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  1 / 141 MEDLINE  
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[PMID]:26226626
[Au] Autor:Heinisch T; Pellizzoni M; Dürrenberger M; Tinberg CE; Köhler V; Klehr J; Häussinger D; Baker D; Ward TR
[Ad] Endereço:†Department of Chemistry, University of Basel, 4056 Basel, Switzerland.
[Ti] Título:Improving the Catalytic Performance of an Artificial Metalloenzyme by Computational Design.
[So] Source:J Am Chem Soc;137(32):10414-9, 2015 Aug 19.
[Is] ISSN:1520-5126
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:Artifical metalloenzymes combine the reactivity of small molecule catalysts with the selectivity of enzymes, and new methods are required to tune the catalytic properties of these systems for an application of interest. Structure-based computational design could help to identify amino acid mutations leading to improved catalytic activity and enantioselectivity. Here we describe the application of Rosetta Design for the genetic optimization of an artificial transfer hydrogenase (ATHase hereafter), [(η(5)-Cp*)Ir(pico)Cl] ⊂ WT hCA II (Cp* = Me5C5(-)), for the asymmetric reduction of a cyclic imine, the precursor of salsolsidine. Based on a crystal structure of the ATHase, computational design afforded four hCAII variants with protein backbone-stabilizing and hydrophobic cofactor-embedding mutations. In dansylamide-competition assays, these designs showed 46-64-fold improved affinity for the iridium pianostool complex [(η(5)-Cp*)Ir(pico)Cl]. Gratifyingly, the new designs yielded a significant improvement in both activity and enantioselectivity (from 70% ee (WT hCA II) to up to 92% ee and a 4-fold increase in total turnover number) for the production of (S)-salsolidine. Introducing additional hydrophobicity in the Cp*-moiety of the Ir-catalyst provided by adding a propyl substituent on the Cp* moiety yields the most (S)-selective (96% ee) ATHase reported to date. X-ray structural data indicate that the high enantioselectivity results from embedding the piano stool moiety within the protein, consistent with the computational model.
[Mh] Termos MeSH primário: Anidrase Carbônica II/química
Irídio/química
Engenharia de Proteínas/métodos
Proteínas Recombinantes/química
[Mh] Termos MeSH secundário: Anidrase Carbônica II/genética
Anidrase Carbônica II/metabolismo
Catálise
Coenzimas/química
Coenzimas/metabolismo
Cristalografia por Raios X
Compostos de Dansil/química
Compostos de Dansil/metabolismo
Seres Humanos
Interações Hidrofóbicas e Hidrofílicas
Iminas/química
Irídio/metabolismo
Metaloproteínas/química
Metaloproteínas/genética
Metaloproteínas/metabolismo
Mutação
Proteínas Recombinantes/genética
Proteínas Recombinantes/metabolismo
Alcaloides de Salsolina/metabolismo
Software
Relação Estrutura-Atividade
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (Coenzymes); 0 (Dansyl Compounds); 0 (Imines); 0 (Metalloproteins); 0 (Recombinant Proteins); 0 (Salsoline Alkaloids); 1431-39-6 (5-dimethylaminonaphthalene-1-sulfonamide); 44448S9773 (Iridium); EC 4.2.1.- (Carbonic Anhydrase II); QMS4D62O1I (salsolidine)
[Em] Mês de entrada:1709
[Cu] Atualização por classe:170908
[Lr] Data última revisão:
170908
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:150731
[St] Status:MEDLINE
[do] DOI:10.1021/jacs.5b06622


  2 / 141 MEDLINE  
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[PMID]:24252728
[Au] Autor:Arshad A; Chen X; Cong Z; Qing H; Deng Y
[Ad] Endereço:Cell Biology Laboratory, School of Life Science, Beijing Institute of Technology, Beijing 100081, China.
[Ti] Título:TRPC1 protects dopaminergic SH-SY5Y cells from MPP+, salsolinol, and N-methyl-(R)-salsolinol-induced cytotoxicity.
[So] Source:Acta Biochim Biophys Sin (Shanghai);46(1):22-30, 2014 Jan.
