Base de dados : MEDLINE
Pesquisa : D09.408.210 [Categoria DeCS]
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[PMID]:26466995
[Au] Autor:Aftab U; Zechel DL; Sajid I
[Ad] Endereço:Department of Microbiology and Molecular Genetics, University of the Punjab, Quaid-e-Azam Campus, Lahore, 54590, Pakistan. usmanaftab.mmg@gmail.com.
[Ti] Título:Antitumor compounds from Streptomyces sp. KML-2, isolated from Khewra salt mines, Pakistan.
[So] Source:Biol Res;48:58, 2015 Oct 14.
[Is] ISSN:0717-6287
[Cp] País de publicação:England
[La] Idioma:eng
[Ab] Resumo:BACKGROUND: Actinomycetes are gram positive bacteria with high G + C content in their DNA and are capable of producing variety of secondary metabolites. Many of these metabolites possess different biological activities and have the potential to be developed as therapeutic agents. The aim of the present study was to screen actinomycetes inhabiting halophilic environment such as Khewra salt mines present in Pakistan for cytotoxic and antitumor compounds. RESULTS: An actiomycetes strain designated as Streptomyces sp. KML-2 was isolated from a saline soil of Khewra salt mines, Pakistan. The strain Streptomyces sp. KML-2 showed 84 % cytotoxic activity against larvae of Artemia salina. In the screening phase, the strain exhibited significant antitumor activity with IC50 values of 12, 48 and 56 µg/ml against Hela, MDBK and Vero cell lines, respectively. After that extract from 20 l fermentation was used to purify secondary metabolites by several chromatographic techniques. Structure elucidation of isolated compounds revealed that it is highly stable producer of Chromomycin SA (1) and 1-(1H-indol-3-yl)-propane-1,2,3-triol (2). Both of the isolated compounds showed significant antitumor activity against Hela and MCF-7 cancer cell lines (IC50 values 8.9 and 7.8 µg/ml against Hela; 12.6 and 0.97 µg/ml against MCF-7, respectively). The 16S rRNA gene sequence (1437 bp) of the strain confirm its identity (99 %) with Streptomyces griseus. CONCLUSIONS: From this research work we were successful in isolating two potent antitumor compounds, Chromomycin SA and 1-(1H-indol-3-yl)-propane-1,2,3-triol from Streptomyces KML-2 strain, isolated from Khewra salt mine. As such this is the second report which confirms that S. griseus can produce Chromomycin SA without introducing any mutagenesis in its biosynthesizing gene cluster and isolated indole derivative is being reported first time from any member of actinomycetes group with having novel antitumor activity against Hela and MCF-7 cells. Nucleotide sequences: Nucleotide sequence data reported are available in the GenBank database under the accession number: GenBank KJ009562.
[Mh] Termos MeSH primário: Antineoplásicos/farmacologia
Microbiologia do Solo
Streptomyces/química
[Mh] Termos MeSH secundário: Animais
Antibacterianos/isolamento & purificação
Antibacterianos/farmacologia
Antineoplásicos/isolamento & purificação
Artemia/classificação
Artemia/efeitos dos fármacos
Bovinos
Linhagem Celular
Cercopithecus aethiops
Cromatografia/métodos
Cromomicinas/classificação
Cromomicinas/farmacologia
Formazans
Glicerol/análogos & derivados
Glicerol/farmacologia
Células HeLa
Seres Humanos
Concentração Inibidora 50
Larva/efeitos dos fármacos
Células MCF-7
Microscopia Eletrônica de Varredura
Mineração
Paquistão
Filogenia
RNA Ribossômico 16S/genética
Sais
Análise de Sequência de RNA
Solo/química
Streptomyces/isolamento & purificação
Streptomyces/ultraestrutura
Streptomyces griseus/classificação
Sais de Tetrazólio
Células Vero
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (Anti-Bacterial Agents); 0 (Antineoplastic Agents); 0 (Chromomycins); 0 (Formazans); 0 (RNA, Ribosomal, 16S); 0 (Salts); 0 (Soil); 0 (Tetrazolium Salts); 13615-41-3 (3-indolylglycerol); 23305-68-2 (MTT formazan); PDC6A3C0OX (Glycerol)
[Em] Mês de entrada:1605
[Cu] Atualização por classe:171116
[Lr] Data última revisão:
171116
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:151016
[St] Status:MEDLINE
[do] DOI:10.1186/s40659-015-0046-3


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[PMID]:25486109
[Au] Autor:Guimarães LA; Jimenez PC; Sousa Tda S; Freitas HP; Rocha DD; Wilke DV; Martín J; Reyes F; Deusdênia Loiola Pessoa O; Costa-Lotufo LV
[Ad] Endereço:Marine Sciences Institute, Federal University of Ceara, Fortaleza, Ceara 60165-081, Brazil. larissaalvesgui@gmail.com.
