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Pesquisa : D03.633.100.759.758.399 [Categoria DeCS]
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[PMID]:28662469
[Au] Autor:Vanco J; Trávnícek Z; Krikavová R; Gáliková J; Dvorák Z; Chalupová M
[Ad] Endereço:Department of Inorganic Chemistry, Regional Centre of Advanced Technologies and Materials, Faculty of Science, Palacký University, 17. listopadu 12, CZ-771 46 Olomouc, Czech Republic.
[Ti] Título:Molecular, cellular and pharmacological effects of platinum(II) diiodido complexes containing 9-deazahypoxanthine derivatives: A group of broad-spectrum anticancer active agents.
[So] Source:J Photochem Photobiol B;173:423-433, 2017 Aug.
[Is] ISSN:1873-2682
[Cp] País de publicação:Switzerland
[La] Idioma:eng
[Ab] Resumo:The platinum(II) iodido complexes 1-5 of the general formula cis-[PtI (L ) ], where L stands for O-substituted 9-deazahypoxanthine derivatives, were prepared and thoroughly characterized by various techniques, including multinuclear 1D and 2D NMR spectroscopy. The complexes were screened for their anticancer potential in vitro on ten human cancer cell lines, concretely breast adenocarcinoma (MCF7), osteosarcoma (HOS), lung carcinoma (A549), cervix epithelioid carcinoma (HeLa), malignant melanoma (G-361), prostate carcinoma (22Rv1, PC-3), hepatocellular carcinoma (HepG2), ovarian carcinoma (A2780) and cisplatin-resistant ovarian carcinoma (A2780R). The complexes exhibited significant wide-spectrum anticancer activity in vitro against all the employed cell lines, with IC ≈0.5-24.0µM. Very good correlation between the lipophilicity parameter log P and IC values of anticancer activity in vitro were obtained by simple QSAR analysis. The most lipophilic complexes 2, 4 and 5 showed the best results, as they reached the sub-micromolar IC values against the A2780 and A2780R sub-lines, with the best result equal 0.5±0.1µM on A2780 for complex 5. The in vivo testing of the representative complexes 1, 4 and 5 (applied at the same dose of Pt as 2mg/kg dose of cisplatin) on a L1210 leukaemia model revealed their positive effect on the prolongation of the mean survival time, even if it was lower than that of cisplatin. The H NMR interaction study revealed the ability of complexes to interact with glutathione (GSH) and 5'-guanosine monophosphate (GMP) and overall higher stability of the complexes 1-5 as compared to cisplatin. The electrospray-ionization mass spectrometry experiments with complex 1 identified the formation of a rich collection of hydrolytic species in water-containing media after 24h and the interaction intermediates with sulfur-containing biomolecule l-cysteine, but not with the reduced glutathione at physiologically relevant concentration levels.
[Mh] Termos MeSH primário: Antineoplásicos/química
Complexos de Coordenação/química
Hipoxantinas/química
Iodo/química
Platina/química
[Mh] Termos MeSH secundário: Animais
Antineoplásicos/uso terapêutico
Antineoplásicos/toxicidade
Apoptose/efeitos dos fármacos
Linhagem Celular Tumoral
Complexos de Coordenação/uso terapêutico
Complexos de Coordenação/toxicidade
Ensaios de Seleção de Medicamentos Antitumorais
Feminino
Células HeLa
Células Hep G2
Seres Humanos
Estimativa de Kaplan-Meier
Células MCF-7
Camundongos
Camundongos Endogâmicos DBA
Neoplasias/tratamento farmacológico
Neoplasias/mortalidade
Neoplasias/patologia
Transplante Heterólogo
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (9-deazahypoxanthine); 0 (Antineoplastic Agents); 0 (Coordination Complexes); 0 (Hypoxanthines); 49DFR088MY (Platinum); 9679TC07X4 (Iodine)
[Em] Mês de entrada:1710
[Cu] Atualização por classe:171010
[Lr] Data última revisão:
171010
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:170630
[St] Status:MEDLINE


  2 / 3237 MEDLINE  
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[PMID]:28628279
[Au] Autor:Kaiser MM; Baszczynski O; Hocková D; Postová-Slavetínská L; Dracínský M; Keough DT; Guddat LW; Janeba Z
[Ad] Endereço:The Institute of Organic Chemistry and Biochemistry of the Czech Academy of Sciences, Flemingovo nám. 2, 16610, Prague 6, Czech Republic.
