ArticleThe Journal of organic chemistry2011
Probing autoinducer-2 based quorum sensing: the biological consequences of molecules unable to traverse equilibrium states.
Article in The Journal of organic chemistry, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
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Who cites it
11 citing papers in PubMed, 24 citations in OpenAlex.
- Co-Culture Reveals the Quorum-Sensing Regulatory Mechanism of Bacteriocin PlnJK Synthesis inMicroorganisms · 2026Article
- Activity of Organoboron Compounds against Biofilm-Forming Pathogens.Antibiotics (Basel, Switzerland) · 2024Review
- Clinical and environmental genotypes of Vibrio vulnificus display distinct, quorum-sensing-mediated, chitin detachment dynamics.Pathogens and disease · 2015Article
- Dissecting AI-2-mediated quorum sensing through C5-analogue synthesis and biochemical analysis.Tetrahedron · 2015Article
- Interspecific quorum sensing mediates the resuscitation of viable but nonculturable vibrios.Applied and environmental microbiology · 2014Article
- Phenotypes of Campylobacter jejuni luxS mutants are depending on strain background, kind of mutation and experimental conditions.PloS one · 2014Article
- Small molecule inhibitors of AI-2 signaling in bacteria: state-of-the-art and future perspectives for anti-quorum sensing agents.International journal of molecular sciences · 2013Article
- C4-alkoxy-HPD: a potent class of synthetic modulators surpassing nature in AI-2 quorum sensing.Journal of the American Chemical Society · 2012Article
- Analysis of bacterial biofilms using NMR-based metabolomics.Future medicinal chemistry · 2012Review
- Uncharacterized 4,5-dihydroxy-2,3-pentanedione (DPD) molecules revealed through NMR spectroscopy: implications for a greater signaling diversity in bacterial species.Angewandte Chemie (International ed. in English) · 2012Article
- A pro-drug approach for selective modulation of AI-2-mediated bacterial cell-to-cell communication.Sensors (Basel, Switzerland) · 2012Article
Corrections and comments
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
Abstract
Bacteria have developed a cell-to-cell communication system, termed quorum sensing (QS), which allows for the population-dependent coordination of their behavior via the exchange of chemical signals. Autoinducer-2 (AI-2), a class of QS signals derived from 4,5-dihydroxy-2,3-pentandione (DPD), has been revealed as a universal signaling molecule in a variety of bacterial species. In spite of considerable interest, the study of putative AI-2 based QS systems remains a challenging topic in part due to the rapid interconversion between the linear and cyclic forms of DPD. Herein, we report the design and development of efficient syntheses of carbocyclic analogues of DPD, which are locked in the cyclic form. The synthetic analogues were evaluated for the modulation of AI-2-based QS in Vibrio harveyi and Salmonella typhimurium. No agonists were uncovered in either V. harveyi or S. typhimurium assay, whereas weak to moderate antagonists were found against V. harveyi. On the basis of NMR analyses and DFT calculations, the heterocyclic oxygen atom within DPD appears necessary to promote hydration at the C3 position of cyclic DPD to afford the active tetrahydroxy species. These results also shed light on the interaction between the heterocyclic oxygen atom and receptor proteins as well as the importance of the linear form and dynamic equilibrium of DPD as crucial requirements for activation of AI-2 based QS circuits.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.