[Ti] Título:Chromomycin A2 induces autophagy in melanoma cells.
[So] Source:Mar Drugs;12(12):5839-55, 2014 Dec 04.
[Is] ISSN:1660-3397
[Cp] País de publicação:Switzerland
[La] Idioma:eng
[Ab] Resumo:The present study highlights the biological effects of chromomycin A2 toward metastatic melanoma cells in culture. Besides chromomycin A2, chromomycin A3 and demethylchromomycin A2 were also identified from the extract derived from Streptomyces sp., recovered from Paracuru Beach, located in the northeast region of Brazil. The cytotoxic activity of chromomycin A2 was evaluated across a panel of human tumor cell lines, which found IC50 values in the nM-range for exposures of 48 and 72 h. MALME-3M, a metastatic melanoma cell line, showed the highest sensitivity to chromomycin A2 after 48h incubation, and was chosen as a model to investigate this potent cytotoxic effect. Treatment with chromomycin A2 at 30 nM reduced cell proliferation, but had no significant effect upon cell viability. Additionally, chromomycin A2 induced accumulation of cells in G0/G1 phase of the cell cycle, with consequent reduction of S and G2/M and unbalanced expression of cyclins. Chromomycin A2 treated cells depicted several cellular fragments resembling autophagosomes and increased expression of proteins LC3-A and LC3-B. Moreover, exposure to chromomycin A2 also induced the appearance of acidic vacuolar organelles in treated cells. These features combined are suggestive of the induction of autophagy promoted by chromomycin A2, a feature not previously described for chromomycins.
[Mh] Termos MeSH primário: Autofagia/efeitos dos fármacos
Melanoma/tratamento farmacológico
Plicamicina/análogos & derivados
[Mh] Termos MeSH secundário: Brasil
Ciclo Celular/efeitos dos fármacos
Linhagem Celular Tumoral
Proliferação Celular/efeitos dos fármacos
Sobrevivência Celular/efeitos dos fármacos
Cromomicina A3/metabolismo
Cromomicinas/farmacologia
Células HCT116
Células HL-60
Seres Humanos
Melanoma/metabolismo
Proteínas Associadas aos Microtúbulos/metabolismo
Plicamicina/farmacologia
Streptomyces/química
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (Chromomycins); 0 (MAP1LC3B protein, human); 0 (Microtubule-Associated Proteins); 0 (chromomycin A2); 0 (light chain 3, human); 86917-62-6 (demethylchromomycin A2); DVW027E7NL (Chromomycin A3); NIJ123W41V (Plicamycin)
[Em] Mês de entrada:1603
[Cu] Atualização por classe:150113
[Lr] Data última revisão:
150113
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:141209
[St] Status:MEDLINE
[do] DOI:10.3390/md12125839


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[PMID]:24415481
[Au] Autor:Siljak-Yakovlev S; Pustahija F; Vicic V; Robin O
[Ad] Endereço:Laboratory Ecology, Systematic and Evolution, UMR 8079, CNRS-UPS-AgroParisTech, University Paris-Sud, Orsay, France.
[Ti] Título:Molecular cytogenetics (FISH and fluorochrome banding): resolving species relationships and genome organization.
