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  1. AU="Alicia Reyes-Arellano"
  2. AU="L. Marcus Wilhelmsson"
  3. AU=Filocamo Giovanni
  4. AU="Andrea Terán-Valdez"
  5. AU=Cleverley Joanne AU=Cleverley Joanne
  6. AU="Feng, Shiguang"
  7. AU="De Falco, Antonio"
  8. AU="Plenter, R J"
  9. AU="Malarz, Janusz"

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  1. Artikel ; Online: GELES MOLECULARES Y ORGANOGELANTES

    ALICIA REYES-ARELLANO

    TIP Revista Especializada en Ciencias Químico-Biológicas, Vol 11, Iss 2, Pp 101-

    2008  Band 104

    Schlagwörter Biology (General) ; QH301-705.5 ; Zoology ; QL1-991 ; Chemistry ; QD1-999
    Sprache Englisch
    Erscheinungsdatum 2008-01-01T00:00:00Z
    Verlag Universidad Nacional Autónoma de México
    Dokumenttyp Artikel ; Online
    Datenquelle BASE - Bielefeld Academic Search Engine (Lebenswissenschaftliche Auswahl)

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  2. Artikel ; Online: Effect of New Analogs of Hexyloxy Phenyl Imidazoline on Quorum Sensing in Chromobacterium violaceum and In Silico Analysis of Ligand-Receptor Interactions

    José Luis Herrera-Arizmendi / Everardo Curiel-Quesada / José Correa-Basurto / Martiniano Bello / Alicia Reyes-Arellano

    Journal of Chemistry, Vol

    2020  Band 2020

    Abstract: The increasing common occurrence of antibiotic-resistant bacteria has become an urgent public health issue. There are currently some infections without any effective treatment, which require new therapeutic strategies. An attractive alternative is the ... ...

    Abstract The increasing common occurrence of antibiotic-resistant bacteria has become an urgent public health issue. There are currently some infections without any effective treatment, which require new therapeutic strategies. An attractive alternative is the design of compounds capable of disrupting bacterial communication known as quorum sensing (QS). In Gram-negative bacteria, such communication is regulated by acyl-homoserine lactones (AHLs). Triggering of QS after bacteria have reached a high cell density allows them to proliferate before expressing virulence factors. Our group previously reported that hexyloxy phenylimidazoline (9) demonstrated 71% inhibitory activity of QS at 100 μM (IC50 = 90.9 μM) in Chromobacterium violaceum, a Gram-negative bacterium. The aim of the present study was to take 9 as a lead compound to design and synthesize three 2-imidazolines (13–15) and three 2-oxazolines (16–18), to be evaluated as quorum-sensing inhibitors on C. violaceum CV026. We were looking for compounds with a higher affinity towards the Cvi receptor of this bacterium and the ability to inhibit QS. The binding mode of the test compounds on the Cvi receptor was explored with docking studies and molecular dynamics. It was found that 8-pentyloxyphenyl-2-imidazoline (13) reduced the production of violacein (IC50 = 56.38 μM) without affecting bacterial growth, suggesting inhibition of quorum sensing. Indeed, compound 13 is apparently one of the best QS inhibitors known to date. Molecular docking revealed the affinity of compound 13 for the orthosteric site of N-hexanoyl homoserine lactone (C6-AHL) on the CviR protein. Ten amino acid residues in the active binding site of C6-AHL in the Cvi receptor interacted with 13, and 7 of these are the same as those interacting with AHL. Contrarily, 8-octyloxyphenyl-2-imidazoline (14), 8-decyloxyphenyl-2-imidazoline (15), and 9-decyloxyphenyl-2-oxazoline (18) bound only to an allosteric site and thus did not compete with C6-AHL for the orthosteric site.
    Schlagwörter Chemistry ; QD1-999
    Thema/Rubrik (Code) 540
    Sprache Englisch
    Erscheinungsdatum 2020-01-01T00:00:00Z
    Verlag Hindawi Limited
    Dokumenttyp Artikel ; Online
    Datenquelle BASE - Bielefeld Academic Search Engine (Lebenswissenschaftliche Auswahl)

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  3. Artikel ; Online: N -Heterocycles Scaffolds as Quorum Sensing Inhibitors. Design, Synthesis, Biological and Docking Studies

    Alfredo Fuentes-Gutiérrez / Everardo Curiel-Quesada / José Correa-Basurto / Alberto Martínez-Muñoz / Alicia Reyes-Arellano

    International Journal of Molecular Sciences, Vol 21, Iss 9512, p

    2020  Band 9512

    Abstract: Quorum sensing is a communication system among bacteria to sense the proper time to express their virulence factors. Quorum sensing inhibition is a therapeutic strategy to block bacterial mechanisms of virulence. The aim of this study was to synthesize ... ...

