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Search for "virulence" in Full Text gives 48 result(s) in Beilstein Journal of Organic Chemistry.

Development of a chemical scaffold for inhibiting nonribosomal peptide synthetases in live bacterial cells

  • Fumihiro Ishikawa,
  • Sho Konno,
  • Hideaki Kakeya and
  • Genzoh Tanabe

Beilstein J. Org. Chem. 2024, 20, 445–451, doi:10.3762/bjoc.20.39

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  • University, Sakyo, Kyoto 606-8501, Japan 10.3762/bjoc.20.39 Abstract The adenylation (A) domain is essential for non-ribosomal peptide synthetases (NRPSs), which synthesize various peptide-based natural products, including virulence factors, such as siderophores and genotoxins. Hence, the inhibition of A
  • -domains could attenuate the virulence of pathogens. 5’-O-N-(Aminoacyl or arylacyl)sulfamoyladenosine (AA-AMS) is a bisubstrate small-molecule inhibitor of the A-domains of NRPSs. However, the bacterial cell permeability of AA-AMS is typically a problem owing to its high hydrophilicity. In this study, we
  • ; Introduction Nonribosomal peptides (NRPs) exhibit various biological activities and have been used as therapeutic agents, such as antibiotics, anticancer agents, and immunosuppressants [1]. Additionally, NRPs function as virulence factors, such as siderophores and genotoxins [2]. Therefore, inhibiting their
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Published 26 Feb 2024

Synthetic approach to 2-alkyl-4-quinolones and 2-alkyl-4-quinolone-3-carboxamides based on common β-keto amide precursors

  • Yordanka Mollova-Sapundzhieva,
  • Plamen Angelov,
  • Danail Georgiev and
  • Pavel Yanev

Beilstein J. Org. Chem. 2023, 19, 1804–1810, doi:10.3762/bjoc.19.132

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  • great research interest, with many reviews published in the recent years [20][21][22]. Some of the compounds are known to act as antibiotics [23][24][25][26], while others function as quorum-sensing signal molecules which regulate the production and release of virulence factors in bacteria, thus helping
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Published 23 Nov 2023

Intermediates and shunt products of massiliachelin biosynthesis in Massilia sp. NR 4-1

  • Till Steinmetz,
  • Blaise Kimbadi Lombe and
  • Markus Nett

Beilstein J. Org. Chem. 2023, 19, 909–917, doi:10.3762/bjoc.19.69

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  • -affinity siderophore, which further acts as a signal molecule for the production of virulence factors [26]. Similar to P. aeruginosa, the causative agent of splenic fever, Bacillus anthracis, is also known to synthesize two structurally different siderophores. The corresponding compounds were found to
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Published 23 Jun 2023

Navigating and expanding the roadmap of natural product genome mining tools

  • Friederike Biermann,
  • Sebastian L. Wenski and
  • Eric J. N. Helfrich

Beilstein J. Org. Chem. 2022, 18, 1656–1671, doi:10.3762/bjoc.18.178

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  • bioinformatic analysis of (meta-)genomes to identify gene clusters involved in the biosynthesis of NPs [3]. NPs have been shown to act as signaling metabolites (e.g., acylhomoserine lactones (1) [6]), siderophores (e.g., pyoverdines (2) [7]), virulence factors (e.g., malleicyprol (3) [8][9][10]), toxins (e.g
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Perspective
Published 06 Dec 2022

Synthesis of C6-modified mannose 1-phosphates and evaluation of derived sugar nucleotides against GDP-mannose dehydrogenase

  • Sanaz Ahmadipour,
  • Alice J. C. Wahart,
  • Jonathan P. Dolan,
  • Laura Beswick,
  • Chris S. Hawes,
  • Robert A. Field and
  • Gavin J. Miller

Beilstein J. Org. Chem. 2022, 18, 1379–1384, doi:10.3762/bjoc.18.142

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  • 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
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Letter
Published 30 Sep 2022

Anomeric 1,2,3-triazole-linked sialic acid derivatives show selective inhibition towards a bacterial neuraminidase over a trypanosome trans-sialidase

  • Peterson de Andrade,
  • Sanaz Ahmadipour and
  • Robert A. Field

Beilstein J. Org. Chem. 2022, 18, 208–216, doi:10.3762/bjoc.18.24

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  • acid from the human host glycoconjugates onto its surface mucins to generate α-2,3-linked sialylated β-galactopyranose units, thus contributing directly to the parasite adhesion and invasion of host cells [12]. Although TcTS is the major parasite virulence factor [13], there is no nanomolar inhibitor
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Published 17 Feb 2022

