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PubMed2000

Production of N-acyl-L-homoserine lactones by P. aeruginosa isolates from chronic lung infections associated with cystic fibrosis.

The N-acyl-L-homoserine lactones (AHLs) produced by sequential Pseudomonas aeruginosa isolates from chronically infected patients with cystic fibrosis were analyzed by thin-layer chromatography. It is demonstrated that both the amounts and the types of molecules synthesized by isolates from patients who were monitored over periods of up to 11 years do not change significantly during chronic colonization. However, in the case of a patient who became co-infected with an AHL-producing Burkholderia cepacia strain a dramatic reduction in the amounts of AHLs produced by the co-residing P. aeruginosa isolates was observed.

4-Butyrolactone↗
PubMed2002

Characterization of N-acyl homoserine lactone overproducing mutants of Burkholderia multivorans ATCC 17616.

Burkholderia multivorans ATCC 17616 ordinarily produces insufficient amounts of N-acyl homoserine lactones (AHLs) to promote AHL-dependent formation of the pigment violacein by the reporter strain Chromobacterium violaceum CV026. We have isolated AHL-overproducing mutants of strain 17616 by screening for variants which do cross-feed AHLs to strain CV026. Nucleotide-sequence analysis of the bmuIR locus which specifies AHL synthase (BmuI) and AHL-binding transcriptional activator protein (BmuR) indicated that the increased capacity to produce AHLs was not a consequence of changes upstream or internal to the bmuI or bmuR genes. We conclude that the mutations leading to AHL overproduction lie outside the bmuI/bmuR locus.

4-Butyrolactone↗
PubMed2007

Detection of quorum-sensing N-acyl homoserine lactone signal molecules by bacterial biosensors.

Many Gram-negative bacteria use N-acyl homoserine lactones (AHLs) as quorum-sensing (QS) signal molecules. AHL QS has been the subject of extensive investigation in the last decade and has become a paradigm for bacterial intercellular signaling. Research in AHL QS has been considerably aided by simple methods devised to detect AHLs using bacterial biosensors that phenotypically respond when exposed to exogenous AHLs. This article reviews and discusses the currently available bacterial biosensors which can be used in detecting and studying the different AHLs.

4-Butyrolactone↗
PubMed1994

Sesquiterpene lactone mix is not an adequate screen for Compositae allergy.

70 patients suspected or known to have contact allergy to Compositae were patch tested with 0.1% sesquiterpene lactone mix (SL mix) and individual Compositae oleoresins. There were no apparent cases of active sensitization by, or irritancy from, the SL mix. 6 patients had allergic reactions to both SL mix and Compositae oleoresins, while 11 patients had allergic reactions to Compositae oleoresins with a negative reaction to the SL mix. In all but 2 of these, Compositae allergy was considered clinically relevant. As 0.1% SL mix picked up only 35% of cases of Compositae allergy, we do not consider it an adequate screen.

Adolescent↗
PubMed1999

A study of the sensitization rate to sesquiterpene lactone mix in Singapore.

We report a study of the sensitization rate to sesquiterpene lactone (SL) mix at the National Skin Centre, Singapore. This is a retrospective review of 1256 patients who were patch tested to SL mix (0.1%) from January 1995 to December 1997. 18 out of 1256 patients (1.43%) reacted positively to SL mix. Their ages ranged from 13 to 58 years (average 33.8 years). There were 15 Chinese, 2 Indian and 1 Malay patients. There was a female preponderance, with a female: male ratio of 3.5:1. The most common clinical presentation were dermatitis of the hands (8; 44%), face (5; 28%), and generalized involvement (5; 28%). After extensive evaluation, only 2 patients had a positive patch test reaction that was of current clinical relevance. 13 patients had concomitant sensitization to other allergens. The 3 commonest concomitant allergens were nickel, balsam of Peru and fragrance mix. In our series, SL allergy is observed to be more common in females and the mean age is lower compared to the classical Compositae dermatitis. The sensitization rate is comparable to other studies, although the clinical relevance is only 11%.

Adolescent↗
PubMed2001

Efficacy of macrocyclic lactones for the control of larvae of the Old World screw-worm fly (Chrysomya bezziana).