    Abstract Quorum sensing is a communication system among bacteria to sense the proper time to express their virulence factors. Quorum sensing inhibition is a therapeutic strategy to block bacterial mechanisms of virulence. The aim of this study was to synthesize and evaluate new bioisosteres of N -acyl homoserine lactones as Quorum sensing inhibitors in Chromobacterium violaceum CV026 by quantifying the specific production of violacein. Five series of compounds with different heterocyclic scaffolds were synthesized in good yields: thiazoles, 16a – c , thiazolines 17a – c , benzimidazoles 18a – c , pyridines 19a – c and imidazolines 32a – c . All 15 compounds showed activity as Quorum sensing inhibitors except 16a . Compounds 16b , 17a – c , 18a , 18c , 19c and 32b exhibited activity at concentrations of 10 µM and 100 µM, highlighting the activity of benzimidazole 18a (IC 50 = 36.67 µM) and 32b (IC 50 = 85.03 µM). Pyridine 19c displayed the best quorum sensing inhibition activity (IC 50 = 9.66 µM). Molecular docking simulations were conducted for all test compounds on the Chromobacterium violaceum CviR protein to gain insight into the process of quorum sensing inhibition. The in-silico data reveal that all 15 the compounds have higher affinity for the protein than the native AHL ligand ( 1 ). A strong correlation was found between the theoretical and experimental results.
    Schlagwörter heterocycles synthesis ; new AHL bioisosteres ; π–π interactions ; quorum sensing ; Biology (General) ; QH301-705.5 ; Chemistry ; QD1-999
    Thema/Rubrik (Code) 540
    Sprache Englisch
    Erscheinungsdatum 2020-12-01T00:00:00Z
    Verlag MDPI AG
    Dokumenttyp Artikel ; Online
    Datenquelle BASE - Bielefeld Academic Search Engine (Lebenswissenschaftliche Auswahl)

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  4. Artikel ; Online: Design, Synthesis, and Evaluation of Alkyl-Quinoxalin-2(1 H )-One Derivatives as Anti- Quorum Sensing Molecules, Inhibiting Biofilm Formation in Aeromonas caviae Sch3

    René Blöcher / Ariel Rodarte Ramírez / Graciela Castro-Escarpulli / Everardo Curiel-Quesada / Alicia Reyes-Arellano

    Molecules, Vol 23, Iss 12, p

    2018  Band 3075

    Abstract: With the increasing antibiotic resistance of bacterial strains, alternative methods for infection control are in high demand. Quorum sensing (QS) is the bacterial communication system based on small molecules. QS is enables bacterial biofilm formation ... ...

    Abstract With the increasing antibiotic resistance of bacterial strains, alternative methods for infection control are in high demand. Quorum sensing (QS) is the bacterial communication system based on small molecules. QS is enables bacterial biofilm formation and pathogenic development. The interruption of QS has become a target for drug discovery, but remains in the early experimental phase. In this study, we synthesized a set of six compounds based on a scaffold (alkyl-quinoxalin-2(1 H )-one), new in the anti-QS of Gram-negative bacteria Aeromonas caviae Sch3. By quantifying biofilm formation, we were able to monitor the effect of these compounds from concentrations of 1 to 100 µM. Significant reduction in biofilm formation was achieved by 3-hexylylquinoxalin-2(1 H )-one ( 11 ), 3-hexylylquinoxalin-2(1 H )-one-6-carboxylic acid ( 12 ), and 3-heptylylquinoxalin-2(1 H )-one-6-carboxylic acid ( 14 ), ranging from 11% to 59% inhibition of the biofilm. This pilot study contributes to the development of anti-QS compounds to overcome the clinical challenge of resistant bacteria strains.
    Schlagwörter anti-quorum sensing ; biofilm ; quinoxalin-2(1 H )-one ; Aeromonas caviae ; bioisosteres ; Grignard reaction ; Organic chemistry ; QD241-441
    Thema/Rubrik (Code) 540
    Sprache Englisch
    Erscheinungsdatum 2018-11-01T00:00:00Z
    Verlag MDPI AG
    Dokumenttyp Artikel ; Online
    Datenquelle BASE - Bielefeld Academic Search Engine (Lebenswissenschaftliche Auswahl)

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  5. Artikel ; Online: trans-Chlorido(4-fluorobenzenethiolato-κS)bis(triphenylphosphane-κP)palladium(II) methanol hemisolvate

    Alcives Avila-Sorrosa / Ericka Santacruz-Juárez / Alicia Reyes-Arellano / Reyna Reyes-Martínez / David Morales-Morales

    Acta Crystallographica Section E, Vol 70, Iss 3, Pp m92-m

    2014  Band 93

    Abstract: The title compound, [Pd(SC6H4F-p)Cl(PPh3)2]·0.5CH3OH, features a PdII complex with two triphenylphosphane (PPh3) ligands arranged in a trans conformation, with one chloride and one 4-fluorobenzenethiolate ligand completing the coordination sphere, giving ...

