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[PMID]:28650656
[Au] Autor:Wang P; Amato NJ; Wang Y
[Ad] Endereço:Environmental Toxicology Graduate Program and ‡Department of Chemistry, University of California , Riverside, California 92521-0403, United States.
[Ti] Título:Cytotoxic and Mutagenic Properties of C3'-Epimeric Lesions of 2'-Deoxyribonucleosides in Escherichia coli Cells.
[So] Source:Biochemistry;56(29):3725-3732, 2017 Jul 25.
[Is] ISSN:1520-4995
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:Reactive oxygen species (ROS), resulting from endogenous metabolism and/or environmental exposure, can induce damage to the 2-deoxyribose moiety in DNA. Specifically, a hydrogen atom from each of the five carbon atoms in 2-deoxyribose can be abstracted by hydroxyl radical, and improper chemical repair of the ensuing radicals formed at the C1', C3', and C4' positions can lead to the stereochemical inversion at these sites to yield epimeric 2-deoxyribose lesions. Although ROS-induced single-nucleobase lesions have been well studied, the biological consequences of the C3'-epimeric lesions of 2'-deoxynucleosides, i.e., 2'-deoxyxylonucleosides (dxN), have not been comprehensively investigated. Herein, we assessed the impact of dxN lesions on the efficiency and fidelity of DNA replication in Escherichia coli cells by conducting a competitive replication and adduct bypass assay with single-stranded M13 phage containing a site-specifically incorporated dxN. Our results revealed that, of the four dxN lesions, only dxG constituted a strong impediment to DNA replication, and intriguingly, dxT and dxC conferred replication bypass efficiencies higher than those of the unmodified counterparts. In addition, the three SOS-induced DNA polymerases (Pol II, Pol IV, and Pol V) did not play any appreciable role in bypassing these lesions. Among the four dxNs, only dxA directed a moderate frequency of dCMP misincorporation. These results provided important insights into the impact of the C3'-epimeric lesions on DNA replication in E. coli cells.
[Mh] Termos MeSH primário: Adutos de DNA
Replicação do DNA
DNA Bacteriano
Desoxirribonucleosídeos
Escherichia coli
Mutagênese
[Mh] Termos MeSH secundário: Adutos de DNA/genética
Adutos de DNA/metabolismo
DNA Bacteriano/biossíntese
DNA Bacteriano/genética
DNA Polimerase Dirigida por DNA/genética
DNA Polimerase Dirigida por DNA/metabolismo
Desoxirribonucleosídeos/genética
Desoxirribonucleosídeos/metabolismo
Escherichia coli/genética
Escherichia coli/metabolismo
Proteínas de Escherichia coli/genética
Proteínas de Escherichia coli/metabolismo
Resposta SOS (Genética)
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (DNA Adducts); 0 (DNA, Bacterial); 0 (Deoxyribonucleosides); 0 (Escherichia coli Proteins); EC 2.7.7.7 (DNA-Directed DNA Polymerase)
[Em] Mês de entrada:1707
[Cu] Atualização por classe:170929
[Lr] Data última revisão:
170929
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:170627
[St] Status:MEDLINE
[do] DOI:10.1021/acs.biochem.7b00146


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[PMID]:28628209
[Au] Autor:Meher G; Meher NK; Iyer RP
[Ad] Endereço:Spring Bank Pharmaceuticals, Inc., Milford, Massachusetts.
[Ti] Título:Nucleobase Protection of Deoxyribo- and Ribonucleosides.
[So] Source:Curr Protoc Nucleic Acid Chem;69:2.1.1-2.1.40, 2017 Jun 19.
