxic to SH-SY5Y cells, therefore, they were used as nanocarriers for UDA. Moreover, studies with ROD/FITC-labeled polyelectrolytes demonstrated approximately 20% cellular uptake of synthetized nanocapsules. Further studies showed that nanoencapsulated form of UDA was biocompatible and protected SH-SY5Y cells against the staurosporine-induced damage in lower concentrations than those of the same drug added directly to the culture medium. These data suggest that designed nanocapsules might serve as novel, promising delivery systems for neuroprotective agents.
[Mh] Termos MeSH primário: Eletrólitos/química
Nanocápsulas/química
Fármacos Neuroprotetores/química
Fármacos Neuroprotetores/farmacologia
Ácidos Undecilênicos/química
Ácidos Undecilênicos/farmacologia
[Mh] Termos MeSH secundário: Materiais Biocompatíveis/síntese química
Materiais Biocompatíveis/farmacologia
Morte Celular/efeitos dos fármacos
Linhagem Celular Tumoral
Sobrevivência Celular/efeitos dos fármacos
Portadores de Fármacos
Estabilidade de Medicamentos
Seres Humanos
Teste de Materiais
Fármacos Neuroprotetores/síntese química
Tamanho da Partícula
Estaurosporina/antagonistas & inibidores
Estaurosporina/toxicidade
Ácidos Undecilênicos/síntese química
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (Biocompatible Materials); 0 (Drug Carriers); 0 (Electrolytes); 0 (Nanocapsules); 0 (Neuroprotective Agents); 0 (Undecylenic Acids); H88EPA0A3N (Staurosporine); K3D86KJ24N (undecylenic acid)
[Em] Mês de entrada:1609
[Cu] Atualização por classe:151228
[Lr] Data última revisão:
151228
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:150802
[St] Status:MEDLINE


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[PMID]:26012840
[Au] Autor:Jantas D; Piotrowski M; Lason W
[Ad] Endereço:Department of Experimental Neuroendocrinology, Institute of Pharmacology, Polish Academy of Sciences, Krakow, Poland.
[Ti] Título:An Involvement of PI3-K/Akt Activation and Inhibition of AIF Translocation in Neuroprotective Effects of Undecylenic Acid (UDA) Against Pro-Apoptotic Factors-Induced Cell Death in Human Neuroblastoma SH-SY5Y Cells.
[So] Source:J Cell Biochem;116(12):2882-95, 2015 Dec.
[Is] ISSN:1097-4644
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:Undecylenic acid (UDA), a naturally occurring 11-carbon unsaturated fatty acid, has been used for several years as an economical antifungal agent and a nutritional supplement. Recently, the potential usefulness of UDA as a neuroprotective drug has been suggested based on the ability of this agent to inhibit µ-calpain activity. In order to verify neuroprotective potential of UDA, we tested protective efficacy of this compound against cell damage evoked by pro-apoptotic factors (staurosporine and doxorubicin) and oxidative stress (hydrogen peroxide) in human neuroblastoma SH-SY5Y cells. We showed that UDA partially protected SH-SY5Y cells against the staurosporine- and doxorubicin-evoked cell death; however, this effect was not connected with its influence on caspase-3 activity. UDA decreased the St-induced changes in mitochondrial and cytosolic AIF level, whereas in Dox-model it affected only the cytosolic AIF content. Moreover, UDA (1-40 µM) decreased the hydrogen peroxide-induced cell damage which was connected with attenuation of hydrogen peroxide-mediated necrotic (PI staining, ADP/ATP ratio) and apoptotic (mitochondrial membrane potential, caspase-3 activation, AIF translocation) changes. Finally, we demonstrated that an inhibitor of PI3-K/Akt (LY294002) but not MAPK/ERK1/2 (U0126) pathway blocked the protection mediated by UDA in all tested models of SH-SY5Y cell injury. These in vitro data point to UDA as potentially effective neuroprotectant the utility of which should be further validated in animal studies.