[So] Source:Methods Mol Biol;1115:309-23, 2014.
[Is] ISSN:1940-6029
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:Fluorochrome banding (chromomycin, Hoechst, and DAPI) and fluorescence in situ hybridization (FISH) are excellent molecular cytogenetic tools providing various possibilities in the study of chromosomal evolution and genome organization. The constitutive heterochromatin and rRNA genes are the most widely used FISH markers. The rDNA is organized into two distinct gene families (18S-5.8S-26S and 5S) whose number and location vary within the complex of closely related species. Therefore, they are widely used as chromosomal landmarks to provide valuable evidence concerning genome evolution at chromosomal levels.
[Mh] Termos MeSH primário: Bandeamento Cromossômico/métodos
Hibridização in Situ Fluorescente/métodos
Filogenia
[Mh] Termos MeSH secundário: Cromomicinas/metabolismo
Raízes de Plantas/citologia
Raízes de Plantas/genética
Fixação de Tecidos
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Chromomycins)
[Em] Mês de entrada:1408
[Cu] Atualização por classe:140113
[Lr] Data última revisão:
140113
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:140114
[St] Status:MEDLINE
[do] DOI:10.1007/978-1-62703-767-9_15


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[PMID]:23635472
[Au] Autor:Barros E Silva AE; Dos Santos Soares Filho W; Guerra M
[Ad] Endereço:Department of Biology, Federal University of Paraíba, Areia, Brazil.
[Ti] Título:Linked 5S and 45S rDNA sites are highly conserved through the subfamily Aurantioideae (Rutaceae).
[So] Source:Cytogenet Genome Res;140(1):62-9, 2013.
[Is] ISSN:1424-859X
[Cp] País de publicação:Switzerland
[La] Idioma:eng
[Ab] Resumo:Sites of 5S and 45S rDNA are more commonly located on different chromosomes of most angiosperms. Previous investigations have shown that in the subfamily Aurantioideae these sites may appear closely linked (adjacent sites), as in Poncirustrifoliata, or completely isolated, as in some species of Citrus. In the present work, the distribution of rDNA sites was investigated in representatives of 9 genera of Aurantioideae by FISH and CMA banding, aiming to understand the evolution of adjacent sites in the subfamily. A total of 57 rDNA sites were observed, 40 of them being adjacent to each other. All adjacent sites displayed the 45S rDNA array more terminally located. Assuming that the linked 5S-45S rDNA arrangement was the ancestral condition in Aurantioideae, the isolated rDNA sites observed in Clausena excavata,Bergera koenigii, and Fortunella obovata, as well as the complete linkage loss in Citrus maxima and C. medica indicates that unlinked sites arose independently several times in the evolution of the group. The linkage loss may be due to independent dispersion of one or both rDNA sequence families followed by deletion of the corresponding array in the adjacent site. The possible mechanisms behind these events and their occurrence in other groups are discussed.
[Mh] Termos MeSH primário: Cromossomos de Plantas/genética
Sequência Conservada
DNA de Plantas/análise
RNA Ribossômico 5S/genética
RNA Ribossômico/genética
Rutaceae/genética
[Mh] Termos MeSH secundário: Sequência de Bases
Cromomicinas/metabolismo
Cromossomos de Plantas/metabolismo
DNA de Plantas/genética
DNA Ribossômico/genética
DNA Ribossômico/metabolismo
Evolução Molecular
Ligação Genética
Variação Genética
Hibridização in Situ Fluorescente
Indóis/metabolismo
Cariótipo
Cariotipagem
Metáfase
RNA de Plantas/análise
RNA de Plantas/genética
Rutaceae/metabolismo
Especificidade da Espécie
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Chromomycins); 0 (DNA, Plant); 0 (DNA, Ribosomal); 0 (Indoles); 0 (RNA, Plant); 0 (RNA, Ribosomal); 0 (RNA, Ribosomal, 5S); 0 (RNA, ribosomal, 45S); 47165-04-8 (DAPI)
[Em] Mês de entrada:1307
[Cu] Atualização por classe:130528
[Lr] Data última revisão:
130528
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:130503
[St] Status:MEDLINE
[do] DOI:10.1159/000350695


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[PMID]:22789867
[Au] Autor:Lu J; Ma Y; Liang J; Xing Y; Xi T; Lu Y
[Ad] Endereço:State Key Laboratory of Natural Medicines, China Pharmaceutical University, Nanjing, Jiangsu 210009, China.
