14 research outputs found

    Revisiting the thiosemicarbazonecopper(II) reaction with glutathione. Activity against colorectal carcinoma cell lines

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    Thiosemicarbazones (TSCs), and their copper derivatives, have been extensively studied mainly due to the potential applications as antitumor compounds. A part of the biological activity of the TSC-CuII complexes rests on their reactivity against cell reductants, as glutathione (GSH). The present paper describes the structure of the [Cu(PTSC)(ONO2)]n compound (1) (HPTSC =pyridine-2-carbaldehyde thiosemicarbazone) and its spectroscopic and magnetic properties. ESI studies performed on the reaction of GSH with 1 and the analogous [{Cu (PTSC*)(ONO2)}2] derivative (2, HPTSC* =pyridine-2-carbaldehyde 4N-methylthiosemicarbazone) show the absence of peaks related with TSC-Cu-GSH species. However GSH-Cu ones are detected, in good agreement with the release of CuI ions after reduction in the experimental conditions. The reactivity of 1 and 2 with cytochrome c and myoglobin and their activities against HT-29 and SW-480 colon carcinoma cell lines are compared with those shown by the free HPTSC and HPTSC* ligands.Obra Social “la Caixa” (OSLC-2012-007), Ministerio de Economía y Competitividad and FEDER funds (CTQ2013-48937-C2-1-P, CTQ2015-70371-REDT, MAT2015-66441-P, BIO2015-67358-C2-2-P), Junta de Castilla y León (BU237U13), Gerencia Regional de Salud, Consejería de Sanidad, Junta de Castilla y León (GRS 1023/A/14), the Basque Government (project IT-779-13

    Xenortide biosynthesis by entomopathogenic xenorhabdus nematophila

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    The biosynthesis gene cluster of the xenortides and a new derivative, xenortide D, which is produced in only trace amounts, was identified in Xenorhabdus nematophila. The structure of xenortide D was elucidated using a combination of labeling experiments followed by MS analysis and was confirmed by synthesis. Bioactivity tests revealed a weak activity of tryptamine-carrying xenortides against Plasmodium falciparum and Trypanosoma brucei

    Synthesis of szentiamide, a depsipeptide from entomopathogenic Xenorhabdus szentirmaii with activity against Plasmodium falciparum

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    The synthesis of the recently characterized depsipeptide szentiamide (1), which is produced by the entomopathogenic bacterium Xenorhabdus szentirmaii, is described. Whereas no biological activity was previously identified for 1, the material derived from the efficient synthesis enabled additional bioactivity tests leading to the identification of a notable activity against insect cells and Plasmodium falciparum, the causative agent of malaria

    Xenortide Biosynthesis by Entomopathogenic <i>Xenorhabdus nematophila</i>

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    The biosynthesis gene cluster of the xenortides and a new derivative, xenortide D, which is produced in only trace amounts, was identified in <i>Xenorhabdus nematophila</i>. The structure of xenortide D was elucidated using a combination of labeling experiments followed by MS analysis and was confirmed by synthesis. Bioactivity tests revealed a weak activity of tryptamine-carrying xenortides against <i>Plasmodium falciparum</i> and <i>Trypanosoma brucei</i>

    Rhabdopeptides as insect-specific virulence factors from entomopathogenic bacteria

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    Six novel linear peptides, named "rhabdopeptides", have been identified in the entomopathogenic bacterium Xenorhabdus nematophila after the discovery of the corresponding rdp gene cluster by using a promoter trap strategy for the detection of insect-inducible genes. The structures of these rhabdopeptides were deduced from labeling experiments combined with detailed MS analysis. Detailed analysis of an rdp mutant revealed that these compounds participate in virulence towards insects and are produced upon bacterial infection of a suitable insect host. Furthermore, two additional rhabdopeptide derivatives produced by Xenorhabdus cabanillasii were isolated, these showed activity against insect hemocytes thereby confirming the virulence of this novel class of compounds

    Neutral Loss Fragmentation Pattern Based Screening for Arginine-Rich Natural Products in <i>Xenorhabdus</i> and <i>Photorhabdus</i>

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    Although sharing a certain degree of structural uniformity, natural product classes exhibit variable functionalities such as different amino acid or acyl residues. During collision induced dissociation, some natural products exhibit a conserved fragmentation pattern close to the precursor ion. The observed fragments result from a shared set of neutral losses, creating a unique fragmentation pattern, which can be used as a fingerprint for members of these natural product classes. The culture supernatants of 69 strains of the entomopathogenic bacteria <i>Photorhabdus</i> and <i>Xenorhabdus</i> were analyzed by MALDI-MS<sup>2</sup>, and a database comprising MS<sup>2</sup> data from each strain was established. This database was scanned for concordant fragmentation patterns of different compounds using a customized software, focusing on relative mass differences of the fragment ions to their precursor ion. A novel group of related natural products comprising 25 different arginine-rich peptides from 16 different strains was identified due to its characteristic neutral loss fragmentation pattern, and the structures of eight compounds were elucidated. Two biosynthesis gene clusters encoding nonribosomal peptide synthetases were identified, emphasizing the possibility to identify a group of structurally and biosynthetically related natural products based on their neutral loss fragmentation pattern

    The genus <i>Photorhabdus</i> contains three predominant species.

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    <p>A stylized representation of a previous six gene MLST phylogeny (<i>adk</i>, <i>ghd</i>, <i>mdk</i>, <i>ndh</i>, <i>pgm</i> and <i>recA</i>) of <i>Photorhabdus</i> (adapted from [<a href="http://www.plosone.org/article/info:doi/10.1371/journal.pone.0144937#pone.0144937.ref005" target="_blank">5</a>]) is shown. The grey areas indicate species that consist of multiple strains, the majority of which are unable to grow above 34°C, with only a few <i>P</i>. <i>luminescens</i> strains capable of growth at temperatures up to 37°C. Example strains are <i>P</i>. <i>luminescens</i><sup>TT01</sup> and <i>P</i>. <i>temperata</i><sup>K122</sup>. The clinical strains adapted to 37°C are boxed. The stars and circles indicate the potential historical timing of temperature adaptation, which could have occurred ancestrally (star) or independently (circles) in different geographical isolates.</p

    Clinical <i>Photorhabdus</i> isolates are able to survive exposure to higher temperatures than most non-clinical isolates.

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    <p>The optical density achieved by representative strains after overnight growth in static conditions (at 28°C in LB medium) after prior 18 h exposure to a range of temperatures. A range of clinical (N. American and Australian) and non-clinical (European) strains of <i>P</i>. <i>asymbiotica (Pa)</i> were tested, and the well-studied <i>P</i>. <i>luminescens</i> strain (<i>Pl</i><sup>TT01</sup>) was included for comparison. Green stars and red diamonds indicate thermal tolerance and intolerance respectively. <i>Pa</i> strain designations are indicated as superscripts.</p
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