[Is] ISSN:1934-9289
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:Oligonucleotides carrying a variety of chemical modifications including conjugates are finding increasing applications in therapeutics, diagnostics, functional genomics, proteomics, and as research tools in chemical and molecular biology. The successful synthesis of oligonucleotides primarily depends on the use of appropriately protected nucleoside building blocks including the exocyclic amino groups of the nucleobases, the hydroxyl groups at the 2'-, 3'-, and 5'-positions of the sugar moieties, and the internucleotide phospho-linkage. This unit is a thoroughly revised update of the previously published version and describes the recent development of various protecting groups that facilitate reliable oligonucleotide synthesis. In addition, various protecting groups for the imide/lactam function of thymine/uracil and guanine, respectively, are described to prevent irreversible nucleobase modifications that may occur in the presence of reagents used in oligonucleotide synthesis. © 2017 by John Wiley & Sons, Inc.
[Mh] Termos MeSH primário: Desoxirribonucleosídeos/química
Ribonucleosídeos/química
[Mh] Termos MeSH secundário: Acetilação
Fotoquímica
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Deoxyribonucleosides); 0 (Ribonucleosides)
[Em] Mês de entrada:1708
[Cu] Atualização por classe:170802
[Lr] Data última revisão:
170802
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:170620
[St] Status:MEDLINE
[do] DOI:10.1002/cpnc.32


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[PMID]:28388097
[Au] Autor:Williams NL; Amato NJ; Wang Y
[Ad] Endereço:Environmental Toxicology Graduate Program and ‡Department of Chemistry, University of California , 501 Big Springs Road, Riverside, California 92521-0403, United States.
[Ti] Título:Replicative Bypass Studies of α-Anomeric Lesions of 2'-Deoxyribonucleosides in Vitro.
[So] Source:Chem Res Toxicol;30(5):1127-1133, 2017 May 15.
[Is] ISSN:1520-5010
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:Genomic integrity is constantly challenged by a variety of endogenous and exogenous DNA damaging agents, which can lead to the formation of 10 -10 DNA lesions per cell per day. Reactive oxygen species (ROS) represent a major type of DNA damaging agent. Specifically, a hydroxyl radical can attack the C1' position of 2-deoxyribose, and the ensuing carbon-centered radical, if improperly repaired, can cause the inversion of stereochemical configuration at the C1' to give α-anomeric lesions. In this study, we assessed the replicative bypass of α-dA, α-dT, α-dC, and α-dG in template DNA by conducting primer extension assays with the use of purified translesion synthesis DNA polymerases. Our results revealed that human polymerase (Pol) η, but not human Pol κ, Pol ι, or yeast Pol ζ, was capable of bypassing all of the α-dN lesions and extending the primer to generate full-length replication products. Data from steady-state kinetic measurements showed that Pol η was the most efficient in inserting the correct nucleotides opposite the modified nucleosides, with the relative efficiencies of nucleotide incorporation following the order of α-dA > α-dG > α-dT > α-dC. Additionally, human Pol η was found to misincorporate dTMP opposite α-dT and dCMP opposite α-dC at frequencies of 66% and 24%, respectively, whereas α-dA and α-dG were weakly miscoding. These findings provided important knowledge about the effects these α-dN lesions have on the fidelity and efficiency of DNA replication mediated by human Pol η.
[Mh] Termos MeSH primário: Replicação do DNA
Desoxirribonucleosídeos/química
[Mh] Termos MeSH secundário: Dano ao DNA
Primers do DNA
DNA Polimerase Dirigida por DNA/metabolismo
Seres Humanos
Técnicas In Vitro
Cinética
Espécies Reativas de Oxigênio/metabolismo
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (DNA Primers); 0 (Deoxyribonucleosides); 0 (Reactive Oxygen Species); EC 2.7.7.7 (DNA-Directed DNA Polymerase)
[Em] Mês de entrada:1706
[Cu] Atualização por classe:170927
[Lr] Data última revisão:
170927
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:170408
[St] Status:MEDLINE
[do] DOI:10.1021/acs.chemrestox.6b00439


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[PMID]:28328490
[Au] Autor:Mertz L
[Ti] Título:The Coming Gray Tide: Wanted: Health Innovations for an Increasingly Older Population.