[Ti] Título:Aureolic acids from a marine-derived Streptomyces sp. WBF16.
[So] Source:Microbiol Res;167(10):590-5, 2012 Dec 20.
[Is] ISSN:1618-0623
[Cp] País de publicação:Germany
[La] Idioma:eng
[Ab] Resumo:A marine-derived actinomycete (Streptomyces sp. WBF16) exhibiting antitumor activities was investigated. The strain was identified using morphological, biochemical and genetic techniques. 16S rDNA sequence of the isolate indicated that it was most closely related to Streptomyces coelicolor A3 (2). Furthermore, a new aureolic acid (Chromomycin B, 1), along with Chromomycin A(2) (2) and Chromomycin A(3) (3) were isolated from its secondary metabolites. Their structures were determined by chemical and spectroscopic methods including 1D, 2D NMR and HRMS. Compounds 1-3 showed strong cytotoxicity against SGC7901, HepG2, A549, HCT116 and COC1 and HUVEC.
[Mh] Termos MeSH primário: Cromomicinas/química
Cromomicinas/farmacologia
Plicamicina/química
Plicamicina/farmacologia
Streptomyces/metabolismo
[Mh] Termos MeSH secundário: Linhagem Celular
Linhagem Celular Tumoral
Cromomicinas/metabolismo
Ensaios de Seleção de Medicamentos Antitumorais/métodos
Células HCT116
Células Hep G2
Células Endoteliais da Veia Umbilical Humana
Seres Humanos
Espectroscopia de Ressonância Magnética/métodos
Biologia Marinha
Plicamicina/metabolismo
Streptomyces/química
Streptomyces/classificação
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (Chromomycins); NIJ123W41V (Plicamycin)
[Em] Mês de entrada:1306
[Cu] Atualização por classe:131121
[Lr] Data última revisão:
131121
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:120714
[St] Status:MEDLINE


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[PMID]:21807523
[Au] Autor:Hu Y; Espindola AP; Stewart NA; Wei S; Posner BA; MacMillan JB
[Ad] Endereço:Department of Biochemistry, Division of Chemistry, University of Texas Southwestern Medical Center, Dallas, TX 75390-9038, USA.
[Ti] Título:Chromomycin SA analogs from a marine-derived Streptomyces sp.
[So] Source:Bioorg Med Chem;19(17):5183-9, 2011 Sep 01.
[Is] ISSN:1464-3391
[Cp] País de publicação:England
[La] Idioma:eng
[Ab] Resumo:Two chromomycin SA analogs, chromomycin SA(3) and chromomycin SA(2), along with deacetylchromomycin A(3) and five previously reported chromomycin analogs were isolated from a marine-derived Streptomyces sp. The structures of the new compounds were determined by spectroscopic methods including 1D and 2D NMR techniques, HRMS and chemical methods. Chromomycin SA(3) and chromomycin SA(2) are the first naturally occuring chromomycin analogs with truncated side-chains. Biological evaluation of chromomycin analogs for cytotoxicity against two non-small cell lung cancer (NSCLC) cell-lines, A549 and HCC44, demonstrated a decrease in cytotoxicity for the truncated sides chain chromomycin analogs.
