147795-40-2

Usage

Uses

Used in Research Applications:
N-(3-Oxodecanoyl)-L-homoserine lactone is used as a research tool for studying the signaling involved in the regulation of bacterial quorum sensing. This application is important for understanding how bacteria communicate and coordinate their actions, which can have implications for developing new strategies to control bacterial infections and biofilm formation.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, N-(3-Oxodecanoyl)-L-homoserine lactone may be used as a potential therapeutic target or as a component in the development of new drugs aimed at disrupting bacterial quorum sensing. By targeting this signaling molecule, it may be possible to inhibit bacterial communication and reduce their ability to cause disease or form resistant biofilms.
Used in Biotechnology Applications:
N-(3-Oxodecanoyl)-L-homoserine lactone could also be utilized in biotechnology applications, such as the development of biosensors or the engineering of bacteria with altered quorum sensing capabilities. This could lead to novel applications in areas such as environmental monitoring, bioremediation, or the production of bioactive compounds.

Biochem/physiol Actions

Acyl homoserine lactone used as an autoinducer of quorum signaling by Pseudomonas putida, Yersinia enterocolitica, and other Gram-negative bacteria.

Upstream product

• 2185-03-7 L-homoserine lactone hydrochloride 
• 66696-81-9 5-(1-hydroxyoctylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione 
• 13283-92-6 β-ketodecanoic acid 
• 2185-02-6 L-homoserine lactone 
• 103576-44-9 2,2-dimethyl-5-octanoyl-1,3-dioxane-4,6-dione 
• 6305-38-0 (S)-(-)-α-amino-γ-butyrolactone hydrobromide 
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• 868054-76-6 2-(2-heptyl-1,3-dioxolan-2-yl)acetic acid 
• 124-07-2 Octanoic acid 
• 111-64-8 n-octanoic acid chloride 
• 22348-96-5 methyl 3-oxodecanoate 
• 821-55-6 2-Nonanone 
• 71989-28-1 N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine 

Downstream Products

• 192883-12-8 N-(3-hydroxy-decanoyl)-L-homoserine lactone 

Relevant academic research and scientific papers

Disruption of biofilm formation by the human pathogen Acinetobacter baumannii using engineered quorum-quenching lactonases

Acinetobacter baumannii is a major human pathogen associated with multidrug-resistant nosocomial infections; its virulence is attributed to quorum-sensing-mediated biofilm formation, and disruption of biofilm formation is an attractive antivirulence strategy. Here, we report the first successful demonstration of biofilm disruption in a clinical isolate of A. baumannii S1, using a quorum-quenching lactonase obtained by directed evolution; this engineered lactonase significantly reduced the biomass of A. baumannii-associated biofilms, demonstrating the utility of this antivirulence strategy. Copyright

Robust routes for the synthesis of N-acylated-l-homoserine lactone (AHL) quorum sensing molecules with high levels of enantiomeric purity

The ready availability of native quorum sensing molecules and related structural analogues is of significant biological interest in the development of methods to manipulate bacterial quorum sensing systems in a useful fashion. In this Letter we report robust routes for the synthesis of a range of N-acylated-l-homoserine lactone (AHL) quorum sensing molecules. Crucially, we have analysed the enantiopurity of the final AHLs and in all cases, excellent levels were observed.

Identification and Quantification of N-Acyl Homoserine Lactones Involved in Bacterial Communication by Small-Scale Synthesis of Internal Standards and Matrix-Assisted Laser Desorption/Ionization Mass Spectrometry

