76924-95-3

Usage

Uses

Used in Diagnostic Applications:
N-(Ketocaproyl)-D,L-homoserine lactone (CAS# 76924-95-3) is used in systems, methods, and kits for the diagnosis and monitoring of bacteria-related conditions. It aids in detecting the binding of a quorum sensing molecule in biological samples, which is crucial for understanding and managing bacterial infections and diseases.
Used in Research Applications:
N-(Ketocaproyl)-D,L-homoserine lactone is used as a research tool to study the mechanisms of quorum sensing in bacteria. This knowledge can help in developing new strategies for controlling bacterial communication and virulence, ultimately leading to the development of novel antimicrobial agents and therapies.

InChI:InChI=1/C10H15NO4/c1-4(2)6(12)10-7(15-9(10)14)5(3)8(13)11-10/h4-7,12H,1-3H3,(H,11,13)/t5-,6+,7+,10-/m1/s1

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Relevant academic research and scientific papers

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

Synthesis of a biotin-labeled quorum-sensing molecule: Towards a general method for target identification

The synthesis of bacterial quorum-sensing regulator N- (3-oxohexanoyl)-L- homoserine lactone (OHHL) and biotin-tagged OHHL is reported. The latter will be applied to developing a general method to address the 'target identification problem' in chemical genetics. Georg Thieme Verlag Stuttgart.

ACYL HOMOSERINE LACTONES FOR INHIBITION OF CELL GROWTH

The present invention provides a method for inhibiting the growth of cancer cells using AHLs of the general formula CX-homoserine lactone where "X" represents a number of between 5 and 14 carbon atoms in the acyl chain of the AHL. The method comprises the step of administering to an individual an amount of an AHL effective to inhibit the growth of cancer cells. Also provided is a method for enhancing the effect of a chemotherapeutic agent comprising the step of administering to an individual the chemotherapeutic agent and an amount of an AHL effective to enhance the cancer cell growth inhibitory effect of the chemotherapeutic agent.

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.

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

A novel convenient route to the naturally occurring 3-oxoacyl-L-homoserinelactones and related bacterial autoinducers

The naturally occurring 3-oxohexanoyl-L-homoserinelactone (1a), a bacterial autoinducer has been prepared in 47% overall yield by condensing stable 3-oxohexanoic acid (2), prepared by hydrolysis from the corresponding ester (3), with L-homoserinelactone using hydroxybenzotriazole (HOBT) and dicyclohexylcarbodiimide (DCC) in non-aqueous media.