[Mh] Termos MeSH primário: Fator de Indução de Apoptose/biossíntese
Apoptose/efeitos dos fármacos
Neuroblastoma/metabolismo
Fármacos Neuroprotetores/administração & dosagem
Ácidos Undecilênicos/administração & dosagem
[Mh] Termos MeSH secundário: Animais
Fator de Indução de Apoptose/metabolismo
Calpaína/metabolismo
Linhagem Celular Tumoral
Cromonas/administração & dosagem
Doxorrubicina/administração & dosagem
Seres Humanos
Morfolinas/administração & dosagem
Neuroblastoma/tratamento farmacológico
Neuroblastoma/patologia
Neurônios/efeitos dos fármacos
Estresse Oxidativo/efeitos dos fármacos
Fosfatidilinositol 3-Quinases/antagonistas & inibidores
Proteínas Proto-Oncogênicas c-akt/antagonistas & inibidores
Transdução de Sinais/efeitos dos fármacos
Estaurosporina/administração & dosagem
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (AIFM1 protein, human); 0 (Apoptosis Inducing Factor); 0 (Chromones); 0 (Morpholines); 0 (Neuroprotective Agents); 0 (Undecylenic Acids); 31M2U1DVID (2-(4-morpholinyl)-8-phenyl-4H-1-benzopyran-4-one); 80168379AG (Doxorubicin); EC 2.7.1.- (Phosphatidylinositol 3-Kinases); EC 2.7.11.1 (Proto-Oncogene Proteins c-akt); EC 3.4.22.- (Calpain); EC 3.4.22.- (mu-calpain); H88EPA0A3N (Staurosporine); K3D86KJ24N (undecylenic acid)
[Em] Mês de entrada:1608
[Cu] Atualização por classe:161125
[Lr] Data última revisão:
161125
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:150528
[St] Status:MEDLINE
[do] DOI:10.1002/jcb.25236


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[PMID]:25818921
[Au] Autor:Nie Y; Duan Y; Gong R; Yu S; Lu M; Yu F; Ji J
[Ad] Endereço:Zhejiang Province Key Lab of Biofuel, Zhejiang University of Technology, Hangzhou, Zhejiang 310014, China.
[Ti] Título:Microwave-assisted pyrolysis of methyl ricinoleate for continuous production of undecylenic acid methyl ester (UAME).
[So] Source:Bioresour Technol;186:334-7, 2015 Jun.
[Is] ISSN:1873-2976
[Cp] País de publicação:England
[La] Idioma:eng
[Ab] Resumo:Undecylenic acid methyl ester (UAME) was continuously produced from methyl ricinoleate using a microwave-assisted pyrolysis system with atomization feeding. The UAME yield of 77 wt.% was obtained at 500°C using SiC as the microwave absorbent and heating medium. The methyl ricinoleate conversion and UAME yield from microwave-assisted pyrolysis process were higher than those from conventional pyrolysis. The effect of temperature on the pyrolysis process was also investigated. The methyl ricinoleate conversion increased but the cracking liquid yield decreased when the temperature increased from 460°C to 560°C. The maximum UAME yield was obtained at the temperature of 500°C.
[Mh] Termos MeSH primário: Temperatura Alta
Micro-Ondas
Ácidos Ricinoleicos/química
Ácidos Undecilênicos/isolamento & purificação
[Pt] Tipo de publicação:EVALUATION STUDIES; JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (Ricinoleic Acids); 0 (Undecylenic Acids); 90FDR3O96Y (methyl ricinoleate)
[Em] Mês de entrada:1601
[Cu] Atualização por classe:150422
[Lr] Data última revisão:
150422
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:150331
[St] Status:MEDLINE


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[PMID]:25737121
[Au] Autor:Cho YH; Lee HJ; Lee JE; Kim SJ; Park K; Lee DY; Park YC
[Ad] Endereço:Department of Bio and Fermentation Convergence Technology, Kookmin University, Seoul 136-702, Republic of Korea.
[Ti] Título:Fast determination of multiple-reaction intermediates for long-chain dicarboxylic Acid biotransformation by gas chromatography-flame ionization detector.
[So] Source:J Microbiol Biotechnol;25(5):704-8, 2015 May.
[Is] ISSN:1738-8872
[Cp] País de publicação:Korea (South)
[La] Idioma:eng
[Ab] Resumo:For the analysis of multiple-reaction intermediates for long-chain dicarboxylic acid biotransformation, simple and reproducible methods of extraction and derivatization were developed on the basis of gas chromatography with flame ionization detector (GC-FID) instead of mass spectrometry. In the derivatization step, change of the ratio of pyridine to MSTFA from 1:3 to 9:1 resulted in higher peak intensity (p = 0.021) and reproducibility (0.6%CV) when analyzing 32 g/l ricinoleic acid (RA). Extraction of RA and ω-hydroxyundec- 9-enoic acid with water containing 100 mM Tween 80 showed 90.4-99.9% relative extraction efficiency and 2-7%CV compared with those with hydrophobic ethyl acetate. In conclusion, reduction of the pyridine content and change of the extraction solvent to water with Tween 80 provided compatible derivatization and extraction methods to GC-FID-based analysis of longchain carboxylic acids.
