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  1 / 105 MEDLINE  
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[PMID]:28243820
[Au] Autor:Tomonaga N; Manabe Y; Sugawara T
[Ad] Endereço:Laboratory of Technology of Marine Bioproducts, Division of Applied Biosciences, Graduate School of Agriculture, Kyoto University, Kitashirakawaoiwakecho, Sakyo-ku, Kyoto, 606-8502, Japan.
[Ti] Título:Digestion of Ceramide 2-Aminoethylphosphonate, a Sphingolipid from the Jumbo Flying Squid Dosidicus gigas, in Mice.
[So] Source:Lipids;52(4):353-362, 2017 Apr.
[Is] ISSN:1558-9307
[Cp] País de publicação:Germany
[La] Idioma:eng
[Ab] Resumo:Ceramide 2-aminoethylphosphonate (CAEP), a sphingophosphonolipid containing a carbon-phosphorus bond, is frequently found in marine organisms and has a unique triene type of sphingoid base in its structure. CAEP has not been evaluated as a food ingredient, although it is generally contained in Mollusca organisms such as squids and shellfish, which are consumed worldwide. In this study, we aimed to elucidate the effects of CAEP as a food component by evaluating the digestion of CAEP extracted from the skin of the jumbo flying squid Dosidicus gigas. Our results revealed that dietary CAEP was digested to free sphingoid bases via ceramides by the mouse small intestinal mucosa. At pH 7.2, CAEP was hydrolyzed more rapidly than the major mammalian sphingolipid sphingomyelin; however, the hydrolysis of CAEP was similar to that of sphingomyelin at pH 9.0. Thus, the digestion of CAEP may be catalyzed by alkaline spingomyelinase and other enzymes. Our findings provide important insights into the digestion of the dietary sphingophosphonolipid CAEP in marine foods.
[Mh] Termos MeSH primário: Ácido Aminoetilfosfônico/análogos & derivados
Ceramidas/administração & dosagem
Decapodiformes/química
Intestino Delgado/metabolismo
[Mh] Termos MeSH secundário: Ácido Aminoetilfosfônico/administração & dosagem
Ácido Aminoetilfosfônico/farmacologia
Animais
Ceramidas/farmacologia
Suplementos Nutricionais
Hidrólise
Camundongos
Esfingomielina Fosfodiesterase/metabolismo
Esfingomielinas/química
[Pt] Tipo de publicação:COMPARATIVE STUDY; JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Ceramides); 0 (Sphingomyelins); 0 (ceramide aminoethylphosphonate); AH00YJQ334 (Aminoethylphosphonic Acid); EC 3.1.4.12 (Sphingomyelin Phosphodiesterase); EC 3.1.4.12 (alkaline sphingomyelinase, mouse)
[Em] Mês de entrada:1707
[Cu] Atualização por classe:171105
[Lr] Data última revisão:
171105
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:170301
[St] Status:MEDLINE
[do] DOI:10.1007/s11745-017-4239-0


  2 / 105 MEDLINE  
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[PMID]:27837996
[Au] Autor:Skeff W; Recknagel C; Schulz-Bull DE
[Ad] Endereço:Leibniz Institute for Baltic Sea Research Warnemuende, Department of Marine Chemistry, Seestrasse 15, 18119 Rostock, Germany. Electronic address: wael.skeff@io-warnemuende.de.
[Ti] Título:The influence of salt matrices on the reversed-phase liquid chromatography behavior and electrospray ionization tandem mass spectrometry detection of glyphosate, glufosinate, aminomethylphosphonic acid and 2-aminoethylphosphonic acid in water.
[So] Source:J Chromatogr A;1475:64-73, 2016 Dec 02.