[Ti] Título:Acyclic Nucleoside Phosphonates Containing 9-Deazahypoxanthine and a Five-Membered Heterocycle as Selective Inhibitors of Plasmodial 6-Oxopurine Phosphoribosyltransferases.
[So] Source:ChemMedChem;12(14):1133-1141, 2017 Jul 20.
[Is] ISSN:1860-7187
[Cp] País de publicação:Germany
[La] Idioma:eng
[Ab] Resumo:Acyclic nucleoside phosphonates (ANPs) are an important class of therapeutic drugs that act as antiviral agents by inhibiting viral DNA polymerases and reverse transcriptases. ANPs containing a 6-oxopurine unit instead of a 6-aminopurine or pyrimidine base are inhibitors of the purine salvage enzyme, hypoxanthine-guanine-[xanthine] phosphoribosyltransferase (HG[X]PRT). Such compounds, and their prodrugs, are able to arrest the growth of Plasmodium falciparum (Pf) in cell culture. A new series of ANPs were synthesized and tested as inhibitors of human HGPRT, PfHGXPRT, and Plasmodium vivax (Pv) HGPRT. The novelty of these compounds is that they contain a five-membered heterocycle (imidazoline, imidazole, or triazole) inserted between the acyclic linker(s) and the nucleobase, namely, 9-deazahypoxanthine. Five of the compounds were found to be micromolar inhibitors of PfHGXPRT and PvHGPRT, but no inhibition of human HGPRT was observed under the same assay conditions. This demonstrates selectivity of these types of compounds for the two parasitic enzymes compared to the human counterpart and confirms the importance of the chemical nature of the acyclic moiety in conferring affinity/selectivity for these three enzymes.
[Mh] Termos MeSH primário: Antimaláricos/síntese química
Hipoxantinas/química
Nucleosídeos/síntese química
Organofosfonatos/síntese química
Pentosiltransferases/antagonistas & inibidores
Plasmodium falciparum/enzimologia
Plasmodium vivax/enzimologia
[Mh] Termos MeSH secundário: Antimaláricos/química
Seres Humanos
Hipoxantina Fosforribosiltransferase/antagonistas & inibidores
Modelos Moleculares
Nucleosídeos/química
Organofosfonatos/química
Relação Estrutura-Atividade
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (9-deazahypoxanthine); 0 (Antimalarials); 0 (Hypoxanthines); 0 (Nucleosides); 0 (Organophosphonates); EC 2.4.2.- (Pentosyltransferases); EC 2.4.2.- (hypoxanthine-guanine-xanthine phosphoribosyltransferase); EC 2.4.2.8 (Hypoxanthine Phosphoribosyltransferase)
[Em] Mês de entrada:1709
[Cu] Atualização por classe:170925
[Lr] Data última revisão:
170925
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:170620
[St] Status:MEDLINE
[do] DOI:10.1002/cmdc.201700293


  3 / 3237 MEDLINE  
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[PMID]:28238512
[Au] Autor:Koul S; Ramdas V; Barawkar DA; Waman YB; Prasad N; Madadi SK; Shejul YD; Bonagiri R; Basu S; Menon S; Reddy SB; Chaturvedi S; Chennamaneni SR; Bedse G; Thakare R; Gundu J; Chaudhary S; De S; Meru AV; Palle V; Chugh A; Mookhtiar KA
[Ad] Endereço:Drug Discovery Unit, Advinus Therapeutics Ltd., Hinjewadi, Pune 411 057, India. Electronic address: summon.koul@advinus.com.
[Ti] Título:Design and synthesis of novel, potent and selective hypoxanthine analogs as adenosine A receptor antagonists and their biological evaluation.
[So] Source:Bioorg Med Chem;25(6):1963-1975, 2017 Mar 15.
[Is] ISSN:1464-3391
[Cp] País de publicação:England
[La] Idioma:eng
[Ab] Resumo:Multipronged approach was used to synthesize a library of diverse C-8 cyclopentyl hypoxanthine analogs from a common intermediate III. Several potent and selective compounds were identified and evaluated for pharmacokinetic (PK) properties in Wistar rats. One of the compounds 14 with acceptable PK parameters was selected for testing in in vivo primary acute diuresis model. The compound demonstrated significant diuretic activity in this model.
