Base de dados : MEDLINE
Pesquisa : D09.947.875.465 [Categoria DeCS]
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[PMID]:28198624
[Au] Autor:Haase PT; Kanzler C; Hildebrandt J; Kroh LW
[Ad] Endereço:Institut für Lebensmitteltechnologie und Lebensmittelchemie, Lebensmittelchemie und Analytik, Technische Universität Berlin , Gustav-Meyer-Allee 25, TIB 4/3-1, D-13355 Berlin, Germany.
[Ti] Título:Browning Potential of C -α-Dicarbonyl Compounds under Maillard Conditions.
[So] Source:J Agric Food Chem;65(9):1924-1931, 2017 Mar 08.
[Is] ISSN:1520-5118
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:In this work, the three major C -α-dicarbonyl compounds glucosone (GLUC), 1-deoxyglucosone (1-DG), and 3-deoxyglucosone (3-DG) were synthesized and examined under Maillard conditions (aqueous solutions with the addition of l-alanine at 130 °C and pH 5/8). For the first time, the resulting color formation, antioxidant activity, and generation of short-chained α-dicarbonyls were investigated and compared to incubations of d-glucose and d-fructose. An additive effect on the formation of color, an antagonistic effect on the generation of α-dicarbonyl compounds, and a synergistic effect on the antioxidant activity could be observed for the 1-DG/GLUC combination. Despite their common degradation products, different extinctions could be measured, with 3-DG showing the strongest color formation, followed by GLUC and 1-DG. The analyzed α-dicarbonyl compounds have no direct impact on the formation of color but are precursors for most of the colored compounds. The main difference between the three substances is their ability to form different heterocyclic degradation products, such as pyranones (1-DG), furanones (1-DG), furans (GLUC and 3-DG), and the corresponding N-heterocycles in the presence of amino components. This seems to be the main reason for their varying browning potential and antioxidant activity.
[Mh] Termos MeSH primário: Cetoses/química
[Mh] Termos MeSH secundário: Frutose/química
Glucose/química
Temperatura Alta
Cinética
Reação de Maillard
Estrutura Molecular
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Ketoses); 26345-59-5 (glucosone); 30237-26-4 (Fructose); IY9XDZ35W2 (Glucose)
[Em] Mês de entrada:1705
[Cu] Atualização por classe:170531
[Lr] Data última revisão:
170531
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:170216
[St] Status:MEDLINE
[do] DOI:10.1021/acs.jafc.6b04512


  2 / 311 MEDLINE  
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[PMID]:27998065
[Au] Autor:Yang J; Zhu Y; Men Y; Sun S; Zeng Y; Zhang Y; Sun Y; Ma Y
[Ad] Endereço:National Engineering Laboratory for Industrial Enzymes, Tianjin Institute of Industrial Biotechnology, Chinese Academy of Sciences , Tianjin 300308, China.
[Ti] Título:Pathway Construction in Corynebacterium glutamicum and Strain Engineering To Produce Rare Sugars from Glycerol.
[So] Source:J Agric Food Chem;64(50):9497-9505, 2016 Dec 21.
[Is] ISSN:1520-5118
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:Rare sugars are valuable natural products widely used in pharmaceutical and food industries. In this study, we expected to synthesize rare ketoses from abundant glycerol using dihydroxyacetone phosphate (DHAP)-dependent aldolases. First, a new glycerol assimilation pathway was constructed to synthesize DHAP. The enzymes which convert glycerol to 3-hydroxypropionaldehyde and l-glyceraldehyde were selected, and their corresponding aldehyde synthesis pathways were constructed in vivo. Four aldol pathways based on different aldolases and phosphorylase were gathered. Next, three pathways were assembled and the resulting strains synthesized 5-deoxypsicose, 5-deoxysorbose, and 5-deoxyfructose from glucose and glycerol and produce l-fructose, l-tagatose, l-sorbose, and l-psicose with glycerol as the only carbon source. To achieve higher product titer and yield, the recombinant strains were further engineered and fermentation conditions were optimized. Fed-batch culture of engineered strains obtained 38.1 g/L 5-deoxypsicose with a yield of 0.91 ± 0.04 mol product per mol of glycerol and synthesized 20.8 g/L l-fructose, 10.3 g/L l-tagatose, 1.2 g/L l-sorbose, and 0.95 g/L l-psicose.
