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Search for "biofilm" in Full Text gives 33 result(s) in Beilstein Journal of Organic Chemistry.
Synthesis of C6-modified mannose 1-phosphates and evaluation of derived sugar nucleotides against GDP-mannose dehydrogenase
Beilstein J. Org. Chem. 2022, 18, 1379–1384, doi:10.3762/bjoc.18.142
- of alginate overproduction contributes to the PA biofilm environment and the resultant and deleterious bacterial resistance to current antibiotic treatments [2]. Alginate production is therefore established as a major virulence factor within PA respiratory tract infections for CF sufferers, and
Make or break: the thermodynamic equilibrium of polyphosphate kinase-catalysed reactions
Beilstein J. Org. Chem. 2022, 18, 1278–1288, doi:10.3762/bjoc.18.134
- ; Introduction Polyphosphate (polyP, Figure 1) is a linear polymer of up to thousands of phosphate residues connected by phosphate anhydride bonds. It serves as a phosphate storage molecule and plays a crucial role in biofilm formation and stress responses of cells [1]. So far polyP has been detected in every
A new glance at the chemosphere of macroalgal–bacterial interactions: In situ profiling of metabolites in symbiosis by mass spectrometry
Beilstein J. Org. Chem. 2021, 17, 1313–1322, doi:10.3762/bjoc.17.91
- zwitterion dimethylsulphoniopropionate (DMSP), resulting in biofilm formation on the algal surrounding [9]. The bacterium subsequently uses the provided glycerol for growth and transforms DMSP into methanethiol and dimethyl sulphide [9]. The metabolic activities of marine bacteria and algae can be surveyed
- SYBR Gold staining (Figure 3a) as previously described [8][37]. These findings indicated that bacteria are associated with their algal host during symbiosis. In parallel, we visualised the metabolites produced by the biofilm formed around U. mutabilis by imaging analysis with AP-SMALDI-HRMS. Three
- spectrometry. Notably, ectoine was used as a metabolic marker to identify bacteria in the biofilm associated with U. mutabilis and the algal surface. Visualising the spatial distribution of epiphytic bacteria in the phycosphere will contribute to the general understanding of the chemically mediated cross
Secondary metabolites of Bacillus subtilis impact the assembly of soil-derived semisynthetic bacterial communities
Beilstein J. Org. Chem. 2020, 16, 2983–2998, doi:10.3762/bjoc.16.248
- neighbouring organisms induce and increase the SM production in the tested strains. Bacillus subtilis is a well-studied soil bacterium and is used as a model organism for biofilm formation and sporulation [30]. It has been shown that several members of the B. subtilis species complex have exceptional plant
- soil and demonstrated to impact the biofilm colony development of B. subtilis [54]. Interestingly, the modulation of the biofilm development was mediated by the primary metabolite hypoxanthine secreted by L. fusiformis. Of note, the impact of B. subtilis was not noticed on L. fusiformis in the mixed
- colony biofilm communities, possibly due to the use of the NRP-negative B. subtilis strain 168, which harbours a spontaneous frameshift mutation in the sfp gene [54]. Testing the impact of the natural isolate B. subtilis P5_B1 and the corresponding NRP mutant derivatives revealed that the spent media
Antibacterial scalarane from Doriprismatica stellata nudibranchs (Gastropoda, Nudibranchia), egg ribbons, and their dietary sponge Spongia cf. agaricina (Demospongiae, Dictyoceratida)
Beilstein J. Org. Chem. 2020, 16, 1596–1605, doi:10.3762/bjoc.16.132
- mentioned in previous studies on nudibranch egg ribbons [17][34][35][36]. The antibacterial activity of 12-deacetoxy-4-demethyl-11,24-diacetoxy-3,4-methylenedeoxoscalarin could point towards a potential protective role against bacterial biofilm formation. Unfortunately, the metabolite was unstable over time
Pigmentosins from Gibellula sp. as antibiofilm agents and a new glycosylated asperfuran from Cordyceps javanica
Beilstein J. Org. Chem. 2019, 15, 2968–2981, doi:10.3762/bjoc.15.293