[Is] ISSN:1873-3778
[Cp] País de publicação:Netherlands
[La] Idioma:eng
[Ab] Resumo:The analysis of highly polar and amphoteric compounds in seawater is a continuing challenge in analytical chemistry due to the possible formation of complexes with the metal cations present in salt-based matrices. Here we provide information for the development of analytical methods for glyphosate, glufosinate, AMPA, and 2-AEP in salt water, based on studies of the effects of salt matrices on reversed-phase liquid chromatography-heated electrospray ionization-tandem mass spectrometry (RP-LC-HESI-MS/MS) after derivatization of the target compounds with FMOC-Cl. The results showed that glyphosate was the only analyte with a strong tendency to form glyphosate-metal complexes (GMC), which clearly influenced the analysis. The retention times (RTs) of GMC and free glyphosate differed by approximately 7.00min, reflecting their distinct RP-LC behaviors. Divalent cations, but not monovalent (Na , K ) or trivalent (Al , Fe ) cations, contributed to this effect and their influence was concentration-dependent. In addition, Cu , Co , Zn , and Mn prevented glyphosate detection whereas Ca , Mg , and Sr altered the retention time. At certain tested concentrations of Ca and Sr glyphosate yielded two peaks, which violated the fundamental rule of LC, that under the same analytical conditions a single substance yields only one LC-peak with a specific RT. Salt-matrix-induced ion suppression was observed for all analytes, especially under high salt concentrations. For glyphosate and AMPA, the use of isotopically labeled internal standards well-corrected the salt-matrix effects, with better results achieved for glufosinate and 2-AEP with the AMPA internal standard than with the glyphosate internal standard. Thus, our study demonstrated that Ca , Mg , and Sr can be used together with FMOC-Cl to form GMC-FMOC which is suitable for RP-LC-HESI-MS/MS analysis.
[Mh] Termos MeSH primário: Aminobutiratos/análise
Cromatografia Líquida
Glicina/análogos & derivados
Herbicidas/análise
Espectrometria de Massas por Ionização por Electrospray
Poluentes Químicos da Água/análise
[Mh] Termos MeSH secundário: Ácido Aminoetilfosfônico/análise
Cátions Bivalentes
Cromatografia de Fase Reversa
Fluorenos/química
Glicina/análise
Glicina/química
Herbicidas/química
Organofosfonatos/análise
Sais/química
Espectrometria de Massas em Tandem
Água/química
Poluentes Químicos da Água/química
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Aminobutyrates); 0 (Cations, Divalent); 0 (Fluorenes); 0 (Herbicides); 0 (Organophosphonates); 0 (Salts); 0 (Water Pollutants, Chemical); 0 (aminomethylphosphonic acid); 059QF0KO0R (Water); 4632WW1X5A (glyphosate); 51276-47-2 (phosphinothricin); 9PLB0BTT90 (1-(9-fluorenyl)methyl chloroformate); AH00YJQ334 (Aminoethylphosphonic Acid); TE7660XO1C (Glycine)
[Em] Mês de entrada:1704
[Cu] Atualização por classe:170817
[Lr] Data última revisão:
170817
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:161114
[St] Status:MEDLINE


  3 / 105 MEDLINE  
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[PMID]:27268308
[Au] Autor:Bovill R; Evans PG; Howse GL; Osborn HM
[Ad] Endereço:Thermofisher Scientific, Wade Road, Basingstoke, Hampshire RG24 8PW, UK.
[Ti] Título:Synthesis and biological analysis of novel glycoside derivatives of l-AEP, as targeted antibacterial agents.
[So] Source:Bioorg Med Chem Lett;26(15):3774-9, 2016 08 01.
[Is] ISSN:1464-3405
[Cp] País de publicação:England
[La] Idioma:eng
[Ab] Resumo:To develop targeted methods for treating bacterial infections, the feasibility of using glycoside derivatives of the antibacterial compound l-R-aminoethylphosphonic acid (l-AEP) has been investigated. These derivatives are hypothesized to be taken up by bacterial cells via carbohydrate uptake mechanisms, and then hydrolyzed in situ by bacterial borne glycosidase enzymes, to selectively afford l-AEP. Therefore the synthesis and analysis of ten glycoside derivatives of l-AEP, for selective targeting of specific bacteria, is reported. The ability of these derivatives to inhibit the growth of a panel of Gram-negative bacteria in two different media is discussed. ß-Glycosides (12a) and (12b) that contained l-AEP linked to glucose or galactose via a carbamate linkage inhibited growth of a range of organisms with the best MICs being <0.75mg/ml; for most species the inhibition was closely related to the hydrolysis of the equivalent chromogenic glycosides. This suggests that for (12a) and (12b), release of l-AEP was indeed dependent upon the presence of the respective glycosidase enzyme.