OBJECTIVE: To assess the efficacy of four macrocyclic lactones for the control of larvae of the Old World Screw-worm Fly (OWS), Chrysomya bezziana, and to examine the effects of excreted residues on the dung fauna. ANIMALS: 100 heifers were divided into five groups of 20 animals. One group remained untreated, whereas the other groups were treated respectively with pour-on formulations of moxidectin, eprinomectin or doramectin, or a sustained-release bolus of ivermectin. PROCEDURES: At intervals of 1 to 15 weeks after treatment, five cattle from each group were challenged with newly-laid eggs of OWS. The efficacy of each treatment was determined 48 h later by comparing the number of myiases in the treated and untreated groups. Abundance of fly larvae in naturally-voided dung pads and the survival of a species of dung beetle, Onthophagus sagittarius, were used to assess the effects of drug residues on the dung fauna. RESULTS AND CONCLUSIONS: Moxidectin showed no activity against larvae of OWS during the first 14 days after treatment. Eprinomectin provided protection for 3 days after dosing, but failed at days 7 and 14, whereas doramectin was effective at day 7, but not at days 14 or 21. In contrast, no myiases were established on bolus-treated cattle from 14 to 102 days after treatment. Faecal residues of moxidectin had no effect on the survival of larvae of dung-feeding flies, whereas those of eprinomectin and doramectin reduced survival for 1 to 2 weeks. Dung voided by bolus-treated cattle inhibited fly breeding and had adverse effects on the development and survival of O sagittarius for up to 15 weeks after treatment.

Animals↗
PubMed2001

Principles for the use of macrocyclic lactones to minimise selection for resistance.

OBJECTIVE: To provide principles for the appropriate use of avermectin/milbemycin or macrocyclic lactone (ML) anthelmintics in sheep, to ensure effective worm control and to minimise selection for ML resistance. STRATEGY: The principles were based on an assessment of the information currently available. The MLs were categorised into three groups (ivermectin [IVM], abamectin [ABA] and moxidectin [MOX]) based on structural differences, persistence and efficacy against ML resistant strains. The reported order of activity or efficacy against ML resistant worm strains was IVM<ABA<MOX. General treatment schemes were considered for Australian conditions and were divided into the following situations: 1. quarantine treatment, 2. treatment on/to clean pasture, 3. treatment on/to safe pasture, 4. treatment on/to moderate/heavily contaminated pasture. For each of these situations a strategy was considered for farms where ML resistance was present or absent. It was assumed that resistance commonly occurs in some or all other broad spectrum anthelmintics, and even where ML resistance has been detected, the ML group remains the most effective. The guidelines provided are general and it is expected that state agencies and sheep/veterinary advisers would give specific advice to suit their environments and drug resistance/worm problems. CONCLUSIONS: The primary recommendation is to use a mixture of effective drugs when treating sheep. However, unless the combination treatment is highly effective it is unlikely to delay selection for ML resistance if sheep are being treated and moved to a clean or safe pasture. Where possible, reliance on the ML anthelmintics should be reduced by not using them every year, not using them in low risk stock or by using narrow spectrum and low efficacy drugs such as naphthalophos when appropriate. Anthelmintic treatment should be given as part of a strategic worm control program. It is suggested that IVM-oral and IVM-capsules should not be used when ML resistance is present. In this situation MOX or ABA should be used in combination with other drugs, provided that the chosen ML is effective against the resistant parasite. It is essential to monitor the efficacy of ML and drug combinations by post-treatment worm egg counts, particularly when ML resistance has been detected.

Animals↗
PubMed2004

In vitro and in vivo correlation of the inhibitory effect of cyclosporin A on the transporter-mediated hepatic uptake of cerivastatin in rats.

Previously, we have shown that the inhibition of the transporter-mediated hepatic uptake of cerivastatin (CER) by cyclosporin A (CsA) could, at least partly, explain a pharmacokinetic interaction between these drugs in humans. In the present study, we have examined the effect of CsA on the in vivo disposition of CER in rats and the in vitro uptake of [14C]CER in isolated rat hepatocytes in an attempt to evaluate the effect of inhibition of transporter-mediated hepatic uptake on the in vivo CER disposition. The steady-state plasma concentration of CER increased 1.4-fold when coadministered with CsA up to a steady-state blood concentration of 4 microM. Studies of [14C]CER uptake into isolated rat hepatocytes showed saturable transport, with the saturable portion accounting for more than 80% of the total uptake. CsA competitively inhibited the uptake of [14C]CER with a Ki of 0.3 microM. The IC50 for the uptake of [14C]CER in the absence and presence of rat plasma was 0.2 and 2.3 microM, respectively. The in vivo hepatic uptake of [14C]CER evaluated by the liver uptake index method was also inhibited by CsA in a dose-dependent manner. On the other hand, CsA did not inhibit the metabolism of [14C]CER in rat microsomes. The in vitro and in vivo correlation analysis revealed that this pharmacokinetic interaction between these drugs in rats could be quantitatively explained by the inhibition of transporter-mediated hepatic uptake. Thus, this drug-drug interaction in rats is predominantly caused by the transporter-mediated uptake process.