[Mh] Termos MeSH primário: Antagonistas do Receptor A1 de Adenosina/química
Antagonistas do Receptor A1 de Adenosina/farmacologia
Hipoxantinas/química
Hipoxantinas/farmacologia
[Mh] Termos MeSH secundário: Antagonistas do Receptor A1 de Adenosina/síntese química
Antagonistas do Receptor A1 de Adenosina/farmacocinética
Animais
Espectroscopia de Ressonância Magnética Nuclear de Carbono-13
Cromatografia Líquida
Desenho de Drogas
Células HEK293
Seres Humanos
Hipoxantinas/síntese química
Hipoxantinas/farmacocinética
Masculino
Espectrometria de Massas
Espectroscopia de Prótons por Ressonância Magnética
Ensaio Radioligante
Ratos
Ratos Wistar
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Adenosine A1 Receptor Antagonists); 0 (Hypoxanthines)
[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:170228
[St] Status:MEDLINE


  4 / 3237 MEDLINE  
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[PMID]:27389219
[Au] Autor:Guo X; Yuan H; An B; Zhu Q; Zhang J
[Ad] Endereço:Institute of Environmental and Analytical Sciences, College of Chemistry and Chemical Engineering, Henan University, Kaifeng 475004, People's Republic of China.
[Ti] Título:Ultrafast excited-state deactivation of 9-methylhypoxanthine in aqueous solution: A QM/MM MD study.
[So] Source:J Chem Phys;144(15):154306, 2016 Apr 21.
[Is] ISSN:1089-7690
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:Photoinduced ultrafast non-adiabatic decay of 9-methylhypoxanthine (9MHPX) in aqueous solution was investigated by ab initio surface-hopping dynamics calculations using a combined quantum mechanical/molecular mechanical approach. The absorption spectra of 9MHPX in aqueous solution were also explored by the hybrid cluster-continuum model at the level of time-dependent density functional theory along with the polarizable continuum model (PCM). The static electronic-structure calculations indicate that the absorption spectra of 9MHPX simulated by TD-B3LYP/PCM and TD-X3LYP/PCM can reproduce very well the experimental findings, with the accuracy of about 0.20 eV. According to dynamics simulations, irradiation of 9MHPX populates the bright excited singlet S1 state, which may undergo an ultrafast non-radiative deactivation to the S0 state. The lifetime of the S1 state of 9MHPX in aqueous solution is predicted to be 115.6 fs, slightly longer than that in the gas phase (88.8 fs), suggesting that the solventwater has no significant influence on the excited-state lifetime of 9MHPX. Such a behavior in 9MHPX is distinctly different from its parent hypoxanthine keto-N9H tautomer in which the excited-state lifetime of the latter in watersolution was remarkably enhanced as compared to the gas phase. The significant difference of the photodynamical behaviors between 9MHPX and keto-N9H can be ascribed to their different hydrogen bond environment in aqueous solution.
[Mh] Termos MeSH primário: Hipoxantinas/química
[Mh] Termos MeSH secundário: Ligações de Hidrogênio
Luz
Simulação de Dinâmica Molecular
Teoria Quântica
Espectrofotometria
Água/química
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (9-methylhypoxanthine); 0 (Hypoxanthines); 059QF0KO0R (Water)
[Em] Mês de entrada:1702
[Cu] Atualização por classe:170223
[Lr] Data última revisão:
170223
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:160709
[St] Status:MEDLINE
[do] DOI:10.1063/1.4946103


  5 / 3237 MEDLINE  
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[PMID]:27387894
[Au] Autor:Choi JH; Kikuchi A; Pumkaeo P; Hirai H; Tokuyama S; Kawagishi H
[Ad] Endereço:a College of Agriculture , Academic Institute, Shizuoka University , Shizuoka , Japan.
[Ti] Título:Bioconversion of AHX to AOH by resting cells of Burkholderia contaminans CH-1.
[So] Source:Biosci Biotechnol Biochem;80(10):2045-50, 2016 Oct.