- ) derivative, pigmentosin B (2), were isolated from the spider-associated fungus Gibellula sp. Furthermore, a new glycosylated asperfuran 3, together with one new (6) and two known (4 and 5) cyclodepsipeptides, was isolated from Cordyceps javanica. The pigmentosins 1 and 2 showed to be active against biofilm
- formation of Staphylococcus aureus DSM1104. The lack of toxicity toward the studied microorganism and cell lines of pigmentosin B (2), as well as the antimicrobial effect of pigmentosin A (1), made them good candidates for further development for use in combination therapy of infections involving biofilm
- , in particular orthopedic implant-related infections, since implants coated with proteins facilitate bacterial attachment and biofilm development [1]. In general, bacteria are known to employ different strategies to cope with the presence of antibiotics, of which a biofilm, an aggregate of
Skeletocutins M–Q: biologically active compounds from the fruiting bodies of the basidiomycete Skeletocutis sp. collected in Africa
Beilstein J. Org. Chem. 2019, 15, 2782–2789, doi:10.3762/bjoc.15.270
- , compound 3 moderately inhibited the biofilm formation of Staphylococcus aureus (S. aureus), while compounds 3 and 4 performed moderately in the ʟ-leucine-7-amido-4-methylcoumarin (ʟ-Leu-AMC) inhibition assay. These compounds represent the first secondary metabolites reported to occur in the fruiting bodies
- (B. subtilis), S. aureus, methicillin-resistant S. aureus (MRSA), and Micrococcus luteus (M. luteus). In the antimicrobial assay, compounds 3 and 5 were observed to interfere with the formation of biofilms commonly associated with S. aureus. When compounds 3 and 5 were evaluated for biofilm
- inhibition activity against S. aureus, they showed only weak activity with 20 and 56% inhibition of the biofilm, respectively, at a concentration 256 µg/mL. Tyromycin A (6) was previously reported to be an inhibitor of leucine aminopeptidase in HeLa S3 cells [6]. Accordingly, all compounds 1–5 were tested
Novel (2-amino-4-arylimidazolyl)propanoic acids and pyrrolo[1,2-c]imidazoles via the domino reactions of 2-amino-4-arylimidazoles with carbonyl and methylene active compounds
Beilstein J. Org. Chem. 2019, 15, 1032–1045, doi:10.3762/bjoc.15.101
- -aminoimidazoles from α-bromocarbonyl compounds and substituted 2-aminopyrimidines. This methodology allowed the rapid synthesis of alkaloids of the isonaamine series [20] and other polysubstituted 2-aminoimidazoles with moderate cytostatic activity [21] and biofilm inhibitory activity against S. Typhimurium and P
Convergent synthesis of the pentasaccharide repeating unit of the biofilms produced by Klebsiella pneumoniae
Beilstein J. Org. Chem. 2019, 15, 431–436, doi:10.3762/bjoc.15.37
- acid corresponding to the repeating unit of the biofilm producing polysaccharide secreted by K. pneumoniae. The unique feature of this pentasaccharide is that it contains a β-D-mannosidic moiety and a α-D-glucuronic acid moiety, which are known to be challenging from the synthetic point of view. In
- the biofilm producing polysaccharide secreted by K. pneumoniae. A convergent synthesis of a pentasaccharide as its 2-aminoethyl glycoside containing a β-D-mannosidic moiety and a α-D-glucuronic acid moiety is presented herein. The presence of a 2-aminoethyl group at the reducing end of the
- convergent synthesis of a pentasaccharide corresponding to the repeating unit of the biofilm producing polysaccharide secreted by K. pneumoniae as its 2-aminoethyl glycoside has been achieved in good yield. The noteworthy points of the synthetic strategy include stereoselective construction of a β-D
Lectins of Mycobacterium tuberculosis – rarely studied proteins
Beilstein J. Org. Chem. 2019, 15, 1–15, doi:10.3762/bjoc.15.1
- Abstract The importance of bacterial lectins for adhesion, pathogenicity, and biofilm formation is well established for many Gram-positive and Gram-negative bacteria. However, there is very little information available about lectins of the tuberculosis-causing bacterium, Mycobacterium tuberculosis (Mtb