Algorithms↗
PubMed2004

Azithromycin inhibits MUC5AC production induced by the Pseudomonas aeruginosa autoinducer N-(3-Oxododecanoyl) homoserine lactone in NCI-H292 Cells.

The features of chronic airway diseases, including chronic bronchitis, cystic fibrosis, bronchiectasis, and diffuse panbronchiolitis, include chronic bacterial infection and airway obstruction by mucus. Pseudomonas aeruginosa is one of the most common pathogens in chronic lung infection, and quorum-sensing systems contribute to the pathogenesis of this disease. The quorum-sensing signal molecule [N-(3-oxododecanoyl) homoserine lactone (3O-C(12)-HSL)] not only regulates bacterial virulence but also is associated with the immune response. In this study, we investigated whether 3O-C(12)-HSL could stimulate the production of a major mucin core protein, MUC5AC. The effect of a macrolide on MUC5AC production was also studied. 3O-C(12)-HSL induced NCI-H292 cells to express MUC5AC at both the mRNA and the protein levels in time- and dose-dependent manners. A 15-membered macrolide, azithromycin, inhibited MUC5AC production that was activated by 3O-C(12)-HSL. 3O-C(12)-HSL induced extracellular signal-regulated kinase (ERK) 1/2 and I-kappa B phosphorylation in cells, and this induction was suppressed by azithromycin. 3O-C(12)-HSL-induced MUC5AC production was blocked by the ERK pathway inhibitor PD98059. Our findings suggest that the P. aeruginosa autoinducer 3O-C(12)-HSL contributes to excessive mucin production in chronic bacterial infection. Azithromycin seems to reduce this mucin production by interfering with intracellular signal transduction.

4-Butyrolactone↗
PubMed1976

Effects of sesquiterpene lactones on the growth of Bacillus thuringiensis.

Two sesquiterpene lactones, hymenovin and tenulin, were tested for their effect on growth of two strains of Bacillus thuringiensis. Growth of both strains was 98% inhibited by 0.6 mg of tenulin per ml, but only 15 to 20% was inhibited by the same level of hymenovin. Hymenovin appeared to have a mutagenic effect on B. thuringiensis cultures resulting in production of several variant strains. Some of the variant strains had lost their ability to form spores and crystals. Hymenovin also induced B. thuringiensis to produce significant levels of bacteriophage. All variant strains were as susceptible to phage as the parent strain. Although the bactericidal activity of tenulin was two times as great as of hymenovin, tenulin did not appear to have a mutagenic effect on the bacteria.

Bacillus thuringiensis↗
PubMed2006

Disruption of N-acyl homoserine lactone-mediated cell signaling and iron acquisition in epiphytic bacteria by leaf surface compounds.

Since N-acyl homoserine lactones (AHLs) are key mediators of cell density-dependent regulation of traits involved in virulence and epiphytic fitness in gram-negative bacteria such as Pseudomonas syringae, a variety of plant species were examined to determine their production of leaf surface compounds that could interact with these signaling systems. Leaf washings of 17 of 52 plant species tested stimulated or inhibited AHL-dependent traits in at least one of the bacterial reporter strains used. The active compounds from most plants could be distinguished from known AHLs due to different patterns of mobility during C8 and C18 reverse-phase thin-layer chromatography (TLC) and normal-phase TLC compared to the patterns for authentic bacterial AHLs. All plant extracts were also tested to determine their abilities to sequester iron and trigger bacterial siderophore synthesis on a medium containing abundant iron. Leaf washings from 16 of the 52 plant species, as well as tannic acid solutions, stimulated pyoverdine synthesis in P. syringae in a high-iron medium. These preparations also inhibited the growth of a P. syringae mutant unable to produce pyoverdine siderophores but not the growth of the wild-type bacterium. The stimulation of siderophore production and the growth inhibition by plant extracts and purified tannins were both reversed by addition of ferric chloride to culture media, indicating that iron was made unavailable by the compounds released onto the leaf surface.

4-Butyrolactone↗
PubMed2006

Synthesis of N-acyl homoserine lactone analogues reveals strong activators of SdiA, the Salmonella enterica serovar Typhimurium LuxR homologue.