[Mh] Termos MeSH primário: Corynebacterium glutamicum/metabolismo
Glicerol/metabolismo
Cetoses/biossíntese
Engenharia Metabólica
[Mh] Termos MeSH secundário: Aldeído Liases/metabolismo
Técnicas de Cultura Celular por Lotes
Biomassa
Vias Biossintéticas
Cromatografia Líquida de Alta Pressão
Corynebacterium glutamicum/genética
Escherichia coli/genética
Fermentação
Frutose/biossíntese
Glucose/metabolismo
Gliceraldeído/análogos & derivados
Gliceraldeído/metabolismo
Hexoses/biossíntese
Hidroliases/metabolismo
Espectroscopia de Ressonância Magnética
Propano/metabolismo
Sorbose/biossíntese
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Hexoses); 0 (Ketoses); 2134-29-4 (3-hydroxypropionaldehyde); 23140-52-5 (psicose); 30237-26-4 (Fructose); 367-47-5 (Glyceraldehyde); EC 4.1.2.- (Aldehyde-Lyases); EC 4.2.1.- (Hydro-Lyases); EC 4.2.1.30 (glycerol dehydratase); IY9XDZ35W2 (Glucose); NV2001607Y (Sorbose); PDC6A3C0OX (Glycerol); T75W9911L6 (Propane); T7A20Y888Y (tagatose)
[Em] Mês de entrada:1704
[Cu] Atualização por classe:170417
[Lr] Data última revisão:
170417
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:161222
[St] Status:MEDLINE
[do] DOI:10.1021/acs.jafc.6b03423


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[PMID]:27264558
[Au] Autor:Quiñones JL; Demple B
[Ad] Endereço:Stony Brook University School of Medicine, Department of Pharmacological Sciences, Stony Brook, NY, 11794, USA.
[Ti] Título:When DNA repair goes wrong: BER-generated DNA-protein crosslinks to oxidative lesions.
[So] Source:DNA Repair (Amst);44:103-109, 2016 Aug.
[Is] ISSN:1568-7856
[Cp] País de publicação:Netherlands
[La] Idioma:eng
[Ab] Resumo:Free radicals generate an array of DNA lesions affecting all parts of the molecule. The damage to deoxyribose receives less attention than base damage, even though the former accounts for ∼20% of the total. Oxidative deoxyribose fragments (e.g., 3'-phosphoglycolate esters) are removed by the Ape1 AP endonuclease and other enzymes in mammalian cells to enable DNA repair synthesis. Oxidized abasic sites are initially incised by Ape1, thus recruiting these lesions into base excision repair (BER) pathways. Lesions such as 2-deoxypentos-4-ulose can be removed by conventional (single-nucleotide) BER, which proceeds through a covalent Schiff base intermediate with DNA polymerase ß (Polß) that is resolved by hydrolysis. In contrast, the lesion 2-deoxyribonolactone (dL) must be processed by multinucleotide ("long-patch") BER: attempted repair via the single-nucleotide pathway leads to a dead-end, covalent complex with Polß cross- linked to the DNA by an amide bond. We recently detected these stable DNA-protein crosslinks (DPC) between Polß and dL in intact cells. The features of the DPC formation in vivo are exactly in keeping with the mechanistic properties seen in vitro: Polß-DPC are formed by oxidative agents in line with their ability to form the dL lesion; they are not formed by non-oxidative agents; DPC formation absolutely requires the active-site lysine-72 that attacks the 5'-deoxyribose; and DPC formation depends on Ape1 to incise the dL lesion first. The Polß-DPC are rapidly processed in vivo, the signal disappearing with a half-life of 15-30min in both mouse and human cells. This removal is blocked by inhibiting the proteasome, which leads to the accumulation of ubiquitin associated with the Polß-DPC. While other proteins (e.g., topoisomerases) also form DPC under these conditions, 60-70% of the trapped ubiquitin depends on Polß. The mechanism of ubiquitin targeting to Polß-DPC, the subsequent processing of the expected 5'-peptidyl-dL, and the biological consequences of unrepaired DPC are important to assess. Many other lyase enzymes that attack dL can also be trapped in DPC, so the processing mechanisms may apply quite broadly.
