Ketones 2-heptanone, 2-nonanone, and 2-undecanone inhibit DnaK-dependent refolding of heat-inactivated bacterial luciferases in Escherichia coli cells lacking small chaperon IbpB

Melkina, O. E.; Khmel, I. A.; Plyuta, V. A.; Кокшарова, О. А.; Zavilgelsky, G. B.

doi:10.1007/s00253-017-8350-1

Cited by 21 publications

(13 citation statements)

References 24 publications

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“…These molecules freely pass also through biological membranes of target organisms and may elicit changes in plasma membrane potential depolarization and activate regulatory proteins [37]. VOCs can interact with and damage lipid membranes [38] and interact with hydrophobic segments in proteins [13,39]. In our study, we found for the first time that ketone 2-nonanone can act on bacterial cells through different targets and by different mechanisms.…”

Section: Three Genes (Synpcc7942_1362 Synpcc7942_0351 Synpcc7942_07mentioning

confidence: 56%

“…It was demonstrated that ketones bind with protein (bovine serum albumin) [12]. Moreover, 2-nonanone and 2-undecanone demonstrated an inhibitory action on protein refolding in bacteria [13], which can suppress the expression of genes involved in Quorum Sensing regulation in bacterial cells [14] and negatively affected biofilm formation by Agrobacterium tumefaciens [15].…”

Section: Introductionmentioning

confidence: 99%

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Four New Genes of Cyanobacterium Synechococcus elongatus PCC 7942 Are Responsible for Sensitivity to 2-Nonanone

et al. 2020

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Microbial volatile organic compounds (VOCs) are cell metabolites that affect many physiological functions of prokaryotic and eukaryotic organisms. Earlier we have demonstrated the inhibitory effects of soil bacteria volatiles, including ketones, on cyanobacteria. Cyanobacteria are very sensitive to ketone action. To investigate the possible molecular mechanisms of the ketone 2-nonanone influence on cyanobacterium Synechococcus elongatus PCC 7942, we applied a genetic approach. After Tn5-692 transposon mutagenesis, several 2-nonanone resistant mutants have been selected. Four different mutant strains were used for identification of the impaired genes (Synpcc7942_1362, Synpcc7942_0351, Synpcc7942_0732, Synpcc7942_0726) that encode correspondingly: 1) a murein-peptide ligase Mpl that is involved in the biogenesis of cyanobacteria cell wall; 2) a putative ABC transport system substrate-binding proteins MlaD, which participates in ABC transport system that maintains lipid asymmetry in the gram-negative outer membrane by aberrantly localized phospholipids transport from outer to inner membranes of bacterial cells; 3) a conserved hypothetical protein that is encoding by gene belonging to phage gene cluster in Synechococcus elongatus PCC 7942 genome; 4) a protein containing the VRR-NUC (virus-type replication-repair nuclease) domain present in restriction-modification enzymes involved in replication and DNA repair. The obtained results demonstrated that 2-nonanone may have different targets in Synechococcus elongatus PCC 7942 cells. Among them are proteins involved in the biogenesis and functioning of the cyanobacteria cell wall (Synpcc7942_1362, Synpcc7942_0351, Synpcc7942_0732) and protein participating in stress response at DNA restriction-modification level (Synpcc7942_0726). This paper is the first report about the genes that encode protein products, which can be affected by 2-nonanone.

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Section: Three Genes (Synpcc7942_1362 Synpcc7942_0351 Synpcc7942_07mentioning

confidence: 56%

Section: Introductionmentioning

confidence: 99%

Four New Genes of Cyanobacterium Synechococcus elongatus PCC 7942 Are Responsible for Sensitivity to 2-Nonanone

et al. 2020

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“…Many of the volatiles of interest to us as potential Pa inhibitors (Table 3) have been noted previously among Pa volatiles, including 2-undecanone [57,[63][64][65][66][67]71,76], 2-heptanone [64][65][66][67]71,76], and methyl thiocyanate [67]. 2-heptanone has been noted to be an inhibitor of micro-organisms (bacteria) [78]. An important confounder in volatile studies, as also noted by others [63], is that uninoculated culture medium produces volatiles that could be confused with those of the micro-organisms of interest; in those of our four chromatographic studies described which required such controls, we have noted many of these, and whereas the media themselves, when exposed to Af, were not inhibitory, those volatiles were excluded from our group of candidates as Pa inhibitors.…”