[Is] ISSN:1347-6947
[Cp] País de publicação:England
[La] Idioma:eng
[Ab] Resumo:Fairy rings are zones of stimulated grass growth owing to the interaction between a fungus and a plant. We previously reported the discovery of two novel plant-growth regulating compounds related to forming fairy rings, 2-azahypoxanthine (AHX) and 2-aza-8-oxohypoxanthine (AOH). In this study, a bacterial strain CH-1 was isolated from an airborne-contaminated nutrient medium containing AHX. The strain converted AHX to AOH and identified as Burkholderia contaminans based on the gene sequence of its 16S rDNA. The quantitative production of AOH by resting cells of the strain was achieved. Among seven Burkholderia species, two bacteria and two yeasts tested, B. contaminans CH-1 showed the highest rate of conversion of AHX to AOH. By batch system, up to 10.6 mmol AHX was converted to AOH using the resting cells. The yield of this process reached at 91%.
[Mh] Termos MeSH primário: Burkholderia/citologia
Burkholderia/metabolismo
Hipoxantinas/metabolismo
[Mh] Termos MeSH secundário: Microbiologia do Ar
Biotransformação
Burkholderia/isolamento & purificação
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (2-aza-8-oxohypoxanthine); 0 (Hypoxanthines); TGZ8A8PWEX (2-azahypoxanthine)
[Em] Mês de entrada:1701
[Cu] Atualização por classe:170130
[Lr] Data última revisão:
170130
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:160709
[St] Status:MEDLINE
[do] DOI:10.1080/09168451.2016.1189314


  6 / 3237 MEDLINE  
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[PMID]:27318977
[Au] Autor:Kubesová K; Trávnícek Z; Dvorák Z
[Ad] Endereço:Department of Cell Biology and Genetics, Faculty of Science, Palacký University, Slechtitelu 27, CZ-783 71, Olomouc, Czech Republic.
[Ti] Título:Pleiotropic effects of gold(I) mixed-ligand complexes of 9-deazahypoxanthine on transcriptional activity of receptors for steroid hormones, nuclear receptors and xenoreceptors in human hepatocytes and cell lines.
[So] Source:Eur J Med Chem;121:530-540, 2016 Oct 04.
[Is] ISSN:1768-3254
[Cp] País de publicação:France
[La] Idioma:eng
[Ab] Resumo:Development of metal-based compounds is an important research avenue in anti-cancer and anti-inflammatory drug discovery. Here we examined the effects of three gold (I) mixed-ligand complexes with the general formula [Au(Ln)(PPh3)] (1, 2, 3) involving triphenylphosphine (PPh3) and a deprotonated form of O-substituted derivatives of 9-deazahypoxanthine (Ln) on the transcriptional activity of aryl hydrocarbon receptor (AhR), androgen receptor (AR), glucocorticoid receptor (GR), thyroid receptor (TR), pregnane X receptor (PXR) and vitamin D receptor (VDR), employing gene reporter assays. In addition, we measured mRNA (RT-PCR) and protein (western blot) expression of target genes for those receptors, including drug-metabolizing P450s, in primary human hepatocytes and cancer cell lines LS180 and HepG2. The tested compounds displayed anti-glucocorticoid effects, as revealed by inhibition of dexamethasone-inducible transcriptional activity of GR and down-regulation of tyrosine aminotransferase. All the compounds slightly and dose-dependently activated PXR and AhR, and moderately induced CYP3A4 and CYP1A1/2 genes in human hepatocytes and LS180 cells. The complexes antagonized basal and ligand-activated AR and VDR, indicating inverse agonist behaviour. Both basal and thyroid hormone-inducible transcriptional activity of TR was dose-dependently increased by all tested compounds. In contrast, the expression of SPOT14 mRNA was decreased by tested compounds in human hepatocytes and HepG2 cells. In conclusion, if intended for human pharmacotherapy, the potential of the complexes 1-3 to influence studied receptors should be taken in account.