[Mh] Termos MeSH primário: DNA Polimerase beta/metabolismo
Reparo do DNA
DNA Liase (Sítios Apurínicos ou Apirimidínicos)/metabolismo
DNA/metabolismo
Desoxirribose/metabolismo
[Mh] Termos MeSH secundário: Animais
Dano ao DNA
DNA Polimerase beta/genética
DNA Liase (Sítios Apurínicos ou Apirimidínicos)/genética
Desoxirribose/química
Meia-Vida
Seres Humanos
Cetoses/metabolismo
Cinética
Camundongos
Estresse Oxidativo
Complexo de Endopeptidases do Proteassoma/metabolismo
Ligação Proteica
Proteólise
Açúcares Ácidos/metabolismo
[Pt] Tipo de publicação:JOURNAL ARTICLE; REVIEW
[Nm] Nome de substância:
0 (Ketoses); 0 (Sugar Acids); 34371-14-7 (2,4,5-trihydroxypentanoic acid gamma-lactone); 533-67-5 (Deoxyribose); 9007-49-2 (DNA); EC 2.7.7.- (DNA Polymerase beta); EC 3.4.25.1 (Proteasome Endopeptidase Complex); EC 4.2.99.18 (APEX1 protein, human); EC 4.2.99.18 (DNA-(Apurinic or Apyrimidinic Site) Lyase)
[Em] Mês de entrada:1705
[Cu] Atualização por classe:171110
[Lr] Data última revisão:
171110
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:160607
[St] Status:MEDLINE


  4 / 311 MEDLINE  
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[PMID]:27152632
[Au] Autor:Kaufmann M; Meissner PM; Pelke D; Mügge C; Kroh LW
[Ad] Endereço:Department of Food Chemistry and Food Analysis, Berlin Institute of Technology, Gustav-Meyer-Allee 25, TIB 4/3-1, D-13355 Berlin, Germany. Electronic address: martin.kaufmann@tu-berlin.de.
[Ti] Título:Structure-reactivity relationship of Amadori rearrangement products compared to related ketoses.
[So] Source:Carbohydr Res;428:87-99, 2016 Jun 16.
[Is] ISSN:1873-426X
[Cp] País de publicação:Netherlands
[La] Idioma:eng
[Ab] Resumo:Structure-reactivity relationships of Amadori rearrangement products compared to their related ketoses were derived from multiple NMR spectroscopic techniques. Besides structure elucidation of six Amadori rearrangement products derived from d-glucose and d-galactose with l-alanine, l-phenylalanine and l-proline, especially quantitative (13)C selective saturation transfer NMR spectroscopy was applied to deduce information on isomeric systems. It could be shown exemplarily that the Amadori compound N-(1-deoxy-d-fructos-1-yl)-l-proline exhibits much higher isomerisation rates than d-fructose, which can be explained by C-1 substituent mediated intramolecular catalysis. In combination with a reduced carbonyl activity of Amadori compounds compared to their related ketoses which results in an increased acyclic keto isomer concentration, the results on isomerisation dynamics lead to a highly significant increased reactivity of Amadori compounds. This can be clearly seen, comparing approximated carbohydrate milieu stability time constants (ACuSTiC) which is 1 s for N-(1-deoxy-d-fructos-1-yl)-l-proline and 10 s for d-fructose at pD 4.20 ± 0.05 at 350 K. In addition, first NMR spectroscopic data are provided, which prove that α-pyranose of (amino acid substituted) d-fructose adopts both, (2)C5 and (5)C2 conformation.
[Mh] Termos MeSH primário: Aminoácidos/química
Cetoses/química
Monossacarídeos/química
[Mh] Termos MeSH secundário: Isomerismo
Espectroscopia de Ressonância Magnética
Estrutura Molecular
[Pt] Tipo de publicação:COMPARATIVE STUDY; JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Amino Acids); 0 (Ketoses); 0 (Monosaccharides)
[Em] Mês de entrada:1702
[Cu] Atualização por classe:170203
[Lr] Data última revisão:
170203
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:160507
[St] Status:MEDLINE


  5 / 311 MEDLINE  
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[PMID]:26620578
[Au] Autor:Jiang Z; Zhang X; Yang L; Li Z; Qin W
[Ad] Endereço:West China School of Medicine, Sichuan University, Chengdu, Sichuan, China.
[Ti] Título:Effect of restricted protein diet supplemented with keto analogues in chronic kidney disease: a systematic review and meta-analysis.
[So] Source:Int Urol Nephrol;48(3):409-18, 2016 Mar.