Section: Discussionmentioning

confidence: 82%

“…Microbial volatiles are typically small lipophilic organic molecules [ 77 ]. The mechanism of inhibitory action of such volatiles has been ascribed to interactions with the hydrophobic segments of proteins [ 78 ]. Regarding our observations with the quorum-sensing mutants, that the lasR -/ rhlR - mutant was noninhibitory, the lasR- mutant was only somewhat inhibitory, and the rhlR- mutant was fully inhibitory, opens the possibility of now defining which downstream pathways in Pa are responsible for these differences.…”

Section: Discussionmentioning

confidence: 99%

Aspergillus Is Inhibited by Pseudomonas aeruginosa Volatiles

Nazik

Sass

Déziel

et al. 2020

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Background: Pseudomonas aeruginosa (Pa) and Aspergillus fumigatus (Af) compete with each other for nutrients and survival in natural environments, and have been extensively studied because of their intermicrobial interactions in the human microbiome. These are the principal microbes infecting immunocompromised patients and persons with cystic fibrosis, particularly the airways. These intermicrobial studies have largely been conducted in liquid medium or on agar, and thus focus on soluble or diffusible microbial products. Several key inhibitory molecules were defined in such studies. Methods: in the present report, we examine several methodologies which can be conveniently used to study the interaction of microbial volatiles, including capture methods and kinetics. Results: Pa volatiles inhibit Af, and the inhibitory mechanism appears to be the incorporation of the inhibitory molecules into the substrate nourishing the Af, rather than directly onto Af structures. We define by mass spectroscopy some specific volatile Pa products that can inhibit Af. Some of these molecules are selected for interest by the study of gene deletion mutants, producing a few Pa strains that were impaired in inhibition. We presumed the volatiles of these latter strains could be excluded from the search for inhibitors. Conclusion: the Pa inhibition of Af via a gaseous phase could be critical components in their competition, particularly in airways, where more direct contact may not be extensive.

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“…It was shown that such VOCs as ketones 2-heptanone, 2-nonanone, and 2-undecanone effectively inhibit the DnaKJE-dependent refolding of heat-inactivated bacterial luciferases only in the E. coli ∆ibpB mutant strain lacking small chaperone IbpB [36]. Chaperone IbpB, which forms a complex with hydrophobic sites in proteins [37][38][39], appears to inhibit the complexation of these sites with hydrophobic ketones.…”

Section: Effect Of (−)-Limonene and (+)-α-Pinene On The Dnakje-dependent Refolding Of Heat-inactivated Bacterial Luciferasementioning

confidence: 99%

The Mode of Action of Cyclic Monoterpenes (−)-Limonene and (+)-α-Pinene on Bacterial Cells

et al. 2021

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A broad spectrum of volatile organic compounds’ (VOCs’) biological activities has attracted significant scientific interest, but their mechanisms of action remain little understood. The mechanism of action of two VOCs—the cyclic monoterpenes (−)-limonene and (+)-α-pinene—on bacteria was studied in this work. We used genetically engineered Escherichia coli bioluminescent strains harboring stress-responsive promoters (responsive to oxidative stress, DNA damage, SOS response, protein damage, heatshock, membrane damage) fused to the luxCDABE genes of Photorhabdus luminescens. We showed that (−)-limonene induces the PkatG and PsoxS promoters due to the formation of reactive oxygen species and, as a result, causes damage to DNA (SOSresponse), proteins (heat shock), and membrane (increases its permeability). The experimental data indicate that the action of (−)-limonene at high concentrations and prolonged incubation time makes degrading processes in cells irreversible. The effect of (+)-α-pinene is much weaker: it induces only heat shock in the bacteria. Moreover, we showed for the first time that (−)-limonene completely inhibits the DnaKJE–ClpB bichaperone-dependent refolding of heat-inactivated bacterial luciferase in both E. coli wild type and mutant ΔibpB strains. (+)-α-Pinene partially inhibits refolding only in ΔibpB mutant strain.

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Ketones 2-heptanone, 2-nonanone, and 2-undecanone inhibit DnaK-dependent refolding of heat-inactivated bacterial luciferases in Escherichia coli cells lacking small chaperon IbpB

Cited by 21 publications

References 24 publications

Four New Genes of Cyanobacterium Synechococcus elongatus PCC 7942 Are Responsible for Sensitivity to 2-Nonanone

Four New Genes of Cyanobacterium Synechococcus elongatus PCC 7942 Are Responsible for Sensitivity to 2-Nonanone

Aspergillus Is Inhibited by Pseudomonas aeruginosa Volatiles

The Mode of Action of Cyclic Monoterpenes (−)-Limonene and (+)-α-Pinene on Bacterial Cells

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