[Mh] Termos MeSH primário: Ácidos Dicarboxílicos/análise
Ácidos Dicarboxílicos/metabolismo
Ácidos Graxos Insaturados/análise
Ácidos Graxos Insaturados/metabolismo
Ionização de Chama/métodos
[Mh] Termos MeSH secundário: Ácidos Dicarboxílicos/química
Ácidos Graxos Insaturados/química
Piridinas/metabolismo
Ácidos Ricinoleicos/metabolismo
Ácidos Undecilênicos/metabolismo
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (Dicarboxylic Acids); 0 (Fatty Acids, Unsaturated); 0 (Pyridines); 0 (Ricinoleic Acids); 0 (Undecylenic Acids); 0 (omega-hydroxyundec-9-enoic acid); I2D0F69854 (ricinoleic acid); NH9L3PP67S (pyridine)
[Em] Mês de entrada:1602
[Cu] Atualização por classe:160909
[Lr] Data última revisão:
160909
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:150305
[St] Status:MEDLINE


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[PMID]:25369173
[Au] Autor:Geethanjali G; Padmaja KV; Sammaiah A; Prasad RB
[Ad] Endereço:Centre for Lipid Research, CSIR-Indian Institute of Chemical Technology , Hyderabad 500 007, Andhra Pradesh, India.
[Ti] Título:Synthesis, characterization, and evaluation of 10-undecenoic acid-based epithio derivatives as multifunctional additives.
[So] Source:J Agric Food Chem;62(47):11505-11, 2014 Nov 26.
[Is] ISSN:1520-5118
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:Novel epithio compounds from alkyl epoxy undecanoates (n-alkyl, C1, C4, and C6; isoalkyl, C3, C4, and C8) were synthesized using an ammonium thiocyanate in ionic liquid 1-methylimidazolium tetrafluoroborate/H2O (2:1) solvent system in 85-90% yields by gas chromatographic (GC) analysis. The synthesized products were characterized by (1)H and (13)C nuclear magnetic resonance spectroscopy, Fourier transform infrared spectroscopy (FTIR), gas chromatography, and GC mass spectral (GC-MS) analyses and evaluated for their antioxidant, extreme pressure (EP), and antiwear (AW) properties in three different base oils, namely, epoxy jatropha fatty acid n-butyl esters (EJB), di-2-ethylhexyl sebacate (DOS), and mineral oil (S-105). Among the synthesized products, n-butyl epithio undecanoate exhibited superior antioxidant property (229.2 °C) compared to butylated hydroxytoluene (BHT, 193.8 °C) in base oil DOS and comparable performance in EJB and S-105 base oils. All of the epithio derivatives exhibited significantly enhanced weld point for the base oils EJB and DOS at 2 wt % level and displayed moderate enhancement in S-105 base oil. Methyl epithio undecanoate at 0.6% concentration exhibited considerable improvement in the wear scar of DOS base oil. The synthesized epithio derivatives have potential as multifunctional additives in lubricant formulations.
[Mh] Termos MeSH primário: Ácidos Undecilênicos/síntese química
[Mh] Termos MeSH secundário: Antioxidantes/química
Hidroxitolueno Butilado/química
Ácidos Decanoicos/química
Ácidos Graxos/química
Cromatografia Gasosa-Espectrometria de Massas
Jatropha/química
Espectroscopia de Ressonância Magnética
Óleos Vegetais/química
Espectroscopia de Infravermelho com Transformada de Fourier
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Antioxidants); 0 (Decanoic Acids); 0 (Fatty Acids); 0 (Plant Oils); 0 (Undecylenic Acids); 1P9D0Z171K (Butylated Hydroxytoluene); K3D86KJ24N (undecylenic acid); U9LS47Q72Q (di-2-ethylhexyl sebacate)
[Em] Mês de entrada:1507
[Cu] Atualização por classe:141126
[Lr] Data última revisão:
141126
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:141105
[St] Status:MEDLINE
[do] DOI:10.1021/jf5033558


  8 / 157 MEDLINE  
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[PMID]:25329539
[Au] Autor:Yang R; Liu X; Chen Z; Yang C; Lin Y; Wang S
[Ad] Endereço:Sericulture and Agri-Food Research Institute, Guangdong Academy of Agricultural Sciences, Guangzhou, China.