[Is] ISSN:1573-2584
[Cp] País de publicação:Netherlands
[La] Idioma:eng
[Ab] Resumo:BACKGROUND: To evaluate the efficacy and safety of the restricted protein diet (low or very low protein diet) supplemented with keto analogues in the treatment of chronic kidney disease (CKD). METHODS: The Cochrane library, PubMed, Embase, CBM and CENTRAL databases were searched and reviewed up to April 2015. Clinical trials were analyzed using RevMan 5.3 software. RESULTS: Seven random control trials, one cross-over trial and one non-randomized concurrent control trial were selected and included in this study according to our inclusion and exclusion criteria. The changes of eGFR, BUN, Scr, albumin, PTH, triglyceride, cholesterol, calcium, phosphorus and nutrition indexes (BMI, lean body mass and mid-arm muscular circumference) before and after treatment were analyzed. The meta-analysis results indicated that, comparing with normal protein diet, low protein diet (LPD) or very low protein diet (vLPD) supplemented with keto analogues (s(v)LPD) could significantly prevent the deterioration of eGFR (P < 0.001), hyperparathyroidism (P = 0.04), hypertension (P < 0.01) and hyperphosphatemia (P < 0.001). No differences in BUN, Scr, Albumin, triglyceride, cholesterol, hemoglobin, calcium and nutrition indexes were observed between different protein intake groups. CONCLUSION: Restricted protein diet supplemented with keto analogues (s(v)LPD) could delay the progression of CKD effectively without causing malnutrition.
[Mh] Termos MeSH primário: Dieta com Restrição de Proteínas/métodos
Suplementos Nutricionais
Cetoses/farmacologia
Insuficiência Renal Crônica/dietoterapia
[Mh] Termos MeSH secundário: Progressão da Doença
Seres Humanos
[Pt] Tipo de publicação:JOURNAL ARTICLE; META-ANALYSIS; REVIEW
[Nm] Nome de substância:
0 (Ketoses)
[Em] Mês de entrada:1612
[Cu] Atualização por classe:171102
[Lr] Data última revisão:
171102
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:151202
[St] Status:MEDLINE
[do] DOI:10.1007/s11255-015-1170-2


  6 / 311 MEDLINE  
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[PMID]:26451463
[Au] Autor:Richter C; Nguyen Trung M; Mahrwald R
[Ad] Endereço:Institute of Chemistry, Humboldt University Berlin , Brook-Taylor Str. 2, 12484 Berlin, Germany.
[Ti] Título:Multicomponent Cascade Reactions of Unprotected Ketoses and Amino Acids--Access to a Defined Configured Quaternary Stereogenic Center.
[So] Source:J Org Chem;80(21):10849-65, 2015 Nov 06.
[Is] ISSN:1520-6904
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:A highly stereoselective multicomponent cascade reaction of ketones with unprotected amino acids was developed. This operationally simple methodology was expanded to reactions of unprotected ketohexoses and unprotected amino acids. By the careful choice of amino acid and isonitrile, an optional access to all possible enantiomers is given.
[Mh] Termos MeSH primário: Aminoácidos/química
Cetonas/química
Cetoses/química
Nitrilos/química
[Mh] Termos MeSH secundário: Catálise
Estereoisomerismo
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (Amino Acids); 0 (Ketones); 0 (Ketoses); 0 (Nitriles)
[Em] Mês de entrada:1604
[Cu] Atualização por classe:151106
[Lr] Data última revisão:
151106
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:151010
[St] Status:MEDLINE
[do] DOI:10.1021/acs.joc.5b02003


  7 / 311 MEDLINE  
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[PMID]:26406454
[Au] Autor:Zhang F; Wu X; Wang L; Liu H; Zhao Y
[Ad] Endereço:The Key Lab of Chemical Biology and Organic Chemistry, The College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou, China. Electronic address: zhangfy@zzu.edu.cn.
[Ti] Título:General and efficient one-pot synthesis of novel sugar/heterocyclic(aryl) 1,2-diketones from sugar terminal alkynes by Sonogashira/tetra-n- butylammonium permanganate oxidation.
[So] Source:Carbohydr Res;417:41-51, 2015 Nov 19.
[Is] ISSN:1873-426X
[Cp] País de publicação:Netherlands
[La] Idioma:eng
[Ab] Resumo:A new approach for one-pot synthesis of novel sugar/heterocyclic(aryl) 1,2-diketones has been achieved by the reaction of various sugar terminal alkynes with heterocyclic(aryl) iodides at room temperature. This one-pot protocol includes Sonogashira coupling and mild n-Bu4NMnO4 oxidation reaction. This method is mild, general and efficient. Fifty-six examples have been given and the sugar/heterocyclic(aryl) 1,2-diketones were obtained in 71-94% yields. The sugar terminal alkynes include 9 structurally different sugars in pyranose, furanose, and acyclic form which have various protecting groups, sensitive groups, and sterically bulky substituents. The heterocyclic(aryl) iodides include sterically bulky heterocyclic compounds and iodobenzenes with electron-donating, electron-neutral, and electron-withdrawing substituents.