[So] Source:IEEE Pulse;8(2):6-11, 2017 Mar-Apr.
[Is] ISSN:2154-2317
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:The human population is getting older, and technology will play a key role in addressing the pressures this aging will place on healthcare systems. According to the 2015 United Nations' World Population Ageing report [1], the number of people worldwide 60 and older will increase from one in eight in 2015 to one in six by 2030 and to one in five by 2050; in Europe and "Northern America" (mainly the United States and Canada), those 60 and older will make up 25% of the population by 2030, and in Asia and Latin America, the number is predicted to be 17%.
[Mh] Termos MeSH primário: Envelhecimento
Assistência à Saúde
Dinâmica Populacional
[Mh] Termos MeSH secundário: Canadá
Desoxirribonucleosídeos
Europa (Continente)
Seres Humanos
Indóis
[Pt] Tipo de publicação:JOURNAL ARTICLE; REVIEW
[Nm] Nome de substância:
0 (3-acetyl-2-bromo-5,6-dichloro-1-(2-deoxyribofuranosyl)indole); 0 (Deoxyribonucleosides); 0 (Indoles)
[Em] Mês de entrada:1704
[Cu] Atualização por classe:170428
[Lr] Data última revisão:
170428
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:170323
[St] Status:MEDLINE
[do] DOI:10.1109/MPUL.2016.2647058


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[PMID]:28045593
[Au] Autor:Van Ostrand R; Jacobsen C; Delahunty A; Stringer C; Noorbehesht R; Ahmed H; Awad AM
[Ad] Endereço:a Chemistry Program, California State University Channel Islands , Camarillo , CA , USA.
[Ti] Título:Synthesis and antibacterial activity of 5'-tetrachlorophthalimido and 5'-azido 5'-deoxyribonucleosides.
[So] Source:Nucleosides Nucleotides Nucleic Acids;36(3):181-197, 2017 Mar 04.
[Is] ISSN:1532-2335
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:Reported is an efficient synthesis of adenyl and uridyl 5'-tetrachlorophthalimido-5'-deoxyribonucleosides, and guanylyl 5'-azido-5'-deoxyribonucleosides, which are useful in solid-phase synthesis of phosphoramidate and ribonucleic guanidine oligonucleotides. Replacement of 5'-hydroxyl with tetrachlorophthalimido group was performed via Mitsunobu reaction for adenosine and uridine. An alternative method was applied for guanosine which replaced the 5'-hydroxyl with an azido group. The resulting compounds were converted to 5'-amino-5'-deoxyribonucleosides for oligonucleotide synthesis. Synthetic intermediates were tested as antimicrobials against six bacterial strains. All analogs containing the 2',3'-O-isopropylidine protecting group demonstrated antibacterial activity against Neisseria meningitidis, and among those analogs with 5'-tetrachlorophthalimido and 5'-azido demonstrated increased antibacterial effect.
[Mh] Termos MeSH primário: Antibacterianos/química
Antibacterianos/farmacologia
[Mh] Termos MeSH secundário: Adenosina/química
Antibacterianos/síntese química
Azidas/química
Técnicas de Química Sintética
Desoxirribonucleosídeos/síntese química
Desoxirribonucleosídeos/farmacologia
Avaliação Pré-Clínica de Medicamentos/métodos
Testes de Sensibilidade Microbiana
Neisseria meningitidis/efeitos dos fármacos
Ftalimidas/química
Uridina/química
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Anti-Bacterial Agents); 0 (Azides); 0 (Deoxyribonucleosides); 0 (Phthalimides); K72T3FS567 (Adenosine); WHI7HQ7H85 (Uridine)
[Em] Mês de entrada:1703
[Cu] Atualização por classe:170303
[Lr] Data última revisão:
170303
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:170104
[St] Status:MEDLINE
[do] DOI:10.1080/15257770.2016.1250906


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[PMID]:27811125
[Au] Autor:Barrio MJ; Spick C; Radu CG; Lassmann M; Eberlein U; Allen-Auerbach M; Schiepers C; Slavik R; Czernin J; Herrmann K
[Ad] Endereço:Department of Molecular and Medical Pharmacology, David Geffen School of Medicine at UCLA, Los Angeles, California.