[Is] ISSN:1745-7270
[Cp] País de publicação:China
[La] Idioma:eng
[Ab] Resumo:Neurotoxins and alterations in Ca2+ homeostasis have been associated with Parkinson's disease (PD), but the role of store-operated Ca2+ entry channels is not well understood. Previous studies have shown the neurotoxicity of salsolinol and 1-methyl-4-phenylpyridinium ion on SH-SY5Y cells and cytoprotection induced by transient receptor potential protein 1 (TRPC1). In the present study, N-methyl-(R)-salsolinol was tested for its cellular toxicity and effects on TRPC1 expression. MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) assays, DAPI (4',6-diamidino-2-phenylindole), fluorescein isothiocyanate-Annexin-V/propidium iodide, western blot analysis, and JC-1 labeling revealed that the three indicated drugs could induce caspase-dependent, mitochondrial-mediated apoptosis. Exposure of SH-SY5Y cells to the indicated drugs resulted in a significant decrease in thapsigargin-mediated Ca2+ influx and TRPC1 expression. Immunocytochemistry experiments revealed that neurotoxins treatment induced TRPC1 translocation to the cytoplasm. Taken together, our results indicate that treatment with neurotoxins may alter Ca2+ homeostasis and induce mitochondrial-mediated caspase-dependent cytotoxicity, an important characteristic of PD.
[Mh] Termos MeSH primário: 1-Metil-4-fenilpiridínio/toxicidade
Neurônios Dopaminérgicos/efeitos dos fármacos
Isoquinolinas/toxicidade
Neurotoxinas/toxicidade
Alcaloides de Salsolina/toxicidade
Canais de Cátion TRPC/farmacologia
[Mh] Termos MeSH secundário: Apoptose/efeitos dos fármacos
Cálcio/metabolismo
Caspases/metabolismo
Linhagem Celular Tumoral
Sobrevivência Celular/efeitos dos fármacos
Neurônios Dopaminérgicos/metabolismo
Seres Humanos
Potencial da Membrana Mitocondrial/efeitos dos fármacos
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (Isoquinolines); 0 (Neurotoxins); 0 (Salsoline Alkaloids); 0 (TRPC Cation Channels); 0 (transient receptor potential cation channel, subfamily C, member 1); 9ILS801M65 (salsolinol); 9Q83ETU10C (salsoline); EC 3.4.22.- (Caspases); R865A5OY8J (1-Methyl-4-phenylpyridinium); SY7Q814VUP (Calcium)
[Em] Mês de entrada:1408
[Cu] Atualização por classe:131223
[Lr] Data última revisão:
131223
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:131121
[St] Status:MEDLINE
[do] DOI:10.1093/abbs/gmt127


  3 / 141 MEDLINE  
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[PMID]:23677770
[Au] Autor:Li X; Leonori D; Sheikh NS; Coldham I
[Ad] Endereço:Department of Chemistry, University of Sheffield, Brook Hill, Sheffield S3 7HF, UK.
[Ti] Título:Synthesis of 1-substituted tetrahydroisoquinolines by lithiation and electrophilic quenching guided by in situ IR and NMR spectroscopy and application to the synthesis of salsolidine, carnegine and laudanosine.
[So] Source:Chemistry;19(24):7724-30, 2013 Jun 10.
[Is] ISSN:1521-3765
[Cp] País de publicação:Germany
[La] Idioma:eng
[Ab] Resumo:The lithiation of N-tert-butoxycarbonyl (N-Boc)-1,2,3,4-tetrahydroisoquinoline was optimized by in situ IR (ReactIR) spectroscopy. Optimum conditions were found by using n-butyllithium in THF at -50 °C for less than 5 min. The intermediate organolithium was quenched with electrophiles to give 1-substituted 1,2,3,4-tetrahydroisoquinolines. Monitoring the lithiation by IR or NMR spectroscopy showed that one rotamer reacts quickly and the barrier to rotation of the Boc group was determined by variable-temperature NMR spectroscopy and found to be about 60.8 kJ mol(-1), equating to a half-life for rotation of approximately 30 s at -50 °C. The use of (-)-sparteine as a ligand led to low levels of enantioselectivity after electrophilic quenching and the "poor man's Hoffmann test" indicated that the organolithium was configurationally unstable. The chemistry was applied to N-Boc-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline and led to the efficient synthesis of the racemic alkaloids salsolidine, carnegine, norlaudanosine and laudanosine.