Tenacibactins K–M, cytotoxic siderophores from a coral-associated gliding bacterium of the genus Tenacibaculum

  • Yasuhiro Igarashi,
  • Yiwei Ge,
  • Tao Zhou,
  • Amit Raj Sharma,
  • Enjuro Harunari,
  • Naoya Oku and
  • Agus Trianto

Beilstein J. Org. Chem. 2022, 18, 110–119, doi:10.3762/bjoc.18.12

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  • ). Conclusion Considering the productivity of siderophores to be an essential trait for the virulence of many microbial pathogens [37], compounds 1–3 could also be involved in the pathogenesis of Tenacibaculum maritimum in fish, which is not well understood [38]. Although the genome size of Tenacibaculum varies
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Published 13 Jan 2022

Natural products in the predatory defence of the filamentous fungal pathogen Aspergillus fumigatus

  • Jana M. Boysen,
  • Nauman Saeed and
  • Falk Hillmann

Beilstein J. Org. Chem. 2021, 17, 1814–1827, doi:10.3762/bjoc.17.124

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  • ; non-ribosomal peptides; polyketides; secondary metabolism; virulence; Introduction To thrive in their natural habitats all organisms from bacteria and fungi to plants and animals need access to sufficient nutritional sources and have to defend themselves against both, competitors and predators
  • by acting as pathogens. It is firmly established that the ability to produce mycotoxins contributes to the virulence potential of these fungi, but as they all thrive in environmental reservoirs they must also provide an ecological advantage to their producer [18]. Indeed, many of these pathogenic
  • shown for Aspergillus fumigatus and its interactions with Acanthamoeba castellanii [30]. Thus, the adaptations that protect fungi against amoeba that were gained in the ‘environmental school of virulence’ might also protect fungi from the immune system [31]. Therefore, to study their interactions with
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Review
Published 28 Jul 2021

Chemical approaches to discover the full potential of peptide nucleic acids in biomedical applications

  • Nikita Brodyagin,
  • Martins Katkevics,
  • Venubabu Kotikam,
  • Christopher A. Ryan and
  • Eriks Rozners

Beilstein J. Org. Chem. 2021, 17, 1641–1688, doi:10.3762/bjoc.17.116

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Published 19 Jul 2021

Antiviral therapy in shrimp through plant virus VLP containing VP28 dsRNA against WSSV

  • Santiago Ramos-Carreño,
  • Ivone Giffard-Mena,
  • Jose N. Zamudio-Ocadiz,
  • Alfredo Nuñez-Rivera,
  • Ricardo Valencia-Yañez,
  • Jaime Ruiz-Garcia,
  • Maria Teresa Viana and
  • Ruben D. Cadena-Nava

Beilstein J. Org. Chem. 2021, 17, 1360–1373, doi:10.3762/bjoc.17.95

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  • over the VLPs derived from the shrimp virus. The mortality rate of shrimp inoculated with WSSV is dose-dependent [52][63][64]. Dose dependency can be grouped in three virulence levels, according to the dilutions used: high 10−1–10−2 (45–43.5 hpi), medium 10−4–10−6 (51.4–49.5 hpi) and low 10−8–10−10
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Published 01 Jun 2021

19F NMR as a tool in chemical biology

  • Diana Gimenez,
  • Aoife Phelan,
  • Cormac D. Murphy and
  • Steven L. Cobb

Beilstein J. Org. Chem. 2021, 17, 293–318, doi:10.3762/bjoc.17.28

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  • -structural protein 1 (NS1A) homodimer (Figure 9) [64]. Protein NS1A is a highly conserved virulence factor from influenza virus (H3N2) comprised of an N-terminal double-stranded RNA (dsRNA)-binding domain (RBD) and a multifunctional C-terminal effector domain (ED), each of which can independently form
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Published 28 Jan 2021

Synthesis of Streptococcus pneumoniae serotype 9V oligosaccharide antigens

  • Sharavathi G. Parameswarappa,
  • Claney L. Pereira and
  • Peter H. Seeberger

Beilstein J. Org. Chem. 2020, 16, 1693–1699, doi:10.3762/bjoc.16.140

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  • Chemistry and Biochemistry, Arnimallee 22, 14195 Berlin, Germany 10.3762/bjoc.16.140 Abstract Streptococcus pneumoniae (SP) bacteria cause serious invasive diseases. SP bacteria are covered by a capsular polysaccharide (CPS) that is a virulence factor and the basis for SP polysaccharide and glycoconjugate
  • are still of growing concern due to an increase in non-vaccine serotypes and the cost of implementing these expensive vaccines in national immunization programs [4][5][6]. CPS is an important bacterial virulence factor and is critical for the interaction with the host as it helps the bacteria to
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Published 15 Jul 2020