[Mh] Termos MeSH primário: Cromomicinas/química
Streptomyces/química
[Mh] Termos MeSH secundário: Antineoplásicos/química
Antineoplásicos/isolamento & purificação
Antineoplásicos/toxicidade
Cromomicinas/isolamento & purificação
Cromomicinas/toxicidade
Ensaios de Seleção de Medicamentos Antitumorais
Espectroscopia de Ressonância Magnética
Conformação Molecular
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, N.I.H., EXTRAMURAL; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (Antineoplastic Agents); 0 (Chromomycins); 0 (chromomycin SA2); 0 (chromomycin SA3)
[Em] Mês de entrada:1112
[Cu] Atualização por classe:161019
[Lr] Data última revisão:
161019
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:110803
[St] Status:MEDLINE
[do] DOI:10.1016/j.bmc.2011.07.013


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[PMID]:21342468
[Au] Autor:García B; González-Sabín J; Menéndez N; Braña AF; Núñez LE; Morís F; Salas JA; Méndez C
[Ad] Endereço:Departamento de Biología Funcional e Instituto Universitario de Oncología del Principado de Asturias (I.U.O.P.A), Universidad de Oviedo, Oviedo, Spain.
[Ti] Título:The chromomycin CmmA acetyltransferase: a membrane-bound enzyme as a tool for increasing structural diversity of the antitumour mithramycin.
[So] Source:Microb Biotechnol;4(2):226-38, 2011 Mar.
[Is] ISSN:1751-7915
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:Mithramycin and chromomycin A(3) are two structurally related antitumour compounds, which differ in the glycosylation profiles and functional group substitutions of the sugars. Chromomycin contains two acetyl groups, which are incorporated during the biosynthesis by the acetyltransferase CmmA in Streptomyces griseus ssp. griseus. A bioconversion strategy using an engineered S. griseus strain generated seven novel acetylated mithramycins. The newly formed compounds were purified and characterized by MS and NMR. These new compounds differ from their parental compounds in the presence of one, two or three acetyl groups, attached at 3E, 4E and/or 4D positions. All new mithramycin analogues showed antitumour activity at micromolar of lower concentrations. Some of the compounds showed improved activities against glioblastoma or pancreas tumour cells. The CmmA acetyltransferase was located in the cell membrane and was shown to accept several acyl-CoA substrates. All these results highlight the potential of CmmA as a tool to create structural diversity in these antitumour compounds.
[Mh] Termos MeSH primário: Acetiltransferases/metabolismo
Antineoplásicos/química
Antineoplásicos/metabolismo
Proteínas de Bactérias/metabolismo
Membrana Celular/enzimologia
Plicamicina/química
Plicamicina/metabolismo
Streptomyces griseus/enzimologia
[Mh] Termos MeSH secundário: Acetiltransferases/genética
Antineoplásicos/farmacologia
Proteínas de Bactérias/genética
Biotransformação
Linhagem Celular Tumoral
Membrana Celular/genética
Membrana Celular/metabolismo
Cromomicinas/metabolismo
Seres Humanos
Plicamicina/farmacologia
Streptomyces griseus/química
Streptomyces griseus/genética
Streptomyces griseus/metabolismo
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (Antineoplastic Agents); 0 (Bacterial Proteins); 0 (Chromomycins); EC 2.3.1.- (Acetyltransferases); NIJ123W41V (Plicamycin)
[Em] Mês de entrada:1105
[Cu] Atualização por classe:150204
[Lr] Data última revisão:
150204
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:110224
[St] Status:MEDLINE
[do] DOI:10.1111/j.1751-7915.2010.00229.x


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[PMID]:21314600
[Au] Autor:Prusov AN; Smirnova TA; Kurochkina LP; Kolomijtseva GY
[Ad] Endereço:Belozersky Institute of Physico-Chemical Biology, Lomonosov Moscow State University, Moscow 119991, Russia. prusov@belozersky.msu.ru
[Ti] Título:Influence of distamycin, chromomycin, and UV-irradiation on extraction of histone H1 from rat liver nuclei by polyglutamic acid.
[So] Source:Biochemistry (Mosc);75(11):1331-41, 2010 Nov.