[Ti] Título:Highly efficient and enzymatic regioselective undecylenoylation of gastrodin in 2-methyltetrahydrofuran-containing systems.
[So] Source:PLoS One;9(10):e110342, 2014.
[Is] ISSN:1932-6203
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:Highly efficient and regioselective acylation of pharmacologically interesting gastrodin with vinyl undecylenic acid has been firstly performed through an enzymatic approach. The highest catalytic activity and regioselectivity towards the acylation of 7'-hydroxyl of gastrodin was obtained with Pseudomonas cepacia lipase. In addition, it was observed the lipase displayed higher activity in the eco-friendly solvent 2-methyltetrahydrofuran-containing systems than in other organic solvents. In the co-solvent mixture of tetrahydrofuran and 2-methyltetrahydrofuran (3/1, v/v), the reaction rate was 60.6 mM/h, substrate conversion exceeded 99%, and 7'-regioselectivity was 93%. It was also interesting that the lipase-catalyzed acylation couldn't be influenced by the benzylic alcohol in gastrodin. However, pseudomonas cepacia lipase displayed different regioselectivity towards gastrodin and arbutin.
[Mh] Termos MeSH primário: Álcoois Benzílicos/química
Furanos/química
Glucosídeos/química
Lipase/metabolismo
[Mh] Termos MeSH secundário: Acilação
Burkholderia cepacia/enzimologia
Estabilidade Enzimática
Cinética
Lipase/química
Solventes/química
Estereoisomerismo
Especificidade por Substrato
Ácidos Undecilênicos/química
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (Benzyl Alcohols); 0 (Furans); 0 (Glucosides); 0 (Solvents); 0 (Undecylenic Acids); 5YS9U2W3RQ (gastrodin); EC 3.1.1.3 (Lipase); FCD0VD8ALF (2-methyltetrahydrofuran); K3D86KJ24N (undecylenic acid)
[Em] Mês de entrada:1510
[Cu] Atualização por classe:171116
[Lr] Data última revisão:
171116
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:141021
[St] Status:MEDLINE
[do] DOI:10.1371/journal.pone.0110342


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[PMID]:24961919
[Au] Autor:Brayden DJ; Walsh E
[Ad] Endereço:School of Veterinary Medicine, Veterinary Sciences Centre and Conway Institute, University College Dublin, Room 214 Belfield, Dublin 4, Ireland, david.brayden@ucd.ie.
[Ti] Título:Efficacious intestinal permeation enhancement induced by the sodium salt of 10-undecylenic acid, a medium chain fatty acid derivative.
[So] Source:AAPS J;16(5):1064-76, 2014 Sep.
[Is] ISSN:1550-7416
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:10-undecylenic acid (UA) is an OTC antifungal therapy and a nutritional supplement. It is an unsaturated medium chain fatty acid (MCFA) derivative, so our hypothesis was that its 11-mer sodium salt, uC11, would improve intestinal permeation similar to the established enhancer, sodium caprate (C10), but without the toxicity of the parent saturated MCFA, decylenic acid (C11). MTT assay and high-content screening (HCS) confirmed a cytotoxicity ranking in Caco-2 cells: C11 > C10 = uC11. Five to ten millimolars of the three agents reduced TEER and increased the Papp of [(14)C]-mannitol across Caco-2 monolayers and rat intestinal mucosae, a concentration that matched increases in plasma membrane permeability seen in HCS. Although C11 was the most efficacious enhancer in vitro, it damaged monolayers and tissue mucosae more than the other two agents at similar concentrations and exposure times and was therefore not pursued further. Rat jejunal and colonic in situ intestinal instillations of 100 mM C10 or uC11 with FITC-dextran 4000 (FD4) solutions yielded comparable regional enhancement ratios of ~10 and 30%, respectively, for each agent with acceptable tissue histology. Mini-tablets of uC11 and FD4 however delivered more FD4 compared to C10-FD-4 mini-tablets in both regions, as reflected by a statistically higher AUC, and with no evidence of membrane perturbation. The unsaturated bond in uC11 therefore confers a reduction in lipophilicity and cytotoxicity compared to C11, and the resulting permeation enhancement is on a par with or superior to that of C10, a key component of formulations in current phase II oral peptide clinical trials.