Convenient synthesis of the pentasaccharide repeating unit corresponding to the cell wall O-antigen of Escherichia albertii O4

  • Tapasi Manna,
  • Arin Gucchait and
  • Anup Kumar Misra

Beilstein J. Org. Chem. 2020, 16, 106–110, doi:10.3762/bjoc.16.12

Graphical Abstract
  • of devastating diarrheal infections in different countries [9]. The role of cell wall O-polysaccharides in regulating the virulence properties of bacteria is well established [10]. Recently, Naumenko et al. [11] reported the structure of the repeating unit of the cell wall O-polysaccharide of the E
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Published 22 Jan 2020

Pigmentosins from Gibellula sp. as antibiofilm agents and a new glycosylated asperfuran from Cordyceps javanica

  • Soleiman E. Helaly,
  • Wilawan Kuephadungphan,
  • Patima Phainuphong,
  • Mahmoud A. A. Ibrahim,
  • Kanoksri Tasanathai,
  • Suchada Mongkolsamrit,
  • Janet Jennifer Luangsa-ard,
  • Souwalak Phongpaichit,
  • Vatcharin Rukachaisirikul and
  • Marc Stadler

Beilstein J. Org. Chem. 2019, 15, 2968–2981, doi:10.3762/bjoc.15.293

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  • microorganisms held together within a self-produced matrix of extracellular polymeric substances, plays an important role as a main virulence determinant in staph infections [1][2]. Within a biofilm, bacteria become tolerant toward antibiotics and host immune responses greater than their planktonic (free
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Published 16 Dec 2019

Chemical synthesis of tripeptide thioesters for the biotechnological incorporation into the myxobacterial secondary metabolite argyrin via mutasynthesis

  • David C. B. Siebert,
  • Roman Sommer,
  • Domen Pogorevc,
  • Michael Hoffmann,
  • Silke C. Wenzel,
  • Rolf Müller and
  • Alexander Titz

Beilstein J. Org. Chem. 2019, 15, 2922–2929, doi:10.3762/bjoc.15.286

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  • resistances in clinically used bacterial targets, innovative antiinfective strategies comprising new antibiotic classes and virulence-attenuating compounds have been developed [3][4]. The argyrins 1–8 are a family of 8 naturally occurring cyclic peptides isolated by Sasse, Höfle and co-workers from the
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Published 05 Dec 2019

Chemical synthesis of the pentasaccharide repeating unit of the O-specific polysaccharide from Escherichia coli O132 in the form of its 2-aminoethyl glycoside

  • Debasish Pal and
  • Balaram Mukhopadhyay

Beilstein J. Org. Chem. 2019, 15, 2563–2568, doi:10.3762/bjoc.15.249

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  • bacteria present in the guts of human and other warm-blooded animals. It is usually harmless and beneficial to the host’s body, however, there are other variants of E. coli having virulence factors and causing diseases like diarrhea, urinary tract infection, septicaemia etc. E. coli O132 is reported to be
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Published 28 Oct 2019

Synthesis of novel sulfide-based cyclic peptidomimetic analogues to solonamides

  • José Brango-Vanegas,
  • Luan A. Martinho,
  • Lucinda J. Bessa,
  • Andreanne G. Vasconcelos,
  • Alexandra Plácido,
  • Alex L. Pereira,
  • José R. S. A. Leite and
  • Angelo H. L. Machado

Beilstein J. Org. Chem. 2019, 15, 2544–2551, doi:10.3762/bjoc.15.247

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  • prevent the expression of Staphylococcus aureus virulence factors such as α-hemolysin and phenol-soluble modulins without affecting the bacterial growth [3]. Particularly, solonamide B and its analogues revealed no detectable toxicity against erythrocytes or human neutrophils [3][4]. Staphylococcus aureus
  • , methicillin-resistant S. aureus (MRSA) is considered an endemic cause of nosocomial infections and has spread into the community and livestock animals as well [8]. Expression of many S. aureus virulence factors is controlled by a sophisticated intercellular chemical signalling pathway named quorum-sensing (QS
  • structurally related to these natural peptidomimetics has been used as a promising strategy for the attenuation of bacterial virulence in strains of S. aureus [12][13][14][15]. Herein, we report the synthesis of new sulfide-based cyclic peptidomimetics through the allylic nucleophilic substitution (SN2’) of
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Published 25 Oct 2019