[Is] ISSN:1608-3040
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:Rat liver nucleus histone H1 was fractionated by polyglutamic acid (PG) in the presence of distamycin A (DM) or chromomycin A(3) (CM). In the absence of the antibiotics, PG extracts from the nuclei about half of the nuclear H1. DM or CM added to the nuclei in saturating concentrations weakens the binding potential of most of H1. Titration of nuclei with DM shows that the number of binding sites for DM in the nuclei is less than in isolated DNA by only 20-25%, and this difference disappears after treatment of nuclei with PG. The lower CD value of DM complexes with nuclei compared to that of DM complexes with free DNA is evidence of a change in the DM-DNA binding mode in nuclear chromatin. About 25% of total histone H1 is sensitive only to DM and ~5% is sensitive only to CM. Half of the DM-sensitive H1 fraction seems to have a different binding mode in condensed compared relaxed chromatin. A small part of H1 (~3%) remains tightly bound to the nuclear chromatin independent of the presence of the antibiotics. Subfraction H1A is more DM-sensitive and H1B is more CM-sensitive. UV irradiation of nuclei results in dose-dependent cross-linking of up to 50% of total H1, which is neither acid-extractable nor recovered during SDS electrophoresis. PG with DM extracts only about 3% of H1 from UV-stabilized chromatin. DM treatment of the nuclei before UV irradiation results in extraction of the whole DM-sensitive H1 fraction (~25%), which in this case is not stabilized in the nucleus. A hypothesis on possible roles of the found H1 fractions in chromatin structural organization is discussed.
[Mh] Termos MeSH primário: Núcleo Celular/química
Cromomicinas/farmacologia
Distamicinas/farmacologia
Hepatócitos/química
Histonas/isolamento & purificação
Ácido Poliglutâmico
Raios Ultravioleta
[Mh] Termos MeSH secundário: Animais
Antibacterianos/farmacologia
Núcleo Celular/efeitos dos fármacos
Núcleo Celular/efeitos da radiação
Cromatina/química
DNA/química
Feminino
Hepatócitos/efeitos dos fármacos
Hepatócitos/efeitos da radiação
Interfase
Conformação de Ácido Nucleico
Ratos
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Anti-Bacterial Agents); 0 (Chromatin); 0 (Chromomycins); 0 (Distamycins); 0 (Histones); 25513-46-6 (Polyglutamic Acid); 80O63P88IS (stallimycin); 9007-49-2 (DNA)
[Em] Mês de entrada:1105
[Cu] Atualização por classe:121115
[Lr] Data última revisão:
121115
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:110215
[St] Status:MEDLINE


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[PMID]:21067184
[Au] Autor:Barceló F; Ortiz-Lombardía M; Martorell M; Oliver M; Méndez C; Salas JA; Portugal J
[Ad] Endereço:Departament de Biologia Fundamental i Ciencies de la Salut, Universitat de les Illes Balears, Palma de Mallorca, Spain.
[Ti] Título:DNA binding characteristics of mithramycin and chromomycin analogues obtained by combinatorial biosynthesis.
[So] Source:Biochemistry;49(49):10543-52, 2010 Dec 14.
[Is] ISSN:1520-4995
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:The antitumor antibiotics mithramycin A and chromomycin A(3) bind reversibly to the minor groove of G/C-rich regions in DNA in the presence of dications such as Mg(2+), and their antiproliferative activity has been associated with their ability to block the binding of certain transcription factors to gene promoters. Despite their biological activity, their use as anticancer agents is limited by severe side effects. Therefore, in our pursuit of new structurally related molecules showing both lower toxicity and higher biological activity, we have examined the binding to DNA of six analogues that we have obtained by combinatorial biosynthetic procedures in the producing organisms. All these molecules bear a variety of changes in the side chain attached to C-3 of the chromophore. The spectroscopic characterization of their binding to DNA followed by the evaluation of binding parameters and associated thermodynamics revealed differences in their binding affinity. DNA binding was entropically driven, dominated by the hydrophobic transfer of every compound from solution into the minor groove of DNA. Among the analogues, mithramycin SDK and chromomycin SDK possessed the higher DNA binding affinities.