[Ti] Título:Human Biodistribution and Radiation Dosimetry of F-Clofarabine, a PET Probe Targeting the Deoxyribonucleoside Salvage Pathway.
[So] Source:J Nucl Med;58(3):374-378, 2017 Mar.
[Is] ISSN:1535-5667
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:F-clofarabine, a nucleotide purine analog, is a substrate for deoxycytidine kinase (dCK), a key enzyme in the deoxyribonucleoside salvage pathway. F-clofarabine might be used to measure dCK expression and thus serve as a predictive biomarker for tumor responses to dCK-dependent prodrugs or small-molecule dCK inhibitors, respectively. As a prerequisite for clinical translation, we determined the human whole-body and organ dosimetry of F-clofarabine. Five healthy volunteers were injected intravenously with 232.4 ± 1.5 MBq of F-clofarabine. Immediately after tracer injection, a dynamic scan of the entire chest was acquired for 30 min. This was followed by 3 static whole-body scans at 45, 90, and 135 min after tracer injection. Regions of interest were drawn around multiple organs on the CT scan and copied to the PET scans. Organ activity was determined and absorbed dose was estimated with OLINDA/EXM software. The urinary bladder (critical organ), liver, kidney, and spleen exhibited the highest uptake. For an activity of 250 MBq, the absorbed doses in the bladder, liver, kidney, and spleen were 58.5, 6.6, 6.3, and 4.3 mGy, respectively. The average effective dose coefficient was 5.1 mSv. Our results hint that F-clofarabine can be used safely in humans to measure tissue dCK expression. Future studies will determine whether F-clofarabine may serve as a predictive biomarker for responses to dCK-dependent prodrugs or small-molecule dCK inhibitors.
[Mh] Termos MeSH primário: Nucleotídeos de Adenina/farmacocinética
Arabinonucleosídeos/farmacocinética
Desoxicitidina Quinase/metabolismo
Desoxirribonucleosídeos/metabolismo
Radioisótopos de Flúor/farmacocinética
Tomografia por Emissão de Pósitrons/métodos
Transdução de Sinais
[Mh] Termos MeSH secundário: Absorção de Radiação/fisiologia
Idoso
Feminino
Seres Humanos
Masculino
Taxa de Depuração Metabólica
Meia-Idade
Imagem Molecular/métodos
Especificidade de Órgãos/fisiologia
Dose de Radiação
Compostos Radiofarmacêuticos/farmacocinética
Distribuição Tecidual
Contagem Corporal Total
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Adenine Nucleotides); 0 (Arabinonucleosides); 0 (Deoxyribonucleosides); 0 (Fluorine Radioisotopes); 0 (Radiopharmaceuticals); 762RDY0Y2H (clofarabine); EC 2.7.1.74 (Deoxycytidine Kinase)
[Em] Mês de entrada:1705
[Cu] Atualização por classe:170511
[Lr] Data última revisão:
170511
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:161105
[St] Status:MEDLINE
[do] DOI:10.2967/jnumed.116.182394


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[PMID]:27764728
[Au] Autor:Anacker DC; Aloor HL; Shepard CN; Lenzi GM; Johnson BA; Kim B; Moody CA
[Ad] Endereço:Department of Microbiology and Immunology, University of North Carolina at Chapel Hill, North Carolina, USA.
[Ti] Título:HPV31 utilizes the ATR-Chk1 pathway to maintain elevated RRM2 levels and a replication-competent environment in differentiating Keratinocytes.
[So] Source:Virology;499:383-396, 2016 Dec.