[Mh] Termos MeSH primário: Ácido Aminoetilfosfônico/farmacologia
Antibacterianos/farmacologia
Bactérias/efeitos dos fármacos
Glicosídeos/farmacologia
[Mh] Termos MeSH secundário: Ácido Aminoetilfosfônico/química
Antibacterianos/síntese química
Antibacterianos/química
Bactérias/crescimento & desenvolvimento
Relação Dose-Resposta a Droga
Glicosídeos/síntese química
Glicosídeos/química
Testes de Sensibilidade Microbiana
Estrutura Molecular
Relação Estrutura-Atividade
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (Anti-Bacterial Agents); 0 (Glycosides); AH00YJQ334 (Aminoethylphosphonic Acid)
[Em] Mês de entrada:1706
[Cu] Atualização por classe:171122
[Lr] Data última revisão:
171122
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:160609
[St] Status:MEDLINE


  4 / 105 MEDLINE  
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[PMID]:26322863
[Au] Autor:Zhu S; Ye M; Xu J; Guo C; Zheng H; Hu J; Chen J; Wang Y; Xu S; Yan X
[Ad] Endereço:Key Laboratory of Applied Marine Biotechnology of Ministry of Education and ‡Collaborative Innovation Center for Zhejiang Marine High-efficiency and Healthy Aquaculture, Ningbo University , Ningbo 315211, China.
[Ti] Título:Lipid Profile in Different Parts of Edible Jellyfish Rhopilema esculentum.
[So] Source:J Agric Food Chem;63(37):8283-91, 2015 Sep 23.
[Is] ISSN:1520-5118
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:Jellyfish Rhopilema esculentum has been exploited commercially as a delicious food for a long time. Although the edible and medicinal values of R. esculentum have gained extensive attention, the effects of lipids on its nutritional value have rarely been reported. In the present of study, the lipid profile including lipid classes, fatty acyl compositions, and fatty acid (FA) positions in lipids from different parts (oral arms, umbrella, and mouth stalk) of R. esculentum was explored by ultraperformance liquid chromatography--electrospray ionization--quadrupole time-of-flight mass spectrometry (UPLC-ESI-Q-TOF-MS). More than 87 species from 10 major lipid classes including phosphatidylcholine (PC), lysophosphatidylcholine (LPC), phosphatidylethanolamine (PE), lysophosphatidylethanolamine (LPE), phosphatidylinositol (PI), lysophosphatidylinositol (LPI), phosphatidylserine (PS), ceramide (Cer), ceramide 2-aminoethylphosphonate (CAEP), and triacylglycerol (TAG) were separated and characterized. Semiquantification of individual lipid species in different parts of R. esculentum was also conducted. Results showed that glycerophospholipids (GPLs) enriched in highly unsaturated fatty acids (HUFAs) were the major compenents in all parts of R. esculentum, which accounted for 54-63% of total lipids (TLs). Considering the high level of GPLs and the FA compositions in GPLs, jellyfish R. esculentum might have great potential as a health-promoting food for humans and as a growth-promoting diet for some commercial fish and crustaceans. Meanwhile, LPC, LPE, and LPI showed high levels in oral arms when compared with umbrella and mouth stalk, which may be due to the high proportion of phospholipase A2 (PLA2) in oral arms. Moreover, a high CAEP level was detected in oral arms, which may render cell membranes with resistance to chemical hydrolysis by PLA2. The relatively low TAG content could be associated with specific functions of oral arms.
[Mh] Termos MeSH primário: Lipídeos/análise
Cifozoários/química
[Mh] Termos MeSH secundário: Ácido Aminoetilfosfônico/análogos & derivados
Ácido Aminoetilfosfônico/análise
Animais
Ceramidas/análise
Cromatografia Líquida de Alta Pressão
Ácidos Graxos/análise
Alimentos
Glicerofosfolipídeos/análise
Seres Humanos
Valor Nutritivo
Fosfolipases A2/análise
Espectrometria de Massas por Ionização por Electrospray
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (Ceramides); 0 (Fatty Acids); 0 (Glycerophospholipids); 0 (Lipids); 0 (ceramide aminoethylphosphonate); AH00YJQ334 (Aminoethylphosphonic Acid); EC 3.1.1.4 (Phospholipases A2)
[Em] Mês de entrada:1603
[Cu] Atualização por classe:150923
[Lr] Data última revisão:
150923
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:150901
[St] Status:MEDLINE
[do] DOI:10.1021/acs.jafc.5b03145


  5 / 105 MEDLINE  
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[PMID]:24162513
[Au] Autor:Klimek-Ochab M; Mucha A; Zymanczyk-Duda E
[Ad] Endereço:Department of Bioorganic Chemistry, Faculty of Chemistry, Wroclaw University of Technology, Wybrzeze Wyspianskiego 27, 50-370, Wroclaw, Poland, magdalena.klimek-ochab@pwr.wroc.pl.
[Ti] Título:2-Aminoethylphosphonate utilization by the cold-adapted Geomyces pannorum P11 strain.