[Mh] Termos MeSH primário: Isoquinolinas/síntese química
Alcaloides de Salsolina/síntese química
Tetra-Hidroisoquinolinas/síntese química
[Mh] Termos MeSH secundário: Alcaloides/síntese química
Alcaloides/química
Seres Humanos
Isoquinolinas/química
Ligantes
Masculino
Ressonância Magnética Nuclear Biomolecular
Alcaloides de Salsolina/química
Esparteína/química
Espectrofotometria Infravermelho
Estereoisomerismo
Tetra-Hidroisoquinolinas/química
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (Alkaloids); 0 (Isoquinolines); 0 (Ligands); 0 (Salsoline Alkaloids); 0 (Tetrahydroisoquinolines); 0 (carnegine); 1745-07-9 (heliamine); 298897D62S (Sparteine); 56W89FBX3E (1,2,3,4-tetrahydroisoquinoline); DA7R5WVN48 (laudanosine); QMS4D62O1I (salsolidine)
[Em] Mês de entrada:1401
[Cu] Atualização por classe:161125
[Lr] Data última revisão:
161125
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:130517
[St] Status:MEDLINE
[do] DOI:10.1002/chem.201301096


  4 / 141 MEDLINE  
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[PMID]:21470616
[Au] Autor:Wu H; Yuan B; Liu YM
[Ad] Endereço:Department of Chemistry and Biochemistry, Jackson State University, Jackson, MS 39110, USA.
[Ti] Título:Chiral capillary electrophoresis-mass spectrometry of tetrahydroisoquinoline-derived neurotoxins: observation of complex stereoisomerism.
[So] Source:J Chromatogr A;1218(20):3118-23, 2011 May 20.
[Is] ISSN:1873-3778
[Cp] País de publicação:Netherlands
[La] Idioma:eng
[Ab] Resumo:Previous studies have shown that certain 1,2,3,4-tetrahydroisoquinoline derivatives (TIQs) are neurotoxins inducing Parkinsonism. Further, individual enantiomers of these toxins such as (R/S)-N-methylsalsolinol ((R/S)-NMSal) possess distinct neurotoxicological properties. In this work, a chiral capillary electrophoresis (CE) method with electrospray ionization-tandem mass spectrometric (ESI-MS/MS) detection was developed for the quantification of TIQ enantiomers. Enantioseparation was achieved with sulfated ß-cyclodextrin (sulfated ß-CD) as chiral selector. To avoid any potential contamination of MS ionization source by the non-volatile chiral selector, partial filling technique was deployed in the CE separation. TIQ derivatives, including (R/S)-6,7-dihydroxy-1-methy-TIQ (salsolinol, Sal), (R/S)-1-benzyl-TIQ (BTIQ), and (R/S)-NMSal, were base-line resolved with resolution values (R) ranging from 3 (for Sal) to 4.5 (for BTIQ), which were much better than those reported previously by HPLC methods. ESI-MS/MS detection of the resolved TIQ enantiomers was specific and sensitive (LOD=1.2 µM for Sal enantiomers). The proposed chiral CE-MS/MS method was used to study in vitro formation of (R/S)-NMSal. It was found that NMSal was formed from the incubation of epinine (a dopamine metabolite) with acetaldehyde (a metabolite of alcohol). More interestingly, four isomers of NMSal were separated and detected in the incubation solution. They were identified as (R)-e.e-NMSal, (R)-e.a-NMSal, (S)-e.e-NMSal, and (S)-e.a-NMSal. This was the first lab evidence that this Parkinsonian neurotoxin exists in multiple isomeric forms.