[Is] ISSN:1096-0341
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:Productive replication of human papillomaviruses (HPV) is restricted to the uppermost layers of the differentiating epithelia. How HPV ensures an adequate supply of cellular substrates for viral DNA synthesis in a differentiating environment is unclear. Here, we demonstrate that HPV31 positive cells exhibit increased dNTP pools and levels of RRM2, a component of the ribonucleotide reductase (RNR) complex, which is required for de novo synthesis of dNTPs. RRM2 depletion blocks productive replication, suggesting RRM2 provides dNTPs for viral DNA synthesis in differentiating cells. We demonstrate that HPV31 regulates RRM2 levels through expression of E7 and activation of the ATR-Chk1-E2F1 DNA damage response, which is essential to combat replication stress upon entry into S-phase, as well as for productive replication. Our findings suggest a novel way in which viral DNA synthesis is regulated through activation of ATR and Chk1 and highlight an intriguing new virus/host interaction utilized for viral replication.
[Mh] Termos MeSH primário: Quinase do Ponto de Checagem 1/metabolismo
Papillomavirus Humano 31/fisiologia
Queratinócitos/virologia
Infecções por Papillomavirus/enzimologia
Ribonucleosídeo Difosfato Redutase/metabolismo
Replicação Viral
[Mh] Termos MeSH secundário: Proteínas Mutadas de Ataxia Telangiectasia/genética
Proteínas Mutadas de Ataxia Telangiectasia/metabolismo
Quinase do Ponto de Checagem 1/genética
Dano ao DNA
Replicação do DNA
Desoxirribonucleosídeos/metabolismo
Interações Hospedeiro-Patógeno
Papillomavirus Humano 31/genética
Seres Humanos
Queratinócitos/enzimologia
Proteínas E7 de Papillomavirus/química
Proteínas E7 de Papillomavirus/genética
Proteínas E7 de Papillomavirus/metabolismo
Infecções por Papillomavirus/genética
Infecções por Papillomavirus/virologia
Domínios Proteicos
Ribonucleosídeo Difosfato Redutase/genética
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Deoxyribonucleosides); 0 (Papillomavirus E7 Proteins); EC 1.17.4.- (ribonucleotide reductase M2); EC 1.17.4.1 (Ribonucleoside Diphosphate Reductase); EC 2.7.11.1 (ATR protein, human); EC 2.7.11.1 (Ataxia Telangiectasia Mutated Proteins); EC 2.7.11.1 (CHEK1 protein, human); EC 2.7.11.1 (Checkpoint Kinase 1)
[Em] Mês de entrada:1706
[Cu] Atualização por classe:170908
[Lr] Data última revisão:
170908
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:161021
[St] Status:MEDLINE


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[PMID]:27511871
[Au] Autor:Crona M; Codó P; Jonna VR; Hofer A; Fernandes AP; Tholander F
[Ad] Endereço:Department of Medicinal Biochemistry and Biophysics, Karolinska Institutet, 171 77, Stockholm, Sweden.
[Ti] Título:A ribonucleotide reductase inhibitor with deoxyribonucleoside-reversible cytotoxicity.
[So] Source:Mol Oncol;10(9):1375-1386, 2016 Nov.
[Is] ISSN:1878-0261
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:Ribonucleotide Reductase (RNR) is the sole enzyme that catalyzes the reduction of ribonucleotides into deoxyribonucleotides. Even though RNR is a recognized target for antiproliferative molecules, and the main target of the approved drug hydroxyurea, few new leads targeted to this enzyme have been developed. We have evaluated a recently identified set of RNR inhibitors with respect to inhibition of the human enzyme and cellular toxicity. One compound, NSC73735, is particularly interesting; it is specific for leukemia cells and is the first identified compound that hinders oligomerization of the mammalian large RNR subunit. Similar to hydroxyurea, it caused a disruption of the cell cycle distribution of cultured HL-60 cells. In contrast to hydroxyurea, the disruption was reversible, indicating higher specificity. NSC73735 thus defines a potential lead candidate for RNR-targeted anticancer drugs, as well as a chemical probe with better selectivity for RNR inhibition than hydroxyurea.