- shown that MTP is associated with Mtb aggregation and biofilm formation in vitro [116]. The importance of these interactions in patients, however, has yet to be confirmed, as the association of mycobacterial biofilms with bacterial pathogenesis has not yet been conclusively shown in vivo. Besides
- (T4P) are surface-exposed fibers that mediate many functions in both Gram-positive and Gram-negative bacteria, including motility, adhesion to host cells, biofilm formation, DNA uptake, and protein secretion [120][121][122][123][124][125][126][127][128]. Mtb expresses T4P that appear by electron
Repurposing the anticancer drug cisplatin with the aim of developing novel Pseudomonas aeruginosa infection control agents
Beilstein J. Org. Chem. 2018, 14, 3059–3069, doi:10.3762/bjoc.14.284
- 637371 Costerton Biofilm Center, Department of Immunology and Microbiology, University of Copenhagen, 2200 København N, Denmark 10.3762/bjoc.14.284 Abstract Antibiotic resistance threatens effective treatment of microbial infections globally. This situation has spurred the hunt for new antimicrobial
- the secretion of exotoxins. Furthermore, cisplatin was also demonstrated to eradicate in vitro biofilms and in vivo biofilms in a murine keratitis model. This showed that cisplatin could be effectively used to eradicate biofilm infections which were otherwise difficult to be treated by conventional
- infections. Keywords: biofilm; cisplatin; Pseudomonas aeruginosa; resistance; type III secretion; Introduction Pseudomonas aeruginosa is a leading nosocomial pathogen which causes, among others, corneal, chronic otitis media, urinary tract (UTI) and respiratory tract infections [1]. P. aeruginosa is also
N-Acylated amino acid methyl esters from marine Roseobacter group bacteria
Beilstein J. Org. Chem. 2018, 14, 2964–2973, doi:10.3762/bjoc.14.276
- medium polar core structure [8][16]. Nevertheless, the ecological function of NAMEs and its derivatives could also be antagonistic activity against concurrent biofilm microorganisms, suggested by the bioactivity of some of the compounds as observed in this study and the antimicrobial and antialgal
Synthesis of pyrrolidine-based hamamelitannin analogues as quorum sensing inhibitors in Staphylococcus aureus
Beilstein J. Org. Chem. 2018, 14, 2822–2828, doi:10.3762/bjoc.14.260
- developed and delivered the pyrrolidine analogue in 17 steps in high yield. Chemoselective derivatization of the pyrrolidine nitrogen atom resulted in 6 more compounds. The synthesized compounds were evaluated in a biofilm model, but were all inactive. Keywords: hamamelitannin; iminosugar; pyrrolidine
- ), an inhibitor of the RAP/TRAP (RNAIII-activating protein/target of RAP) quorum sensing system in S. aureus (Figure 1) [12][13][14]. Furthermore, hamamelitannin has been shown to inhibit biofilm formation and to potentiate the activity of antibiotics against staphylococcal biofilms in vitro and in vivo
- . aureus biofilm model, but were all inactive (see Supporting Information File 1). Conclusion A convergent synthetic route for the synthesis of pyrrolidine-based hamamelitannin analogues was developed. The originally envisioned strategy failed due to difficulties in the ring-closing metathesis reaction
Synthesis and biological evaluation of 1,2-disubstituted 4-quinolone analogues of Pseudonocardia sp. natural products
Beilstein J. Org. Chem. 2018, 14, 2680–2688, doi:10.3762/bjoc.14.245
- their phenotype in response to changes in population density, regulating virulence and biofilm formation when most impactful to the host organism [5]. This process is mediated by signalling molecules such as PQS, and natural product structures 1–8 analogous to PQS may provide interspecies QS-modulator
Non-native autoinducer analogs capable of modulating the SdiA quorum sensing receptor in Salmonella enterica serovar Typhimurium
Beilstein J. Org. Chem. 2018, 14, 2651–2664, doi:10.3762/bjoc.14.243
- , host colonization, and biofilm formation at high population densities. This cell–cell signaling process is regulated by N-acyl L-homoserine lactone (AHL) signals, or autoinducers, and LuxR-type receptors in Gram-negative bacteria. SdiA is an orphan LuxR-type receptor found in Escherichia, Salmonella