[Mh] Termos MeSH primário: Alquinos/química
Elétrons
Compostos Heterocíclicos/síntese química
Cetoses/síntese química
Compostos Organometálicos/química
Paládio/química
[Mh] Termos MeSH secundário: Catálise
Química Verde
Iodobenzenos/química
Estrutura Molecular
Oxirredução
Estereoisomerismo
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (Alkynes); 0 (Heterocyclic Compounds); 0 (Iodobenzenes); 0 (Ketoses); 0 (Organometallic Compounds); 35638-41-6 (tetrabutylammonium permanganate); 5TWQ1V240M (Palladium)
[Em] Mês de entrada:1608
[Cu] Atualização por classe:151109
[Lr] Data última revisão:
151109
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:150926
[St] Status:MEDLINE


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[PMID]:26275233
[Au] Autor:Wen L; Huang K; Wei M; Meisner J; Liu Y; Garner K; Zang L; Wang X; Li X; Fang J; Zhang H; Wang PG
[Ad] Endereço:Department of Chemistry and Center for Therapeutics and Diagnostics, Georgia State University, Atlanta, GA 30303 (USA).
[Ti] Título:Facile Enzymatic Synthesis of Ketoses.
[So] Source:Angew Chem Int Ed Engl;54(43):12654-8, 2015 Oct 19.
[Is] ISSN:1521-3773
[Cp] País de publicação:Germany
[La] Idioma:eng
[Ab] Resumo:Studies of rare ketoses have been hampered by a lack of efficient preparation methods. A convenient, efficient, and cost-effective platform for the facile synthesis of ketoses is described. This method enables the preparation of difficult-to-access ketopentoses and ketohexoses from common and inexpensive starting materials with high yield and purity and without the need for a tedious isomer separation step.
[Mh] Termos MeSH primário: Cetoses/síntese química
Cetoses/metabolismo
[Mh] Termos MeSH secundário: Biocatálise
Técnicas de Química Sintética/economia
Técnicas de Química Sintética/métodos
Frutoquinases/metabolismo
Seres Humanos
Isomerismo
Cetoses/química
Fosforilação
Fosfotransferases (Aceptor do Grupo Álcool)/metabolismo
Biossíntese de Proteínas
Thermotoga maritima/enzimologia
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, N.I.H., EXTRAMURAL; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (Ketoses); EC 2.7.1.- (Fructokinases); EC 2.7.1.- (Phosphotransferases (Alcohol Group Acceptor)); EC 2.7.1.5 (rhamnulokinase)
[Em] Mês de entrada:1608
[Cu] Atualização por classe:170220
[Lr] Data última revisão:
170220
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:150815
[St] Status:MEDLINE
[do] DOI:10.1002/anie.201505714


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[PMID]:26151084
[Au] Autor:Chumsae C; Hossler P; Raharimampionona H; Zhou Y; McDermott S; Racicot C; Radziejewski C; Zhou ZS
[Ad] Endereço:†Protein Analytics, Process Sciences Department, AbbVie Bioresearch Center, Worcester, Massachusetts 01605, United States.
[Ti] Título:When Good Intentions Go Awry: Modification of a Recombinant Monoclonal Antibody in Chemically Defined Cell Culture by Xylosone, an Oxidative Product of Ascorbic Acid.
[So] Source:Anal Chem;87(15):7529-34, 2015 Aug 04.
[Is] ISSN:1520-6882
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:With the advent of new initiatives to develop chemically defined media, cell culture scientists screen many additives to improve cell growth and productivity. However, the introduction or increase of supplements, typically considered beneficial or protective on their own, to the basal media or feed stream may cause unexpected detrimental consequences to product quality. For instance, because cultured cells are constantly under oxidative stress, ascorbic acid (vitamin C, a potent natural reducing agent) is a common additive to cell culture media. However, as reported herein, a recombinant monoclonal antibody (adalimumab) in cell culture was covalently modified by xylosone (molecular weight 148), an oxidative product of ascorbate. Containing reactive carbonyl groups, xylosone modifies various amines (e.g., the N-termini of the heavy and light chains and susceptible lysines), forming either hemiaminal (+148 Da) or Schiff base (imine, +130 Da) products. Our findings show, for the first time, that ascorbate-derived xylosone can contribute to an increase in molecular heterogeneity, such as acidic species. Our work serves as a reminder that additives to cell culture and their metabolites may become reactive and negatively impact the overall product quality and should be carefully monitored with any changes in cell culture conditions.