N-Acyl homoserine lactones (AHLs) are molecules that are synthesized and detected by many gram-negative bacteria to monitor the population density, a phenomenon known as quorum sensing. Salmonella enterica serovar Typhimurium is an exceptional species since it does not synthesize its own AHLs, while it does encode a LuxR homologue, SdiA, which enables this bacterium to detect AHLs that are produced by other species. To obtain more information about the specificity of the ligand binding by SdiA, we synthesized and screened a limited library of AHL analogues. We identified two classes of analogues that are strong activators of SdiA: the N-(3-oxo-acyl)-homocysteine thiolactones (3O-AHTLs) and the N-(3-oxo-acyl)-trans-2-aminocyclohexanols. To our knowledge, this is the first report of compounds (the 3O-AHTLs) that are able to activate a LuxR homologue at concentrations that are lower than the concentrations of the most active AHLs. SdiA responds with greatest sensitivity to AHTLs that have a keto modification at the third carbon atom and an acyl chain that is seven or eight carbon atoms long. The N-(3-oxo-acyl)-trans-2-aminocyclohexanols were found to be less sensitive to deactivation by lactonase and alkaline pH than the 3O-AHTLs and the AHLs are. We also examined the activity of our library with LuxR of Vibrio fischeri and identified three new inhibitors of LuxR. Finally, we performed preliminary binding experiments which suggested that SdiA binds its activators reversibly. These results increase our understanding of the specificity of the SdiA-ligand interaction, which could have uses in the development of anti-quorum-sensing-based antimicrobials.

4-Butyrolactone↗
PubMed1995

Inactivation of rsmA leads to overproduction of extracellular pectinases, cellulases, and proteases in Erwinia carotovora subsp. carotovora in the absence of the starvation/cell density-sensing signal, N-(3-oxohexanoyl)-L-homoserine lactone.

The soft-rotting bacterium, Erwinia carotovora subsp. carotovora 71, produces extracellular enzymes such as pectate lyase isozymes (Pels), cellulase (Cel), polygalacturonase (Peh), and protease (Prt). While the extracellular levels of these enzymes are extremely low when the bacterium is grown in salts-yeast extract-glycerol (SYG) medium, the enzymatic activities are highly induced in SYG medium supplemented with celery extract. By transposon (mini-Tn5) mutagenesis, we isolated a RsmA- mutant, AC5070, which overproduces extracellular enzymes; the basal levels of Pel, Peh, and Cel in AC5070 are higher than the induced levels in the RsmA+ parent, AC5047. While Peh production is mostly constitutive in AC5070, Pel, Cel, and Prt production is still inducible with celery extract. The high basal levels of pel-1, pel-3, and peh-1 mRNAs in AC5070 demonstrate that overproduction of the pectolytic enzymes is due to the stimulation of transcription. Using chromosomal DNA flanking mini-Tn5 as a probe, we cloned the wild-type rsmA+ allele, which suppresses Pel, Peh, Cel, and Prt production in both RsmA+ and RsmA- strains. The RsmA- mutant, like its parent, produces N-(3-oxohexanoyl)-L-homoserine lactone (HSL), a starvation/cell density-sensing signal required for extracellular enzyme production. To examine the role of HSL, we constructed HSL-deficient strains by replacing hslI, a locus required for HSL production, with hslI::Tn3HoHo1-Spc. While the basal levels of Pel, Peh, Cel, and Prt are comparable in the RsmA- mutant and its HSL- derivative, these enzymes are barely detectable in the Hsl- derivative of the RsmA+ parent strain.(ABSTRACT TRUNCATED AT 250 WORDS)

4-Butyrolactone↗
PubMed2000

Bacterial growth stimulation with exogenous siderophore and synthetic N-acyl homoserine lactone autoinducers under iron-limited and low-nutrient conditions.

The growth of marine bacteria under iron-limited conditions was investigated. Neither siderophore production nor bacterial growth was detected for Pelagiobacter sp. strain V0110 when Fe(III) was present in the culture medium at a concentration of <1.0 microM. However, the growth of V0110 was strongly stimulated by the presence of trace amounts of exogenous siderophore from an alpha proteobacterium, V0902, and 1 nM N-acyl-octanoylhomoserine lactone (C(8)-HSL), which is known as a quorum-sensing chemical signal. Even though the iron-binding functionality of a hydroxamate siderophore was undetected in the supernatant of V0902, a hydroxamate siderophore was detected in the supernatant of V0110 under the above conditions. These results indicated that hydroxamate siderophore biosynthesis by V0110 began in response to the exogenous siderophore from V0902 when in the presence of C(8)-HSL; however, C(8)-HSL production by V0110 and V0902 was not detected. Direct interaction between V0902 and V0110 through siderophore from V0902 was observed in the dialyzing culture. Similar stimulated growth by exogenous siderophore and HSL was also observed in other non-siderophore-producing bacteria isolated from marine sponges and seawater. The requirement of an exogenous siderophore and an HSL for heterologous siderophore production indicated the possibility that cell-cell communication between different species was occurring.