    Abstract The title compound, [Pd(SC6H4F-p)Cl(PPh3)2]·0.5CH3OH, features a PdII complex with two triphenylphosphane (PPh3) ligands arranged in a trans conformation, with one chloride and one 4-fluorobenzenethiolate ligand completing the coordination sphere, giving rise to a slightly distorted square-planar geometry of the PdII ion. The methanol solvent molecule is disordered about an inversion centre with an occupancy of 0.25 for each molecule. In the crystal, weak C—H.Cl hydrogen-bonding interactions between the complex molecules generate chain frameworks parallel to [010].
    Schlagwörter Chemistry ; QD1-999
    Sprache Englisch
    Erscheinungsdatum 2014-03-01T00:00:00Z
    Verlag International Union of Crystallography
    Dokumenttyp Artikel ; Online
    Datenquelle BASE - Bielefeld Academic Search Engine (Lebenswissenschaftliche Auswahl)

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  6. Artikel ; Online: trans-Bis(μ-benzenethiolato-κ2S:S)bis[chlorido(triphenylphosphane-κP)palladium(II)] chloroform disolvate

    David Morales-Morales / Reyna Reyes-Martínez / Juan Manuel Germán-Acacio / Alicia Reyes-Arellano / Alcives Avila-Sorrosa

    Acta Crystallographica Section E, Vol 69, Iss 8, Pp m472-m

    2013  Band 472

    Abstract: The title compound, [Pd2Cl2(C6H5S)2(C18H15P)2]·2CHCl3, contains a centrosymmetric dinuclear palladium complex with the PdII cation in a slightly distorted square-planar coordination environment. The PdII cations are bridged by the S atoms of two ... ...

    Abstract The title compound, [Pd2Cl2(C6H5S)2(C18H15P)2]·2CHCl3, contains a centrosymmetric dinuclear palladium complex with the PdII cation in a slightly distorted square-planar coordination environment. The PdII cations are bridged by the S atoms of two benzenethiolate ligands with different Pd—S distances [2.2970 (11) and 2.3676 (11) Å]. The coordination of the metal atom is completed by a chloride anion [2.3383 (11) Å] and a triphenylphosphane ligand [2.2787 (11) Å]. Weak C—H.Cl interactions are present between complex molecules and the CHCl3 solvent molecule. The latter is disordered over two positions in a 0.792 (8):0.208 (8) ratio. The crystal under investigation was found to be twinned by nonmerohedry, with a fraction of 73.4 (1)% for the major twin component.
    Schlagwörter Chemistry ; QD1-999
    Sprache Englisch
    Erscheinungsdatum 2013-08-01T00:00:00Z
    Verlag International Union of Crystallography
    Dokumenttyp Artikel ; Online
    Datenquelle BASE - Bielefeld Academic Search Engine (Lebenswissenschaftliche Auswahl)

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  7. Artikel ; Online: Imidazolines as Non-Classical Bioisosteres of N-Acyl homoserine lactones and Quorum Sensing Inhibitors

    Mabel Montenegro-Sustaita / Everardo Curiel-Quesada / Héctor Salgado-Zamora / Alicia Reyes-Arellano / Alejandro Bucio-Cano

    International Journal of Molecular Sciences, Vol 13, Iss 2, Pp 1284-

    2012  Band 1299

    Abstract: A series of selected 2-substituted imidazolines were synthesized in moderate to excellent yields by a modification of protocols reported in the literature. They were evaluated as potential non-classical bioisosteres of AHL with the aim of counteracting ... ...

    Abstract A series of selected 2-substituted imidazolines were synthesized in moderate to excellent yields by a modification of protocols reported in the literature. They were evaluated as potential non-classical bioisosteres of AHL with the aim of counteracting bacterial pathogenicity. Imidazolines 18a, 18e and 18f at various concentrations reduced the violacein production by Chromobacterium violaceum, suggesting an anti-quorum sensing profile against Gram-negative bacteria. Imidazoline 18b did not affect the production of violacein, but had a bacteriostatic effect at 100 µM and a bactericidal effect at 1 mM. Imidazoline 18a bearing a hexyl phenoxy moiety was the most active compound of the series, rendering a 72% inhibitory effect of quorum sensing at 100 µM. Imidazoline 18f bearing a phenyl nonamide substituent presented an inhibitory effect on quorum sensing at a very low concentration (1 nM), with a reduction percentage of 28%. This compound showed an irregular performance, decreasing inhibition at concentrations higher than 10 µM, until reaching 100 µM, at which concentration it increased the inhibitory effect with a 49% reduction percentage. When evaluated on Serratia marcescens, compound 18f inhibited the production of prodigiosin by 40% at 100 μM.
    Schlagwörter imidazoline synthesis ; quorum sensing ; Chromobacterium violaceum ; AHL bioisosteres ; Biology (General) ; QH301-705.5 ; Chemistry ; QD1-999
    Sprache Englisch
    Erscheinungsdatum 2012-01-01T00:00:00Z
    Verlag MDPI AG
    Dokumenttyp Artikel ; Online
    Datenquelle BASE - Bielefeld Academic Search Engine (Lebenswissenschaftliche Auswahl)