[So] Source:Curr Microbiol;68(3):330-5, 2014 Mar.
[Is] ISSN:1432-0991
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:Cold-adapted strain of Geomyces pannorum P11 was found to mineralize of phosphorus-carbon bond-containing compound--2-aminoethylphosphonic acid (2-AEP, ciliatine). The biodegradation process proceeded in the phosphate-independent manner. Ciliatine-metabolizing enzymes' activity was detectable in cell-free extracts prepared from psychrophilic G. pannorum pregrown on 4 mM 2-AEP. Phosphonoacetaldehyde hydrolase (phosphonatase) activity in a partially purified extract was demonstrated at 10 °C.
[Mh] Termos MeSH primário: Ácido Aminoetilfosfônico/metabolismo
Ascomicetos/enzimologia
Ascomicetos/metabolismo
Hidrolases/metabolismo
[Mh] Termos MeSH secundário: Biotransformação
Temperatura Baixa
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
AH00YJQ334 (Aminoethylphosphonic Acid); EC 3.- (Hydrolases); EC 3.11.1.1 (phosphonoacetaldehyde hydrolase)
[Em] Mês de entrada:1409
[Cu] Atualização por classe:150422
[Lr] Data última revisão:
150422
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:131029
[St] Status:MEDLINE
[do] DOI:10.1007/s00284-013-0485-4


  6 / 105 MEDLINE  
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[PMID]:23860780
[Au] Autor:Cai Y; Lu Y; Yu C; Lyu H; Miao Z
[Ad] Endereço:State Key Laboratory and Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China.
[Ti] Título:Combined C-H functionalization/O-H insertion reaction to form tertiary ß-alkoxy substituted ß-aminophosphonates catalyzed by [Cu(MeCN)4]PF6.
[So] Source:Org Biomol Chem;11(33):5491-9, 2013 Sep 07.
[Is] ISSN:1477-0539
[Cp] País de publicação:England
[La] Idioma:eng
[Ab] Resumo:The copper-catalyzed C-H functionalization/O-H insertion reaction of α-diazophosphonates with alcohols has been developed with iodine as an additive. In order to understand this reaction, we present here a possible mechanism for the combined reaction. This process provides straightforward access to tertiary ß-alkoxy substituted ß-aminophosphonate derivatives with moderate to good yields.
[Mh] Termos MeSH primário: Álcoois
Ácido Aminoetilfosfônico/síntese química
Compostos Azo/síntese química
Cobre/química
Compostos Organometálicos/química
Organofosfonatos/síntese química
[Mh] Termos MeSH secundário: Álcoois/química
Ácido Aminoetilfosfônico/química
Compostos Azo/química
Catálise
Iodo/química
Estrutura Molecular
Organofosfonatos/química
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (Alcohols); 0 (Azo Compounds); 0 (Organometallic Compounds); 0 (Organophosphonates); 0 (alkoxyl radical); 789U1901C5 (Copper); 9679TC07X4 (Iodine); AH00YJQ334 (Aminoethylphosphonic Acid)
[Em] Mês de entrada:1403
[Cu] Atualização por classe:130731
[Lr] Data última revisão:
130731
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:130718
[St] Status:MEDLINE
[do] DOI:10.1039/c3ob40941d


  7 / 105 MEDLINE  
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[PMID]:23434798
[Au] Autor:Shoguchi E; Tanaka M; Takeuchi T; Shinzato C; Satoh N
[Ad] Endereço:Marine Genomics Unit, Okinawa Institute of Science and Technology, Onna, Okinawa 904-0495, Japan. eiichi@oist.jp
[Ti] Título:Probing a coral genome for components of the photoprotective scytonemin biosynthetic pathway and the 2-aminoethylphosphonate pathway.
[So] Source:Mar Drugs;11(2):559-70, 2013 Feb 22.