[Mh] Termos MeSH primário: Ouro/química
Hepatócitos/efeitos dos fármacos
Hipoxantinas/química
Compostos Organometálicos/química
Compostos Organometálicos/farmacologia
Receptores de Esteroides/genética
Transcrição Genética/efeitos dos fármacos
[Mh] Termos MeSH secundário: Linhagem Celular Tumoral
Hepatócitos/metabolismo
Seres Humanos
RNA Mensageiro/genética
RNA Mensageiro/metabolismo
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (9-deazahypoxanthine); 0 (Hypoxanthines); 0 (Organometallic Compounds); 0 (RNA, Messenger); 0 (Receptors, Steroid); 7440-57-5 (Gold)
[Em] Mês de entrada:1702
[Cu] Atualização por classe:171009
[Lr] Data última revisão:
171009
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:160620
[St] Status:MEDLINE


  7 / 3237 MEDLINE  
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[PMID]:27279530
[Au] Autor:Dai Y; Cui J; Gan P; Li W
[Ad] Endereço:Department of Abdominal Surgery, Third Affiliated Hospital of Kunming Medical University, Kunming, Yunnan 650118, P.R. China.
[Ti] Título:Downregulation of tetrahydrobiopterin inhibits tumor angiogenesis in BALB/c-nu mice with hepatocellular carcinoma.
[So] Source:Oncol Rep;36(2):669-75, 2016 Aug.
[Is] ISSN:1791-2431
[Cp] País de publicação:Greece
[La] Idioma:eng
[Ab] Resumo:Hepatocellular carcinoma (HCC) is a highly vascular tumor, and treatment options for patients of advanced-stage are limited. Nitric oxide (NO), which is derived from endothelial nitric oxide synthase (eNOS), provides crucial signals for angiogenesis in the tumor microenvironment. Tetrahydrobiopterin (BH4) is an essential cofactor eNOS and represents a critical determinant of NO production. To examine whether treatment of 2,4-diamino-6-hydroxypyrimidine (DAHP) inhibits angiogenesis of HCC, BALB/c-nu mice were injected with HepG-2 cells with DAHP. Supplemental DAHP treatment decreased K-ras mRNA transcripts, inhibition of phosphorylation of eNOS and Akt, inhibition of guanosine triphosphate cyclohydrolase (GTPCH), and decreased significantly NO synthesis, and then inhibited angiogenesis, compared with the results observed in the saline group. Histopathology demonstrated angiogenesis and tumor formation were significantly inhibited in HCC. DAHP downregulates GTPCH protein expression, corresponding to decreased levels of BH4 and the contents of NO. In addition, DAHP downregulates eNOS and Akt protein expression, corresponding to decreased eNOS phosphorylation at Ser1177 and Akt phosphorylation, compared with the saline control. We suggest that DAHP, recognized as a specific competitive inhibitor of GTPCH, can decrease tumor BH4 and NO by the inhibition of the wild-type Ras-PI3K/Akt pathway, and then inhibiting angiogenesis, and may provide a novel and promising way to target BH4 synthetic pathways to inhibit angiogenesis and to control potential progression of HCC. Whether DAHP has a therapeutic potential will require more direct testing in humans.
[Mh] Termos MeSH primário: Biopterina/análogos & derivados
Carcinoma Hepatocelular/genética
Regulação para Baixo/genética
Neoplasias Hepáticas/genética
Neovascularização Patológica/genética
[Mh] Termos MeSH secundário: Animais
Biopterina/genética
Linhagem Celular Tumoral
Regulação para Baixo/efeitos dos fármacos
Genes ras/genética
Células Hep G2
Seres Humanos
Hipoxantinas/farmacologia
Camundongos
Camundongos Endogâmicos BALB C
Camundongos Nus
Neovascularização Patológica/patologia
Óxido Nítrico/genética
Óxido Nítrico Sintase Tipo III/genética
Fosfatidilinositol 3-Quinases/genética
Fosforilação/efeitos dos fármacos
Fosforilação/genética
Proteínas Proto-Oncogênicas c-akt/genética
RNA Mensageiro/genética
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Hypoxanthines); 0 (RNA, Messenger); 22150-76-1 (Biopterin); 31C4KY9ESH (Nitric Oxide); EC 1.14.13.39 (Nitric Oxide Synthase Type III); EC 2.7.1.- (Phosphatidylinositol 3-Kinases); EC 2.7.11.1 (Proto-Oncogene Proteins c-akt); EDH7CNS75I (2,4-diaminohypoxanthine); EGX657432I (sapropterin)
[Em] Mês de entrada:1703
[Cu] Atualização por classe:170308
[Lr] Data última revisão:
170308
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:160610
[St] Status:MEDLINE
[do] DOI:10.3892/or.2016.4850


  8 / 3237 MEDLINE  
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[PMID]:27210892
[Au] Autor:Chen H; Zhang K; Wang S; Xu C; Zou Z; Tao A
[Ad] Endereço:The Second Affiliated Hospital of Guangzhou Medical University, The State Key Laboratory of Respiratory Disease, Guangdong Provincial Key Laboratory of Allergy & Clinical Immunology.
