4-Hydroxy-2-nonylquinoline: A Novel Iron Chelator Isolated from a Bacterial Cell Membrane

Royt, Paulette W.; Honeychuck, Robert V.; Ravich, Vadim; Ponnaluri, Padma; Pannell, Lewis K.; Buyer, Jeffrey S.; Chandhoke, Vikas; Stalick, Wayne M.; DeSesso, Leo C.; Donohue, Sean T.; Ghei, Rashmi; Relyea, Joseph D.; Ruiz, Raphael

doi:10.1006/bioo.2001.1225

Cited by 20 publications

(11 citation statements)

References 5 publications

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“…The complexity of QS‐dependent gene regulation has also become apparent from previous observations of additional biological functions of non‐enzymatically formed products of homoserine lactones including binding of iron (Kaufmann et al ., 2005). Moreover, the PQS precursor substance 4‐hydroxy‐alkyl‐quinoline has recently been described to exhibit iron‐chelating activities although this was not be confirmed by the use of the synthesized compound (Royt et al ., 2001). We have now shown that PQS and other 3,4‐(di)hydroxy‐alkyl‐quinoline derivates, but not the 4‐(mono)hydroxy‐alkyl‐quinoline are potent iron chelators.…”

Section: Resultsmentioning

confidence: 99%

The Pseudomonas aeruginosa quinolone signal (PQS) has an iron‐chelating activity

Bredenbruch

Geffers²,

Nimtz

et al. 2006

Environmental Microbiology

247

252

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Summary Virulence factor production and the development of biofilms in Pseudomonas aeruginosa have been shown to be regulated by two hierarchically organized quorum‐sensing systems activated by two types of small acyl‐homoserine lactone signal molecules. Recently, a third type of bacterial signal molecule, the Pseudomonas quinolone signal (PQS), has been identified, which positively regulates a subset of genes dependent on the quorum‐sensing systems. However, the molecular mechanism underlying PQS signalling has remained poorly understood. In this study the global transcriptional profile of P. aeruginosa in response to PQS revealed a marked upregulation of genes belonging to the tightly interdependent functional groups of the iron acquisition and the oxidative stress response. Remarkably, most of the differentially regulated genes, as well as the induction of rhlR, could be traced back to an iron‐chelating effect of PQS. Our results amount to the elucidation of how PQS affects P. aeruginosa and have important implications for the understanding of the complex regulatory circuits involved in P. aeruginosa gene regulation.

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Section: Resultsmentioning

confidence: 99%

The Pseudomonas aeruginosa quinolone signal (PQS) has an iron‐chelating activity

Bredenbruch

Geffers²,

Nimtz

et al. 2006

Environmental Microbiology

247

252

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“…The identified metabolite, 4-hydroxy-2-alkyl-quinoline, comprises a class of heterocyclic molecules produced by P. aeruginosa that demonstrated antimicrobial properties against gram-positive bacteria including methicillin-resistant Staphylococcus aureus (Taylor et al 1995). These types of molecules are known as pseudans (Royt et al 2001). This group of molecules is based on the 4-hydroxy-2-alkyl-quinoline structure and is differentiated based upon the size and degree of saturation of the alkyl chain, as well as the presence or absence of the N-oxide (Taylor et al 1995).…”

Section: Discussionmentioning

confidence: 99%

“…This group of molecules is based on the 4-hydroxy-2-alkyl-quinoline structure and is differentiated based upon the size and degree of saturation of the alkyl chain, as well as the presence or absence of the N-oxide (Taylor et al 1995). Pseudan IX, 4-hydroxy-2-nonyl-quinoline, and pseudan VII, 4-hydroxy-2-heptylquinoline, have been found to act as siderophores and reside in the cytoplasmic membrane of P. aeruginosa (Royt et al 2001). Probably, the 4-hydroxy-2-alkyl-quinoline has supported the siderophore activity of KA19.…”