[Is] ISSN:1660-3397
[Cp] País de publicação:Switzerland
[La] Idioma:eng
[Ab] Resumo:Genome sequences of the reef-building coral, Acropora digitifera, have been decoded. Acropora inhabits an environment with intense ultraviolet exposure and hosts the photosynthetic endosymbiont, Symbiodinium. Acropora homologs of all four genes necessary for biosynthesis of the photoprotective cyanobacterial compound, shinorine, are present. Among metazoans, these genes are found only in anthozoans. To gain further evolutionary insights into biosynthesis of photoprotective compounds and associated coral proteins, we surveyed the Acropora genome for 18 clustered genes involved in cyanobacterial synthesis of the anti-UV compound, scytonemin, even though it had not previously been detected in corals. We identified candidates for only 6 of the 18 genes, including tyrP, scyA, and scyB. Therefore, it does not appear that Acropora digitifera can synthesize scytonemin independently. On the other hand, molecular phylogenetic analysis showed that one tyrosinase gene is an ortholog of vertebrate tyrosinase genes and that the coral homologs, scyA and scyB, are similar to bacterial metabolic genes, phosphonopyruvate (ppyr) decarboxylase and glutamate dehydrogenase (GDH), respectively. Further genomic searches for ppyr gene-related biosynthetic components indicate that the coral possesses a metabolic pathway similar to the bacterial 2-aminoethylphosphonate (AEP) biosynthetic pathway. The results suggest that de novo synthesis of carbon-phosphorus compounds is performed in corals.
[Mh] Termos MeSH primário: Ácido Aminoetilfosfônico/metabolismo
Antozoários/genética
Indóis/metabolismo
Fenóis/metabolismo
[Mh] Termos MeSH secundário: Ácido Aminoetilfosfônico/química
Animais
Bases de Dados Factuais
Regulação da Expressão Gênica
Genoma
Indóis/química
Estrutura Molecular
Fenóis/química
Filogenia
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Indoles); 0 (Phenols); 152075-98-4 (scytonemin); AH00YJQ334 (Aminoethylphosphonic Acid)
[Em] Mês de entrada:1309
[Cu] Atualização por classe:170220
[Lr] Data última revisão:
170220
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:130226
[St] Status:MEDLINE
[do] DOI:10.3390/md11020559


  8 / 105 MEDLINE  
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[PMID]:22068261
[Au] Autor:Chen SP; Hu L; Zhang YQ; Deng P; Li C; Chen X; Yuan LJ
[Ad] Endereço:College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072, PR China.
[Ti] Título:(AEDPH3)·(BtaH): a novel supramolecular plaster with formaldehyde adsorption and formaldehyde/ultraviolet ray-induced luminescence switching performance.
[So] Source:Chem Commun (Camb);48(4):552-4, 2012 Jan 14.
[Is] ISSN:1364-548X
[Cp] País de publicação:England
[La] Idioma:eng
[Ab] Resumo:A novel supramolecular plaster, (AEDPH(3))·(BtaH) (1), is synthesised and characterized. The supramolecular plaster is easy to synthesise and process, and displays good mechanical properties. It can adsorb and eliminate formaldehyde (HCHO) with high efficiency and exhibits very interesting HCHO/ultraviolet ray-induced luminescence switching.
[Mh] Termos MeSH primário: Ácido Aminoetilfosfônico/química
Poluentes Ambientais/isolamento & purificação
Formaldeído/isolamento & purificação
Triazóis/química
[Mh] Termos MeSH secundário: Adsorção
Luminescência
Modelos Moleculares
Raios Ultravioleta
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (Environmental Pollutants); 0 (Triazoles); 1HG84L3525 (Formaldehyde); AH00YJQ334 (Aminoethylphosphonic Acid)
[Em] Mês de entrada:1203
[Cu] Atualização por classe:131121
[Lr] Data última revisão:
131121
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:111110
[St] Status:MEDLINE
[do] DOI:10.1039/c1cc16415e


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[PMID]:21861368
[Au] Autor:Cooley NA; Kulakova AN; Villarreal-Chiu JF; Gilbert JA; McGrath JW; Quinn JP
[Ad] Endereço:School of Biological Science, Queens University, Medical Biology Centre, 97 Lisburn Road, Belfast, BT9 7BL, Northern Ireland, UK.
[Ti] Título:Phosphonoacetate biosynthesis: in vitro detection of a novel NADP(+)-dependent phosphonoacetaldehyde-oxidizing activity in cell-extracts of the marine Roseovarius nubinhibens ISM.
[So] Source:Mikrobiologiia;80(3):329-34, 2011 May-Jun.
[Is] ISSN:0026-3656
[Cp] País de publicação:Russia (Federation)
[La] Idioma:eng
[Ab] Resumo:A novel phosphonoacetaldehyde-oxidizing activity was detected in cell-extracts of the marine bacterium Roseovarius nubinhibens ISM grown on 2-aminoethylphosphonic acid (2-AEP; ciliatine). Extracts also contained 2-AEP transaminase and phosphonoacetate hydrolase activities. These findings indicate the existence of a biological route from 2-AEP via phosphonoacetaldehyde for the production of phosphonoacetate, which has not previously been shown to be a natural product. The three enzymes appear to constitute a previously-unreported pathway for the mineralization of 2-AEP which is a potentially important source of phosphorus in the nutrient-stressed marine environment.