- to coordinate group beneficial behaviors such as virulence factor production, host colonization, and biofilm formation at high population densities [12]. Gram-negative bacteria typically use N-acyl L-homoserine lactone (AHL) signals for QS, which are produced by LuxI-type synthases and sensed by
Targeting the Pseudomonas quinolone signal quorum sensing system for the discovery of novel anti-infective pathoblockers
Beilstein J. Org. Chem. 2018, 14, 2627–2645, doi:10.3762/bjoc.14.241
- well as cell envelope properties or biofilm formation [15]. All the mechanisms described above help to explain the notion that established chronic P. aeruginosa infections are notoriously difficult to eradicate. This ubiquitous opportunistic pathogen is able to cause infections basically in every niche
- pathogenicity traits like the production of virulence factors or biofilm formation are under the control of these systems. Actually, title pathogen makes use of four intertwined QS systems, referred to as las, rhl, pqs, and iqs [22]. These subsystems influence each other establishing an intricate regulatory
- response. In terms of pathogenicity traits, they are involved in the regulation of genes encoding for enzymes responsible for phenazine biosynthesis (pyocyanin production), hydrogen cyanide synthesis, Lectins LecA and LecB and additional genes involved in biofilm formation, enzymes for rhamnolipid
Pathoblockers or antivirulence drugs as a new option for the treatment of bacterial infections
Beilstein J. Org. Chem. 2018, 14, 2607–2617, doi:10.3762/bjoc.14.239
- pathogen [10]. 3. Blocking adhesion and biofilm formation Bacterial adhesion to the host’s tissue is the initial step of every infection. In many cases, microbial adhesion is mediated by carbohydrate-binding proteins, so-called lectins, which recognize glycoconjugates on the surface of cells and tissue
- and invade bladder and kidney tissue, and to promote biofilm formation. Bladder-adhesive FimH is a mannose-specific lectin and the kidney-adhesive PapG binds galactosides. In a second indication, FimH also mediates the attachment of E. coli to the gut, inducing inflammation in Crohn’s disease [13
- that, in addition to antimicrobial resistance, forms biofilms, a complex matrix of extracellular polysaccharides, polypeptides and DNA, which act as an additional protective barrier [30]. P. aeruginosa employs two lectins for biofilm formation and host–cell adhesion: proteins LecA and LecB [31][32
Impact of Pseudomonas aeruginosa quorum sensing signaling molecules on adhesion and inflammatory markers in endothelial cells
Beilstein J. Org. Chem. 2018, 14, 2580–2588, doi:10.3762/bjoc.14.235
- cells were stimulated with 20 µM of main P. aeruginosa QSSMs (OdDHL = N-(3-oxododecanoyl)-L-homoserine lactone, C4HSL = N-butyryl-L-homoserine lactone, PQS = 2-heptyl-3-hydroxy-4(1H)-quinolone and HHQ = 2-heptyl-4-quinolone). Adherence to endothelial cells, inert substratum and biofilm formation was
- evaluated. The expression of adhesion molecules (VE-cadherin, PECAM-1, ICAM-1, and P-selectin) and inflammatory response molecules (IL-1β, IL-6, TNFα, TGFβ, and eNOS) was assessed by qRT-PCR and flow cytometry. Our results showed that bacterial adherence to inert substratum and biofilm were decreased in the
- compromised individuals and in patients with bronchiectasis or cystic fibrosis. The infections become chronic, as P. aeruginosa develops resistance to conventional antibiotics due to its ability to produce virulence factors and modulate immune defenses by quorum sensing (QS) and biofilm production
Defining the hydrophobic interactions that drive competence stimulating peptide (CSP)-ComD binding in Streptococcus pneumoniae
Beilstein J. Org. Chem. 2018, 14, 1769–1777, doi:10.3762/bjoc.14.151
- , swarming, biofilm formation, virulence factor production and competence [3][4][5]. As such, QS has attracted significant attention as a means to control bacterial behaviors (i.e., promote productive processes while attenuating harmful traits). Extensive work aimed at developing small molecule-based QS
