Synthesis of d-desthiobiotin-AI-2 as a novel chemical probe for autoinducer-2 quorum sensing receptors

Miranda, Vanessa; Torcato, Inês M.; Xavier, Karina B.; Ventura, M. Rita

doi:10.1016/j.bioorg.2019.103200

Cited by 13 publications

(8 citation statements)

References 28 publications

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“…1a ) 6 , 7 . DPD is generally synthetized by the enzyme LuxS 1 , 4 , in addition to two non-canonical AI-2 synthesis pathways proposed to be present in some bacteria lacking the luxS gene 8 . To date, two AI-2 forms engaged by corresponding bacterial receptors have been identified, including the boron-containing DPD derivative S -2-methyl-2,3,3,4-tetrahydroxytetrahydrofuran-borate ( S -THMF-borate) recognized by LuxP present only in Vibrio spp.…”

Section: Introductionmentioning

confidence: 99%

“…The AI-2 receptors LuxP and LsrB are both periplasmic binding proteins (PBPs) homologous to ribose binding proteins but share only limited similarity (~11% identity) in their primary sequences 2 , 9 . LuxP bound to AI-2 converts the activity of the transmembrane sensor histidine kinase (HK) LuxQ from kinase to phosphatase, thus regulating gene expression and changing many density-dependent phenotypes such as bioluminescence, biofilm formation and virulence factor production 1 , 4 , 8 , whereas the LsrB-AI-2 complex engages the membrane components of the ATP-binding cassette transporter system Lsr to deliver AI-2 into cells 9 , 11 . In addition, LsrB bound to AI-2 is able to drive chemotactic responses in Escherichia coli through interactions with the periplasmic sensory domain of the chemoreceptor Tsr 14 , 15 .…”

Section: Introductionmentioning

confidence: 99%

“…For example, in bacterial pathogens such as Pseudomonas aeruginosa and Enterococcus faecalis , gene expression and phenotypes such as biofilm formation and the production of virulence factors are regulated by AI-2 16 – 19 . However, earlier efforts to identify potential AI-2 receptors using bioinformatics approaches as well as chemical probes have not been successful 8 , 13 , 20 , suggesting that alternative strategies may be required to resolve this issue. The inability to identify AI-2 sensors in these AI-2-responsive bacteria have greatly hampered our understanding of the role of AI-2 as a universal signal participating in intra- and interspecies communication 3 , 4 , 8 , 13 , 20 .…”

Section: Introductionmentioning

confidence: 99%

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Sensing of autoinducer-2 by functionally distinct receptors in prokaryotes

et al. 2020

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Autoinducer-2 (AI-2) is a quorum sensing signal that mediates communication within and between many bacterial species. However, its known receptors (LuxP and LsrB families) are not found in all the bacteria capable of responding to this signaling molecule. Here, we identify a third type of AI-2 receptor, consisting of a dCACHE domain. AI-2 binds to the dCACHE domain of chemoreceptors PctA and TlpQ of Pseudomonas aeruginosa, thus inducing chemotaxis and biofilm formation. Boron-free AI-2 is the preferred ligand for PctA and TlpQ. AI-2 also binds to the dCACHE domains of histidine kinase KinD from Bacillus subtilis and diguanylate cyclase rpHK1S-Z16 from Rhodopseudomonas palustris, enhancing their enzymatic activities. dCACHE domains (especially those belonging to a subfamily that includes the AI-2 receptors identified in the present work) are present in a large number of bacterial and archaeal proteins. Our results support the idea that AI-2 serves as a widely used signaling molecule in the coordination of cell behavior among prokaryotic species.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Sensing of autoinducer-2 by functionally distinct receptors in prokaryotes

et al. 2020

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“…LsrB, a receptor for signaling molecules, transports AI-2 into cells [18]. To verify the role of lsrB in the signal transmission of the AI-2-induced phage defense mechanism, we employed ΔlsrB to explore the influence of AI-2 on the number of plaques formed, the bacterial growth rate, and metabolic activity.…”

Section: The Role Of Lsrb In Signal Transmissionmentioning

confidence: 99%

Autoinducer‐2‐mediated quorum‐sensing system resists T4 phage infection in Escherichia coli

et al. 2021

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In response to the restriction of nutrients and predation by natural enemies, bacteria have evolved complex coping strategies to ensure the reproduction and survival of individual species. Quorum sensing (QS) is involved in the bacterial response to phage predation and regulation of cellular metabolism. However, to date, no clear evidence exists regarding the involvement of autoinducer‐2 (AI‐2)‐mediated QS systems in Escherichia coli in response to the challenges of nutrient restriction and phage infection. In this study, the role of the AI‐2‐mediated QS system in resisting T4 phage infection and regulating cell mechanisms in E. coli was revealed for the first time. This effect of the AI‐2‐mediated QS was achieved by simultaneously downregulating the T4 absorption site and carbon and glucose metabolism. Additionally, we found that lsrB, a metabolic brake, participates in AI‐2‐mediated regulation and maintenance of the normal metabolic balance of cells. The novel phage defense strategy and regulation and maintenance of cellular metabolism effectively limited the expansion of the phage population.

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“…AI-2 regulates various physiological functions of bacteria, such as bioluminescence, toxin production, and proteome modulation [ 14 , 17 ]. Two types of AI-2 receptors were firstly identified involving LuxP that was only found in Vibrio and LsrB and were detected in E. coli and Salmonella [ 18 , 19 , 20 , 21 , 22 , 23 , 24 ]. The latest research demonstrates that the proteins with a dCACHE (double calcium channels and chemotaxis receptors) domain, including KinD in B. subtilis , serve as a novel type of AI-2 receptors [ 25 ].…”

Section: Introductionmentioning

confidence: 99%

Two Lysine Sites That Can Be Malonylated Are Important for LuxS Regulatory Roles in Bacillus velezensis

Cao

Fan

et al. 2021

Microorganisms

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S-ribosylhomocysteine lyase (LuxS) has been shown to regulate bacterial multicellular behaviors, typically biofilm formation. However, the mechanisms for the regulation are still mysterious. We previously identified a malonylation modification on K124 and K130 of the LuxS in the plant growth-promoting rhizobacterium B. velezensis (FZB42). In this work, we investigated the effects of the two malonylation sites on biofilm formation and other biological characteristics of FZB42. The results showed that the K124R mutation could severely impair biofilm formation, swarming, and sporulation but promote AI-2 production, suggesting inhibitory effects of high-level AI-2 on the features. All mutations (K124R, K124E, K130R, and K130E) suppressed FZB42 sporulation but increased its antibiotic production. The double mutations generally had a synergistic effect or at least equal to the effects of the single mutations. The mutation of K130 but not of K124 decreased the in vitro enzymatic activity of LuxS, corresponding to the conservation of K130 among various Bacillus LuxS proteins. From the results, we deduce that an alternative regulatory circuit may exist to compensate for the roles of LuxS upon its disruption. This study broadens the understanding of the biological function of LuxS in bacilli and underlines the importance of the two post-translational modification sites.

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Synthesis of d-desthiobiotin-AI-2 as a novel chemical probe for autoinducer-2 quorum sensing receptors

Cited by 13 publications

References 28 publications

Sensing of autoinducer-2 by functionally distinct receptors in prokaryotes

Sensing of autoinducer-2 by functionally distinct receptors in prokaryotes

Autoinducer‐2‐mediated quorum‐sensing system resists T4 phage infection in Escherichia coli

Two Lysine Sites That Can Be Malonylated Are Important for LuxS Regulatory Roles in Bacillus velezensis

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