[Mh] Termos MeSH primário: Eletroforese Capilar/métodos
Indóis/química
Neurotoxinas/química
Alcaloides de Salsolina/química
Espectrometria de Massas por Ionização por Electrospray/métodos
[Mh] Termos MeSH secundário: Acetaldeído/química
Desoxiepinefrina/química
Espectrometria de Massas
Estereoisomerismo
Espectrometria de Massas em Tandem
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, N.I.H., EXTRAMURAL
[Nm] Nome de substância:
0 (Indoles); 0 (Neurotoxins); 0 (Salsoline Alkaloids); 0 (indolin-2-one); 9Q83ETU10C (salsoline); GO1N1ZPR3B (Acetaldehyde); R7339QLN1C (Deoxyepinephrine)
[Em] Mês de entrada:1108
[Cu] Atualização por classe:170220
[Lr] Data última revisão:
170220
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:110408
[St] Status:MEDLINE
[do] DOI:10.1016/j.chroma.2011.03.026


  5 / 141 MEDLINE  
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[PMID]:21222065
[Au] Autor:Ramlochansingh C; Taylor RE; Tizabi Y
[Ad] Endereço:Department of Pharmacology, College of Medicine, Howard University, 520 W Street NW, Washington, DC 20059, USA.
[Ti] Título:Toxic effects of low alcohol and nicotine combinations in SH-SY5Y cells are apoptotically mediated.
[So] Source:Neurotox Res;20(3):263-9, 2011 Oct.
[Is] ISSN:1476-3524
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:It is well established that combination of heavy drinking and smoking has severe health consequences. However, at relatively low concentrations, both alcohol and nicotine may have beneficial effects including neuroprotection. Thus, protective effects of low alcohol concentration against beta-amyloid-induced toxicity in organotypic hippocampal slices and protective effects of nicotine against salsolinol-induced toxicity in human-derived neuroblastoma cells (SH-SY5Y) have been reported. In this study, we sought to determine whether alcohol might also be protective against salsolinol-induced toxicity in SH-SY5Y cells and whether the combination of low doses of alcohol and nicotine might have an additive or synergistic effect. Pre-exposure of SH-SY5Y cells to either ethanol (1 or 10 mM) or nicotine (20 or 50 µM) significantly attenuated salsolinol-induced toxicity. However, contrary to the expectation the combination of low doses of alcohol and nicotine not only did not provide any synergistic or additive protective effect, but exacerbated salsolinol-induced toxicity. Indeed, simple combination of low alcohol and nicotine resulted in significant toxicity in SH-SY5Y cells. This toxicity, reflected in a reduction in cell viability was associated with an increase in apoptosis as determined by caspase-3 measurement. These in vitro results suggest that combination of even low concentrations of alcohol and nicotine may activate apoptotic mechanisms that can lead to cell toxicity and detrimental consequences.
[Mh] Termos MeSH primário: Apoptose/efeitos dos fármacos
Depressores do Sistema Nervoso Central/toxicidade
Etanol/toxicidade
Nicotina/toxicidade
Agonistas Nicotínicos/toxicidade
[Mh] Termos MeSH secundário: Análise de Variância
Animais
Caspase 3/metabolismo
Linhagem Celular Tumoral
Sobrevivência Celular/efeitos dos fármacos
Relação Dose-Resposta a Droga
Combinação de Medicamentos
Seres Humanos
Neuroblastoma/patologia
Alcaloides de Salsolina/farmacologia
Sais de Tetrazólio
Tiazóis
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, N.I.H., EXTRAMURAL
[Nm] Nome de substância:
0 (Central Nervous System Depressants); 0 (Drug Combinations); 0 (Nicotinic Agonists); 0 (Salsoline Alkaloids); 0 (Tetrazolium Salts); 0 (Thiazoles); 3K9958V90M (Ethanol); 6M3C89ZY6R (Nicotine); 9Q83ETU10C (salsoline); EC 3.4.22.- (Caspase 3); EUY85H477I (thiazolyl blue)
[Em] Mês de entrada:1111
[Cu] Atualização por classe:161125
[Lr] Data última revisão:
161125
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:110112
[St] Status:MEDLINE
[do] DOI:10.1007/s12640-011-9239-x


  6 / 141 MEDLINE  
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[PMID]:20446293
[Au] Autor:Kuklinski NJ; Berglund EC; Engelbreksson J; Ewing AG
[Ad] Endereço:Department of Chemistry, The Pennsylvania State University, PA, USA.