- threshold concentration, CSP binds and activates the transmembrane histidine kinase receptor ComD. Upon activation, ComD phosphorylates ComE. Phosphorylated ComE then autoactivates the competence QS circuit and upregulates the expression of genes involved in virulence factor production, biofilm formation
Continuous multistep synthesis of 2-(azidomethyl)oxazoles
Beilstein J. Org. Chem. 2018, 14, 506–514, doi:10.3762/bjoc.14.36
- 1,4-disubstituted triazoles 8 through click reaction between 2-azidomethyl-4,5-diaryloxazoles and alkynes in the presence of a copper(I) catalyst (Scheme 2). The authors were able to synthesize an array of small-molecule peptidomimetics that inhibited Porphyromonas gingivalis biofilm formation [34
Binding abilities of polyaminocyclodextrins: polarimetric investigations and biological assays
Beilstein J. Org. Chem. 2017, 13, 2751–2763, doi:10.3762/bjoc.13.271
- resistance genes) and the emergence of multidrug resistant strains [59]. In addition, extracellular DNA has been shown to be important for biofilm establishment and maintenance by pathogenic bacteria, such as Pseudomonas aeruginosa and Staphylococcus aureus [60][61][62]. Some other bacteria, such as E. coli
- further remark, we can outline that the latter apparently negative result is quite intriguing indeed, because we may envisage a possible use of our materials as scavengers of extracellular DNA (eDNA). As a matter of fact, recent studies have shown that eDNA is important for biofilm establishment and
- maintenance by pathogenic bacteria, such as P. aeruginosa and S. aureus [60][61][62]. In addition, eDNA with its negative charge can sequester cationic antibiotics contributing to antibiotic resistance; thus, removing eDNA from the biofilm matrix can weaken the biofilm and can raise its susceptibility to
What contributes to an effective mannose recognition domain?
Beilstein J. Org. Chem. 2017, 13, 2584–2595, doi:10.3762/bjoc.13.255
- lectins, the bacterial adhesins, play an important role in the initial interaction of the bacterium with host tissue [9][10]. This primary contact is a prerequisite for the infection of host cells and subsequent biofilm formation, and grants the bacteria a significant advantage by resisting clearance and
Glyco-gold nanoparticles: synthesis and applications
Beilstein J. Org. Chem. 2017, 13, 1008–1021, doi:10.3762/bjoc.13.100
- -antibiotic conjugates, were prepared and resulted able to overcome antibiotic resistance of microbial biofilms, since CA NPs render streptomycin more accessible to biofilms, thereby more available to interact with biofilm bacteria [89]. Similarly, a novel recyclable E.coli-specific killing GAuNP
Posttranslational isoprenylation of tryptophan in bacteria
Beilstein J. Org. Chem. 2017, 13, 338–346, doi:10.3762/bjoc.13.37
- contributes to the phenotypic characteristics involved in biofilm formation by B. subtilis subsp. natto, which is closely related to the Bacillus laboratory strains and renowned as the producer strain for the quite sticky, traditional Japanese food natto, made from fermented soybeans [23]. B. subtilis subsp
- . natto is obviously distinct from the other laboratory strains with respect to the biofilm formation. The biofilm mainly consists of the highly sticky poly-γ-glutamic acid (γ-PGA) polymer (Figure 2B), and the ComXnatto pheromone activates γ-PGA biosynthesis in B. subtilis subsp. natto at nanomolar levels
Chemical probes for competitive profiling of the quorum sensing signal synthase PqsD of Pseudomonas aeruginosa
Beilstein J. Org. Chem. 2016, 12, 2784–2792, doi:10.3762/bjoc.12.277
- ) are the two best studied AQs (Figure 1A) [7]. A variety of virulence factors are under control of the pqs quorum sensing system, including the production of elastase, pyocyanin, PA-IL lectin, and rhamnolipids, as well as populations dynamic behaviours such as biofilm formation. However, the exact
- inhibitors based on these leads have been described and importantly, some of them also displayed in situ activity by reducing signal production and biofilm formation in live cultures of P. aeruginosa [28][31]. Recently, a synergistic dual PqsD and PqsR inhibitor was developed which also led to a marked
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