N-acyl homoserine lactones (AHL) are small signal molecules involved in the quorum sensing of many gram-negative bacteria, and play an important role in biofilm formation and pathogenesis. Present analytical methods for identification and quantification of AHL require time-consuming sample preparation steps and are hampered by the lack of appropriate standards. By aiming at a fast and straightforward method for AHL analytics, we investigated the applicability of matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF MS). Suitable MALDI matrices, including crystalline and ionic liquid matrices, were tested and the fragmentation of different AHL in collision-induced dissociation MS/MS was studied, providing information about characteristic marker fragments ions. Employing small-scale synthesis protocols, we established a versatile and cost-efficient procedure for fast generation of isotope-labeled AHL standards, which can be used without extensive purification and yielded accurate standard curves. Quantitative analysis was possible in the low pico-molar range, with lower limits of quantification reaching from 1 to 5 pmol for different AHL. The developed methodology was successfully applied in a quantitative MALDI MS analysis of low-volume culture supernatants of Pseudomonas aeruginosa. [Figure not available: see fulltext.].

Haloperoxidase mediated quorum quenching by Nitzschia cf pellucida: Study of the metabolization of N-Acyl homoserine lactones by a benthic diatom

Diatoms are known to produce a variety of halogenated compounds, which were recently shown to have a role in allelopathic interactions between competing species. The production of these compounds is linked to haloperoxidase activity. This research, has shown that this system may also be involved in diatom-bacteria interactions via the H2O2 dependent inactivation of a type of quorum sensing (QS) molecule, i.e., N-β-ketoacylated homoserine lactones (AHLs), by a natural haloperoxidase system from the benthic diatom Nitzschia cf pellucida. The AHL degradation pathway towards corresponding halogenated derivatives was elucidated via HPLC-MS analysis and the synthesis of a broad series of novel halogenated AHL analogues as reference compounds. Furthermore, their biological activity as quorum sensing modulators was directly compared and evaluated against a series of naturally occurring β-keto-AHLs. It has been demonstrated that the loss of the QS activity results from the final cleavage of the halogenated N-acyl chain of the signal molecules.

MODULATION OF BACTERIAL QUORUM SENSING WITH SYNTHETIC LIGANDS

The present invention provides compounds and methods for modulation of the quorum sensing of bacteria. In an embodiment, the compounds of the present invention are able to act as replacements for naturally occurring bacterial quorum sensing ligands in a l

COMPOUNDS AND METHODS FOR MODULATING COMMUNICATION AND VIRULENCE IN QUORUM SENSING BACTERIA

The present invention provides compositions and methods for modulating the communication and virulence of quorum sensing bacteria. In various exemplary embodiments, the invention provides a combinatorial library of quorum sensing compounds including synthetic analogs of naturally occurring and non-naturally occurring acyl-homoserine lactone (AHL) analogs, and methods of synthesizing and using these compounds.

Synthesis of Pseudomonas quorum-sensing autoinducer analogs and structural entities required for induction of apoptosis in macrophages

The synthesis of the analogs of N-3-oxododecanoyl-l-homoserine lactone (1) and their structure-activity relationship for the apoptotic induction in macrophages, P388D1 cells, are described. It was revealed that the position of the oxo group in the acyl si

Small molecule inhibitors of bacterial quorum sensing and biofilm formation

Bacteria monitor their local population densities using small molecules (or autoinducers) in a process known as quorum sensing. Here, we report a new and efficient synthetic route to naturally occurring bacterial autoinducers [N-acyl L-homoserine lactones (AHLs)] that is readily amenable to the synthesis of analogues. This route has been applied in the first synthesis of a library of non-native AHLs. Evaluation of these compounds in bacterial reporter gene and biofilm assays has revealed a potent set of quorum sensing antagonists. These ligands will serve as valuable new tools to explore the role of quorum sensing in bacterial pathogenesis. Copyright

Synthetic analogues of the bacterial signal (quorum sensing) molecule N-(3-oxododecanoyl)-L-homoserine lactone as immune modulators

Comparative immune modulatory activity for a range of synthetic analogues of a Pseudomonas aeruginosa signal molecule, N-(3-oxododecanoyl)-L-homoserine lactone (30, C12-HSL), is described. Twenty-four single or combination systematic alteration