[Mh] Termos MeSH primário: Desoxirribonucleosídeos/farmacologia
Inibidores Enzimáticos/farmacologia
Ribonucleotídeo Redutases/antagonistas & inibidores
[Mh] Termos MeSH secundário: Bioensaio
Ciclo Celular/efeitos dos fármacos
Morte Celular/efeitos dos fármacos
Proliferação Celular/efeitos dos fármacos
Sobrevivência Celular/efeitos dos fármacos
Relação Dose-Resposta a Droga
Inibidores Enzimáticos/química
Citometria de Fluxo
Regulação da Expressão Gênica/efeitos dos fármacos
Células HL-60
Seres Humanos
Hidroxiureia/farmacologia
Estrutura Quaternária de Proteína
Subunidades Proteicas/antagonistas & inibidores
Subunidades Proteicas/química
Subunidades Proteicas/metabolismo
Ribonucleotídeo Redutases/química
Ribonucleotídeo Redutases/metabolismo
Temperatura Ambiente
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Deoxyribonucleosides); 0 (Enzyme Inhibitors); 0 (Protein Subunits); EC 1.17.4.- (Ribonucleotide Reductases); X6Q56QN5QC (Hydroxyurea)
[Em] Mês de entrada:1710
[Cu] Atualização por classe:171030
[Lr] Data última revisão:
171030
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:160812
[St] Status:MEDLINE


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[PMID]:27498304
[Au] Autor:Bosáková A; Perlíková P; Tichý M; Pohl R; Hocek M
[Ad] Endereço:Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Gilead Sciences & IOCB Research Center, Flemingovo nam. 2, CZ-16610 Prague 6, Czech Republic.
[Ti] Título:6-Aryl-4-amino-pyrimido[4,5-b]indole 2'-deoxyribonucleoside triphosphates (benzo-fused 7-deaza-dATP analogues): Synthesis, fluorescent properties, enzymatic incorporation into DNA and DNA-protein binding study.
[So] Source:Bioorg Med Chem;24(19):4528-4535, 2016 Oct 01.
[Is] ISSN:1464-3391
[Cp] País de publicação:England
[La] Idioma:eng
[Ab] Resumo:Four 6-substituted 4-amino-pyrimido[4,5-b]indole 2'-deoxyribonucleoside triphosphates (dA(BX)TPs) were prepared by glycosylation of 4,6-dichloropyrimidoindole followed by ammonolysis, cross-coupling and triphosphorylation. They were found to be moderate to good substrates for DNA polymerases in primer extension. They also exerted fluorescence with emission maxima 335-378nm. When incorporated to oligonucleotide probes, they did not show significant mismatch discrimination but the 6-benzofuryl 4-amino-pyrimido[4,5-b]indole nucleotide displayed a useful sensitivity to protein binding in experiment with SSB protein.