[Ti] Título:Determination of salsolinol, norsalsolinol, and twenty-one biogenic amines using micellar electrokinetic capillary chromatography-electrochemical detection.
[So] Source:Electrophoresis;31(11):1886-93, 2010 Jun.
[Is] ISSN:1522-2683
[Cp] País de publicação:Germany
[La] Idioma:eng
[Ab] Resumo:Micellar electrokinetic chromatography coupled to amperometric electrochemical detection was used to resolve and then quantify biogenic amines and metabolites within the fruit fly Drosophila melanogaster. A new separation scheme was devised to allow resolution of 24 compounds of interest. This was accomplished by precisely controlling the amount of base added to the background buffer, optimizing the resolution of the separation, and then calculating the pH. Here we focused on measurements of six of the analytes that are thought to be involved in the response to alcohol, dopamine, salsolinol, norsalsolinol, N-acetyloctopamine, octopamine, and N-acetyldopamine. These were identified and quantified within the fly head. We believe that the identification of salsolinol and norsalsolinol in the fly brain is novel.
[Mh] Termos MeSH primário: Aminas Biogênicas/análise
Cromatografia Capilar Eletrocinética Micelar/métodos
Drosophila melanogaster/química
Isoquinolinas/análise
Alcaloides de Salsolina/análise
[Mh] Termos MeSH secundário: Animais
Aminas Biogênicas/química
Boratos/química
Proteínas de Drosophila/análise
Proteínas de Drosophila/química
Concentração de Íons de Hidrogênio
Isoquinolinas/química
Masculino
Sistema Nervoso/química
Análise de Regressão
Alcaloides de Salsolina/química
Dodecilsulfato de Sódio/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 (Biogenic Amines); 0 (Borates); 0 (Drosophila Proteins); 0 (Isoquinolines); 0 (Salsoline Alkaloids); 368GB5141J (Sodium Dodecyl Sulfate); 9ILS801M65 (salsolinol); 9SPO03ZH41 (norsalsolinol)
[Em] Mês de entrada:1008
[Cu] Atualização por classe:170220
[Lr] Data última revisão:
170220
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:100507
[St] Status:MEDLINE
[do] DOI:10.1002/elps.200900761


  7 / 141 MEDLINE  
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[PMID]:19526284
[Au] Autor:Das JR; Tizabi Y
[Ad] Endereço:Department of Pharmacology, College of Medicine, Howard University, 520 W Street NW, Washington, DC 20059, USA.
[Ti] Título:Additive protective effects of donepezil and nicotine against salsolinol-induced cytotoxicity in SH-SY5Y cells.
[So] Source:Neurotox Res;16(3):194-204, 2009 Oct.
[Is] ISSN:1476-3524
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:Although the etiology of Parkinson's disease (PD) remains elusive, a number of toxins including elevated salsolinol, an endogenous metabolite of dopamine may contribute to its pathology. It was reported recently that nicotine may have protective effects against salsolinol-induced toxicity in human neuroblastoma derived SH-SY5Y cells and that these effects of nicotine are mediated by nicotinic receptors. Donepezil (Aricept) is a reversible non-competitive acetylcholinesterase inhibitor that is approved for use in mild to moderate Alzheimer's disease. The increase in acetylcholine concentrations is believed to be the major contributory factor in donepezil's therapeutic efficacy. However, cholinesterase inhibitors may also directly interact with nicotinic receptors and possess neuroprotective properties. In this study, we sought to determine whether donepezil may have protective effects against salsolinol-induced toxicity in SH-SY5Y cells and whether the combination of donepezil and nicotine may result in additive protection. Moreover, it was of interest to elucidate the role of nicotinic receptors as well as cell cycle and apoptosis in mechanism of action of these compounds. SH-SY5Y cells were exposed to 0.6 mM salsolinol with and without various drug pretreatments for 48 h. Nicotine (50 muM) resulted in approximately 54% protection and donepezil (5 muM) resulted in approximately 40% protection, and the combination of the two resulted in an additive (approximately 93%) protection against salsolinol-induced toxicity. Salsolinol caused an arrest of the cells in G(1)-phase of cell cycle and an increase in apoptotic indices that were blocked by the combination of donepezil and nicotine. Mecamylamine, a non-selective nicotinic receptor antagonist completely blocked the effects of nicotine and partially attenuated the effects of donepezil. A combination of atropine, a muscarinic receptor antagonist and mecamylamine completely blocked the effects of donepezil, indicating involvement of both nicotinic and muscarinic receptors in donepezil's actions. The findings suggest a therapeutic potential for the combination of donepezil and nicotine in PD.