4-Butyrolactone↗
PubMed2001

Visualization of N-acylhomoserine lactone-mediated cell-cell communication between bacteria colonizing the tomato rhizosphere.

Given that a large proportion of the bacteria colonizing the roots of plants is capable of producing N-acyl-L-homoserine lactone (AHL) molecules, it appears likely that these bacterial pheromones may serve as signals for communication between cells of different species. In this study, we have developed and characterized novel Gfp-based monitor strains that allow in situ visualization of AHL-mediated communication between individual cells in the plant rhizosphere. For this purpose, three Gfp-based AHL sensor plasmids that respond to different spectra of AHL molecules were transferred into AHL-negative derivatives of Pseudomonas putida IsoF and Serratia liquefaciens MG1, two strains that are capable of colonizing tomato roots. These AHL monitor strains were used to visualize communication between defined bacterial populations in the rhizosphere of axenically grown tomato plants. Furthermore, we integrated into the chromosome of AHL-negative P. putida strain F117 an AHL sensor cassette that responds to the presence of long-chain AHLs with the expression of Gfp. This monitor strain was used to demonstrate that the indigenous bacterial community colonizing the roots of tomato plants growing in nonsterile soil produces AHL molecules. The results strongly support the view that AHL signal molecules serve as a universal language for communication between the different bacterial populations of the rhizosphere consortium.

4-Butyrolactone↗
PubMed2002

Genes encoding the N-acyl homoserine lactone-degrading enzyme are widespread in many subspecies of Bacillus thuringiensis.

Gram-negative bacteria can communicate with each other by N-acyl homoserine lactones (AHLs), which are quorum-sensing autoinducers. Recently, the aiiA gene (encoding an enzyme catalyzing the degradation of AHL) has been cloned from Bacillus sp. strain 240B1. During investigations in the course of the ongoing Bacillus thuringiensis subsp. morrisoni genome project, an aiiA homologue gene in the genome sequence was found. These results led to consideration of the possibility of the widespread existence of the gene in B. thuringiensis. aiiA homologue genes were found in 16 subspecies of B. thuringiensis, and their sequences were determined. Comparison of the Bacillus sp. strain 240B1 aiiA gene with the B. thuringiensis aiiA homologue genes showed high homologies of 89 to 95% and 90 to 96% in the nucleotide sequence and deduced amino acid sequence, respectively. Among the subspecies of B. thuringiensis having an aiiA gene, the subspecies aizawai, galleriae, kurstaki, kyushuensis, ostriniae, and subtoxicus were shown to degrade AHL. It was observed that recombinant Escherichia coli producing AiiA proteins also had AHL-degrading activity and could also attenuate the plant pathogenicity of Erwinia carotovora. These results indicate that insecticidal B. thuringiensis strains might have potential to compete with gram-negative bacteria in natural ecosystems by autoinducer-degrading activity.

4-Butyrolactone↗
PubMed2002

Possible quorum sensing in marine snow bacteria: production of acylated homoserine lactones by Roseobacter strains isolated from marine snow.

We report here, for the first time, that bacteria associated with marine snow produce communication signals involved in quorum sensing in gram-negative bacteria. Four of 43 marine microorganisms isolated from marine snow were found to produce acylated homoserine lactones (AHLs) in well diffusion and thin-layer chromatographic assays based on the Agrobacterium tumefaciens reporter system. Three of the AHL-producing strains were identified by 16S ribosomal DNA gene sequence analysis as Roseobacter spp., and this is the first report of AHL production by these alpha-PROTEOBACTERIA: It is likely that AHLs in Roseobacter species and other marine snow bacteria govern phenotypic traits (biofilm formation, exoenzyme production, and antibiotic production) which are required mainly when the population reaches high densities, e.g., in the marine snow community.

4-Butyrolactone↗
PubMed2003

Agrobacterium bioassay strain for ultrasensitive detection of N-acylhomoserine lactone-type quorum-sensing molecules: detection of autoinducers in Mesorhizobium huakuii.

An ultrasensitive bioassay system for the detection of N-acylhomoserine lactones (AHLs) was constructed in Agrobacterium tumefaciens by using the T7 expression system to overproduce the AHL receptor TraR. This strain detected many diverse AHLs, some at extremely low concentrations. We used this strain to detect for the first time AHLs made by Mesorhizobium huakuii, which symbiotically fixes nitrogen in association with the legume Astragalus sinicus, a source of green manure throughout eastern Asia.

4-Butyrolactone↗