[Ti] Título:Generation and purification of monoclonal antibodies against Der f 2, a major allergen from Dermatophagoides farinae.
[So] Source:Drug Discov Ther;10(2):103-8, 2016.
[Is] ISSN:1881-7831
[Cp] País de publicação:Japan
[La] Idioma:eng
[Ab] Resumo:Monoclonal antibodies (mAbs) are needed for the quantitation of environmental allergens for precise diagnosis and immunotherapy. In this study, we produced and purified monoclonal antibodies against Der f 2, one of the major allergens of the house dust mite Dermatophagoides farina, in order to develop an assay for the detection of this allergen. BALB/c mice were immunized four times with the protein Der f 2 together with an adjuvant after which splenocytes were collected and fused with SP2/0 (myeloma cells) in the presence of polyethylene glycol (PEG). The fused cells were selected in the presence of Hypoxanthine-Aminopterin-Thymidine (HAT) and then Hypoxanthine-Thymidine (HT) medium. Positive cells were screened with ELISA and subcloned by limited dilution at least three times to achieve stable mAb-producing clones. Four stable mAb-producing clones were obtained. One clone with IgG1 isotype and another with IgG2b isotype were chosen to produce large amounts of mAb by inoculation of the cells into the abdominal cavity of mice. Ascites were collected and the mAbs were purified using protein A affinity chromatography. Testing of the ascites by ELISA showed the titration of IgG1 and IgG2b to be higher than 1/10(6) dilution. The specificity of both antibodies was confirmed by immunoblotting. Thus, we produced two mAb clones against Der f 2 that can be used to create a precise quantitative method to identify allergen components in dust samples and facilitate further study in Der f 2 component-resolved diagnosis (CRD).
[Mh] Termos MeSH primário: Alérgenos/imunologia
Anticorpos Monoclonais/biossíntese
Antígenos de Dermatophagoides/imunologia
Proteínas de Artrópodes/imunologia
Dermatophagoides farinae/imunologia
Pyroglyphidae/imunologia
[Mh] Termos MeSH secundário: Aminopterina
Animais
Anticorpos Monoclonais/isolamento & purificação
Ascite/imunologia
Fusão Celular
Linhagem Celular
Hibridomas
Hipoxantinas
Imunoglobulina G/imunologia
Camundongos
Camundongos Endogâmicos BALB C
Timidina
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Allergens); 0 (Antibodies, Monoclonal); 0 (Antigens, Dermatophagoides); 0 (Arthropod Proteins); 0 (Dermatophagoides farinae antigen f 2); 0 (Hypoxanthines); 0 (Immunoglobulin G); JYB41CTM2Q (Aminopterin); VC2W18DGKR (Thymidine)
[Em] Mês de entrada:1701
[Cu] Atualização por classe:170124
[Lr] Data última revisão:
170124
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:160524
[St] Status:MEDLINE
[do] DOI:10.5582/ddt.2016.01029


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[PMID]:25894214
[Au] Autor:Karnawat V; Puranik M
[Ad] Endereço:a Chemistry Department , Indian Institute of Science Education and Research , Pune 411008 , Maharashtra , India.
[Ti] Título:Solution structures of purine base analogues 9-deazaguanine and 9-deazahypoxanthine.
[So] Source:J Biomol Struct Dyn;34(3):640-52, 2016.