[Mh] Termos MeSH primário: Apoptose/efeitos dos fármacos
Inibidores da Colinesterase/farmacologia
Indanos/farmacologia
Nicotina/farmacologia
Agonistas Nicotínicos/farmacologia
Piperidinas/farmacologia
Alcaloides de Salsolina/toxicidade
[Mh] Termos MeSH secundário: Análise de Variância
Anexina A5/metabolismo
Atropina/farmacologia
Ciclo Celular/efeitos dos fármacos
Linhagem Celular Tumoral
Sobrevivência Celular/efeitos dos fármacos
Relação Dose-Resposta a Droga
Combinação de Medicamentos
Interações Medicamentosas
Citometria de Fluxo/métodos
Regulação Neoplásica da Expressão Gênica/efeitos dos fármacos
Seres Humanos
Mecamilamina/farmacologia
Neuroblastoma/patologia
Antagonistas Nicotínicos/farmacologia
Propídio
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (Annexin A5); 0 (Cholinesterase Inhibitors); 0 (Drug Combinations); 0 (Indans); 0 (Nicotinic Agonists); 0 (Nicotinic Antagonists); 0 (Piperidines); 0 (Salsoline Alkaloids); 36015-30-2 (Propidium); 6EE945D3OK (Mecamylamine); 6M3C89ZY6R (Nicotine); 7C0697DR9I (Atropine); 8SSC91326P (donepezil); 9Q83ETU10C (salsoline)
[Em] Mês de entrada:1001
[Cu] Atualização por classe:171110
[Lr] Data última revisão:
171110
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:090616
[St] Status:MEDLINE
[do] DOI:10.1007/s12640-009-9040-2


  8 / 141 MEDLINE  
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[PMID]:19523811
[Au] Autor:Zhu W; An Y; Zheng J; Tang L; Zhang W; Jin L; Jiang L
[Ad] Endereço:Department of Chemistry, East China Normal University, 3663 Zhongshan Rd.(N), Shanghai 200062, PR China.
[Ti] Título:A new microdialysis-electrochemical device for in vivo simultaneous determination of acetylcholine and choline in rat brain treated with N-methyl-(R)-salsolinol.
[So] Source:Biosens Bioelectron;24(12):3594-9, 2009 Aug 15.
[Is] ISSN:1873-4235
[Cp] País de publicação:England
[La] Idioma:eng
[Ab] Resumo:Acetylcholine (ACh) and choline (Ch) play a critical role in cholinergic neurotransmission and the abnormalities in their concentrations are related to several neural diseases. Therefore, the in vivo determination of ACh and Ch is important to the research on neurodegenerative disorders. In this work, electrochemical biosensors based on poly(m-(1,3)-phenylenediamine) (pmPD) and polytyramine (PTy) modified enzyme electrodes were fabricated. The electropolymerized pmPD polymer was used to exclude interfering substances and the PTy layer facilitated the immobilization of acetylcholinesterase (AChE) and choline oxidase (ChOx). Then, ACh/Ch sensor and Ch sensor were coupled with microdialysis to produce a novel device, which provides a sensitive and selective method for simultaneous determination of ACh and Ch. This method has detection limits of 63.0+/-3.4 nM for ACh and 25.0+/-1.2 nM for Ch. The integrated device was successfully applied to assessing the impact of endogenous neurotoxin N-methyl-(R)-salsolinol [1(R),2-dimethyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline, (R)-NMSal] on ACh and Ch concentration, which is of great benefit to understand the pathogenesis of Parkinson's disease.