[Mh] Termos MeSH primário: Nucleotídeos de Desoxiadenina/química
Desoxirribonucleosídeos/química
Corantes Fluorescentes/química
Indóis/química
Sondas de Oligonucleotídeos/química
[Mh] Termos MeSH secundário: Pareamento Incorreto de Bases
Sequência de Bases
Proteínas de Ligação a DNA/química
Proteínas de Ligação a DNA/metabolismo
DNA Polimerase Dirigida por DNA/metabolismo
Nucleotídeos de Desoxiadenina/síntese química
Nucleotídeos de Desoxiadenina/metabolismo
Desoxirribonucleosídeos/síntese química
Desoxirribonucleosídeos/metabolismo
Escherichia coli/química
Escherichia coli/metabolismo
Proteínas de Escherichia coli/química
Proteínas de Escherichia coli/metabolismo
Corantes Fluorescentes/síntese química
Corantes Fluorescentes/metabolismo
Indóis/síntese química
Indóis/metabolismo
Sondas de Oligonucleotídeos/síntese química
Sondas de Oligonucleotídeos/metabolismo
Espectrometria de Fluorescência
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (DNA-Binding Proteins); 0 (Deoxyadenine Nucleotides); 0 (Deoxyribonucleosides); 0 (Escherichia coli Proteins); 0 (Fluorescent Dyes); 0 (Indoles); 0 (Oligonucleotide Probes); 0 (SSB protein, E coli); EC 2.7.7.7 (DNA-Directed DNA Polymerase); K8KCC8SH6N (2'-deoxyadenosine triphosphate)
[Em] Mês de entrada:1707
[Cu] Atualização por classe:170919
[Lr] Data última revisão:
170919
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:160808
[St] Status:MEDLINE


  10 / 1074 MEDLINE  
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[PMID]:26945242
[Au] Autor:Schmied-Tobies MI; Paschke H; Reemtsma T
[Ad] Endereço:Helmholtz Centre for Environmental Research - UFZ, Permoserstrasse 15, 04318 Leipzig, Germany.
[Ti] Título:Combined chemoassay and mass spectrometric approach to study the reactive potential of electrophiles towards deoxynucleosides as model for DNA.
[So] Source:Chemosphere;151:263-70, 2016 May.
[Is] ISSN:1879-1298
[Cp] País de publicação:England
[La] Idioma:eng
[Ab] Resumo:The modification of DNA by adduct formation is a potential molecular initiating event of genotoxicity. A chemoassay was established to study adduct formation of electrophiles with deoxynucleosides. Liquid chromatography-mass spectrometry was used to determine the reactivity of the model electrophiles para-benzoquinone, hydroquinone, and 1,4-naphthoquinone with deoxynucleoside (deoxyadenosine (dA), deoxyguanosine (dG), deoxycytidine (dC) and thymidine (dT)) to detect formation of adducts via constant neutral loss scan of deoxyribose (116 Da), and to elucidate adduct structures using high resolution mass spectrometry. Of the four deoxynucleosides dG was most susceptible, followed by dC and para-benzoquinone was the most reactive electrophile. With this approach five dG and four dC adducts were detected, formed by Michael addition and subsequent condensation. Also oxidation occurred with reactive oxygen species (ROS). Three of the adducts formed by benzoquinone have not been reported before. This chemoassay combined with mass spectrometry offers a way (a) to screen a large number of chemicals for their genotoxic potential, (b) to determine novel adducts that may be searched for in in vitro and in vivo studies and thus (c) to better understand the reaction of electrophiles with nucleobases.
[Mh] Termos MeSH primário: Adutos de DNA/análise
Desoxirribonucleosídeos/química
Mutagênicos/química
Oxidantes/química
Espectrometria de Massas em Tandem/métodos
[Mh] Termos MeSH secundário: Benzoquinonas/química
Cromatografia Líquida
DNA/química
Dano ao DNA
Desoxiadenosinas/química
Desoxicitidina/química
Desoxiguanosina/química
Naftoquinonas/química
Timidina/química
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (Benzoquinones); 0 (DNA Adducts); 0 (Deoxyadenosines); 0 (Deoxyribonucleosides); 0 (Mutagens); 0 (Naphthoquinones); 0 (Oxidants); 0W860991D6 (Deoxycytidine); 3T006GV98U (quinone); 9007-49-2 (DNA); G9481N71RO (Deoxyguanosine); P582C98ULC (2'-deoxyadenosine); RBF5ZU7R7K (1,4-naphthoquinone); VC2W18DGKR (Thymidine)
[Em] Mês de entrada:1611
[Cu] Atualização por classe:170103
[Lr] Data última revisão:
170103
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:160306
[St] Status:MEDLINE



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