Bipolenins K–N: New sesquiterpenoids from the fungal plant pathogen Bipolaris sorokiniana

  • Chin-Soon Phan,
  • Hang Li,
  • Simon Kessler,
  • Peter S. Solomon,
  • Andrew M. Piggott and
  • Yit-Heng Chooi

Beilstein J. Org. Chem. 2019, 15, 2020–2028, doi:10.3762/bjoc.15.198

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  • array of secondary metabolites, including sesquiterpenes [1][2][3][4][5][6][7], sesquiterpene-xanthones [8], diterpenes [9], sesterterpenes [10], cochlioquinones and peptides [11]. Moreover, several of these secondary metabolites are known to play important roles in mediating the virulence of these
  • and is a major threat to yield improvement and food security in Central Asia [13]. Recent genome sequencing of 35 Australian strains of B. sorokiniana identified a known proteinaceous necrotrophic effector, ToxA, which confers host-specific virulence proteins and is proposed to be acquired through
  • putative sesquiterpene synthase genes in the genome of B. sorokiniana BRIP10943, allowing the molecular genetic basis for their biosynthesis and their roles in mediating the virulence of B. sorokiniana against wheat to be explored. Experimental General experimental procedures Optical rotations were
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Published 26 Aug 2019

Synthesis and biological activity of methylated derivatives of the Pseudomonas metabolites HHQ, HQNO and PQS

  • Sven Thierbach,
  • Max Wienhold,
  • Susanne Fetzner and
  • Ulrich Hennecke

Beilstein J. Org. Chem. 2019, 15, 187–193, doi:10.3762/bjoc.15.18

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  • are associated with quorum sensing and virulence of the human pathogen Pseudomonas aeruginosa, have been prepared. While the synthesis by direct methylation was successful for 3-unsubstituted 2-heptyl-4(1H)-quinolones, methylated derivatives of the Pseudomonas quinolone signal (PQS) were synthesized
  • (HHQ, 1) are important signaling molecules involved in quorum sensing and as such play an important role in virulence regulation [3][10][11][12]. Another metabolite from the AQ biosynthesis pathway of P. aeruginosa is 2-heptyl-1-hydroxy-4(1H)-quinolone (generally referred to as 2-heptyl-4
  • oxygen atom (6). Quorum sensing activity The compounds HHQ, PQS and HQNO are strongly related to quorum sensing and virulence in P. aeruginosa. HHQ and PQS act as signal molecules and, by interacting with the transcriptional regulator PqsR, induce the expression of the AQ biosynthetic genes. Such
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Published 21 Jan 2019

Lectins of Mycobacterium tuberculosis – rarely studied proteins

  • Katharina Kolbe,
  • Sri Kumar Veleti,
  • Norbert Reiling and
  • Thisbe K. Lindhorst

Beilstein J. Org. Chem. 2019, 15, 1–15, doi:10.3762/bjoc.15.1

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  • infections in humans, presumably through interference with lectin-associated pathogen–host adhesion [67][68]. Besides facilitation of adhesion, some bacterial lectins are also known to act as toxins. The secreted pertussis toxin, for example, is a lectin and an important virulence factor of Bordetella
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Published 02 Jan 2019

Repurposing the anticancer drug cisplatin with the aim of developing novel Pseudomonas aeruginosa infection control agents

  • Mingjun Yuan,
  • Song Lin Chua,
  • Yang Liu,
  • Daniela I. Drautz-Moses,
  • Joey Kuok Hoong Yam,
  • Thet Tun Aung,
  • Roger W. Beuerman,
  • May Margarette Santillan Salido,
  • Stephan C. Schuster,
  • Choon-Hong Tan,
  • Michael Givskov,
  • Liang Yang and
  • Thomas E. Nielsen