[Mh] Termos MeSH primário: Acetilcolina/análise
Encéfalo/efeitos dos fármacos
Encéfalo/metabolismo
Colina/análise
Eletroquímica/instrumentação
Microdiálise/instrumentação
Doença de Parkinson Secundária/metabolismo
[Mh] Termos MeSH secundário: Animais
Técnicas Biossensoriais/instrumentação
Desenho de Equipamento
Análise de Falha de Equipamento
Masculino
Doença de Parkinson Secundária/induzido quimicamente
Doença de Parkinson Secundária/diagnóstico
Ratos
Ratos Sprague-Dawley
Alcaloides de Salsolina
[Pt] Tipo de publicação:EVALUATION STUDIES; JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (Salsoline Alkaloids); 9Q83ETU10C (salsoline); N91BDP6H0X (Choline); N9YNS0M02X (Acetylcholine)
[Em] Mês de entrada:0909
[Cu] Atualização por classe:131121
[Lr] Data última revisão:
131121
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:090616
[St] Status:MEDLINE
[do] DOI:10.1016/j.bios.2009.05.023


  9 / 141 MEDLINE  
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[PMID]:19012744
[Au] Autor:Kobayashi H; Fukuhara K; Tada-Oikawa S; Yada Y; Hiraku Y; Murata M; Oikawa S
[Ad] Endereço:Department of Environmental and Molecular Medicine, Mie University Graduate School of Medicine, Edobashi 2-174, Tsu, Mie, Japan.
[Ti] Título:The mechanisms of oxidative DNA damage and apoptosis induced by norsalsolinol, an endogenous tetrahydroisoquinoline derivative associated with Parkinson's disease.
[So] Source:J Neurochem;108(2):397-407, 2009 Jan.
[Is] ISSN:1471-4159
[Cp] País de publicação:England
[La] Idioma:eng
[Ab] Resumo:Tetrahydroisoquinoline (TIQ) derivatives are putative neurotoxins that may contribute to the degeneration of dopaminergic neurons in Parkinson's disease. One TIQ, norsalsolinol (NorSAL), is present in dopamine-rich areas of human brain, including the substantia nigra. Here, we demonstrate that NorSAL reduces cell viability and induces apoptosis via cytochrome c release and caspase 3 activation in SH-SY5Y human neuroblastoma cells. Cytochrome c release, caspase 3 activation, and apoptosis induction were all inhibited by the antioxidant N-acetylcysteine. Thus, reactive oxygen species (ROS) contribute to apoptosis induced by NorSAL. Treatment with NorSAL also increased levels of oxidative damage to DNA, a stimulus for apoptosis, in SH-SY5Y. To clarify the mechanism of intracellular DNA damage, we examined the DNA damage caused by NorSAL using (32)P-5'-end-labeled isolated DNA fragments. NorSAL induced DNA damage in the presence of Cu(II). Catalase and bathocuproine, a Cu(I) chelator, inhibited this DNA damage, suggesting that ROS such as the Cu(I)-hydroperoxo complex derived from the reaction of H(2)O(2) with Cu(I), promote DNA damage by NorSAL. In summary, NorSAL-generated ROS induced oxidative DNA damage, which led to caspase-dependent apoptosis in neuronal cells.