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  8. Artikel ; Online: Prevention of Aflatoxin B1-Induced DNA Breaks by β-D-Glucan

    Eduardo Madrigal-Bujaidar / José Antonio Morales-González / Manuel Sánchez-Gutiérrez / Jeannett A. Izquierdo-Vega / Alicia Reyes-Arellano / Isela Álvarez-González / Ricardo Pérez-Pasten / Eduardo Madrigal-Santillán

    Toxins, Vol 7, Iss 6, Pp 2145-

    2015  Band 2158

    Abstract: Aflatoxins are a group of naturally-occurring carcinogens that are known to contaminate different human and animal foodstuffs. Aflatoxin B1 (AFB1) is the most genotoxic hepatocarcinogenic compound of all of the aflatoxins. In this report, we explore the ... ...

    Abstract Aflatoxins are a group of naturally-occurring carcinogens that are known to contaminate different human and animal foodstuffs. Aflatoxin B1 (AFB1) is the most genotoxic hepatocarcinogenic compound of all of the aflatoxins. In this report, we explore the capacity of β-D-glucan (Glu) to reduce the DNA damage induced by AFB1 in mouse hepatocytes. For this purpose, we applied the comet assay to groups of animals that were first administered Glu in three doses (100, 400 and 700 mg/kg bw, respectively) and, 20 min later, 1.0 mg/kg of AFB1. Liver cells were obtained at 4, 10 and 16 h after the chemical administration and examined. The results showed no protection of the damage induced by AFB1 with the low dose of the polysaccharide, but they did reveal antigenotoxic activity exerted by the two high doses. In addition, we induced a co-crystallization between both compounds, determined their fusion points and analyzed the molecules by UV spectroscopy. The data suggested the formation of a supramolecular complex between AFB1 and β-D-glucan.
    Schlagwörter aflatoxin B1 ; glucan ; mouse hepatocytes ; antigenotoxicity ; Medicine ; R
    Sprache Englisch
    Erscheinungsdatum 2015-06-01T00:00:00Z
    Verlag MDPI AG
    Dokumenttyp Artikel ; Online
    Datenquelle BASE - Bielefeld Academic Search Engine (Lebenswissenschaftliche Auswahl)

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  9. Artikel ; Online: Investigation on the Protective Effect of α-Mannan against the DNA Damage Induced by Aflatoxin B1 in Mouse Hepatocytes

    Alicia Reyes-Arellano / Eduardo Madrigal-Bujaidar / Manuel Sánchez-Gutiérrez / José Antonio Morales-González / Eduardo Madrigal-Santillán

    International Journal of Molecular Sciences, Vol 10, Iss 2, Pp 395-

    2009  Band 406

    Abstract: Aflatoxin B1 is a contaminant of agricultural and dairy products that can be related to mutagenic and carcinogenic effects. In this report we explore the capacity of α-mannan (Man) to reduce the DNA damage induced by AFB1 in mouse hepatocytes. For this ... ...

    Abstract Aflatoxin B1 is a contaminant of agricultural and dairy products that can be related to mutagenic and carcinogenic effects. In this report we explore the capacity of α-mannan (Man) to reduce the DNA damage induced by AFB1 in mouse hepatocytes. For this purpose we applied the comet assay to groups of animals which were first administered Man (100, 400 and 700 mg/kg, respectively) and 20 min later 1.0 mg/kg of AFB1. Liver cells were obtained at 4, 10, and 16 h after the chemical administration and examined. The results showed no protection of the damage induced by AFB1 with the low dose of the polysaccharide, but they did reveal antigenotoxic activity exerted by the two high doses. In addition, we induced a co-crystallization between both compounds, determined their fusion points and analyzed the molecules by UV spectroscopy. The obtained data suggested the formation of a supramolecular complex between AFB1 and Man.
    Schlagwörter Aflatoxin B1 ; mannan ; mouse hepatocytes ; antigenotoxicity ; Biology (General) ; QH301-705.5 ; Chemistry ; QD1-999
    Thema/Rubrik (Code) 630
    Sprache Englisch
    Erscheinungsdatum 2009-02-01T00:00:00Z
    Verlag MDPI AG
    Dokumenttyp Artikel ; Online
    Datenquelle BASE - Bielefeld Academic Search Engine (Lebenswissenschaftliche Auswahl)

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