Synthesis and evaluation of thiazolidinedione and dioxazaborocane analogues as inhibitors of AI-2 quorum sensing in Vibrio harveyi
Bibliographic Data
| ID | 23462890 |
|---|---|
| Authors | Gilles Brackman, Clarence Adams, Abed Al Aziz Al Quntar, Della Adams, Lewis H Carlson, Claes D Enk, Izet Karalic, Hans J Nelis, Serge Van Calenbergh, Morris Srebnik, Tom Coenye |
| Year | 2013 |
| Volume | 21 |
| Issue | 3 |
| Pages | 660-667 |
| Publication date | 2013-02-01 |
| Open Access | Yes |
| Type | ARTICLE |
| Venue | Bioorganic & Medicinal Chemistry (JOURNAL) |
| Journal identifiers | ISSN: 0968-0896 • E-ISSN: 0968-0896 |
| Publisher | Elsevier BV (PUBLISHER) |
| DOI | 10.1016/j.bmc.2012.11.055 |
| PMID | 23286963 |
| OpenAlex | W23286963 |
| Language | EN |
| Citations received | 4 |
| References cited | 32 |
Two focused libraries based on two types of compounds, that is, thiazolidinediones and dioxazaborocanes were designed. Structural resemblances can be found between thiazolidinediones and well-known furanone type quorum sensing (QS) inhibitors such as N-acylaminofuranones, and/or acyl-homoserine lactone signaling molecules, while dioxazaborocanes structurally resemble previously reported oxazaborolidine derivatives which antagonized autoinducer 2 (AI-2) binding to its receptor. Because of this, we hypothesized that these compounds could affect AI-2 QS in Vibrio harveyi. Although all compounds blocked QS, the thiazolidinediones were the most active AI-2 QS inhibitors, with EC(50) values in the low micromolar range. Their mechanism of inhibition was elucidated by measuring the effect on bioluminescence in a series of V. harveyi QS mutants and by DNA-binding assays with purified LuxR protein. The active compounds neither affected bioluminescence as such nor the production of AI-2. Instead, our results indicate that the thiazolidinediones blocked AI-2 QS in V. harveyi by decreasing the DNA-binding ability of LuxR. In addition, several dioxazaborocanes were found to block AI-2 QS by targeting LuxPQ.
Ancient history · China · Communism · Dream · Geography · Political science · Communism, Protests, Social Movements · History · Law · Psychology
| Citations per year | 0.27 |
|---|---|
| Citation span | 2011 - 2023 (13) |
| Highly cited | No |