[Mh] Termos MeSH primário: Apoptose/efeitos dos fármacos
Dano ao DNA/efeitos dos fármacos
Alcaloides de Salsolina/farmacologia
[Mh] Termos MeSH secundário: Autorradiografia
Benzoquinonas/metabolismo
Caspase 3/metabolismo
Linhagem Celular Tumoral
Cobre/farmacologia
Citocromos c/metabolismo
Desoxiguanosina/análogos & derivados
Desoxiguanosina/metabolismo
Relação Dose-Resposta a Droga
Depuradores de Radicais Livres/farmacologia
Seres Humanos
NAD/metabolismo
Neuroblastoma
Fenantrolinas/farmacologia
Isótopos de Fósforo/metabolismo
Tetra-Hidroisoquinolinas/química
Sais de Tetrazólio
Tiazóis
Fatores de Tempo
Tirosina 3-Mono-Oxigenase/metabolismo
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (Benzoquinones); 0 (Free Radical Scavengers); 0 (Phenanthrolines); 0 (Phosphorus Isotopes); 0 (Salsoline Alkaloids); 0 (Tetrahydroisoquinolines); 0 (Tetrazolium Salts); 0 (Thiazoles); 0U46U6E8UK (NAD); 3T006GV98U (quinone); 789U1901C5 (Copper); 88847-89-6 (8-oxo-7-hydrodeoxyguanosine); 9007-43-6 (Cytochromes c); 9SPO03ZH41 (norsalsolinol); 9THP2V94FX (bathocuproine); EC 1.14.16.2 (Tyrosine 3-Monooxygenase); EC 3.4.22.- (Caspase 3); EUY85H477I (thiazolyl blue); G9481N71RO (Deoxyguanosine); S2QG84156O (cupric chloride)
[Em] Mês de entrada:0904
[Cu] Atualização por classe:161124
[Lr] Data última revisão:
161124
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:081118
[St] Status:MEDLINE
[do] DOI:10.1111/j.1471-4159.2008.05774.x


  10 / 141 MEDLINE  
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[PMID]:19034892
[Au] Autor:Cai M; Liu YM
[Ad] Endereço:Department of Chemistry, Jackson State University, 1400 Lynch St., Jackson, MS 39217, USA.
[Ti] Título:Quantification of salsolinol enantiomers by stable isotope dilution liquid chromatography with tandem mass spectrometric detection.
[So] Source:Rapid Commun Mass Spectrom;22(24):4171-7, 2008 Dec.
[Is] ISSN:0951-4198
[Cp] País de publicação:England
[La] Idioma:eng
[Ab] Resumo:Salsolinol, 1-methyl-6,7-dihydroxy-2,3,4,5-tetrahydroisoquinoline (SAL), is a precursor of a Parkinsonian neurotoxin, N-methysalsolinol (N-methyl-SAL). Previous studies have shown that individual enantiomers of N-methyl-SAL possess distinct neurotoxicological properties. In this work, a chiral high-performance liquid chromatography (HPLC) method with electrospray ionization tandem mass spectrometric (ESI-MS/MS) detection was developed for the quantification of (R/S)-SAL enantiomers. Enantioseparation was achieved on a beta-cyclodextrin-bonded silica gel column, and the resolved enantiomers were detected by ESI-MS/MS operated in positive ion mode. The ESI collision-induced dissociation (CID) mass spectrum of SAL was studied together with that of its deuterium-labeled analog (i.e. salsolinol-alpha,alpha,alpha,1-d(4), SAL-d(4)) so that the fragmentation pathways could be elucidated. Further, using SAL-d(4) as internal standard in HPLC/MS/MS analysis of SAL improved significantly assay accuracy and reliability. Determination of (R/S)-SAL enantiomers present in food samples such as dried banana chips was demonstrated.
[Mh] Termos MeSH primário: Contaminação de Alimentos/análise
Isoquinolinas/análise
Espectrometria de Massas por Ionização por Electrospray/métodos
Espectrometria de Massas em Tandem/métodos
[Mh] Termos MeSH secundário: Cromatografia Líquida de Alta Pressão
Deutério/análise
Musa/química
Reprodutibilidade dos Testes
Alcaloides de Salsolina/toxicidade
Sementes/química
Estereoisomerismo
Vitis/química
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, N.I.H., EXTRAMURAL
[Nm] Nome de substância:
0 (Isoquinolines); 0 (Salsoline Alkaloids); 9ILS801M65 (salsolinol); 9Q83ETU10C (salsoline); AR09D82C7G (Deuterium)
[Em] Mês de entrada:0902
[Cu] Atualização por classe:161122
[Lr] Data última revisão:
161122
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:081127
[St] Status:MEDLINE
[do] DOI:10.1002/rcm.3847



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