[Mh] Termos MeSH primário: Fosfatase Alcalina/metabolismo
Ácido Aminoetilfosfônico/metabolismo
Ácido Fosfonoacéticos/metabolismo
Rhodobacteraceae
[Mh] Termos MeSH secundário: Acetaldeído/análogos & derivados
Acetaldeído/metabolismo
Organismos Aquáticos/enzimologia
Organismos Aquáticos/crescimento & desenvolvimento
Proteínas de Bactérias/metabolismo
Concentração de Íons de Hidrogênio
NADP/metabolismo
Fósforo/metabolismo
Rhodobacteraceae/enzimologia
Rhodobacteraceae/crescimento & desenvolvimento
Rhodobacteraceae/isolamento & purificação
Especificidade por Substrato
Temperatura Ambiente
Transaminases/metabolismo
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (Bacterial Proteins); 16051-76-6 (phosphonoacetaldehyde); 27YLU75U4W (Phosphorus); 53-59-8 (NADP); AH00YJQ334 (Aminoethylphosphonic Acid); EC 2.6.1.- (Transaminases); EC 3.1.3.1 (Alkaline Phosphatase); EC 3.11.1.2 (phosphonoacetate hydrolase); GO1N1ZPR3B (Acetaldehyde); N919E46723 (Phosphonoacetic Acid)
[Em] Mês de entrada:1109
[Cu] Atualização por classe:131121
[Lr] Data última revisão:
131121
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:110825
[St] Status:MEDLINE


  10 / 105 MEDLINE  
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[PMID]:21793197
[Au] Autor:Ross RD; Roeder RK
[Ad] Endereço:Department of Aerospace and Mechanical Engineering, Bioengineering Graduate Program, University of Notre Dame, Notre Dame, Indiana 46556, USA.
[Ti] Título:Binding affinity of surface functionalized gold nanoparticles to hydroxyapatite.
[So] Source:J Biomed Mater Res A;99(1):58-66, 2011 Oct.
[Is] ISSN:1552-4965
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:Gold nanoparticles (Au NPs) have been investigated for a number of biomedical applications, including drug and gene delivery vehicles, thermal ablation therapy, diagnostic sensors, and imaging contrast agents. Surface functionalization with molecular groups exhibiting calcium affinity can enable targeted delivery of Au NPs to calcified tissue, including damaged bone tissue. Therefore, the objective of this study was to investigate the binding affinity of functionalized Au NPs for targeted delivery to bone mineral, using hydroxyapatite (HA) crystals as a synthetic analog in vitro. Au NPs were synthesized to a mean particle size of 10-15 nm and surface functionalized with either L-glutamic acid, 2-aminoethylphosphonic acid, or alendronate, which exhibit a primary amine for binding gold opposite carboxylate, phosphonate, or bisphosphonate groups, respectively, for targeting calcium. Bisphosphonate functionalized Au NPs exhibited the most rapid binding kinetics and greatest binding affinity to HA, followed by glutamic acid and phosphonic acid. All functional groups reached complete binding after 24 h. Equilibrium binding constants in de-ionized water, determined by nonlinear regression of Langmuir isotherms, were 3.40, 0.69, and 0.25 mg/L for bisphosphonate, carboxylate, and phosphonate functionalized Au NPs, respectively. Functionalized Au NPs exhibited lower overall binding in fetal bovine serum compared to de-ionized water, but relative differences between functional groups were similar.
[Mh] Termos MeSH primário: Durapatita/química
Ouro/química
Nanopartículas Metálicas/química
[Mh] Termos MeSH secundário: Alendronato/química
Ácido Aminoetilfosfônico/química
Animais
Cálcio/química
Bovinos
Ácido Glutâmico/química
Soro/química
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, U.S. GOV'T, NON-P.H.S.
[Nm] Nome de substância:
3KX376GY7L (Glutamic Acid); 7440-57-5 (Gold); 91D9GV0Z28 (Durapatite); AH00YJQ334 (Aminoethylphosphonic Acid); SY7Q814VUP (Calcium); X1J18R4W8P (Alendronate)
[Em] Mês de entrada:1112
[Cu] Atualização por classe:131121
[Lr] Data última revisão:
131121
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:110728
[St] Status:MEDLINE
[do] DOI:10.1002/jbm.a.33165



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