[Mh] Termos MeSH primário: Cromomicinas/química
Cromomicinas/metabolismo
Técnicas de Química Combinatória
DNA/metabolismo
Plicamicina/análogos & derivados
Plicamicina/metabolismo
[Mh] Termos MeSH secundário: Animais
Sítios de Ligação/fisiologia
Cromomicinas/biossíntese
Técnicas de Química Combinatória/métodos
DNA/química
Masculino
Modelos Moleculares
Conformação de Ácido Nucleico
Salmão
Testículo/química
Termodinâmica
[Pt] Tipo de publicação:COMPARATIVE STUDY; JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (Chromomycins); 9007-49-2 (DNA); NIJ123W41V (Plicamycin)
[Em] Mês de entrada:1101
[Cu] Atualização por classe:131121
[Lr] Data última revisão:
131121
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:101112
[St] Status:MEDLINE
[do] DOI:10.1021/bi101398s


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[PMID]:20093108
[Au] Autor:Mansilla S; Garcia-Ferrer I; Méndez C; Salas JA; Portugal J
[Ad] Endereço:Instituto de Biologia Molecular de Barcelona, CSIC, Parc Cientific de Barcelona, Baldiri Reixac, Spain.
[Ti] Título:Differential inhibition of restriction enzyme cleavage by chromophore-modified analogues of the antitumour antibiotics mithramycin and chromomycin reveals structure-activity relationships.
[So] Source:Biochem Pharmacol;79(10):1418-27, 2010 May 15.
[Is] ISSN:1873-2968
[Cp] País de publicação:England
[La] Idioma:eng
[Ab] Resumo:Differential cleavage at three restriction enzyme sites was used to determine the specific binding to DNA of the antitumour antibiotics mithramycin A (MTA), chromomycin A(3) (CRO) and six chromophore-modified analogues bearing shorter side chains attached at C-3, instead of the pentyl chain. All these antibiotics were obtained through combinatorial biosynthesis in the producer organisms. MTA, CRO and their six analogues showed differences in their capacity for inhibiting the rate of cleavage by restriction enzymes that recognize C/G-rich tracts. Changes in DNA melting temperature produced by these molecules were also analyzed, as well as their antiproliferative activities against a panel of colon, ovarian and prostate human carcinoma cell lines. Moreover, the cellular uptake of several analogues was examined to identify whether intracellular retention was related to cytotoxicity. These experimental approaches provided mutually consistent evidence of a seeming correlation between the strength of binding to DNA and the antiproliferative activity of the chromophore-modified molecules. Four of the analogues (mithramycin SK, mithramycin SDK, chromomycin SK and chromomycin SDK) showed promising biological profiles.
[Mh] Termos MeSH primário: Antibióticos Antineoplásicos/farmacologia
Cromomicinas/farmacologia
Enzimas de Restrição do DNA/antagonistas & inibidores
Plicamicina/análogos & derivados
[Mh] Termos MeSH secundário: Linhagem Celular Tumoral
Cromomicina A3/farmacologia
Neoplasias do Colo/tratamento farmacológico
Desoxirribonucleases de Sítio Específico do Tipo II/antagonistas & inibidores
Feminino
Citometria de Fluxo
Seres Humanos
Masculino
Neoplasias Ovarianas/tratamento farmacológico
Plicamicina/farmacologia
Neoplasias da Próstata/tratamento farmacológico
Relação Estrutura-Atividade
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (Antibiotics, Antineoplastic); 0 (Chromomycins); 0 (mithramycin SK); 97666-60-9 (mithramycin A); DVW027E7NL (Chromomycin A3); EC 3.1.21.- (DNA Restriction Enzymes); EC 3.1.21.- (endodeoxyribonuclease XmaIII); EC 3.1.21.4 (Deoxyribonucleases, Type II Site-Specific); EC 3.1.21.4 (GACGTC-specific type II deoxyribonucleases); NIJ123W41V (Plicamycin)
[Em] Mês de entrada:1004
[Cu] Atualização por classe:131121
[Lr] Data última revisão:
131121
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:100123
[St] Status:MEDLINE
[do] DOI:10.1016/j.bcp.2010.01.005



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