Beilstein J. Org. Chem. 2018, 14, 3059–3069, doi:10.3762/bjoc.14.284

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  • the main cause of fatal infections in patients with cystic fibrosis (CF) [2] and cancer patients [3][4]. The success of P. aeruginosa as a leading pathogen is attributed to its ability to form resilient biofilms, resist antimicrobials and secrete virulence products. Microbial cells resident in
  • biofilms are encased by an extracellular matrix, which protects them from antimicrobial treatment and the host’s immune clearance [5]. Clinical P. aeruginosa isolates are mostly multidrug-resistant (MDR) strains [6], with robust ability to form biofilms [7]. P. aeruginosa also secretes virulence factors
  • bacteria in the biofilm mode including virulence mechanisms that cripple immune defenses, may offer novel antimicrobial therapies against a variety of otherwise persistent P. aeruginosa infections. Here, we screened our in-house collection of FDA-approved drugs and found that cisplatin was the most potent
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Published 14 Dec 2018

Protein–protein interactions in bacteria: a promising and challenging avenue towards the discovery of new antibiotics

  • Laura Carro

Beilstein J. Org. Chem. 2018, 14, 2881–2896, doi:10.3762/bjoc.14.267

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  • regulation of gene expression, DNA replication, signal transduction, virulence, etc. and therefore represent potential fruitful targets for antibacterial drug discovery. Recently, scientific efforts have helped towards the understanding and the deciphering of the protein-interaction networks (PINs) that
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Review
Published 21 Nov 2018

Synthesis of pyrrolidine-based hamamelitannin analogues as quorum sensing inhibitors in Staphylococcus aureus

  • Jakob Bouton,
  • Kristof Van Hecke,
  • Reuven Rasooly and
  • Serge Van Calenbergh

Beilstein J. Org. Chem. 2018, 14, 2822–2828, doi:10.3762/bjoc.14.260

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  • resistance problem need to be multifactorial. Next to disease prevention and the development of new antibiotics, it is essential to investigate innovative strategies to combat bacterial infections [3][4]. Recently, targeting bacterial virulence has gained a lot of attention [5][6][7]. It has been
  • hypothesized that by “disarming” the pathogen, rather than inhibiting its growth, selective pressure for resistance development will be much lower. Furthermore, reduction of bacterial virulence directly protects the host, and at the same time renders the bacteria more susceptible towards the host defense
  • clinical infections. In S. aureus, virulence is mainly mediated by quorum sensing, a bacterial cell-to-cell communication system based on the secretion of signal molecules [9][10][11]. The natural product hamamelitannin (1) has been identified as a non-peptide analogue of RIP (RNAIII-inhibiting protein
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Published 12 Nov 2018

Synthesis and biological evaluation of 1,2-disubstituted 4-quinolone analogues of Pseudonocardia sp. natural products

  • Stephen M. Geddis,
  • Teodora Coroama,
  • Suzanne Forrest,
  • James T. Hodgkinson,
  • Martin Welch and
  • David R. Spring

Beilstein J. Org. Chem. 2018, 14, 2680–2688, doi:10.3762/bjoc.14.245

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  • analogues was observed to inhibit production of the virulence factor pyocyanin in the human pathogen Pseudomonas aeruginosa, which may be a result of their similarity to the Pseudomonas quinolone signal (PQS) quorum sensing autoinducer. This provided new insights regarding the effect of N-substitution in
  • 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
  • chemical probes. It has been proposed that such a strategy may perturb bacterial virulence and pathogenicity associated with QS, thus conferring a therapeutic benefit, without applying a selection pressure for resistance [6]. Whilst recent experiments suggest that resistance may still emerge, it has been
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Published 19 Oct 2018

Non-native autoinducer analogs capable of modulating the SdiA quorum sensing receptor in Salmonella enterica serovar Typhimurium

  • Matthew J. Styles and
  • Helen E. Blackwell

Beilstein J. Org. Chem. 2018, 14, 2651–2664, doi:10.3762/bjoc.14.243

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  • Matthew J. Styles Helen E. Blackwell Department of Chemistry, University of Wisconsin–Madison, 1101 University Avenue, Madison, WI 53706, USA 10.3762/bjoc.14.243 Abstract Quorum sensing (QS) allows many common bacterial pathogens to coordinate group behaviors such as virulence factor production
  • controlling, virulence in these bacteria. To date, few studies have characterized the features of AHLs and other small molecules capable of SdiA agonism, and no SdiA antagonists have been reported. Herein, we report the screening of a set of AHL analogs to both uncover agonists and antagonists of SdiA and to
  • has lagged behind [4]. In recent years, non-bacteriocidal approaches have emerged as a new therapeutic strategy to treat infection with potentially a lesser propensity for resistance development and spread [4][5][6]. Interfering with the regulation of virulence phenotypes represents one such approach
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Published 17 Oct 2018
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