[Mh] Termos MeSH primário: Anticorpos Monoclonais/metabolismo
Ácido Ascórbico/química
Cetoses/metabolismo
Proteínas Recombinantes/metabolismo
[Mh] Termos MeSH secundário: Anticorpos Monoclonais/química
Ácido Ascórbico/metabolismo
Técnicas de Cultura de Células
Cetoses/química
Estrutura Molecular
Oxirredução
Proteínas Recombinantes/química
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, N.I.H., EXTRAMURAL
[Nm] Nome de substância:
0 (Antibodies, Monoclonal); 0 (Ketoses); 0 (Recombinant Proteins); 26188-06-7 (threo-pentos-2-ulose); PQ6CK8PD0R (Ascorbic Acid)
[Em] Mês de entrada:1603
[Cu] Atualização por classe:171007
[Lr] Data última revisão:
171007
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:150708
[St] Status:MEDLINE
[do] DOI:10.1021/acs.analchem.5b00801


  10 / 311 MEDLINE  
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[PMID]:26086401
[Au] Autor:Pan X; Wang X; Wang L; Xu K; Kong F; Tang B
[Ad] Endereço:†Collaborative Innovation Center of Functionalized Probes for Chemical Imaging in Universities of Shandong, Key Laboratory of Molecular and Nano Probes, Ministry of Education, Shandong Provincial Key Laboratory of Clean Production of Fine Chemicals, College of Chemistry, Chemical Engineering and Mat
[Ti] Título:Near-Infrared Fluorescence Probe for Monitoring the Metabolic Products of Vitamin C in HepG2 Cells under Normoxia and Hypoxia.
[So] Source:Anal Chem;87(14):7092-7, 2015 Jul 21.
[Is] ISSN:1520-6882
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:Vitamin C (ascorbic acid; AA) is a well-known reducing agent and has been evaluated for its antitumor activity. However, the mechanism for its antitumor action remains unclear. Tracking the metabolism of AA may help to elucidate its antitumor mechanism. In this study, a near-infrared fluorescent probe (Arg-Cy) for monitoring the metabolic products of AA in living cells was developed based on the reaction of the guanidine group in Arg-Cy with the adjacent diketone involved in the metabolites of AA. Consequently, the probe can respond to L-xylosone, a metabolite of AA, with high selectivity and sensitivity and was successfully used to visualize the real-time changes of L-xylosone levels in living cells incubated under normoxic conditions. Considering that the tumor microenvironment suffers from hypoxia, the L-xylosone levels in the process of HepG2 cell death induced by pharmacological doses of AA were also monitored under hypoxic conditions. Surprisingly, no obvious fluorescence change appeared during this process. Furthermore, detection of the intracellular redox state using a reported H2O2 probe confirmed that AA can be metabolized to L-xylosone only under normoxic conditions due to the oxidative stress, but not under hypoxic conditions. Therefore, we hypothesize that the mechanism for cell death induced by AA under hypoxia is different from that under normoxia. Thus, the developed probe can provide a tool for monitoring the metabolism of AA and may help to clarify the mechanism for the antitumor activity of vitamin C in the tumor microenvironment.
[Mh] Termos MeSH primário: Ácido Ascórbico/análise
Hipóxia Celular
Microscopia de Fluorescência
Espectrometria de Massas por Ionização por Electrospray
[Mh] Termos MeSH secundário: Apoptose/efeitos dos fármacos
Ácido Ascórbico/química
Dipeptídeos/química
Corantes Fluorescentes/química
Corantes Fluorescentes/metabolismo
Células Hep G2
Seres Humanos
Peróxido de Hidrogênio/química
Peróxido de Hidrogênio/toxicidade
Cetoses/química
Cetoses/metabolismo
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (Dipeptides); 0 (Fluorescent Dyes); 0 (Ketoses); 26188-06-7 (threo-pentos-2-ulose); BBX060AN9V (Hydrogen Peroxide); PQ6CK8PD0R (Ascorbic Acid)
[Em] Mês de entrada:1604
[Cu] Atualização por classe:150721
[Lr] Data última revisão:
150721
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:150619
[St] Status:MEDLINE
[do] DOI:10.1021/acs.analchem.5b00820



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