[Mh] Termos MeSH primário: Absorção Intestinal/efeitos dos fármacos
Mucosa Intestinal/efeitos dos fármacos
Ácidos Undecilênicos/farmacologia
[Mh] Termos MeSH secundário: Animais
Células CACO-2
Sobrevivência Celular/efeitos dos fármacos
Química Farmacêutica
Ácidos Decanoicos/farmacologia
Dextranos/metabolismo
Relação Dose-Resposta a Droga
Condutividade Elétrica
Fluoresceína-5-Isotiocianato/análogos & derivados
Fluoresceína-5-Isotiocianato/metabolismo
Seres Humanos
Mucosa Intestinal/metabolismo
Mucosa Intestinal/patologia
Cinética
Manitol/metabolismo
Permeabilidade
Ratos
Comprimidos
Ácidos Undecilênicos/química
Ácidos Undecilênicos/toxicidade
[Pt] Tipo de publicação:COMPARATIVE STUDY; JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (Decanoic Acids); 0 (Dextrans); 0 (Tablets); 0 (Undecylenic Acids); 0 (fluorescein isothiocyanate dextran); 3OWL53L36A (Mannitol); 4G9EDB6V73 (decanoic acid); I223NX31W9 (Fluorescein-5-isothiocyanate); K3D86KJ24N (undecylenic acid)
[Em] Mês de entrada:1505
[Cu] Atualização por classe:161125
[Lr] Data última revisão:
161125
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:140626
[St] Status:MEDLINE
[do] DOI:10.1208/s12248-014-9634-3


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[PMID]:24938497
[Au] Autor:Kato M; Nguyen D; Gonzalez M; Cortez A; Mullen SE; Cheruzel LE
[Ad] Endereço:San Jose State University, One Washington Square, San José, CA 95192-0101, United States.
[Ti] Título:Regio- and stereoselective hydroxylation of 10-undecenoic acid with a light-driven P450 BM3 biocatalyst yielding a valuable synthon for natural product synthesis.
[So] Source:Bioorg Med Chem;22(20):5687-91, 2014 Oct 15.
[Is] ISSN:1464-3391
[Cp] País de publicação:England
[La] Idioma:eng
[Ab] Resumo:We report herein the selective hydroxylation of 10-undecenoic acid with a light-activated hybrid P450 BM3 enzyme. Under previously developed photocatalytic reaction conditions, only a monohydroxylated product is detected by gas chromatography. Hydroxylation occurs exclusively at the allylic position as confirmed from a synthesized authentic standard. Investigation into the stereochemistry of the reaction indicates that the R enantiomer is obtained in 85% ee. The (R)-9-hydroxy-10-undecenoic acid obtained enzymatically is a valuable synthon en route to various natural products further expanding the light-activated P450 BM3 biocatalysis and highlighting the advantages over traditional methods.
[Mh] Termos MeSH primário: Proteínas de Bactérias/metabolismo
Biocatálise
Produtos Biológicos/metabolismo
Sistema Enzimático do Citocromo P-450/metabolismo
Luz
NADPH-Ferri-Hemoproteína Redutase/metabolismo
Ácidos Undecilênicos/metabolismo
[Mh] Termos MeSH secundário: Proteínas de Bactérias/química
Proteínas de Bactérias/isolamento & purificação
Produtos Biológicos/química
Sistema Enzimático do Citocromo P-450/química
Sistema Enzimático do Citocromo P-450/isolamento & purificação
Hidroxilação
Modelos Moleculares
Estrutura Molecular
NADPH-Ferri-Hemoproteína Redutase/química
NADPH-Ferri-Hemoproteína Redutase/isolamento & purificação
Estereoisomerismo
Ácidos Undecilênicos/química
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, N.I.H., EXTRAMURAL; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (Bacterial Proteins); 0 (Biological Products); 0 (Undecylenic Acids); 9035-51-2 (Cytochrome P-450 Enzyme System); EC 1.6.2.4 (NADPH-Ferrihemoprotein Reductase); EC 1.6.2.4 (flavocytochrome P450 BM3 monoxygenases); K3D86KJ24N (undecylenic acid)
[Em] Mês de entrada:1504
[Cu] Atualização por classe:170220
[Lr] Data última revisão:
170220
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:140619
[St] Status:MEDLINE



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