Section: Discussionmentioning

confidence: 99%

Evaluation of rhizospheric Pseudomonas and Bacillus as biocontrol tool for Xanthomonas campestris pv campestris

Mishra

Arora

2011

World J Microbiol Biotechnol

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Xanthomonas campestris pv campestris (Xcc), causing black rot, is one of the most yield-limiting and destructive pathogens of cruciferous crops. The intention of this study was to evaluate the potential of rhizobacteria in black rot management. Fifty-four isolates from rhizosphere soil of Brassica campestris were screened against Xcc. Two isolates namely, KA19 and SE, with inhibition radius >11 mm were selected. The combined use of them produced an average inhibition zone of 18.1 ± 1.4 mm radius (P < 0.05). 16S rRNA gene sequencing and phylogenetic analysis identified KA19 and SE as the nearest homologs (>99.4%) of Pseudomonas aeruginosa and Bacillus thuringiensis, respectively. In greenhouse study, both isolates were effective (P < 0.05) in reducing black rot lesions compared to untreated control involving either a foliar spray or the combined seed soak and soil drench. However, the combined strains (KA19 + SE) were significantly more effective (P < 0.05) when the mode of application was combined seed and soil drench. The lipid content of seeds increased significantly with the application of these strains, especially with SE alone and in combination. After 9 weeks, the Xcc population was significantly lower in soil treated with combined strains (P < 0.05). KA19 produced extracellular siderophores, influenced by various carbon sources and identified as 4-hydroxy-2-nonyl-quinoline by NMR. In Bacillus SE, two antibacterial factors corresponding to autolysins (β-N-acetylglucosaminidase) and AHL-lactonases were established. This study would strengthen our understanding for application of different rhizobacteria with various active principles like Pseudomonas and Bacillus as ingredients of a biocontrol mixture.

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“…Around 60% of the PQS produced by P. aeruginosa is associated with the cell envelope Diggle et al, 2007), and the membranes of cells grown in iron-rich media are visibly pink due to complexed Fe 31 , possibly stored in AQ-containing inclusion bodies (Royt et al, 2001(Royt et al, , 2007. Therefore, there is the possibility that PQS could act as an iron trap and storage molecule in the cell membrane and that it may be able to deliver iron directly to the cells.…”

Section: Role Of Aqs In Iron Metabolismmentioning

confidence: 99%

Quinolones: from antibiotics to autoinducers

et al. 2011

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Since quinine was first isolated, animals, plants and microorganisms producing a wide variety of quinolone compounds have been discovered, several of which possess medicinally interesting properties ranging from antiallergenic and anticancer to antimicrobial activities. Over the years, these have served in the development of many synthetic drugs, including the successful fluoroquinolone antibiotics. Pseudomonas aeruginosa and related bacteria produce a number of 2-alkyl-4(1H)-quinolones, some of which exhibit antimicrobial activity. However, quinolones such as the Pseudomonas quinolone signal and 2-heptyl-4-hydroxyquinoline act as quorum-sensing signal molecules, controlling the expression of many virulence genes as a function of cell population density. Here, we review selectively this extensive family of bicyclic compounds, from natural and synthetic antimicrobials to signalling molecules, with a special emphasis on the biology of P. aeruginosa. In particular, we review their nomenclature and biochemistry, their multiple properties as membrane-interacting compounds, inhibitors of the cytochrome bc1 complex and iron chelators, as well as the regulation of their biosynthesis and their integration into the intricate quorum-sensing regulatory networks governing virulence and secondary metabolite gene expression.

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4-Hydroxy-2-nonylquinoline: A Novel Iron Chelator Isolated from a Bacterial Cell Membrane

Cited by 20 publications

References 5 publications

The Pseudomonas aeruginosa quinolone signal (PQS) has an iron‐chelating activity

The Pseudomonas aeruginosa quinolone signal (PQS) has an iron‐chelating activity

Evaluation of rhizospheric Pseudomonas and Bacillus as biocontrol tool for Xanthomonas campestris pv campestris

Quinolones: from antibiotics to autoinducers

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