[Is] ISSN:1538-0254
[Cp] País de publicação:England
[La] Idioma:eng
[Ab] Resumo:Deaza analogues of nucleobases are potential drugs against infectious diseases caused by parasites. A caveat is that apart from binding their target parasite enzymes, they also bind and inhibit enzymes of the host. In order to design derivatives of deaza analogues which specifically bind target enzymes, knowledge of their molecular structure, protonation state, and predominant tautomers at physiological conditions is essential. We have employed resonance Raman spectroscopy at an excitation wavelength of 260 nm, to decipher solution structure of 9-deazaguanine (9DAG) and 9-deazahypoxanthine (9DAH). These are analogues of guanine and hypoxanthine, respectively, and have been exploited to study static complexes of nucleobase binding enzymes. Such enzymes are known to perturb pKa of their ligands, and thus, we also determined solution structures of these analogues at two, acidic and alkaline, pH. Structure of each possible protonation state and tautomer was computed using density functional theoretical calculations. Species at various pHs were identified based on isotopic shifts in experimental wavenumbers and by comparing these shifts with corresponding computed isotopic shifts. Our results show that at physiological pH, N1 of pyrimidine ring in 9DAG and 9DAH bears a proton. At lower pH, N3 is place of protonation, and at higher pH, deprotonation occurs at N1 position. The proton at N7 of purine ring remains intact even at pH 12.5. We have further compared these results with naturally occurring nucleotides. Our results identify key vibrational modes which can report on hydrogen bonding interactions, protonation and deprotonation in purine rings upon binding to the active site of enzymes.
[Mh] Termos MeSH primário: Guanina/análogos & derivados
Hipoxantinas/química
Estrutura Molecular
[Mh] Termos MeSH secundário: Guanina/química
Modelos Químicos
Modelos Moleculares
Conformação Molecular
Soluções
Análise Espectral
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (9-deazahypoxanthine); 0 (Hypoxanthines); 0 (Solutions); 5Z93L87A1R (Guanine); 65996-58-9 (9-deazaguanine)
[Em] Mês de entrada:1612
[Cu] Atualização por classe:161230
[Lr] Data última revisão:
161230
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:150421
[St] Status:MEDLINE
[do] DOI:10.1080/07391102.2015.1042916


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[PMID]:26347551
[Au] Autor:Hansson KA; Døving KB; Skjeldal FM
[Ad] Endereço:Department of Biosciences, University of Oslo, Oslo N-0316, Norway k.a.hansson@medisin.uio.no.
[Ti] Título:Mixed input to olfactory glomeruli from two subsets of ciliated sensory neurons does not impede relay neuron specificity in the crucian carp.
[So] Source:J Exp Biol;218(Pt 20):3257-63, 2015 Oct.
[Is] ISSN:1477-9145
[Cp] País de publicação:England
[La] Idioma:eng
[Ab] Resumo:The consensus view of olfactory processing is that the axons of receptor-specific primary olfactory sensory neurons (OSNs) converge to a small subset of glomeruli, thus preserving the odour identity before the olfactory information is processed in higher brain centres. In the present study, we show that two different subsets of ciliated OSNs with different odorant specificities converge to the same glomeruli. In order to stain different ciliated OSNs in the crucian carp Carassius carassius we used two different chemical odorants, a bile salt and a purported alarm substance, together with fluorescent dextrans. The dye is transported within the axons and stains glomeruli in the olfactory bulb. Interestingly, the axons from the ciliated OSNs co-converge to the same glomeruli. Despite intermingled innervation of glomeruli, axons and terminal fields from the two different subsets of ciliated OSNs remained mono-coloured. By 4-6 days after staining, the dye was transported trans-synaptically to separately stained axons of relay neurons. These findings demonstrate that specificity of the primary neurons is retained in the olfactory pathways despite mixed innervation of the olfactory glomeruli. The results are discussed in relation to the emerging concepts about non-mammalian glomeruli.
[Mh] Termos MeSH primário: Carpas/fisiologia
Bulbo Olfatório/metabolismo
Condutos Olfatórios/fisiologia
Neurônios Receptores Olfatórios/efeitos dos fármacos
Olfato
[Mh] Termos MeSH secundário: Animais
Corantes
Dextranos
Hipoxantinas/farmacologia
Bulbo Olfatório/efeitos dos fármacos
Condutos Olfatórios/efeitos dos fármacos
Neurônios Receptores Olfatórios/metabolismo
Sinapses/metabolismo
Ácido Taurolitocólico/farmacologia
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Coloring Agents); 0 (Dextrans); 0 (Hypoxanthines); 516-90-5 (Taurolithocholic Acid)
[Em] Mês de entrada:1701
[Cu] Atualização por classe:170113
[Lr] Data última revisão:
170113
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:150909
[St] Status:MEDLINE
[do] DOI:10.1242/jeb.125476



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