106983-28-2

Usage

Uses

Used in Pharmaceutical Industry:
N-CAPROYL-L-HOMOSERINE LACTONE is used as a signaling molecule for promoting the expression of violacein in Chromobacterium violaceum mutants. This application is particularly relevant in the development of new drugs and therapies, as it can help researchers understand the underlying mechanisms of bacterial communication and potentially exploit them for therapeutic purposes.
Used in Research and Development:
In the field of research and development, N-CAPROYL-L-HOMOSERINE LACTONE serves as a valuable tool for studying the role of homoserine lactones in bacterial communication. By inducing violacein expression in specific bacterial mutants, researchers can gain insights into the complex signaling networks that govern bacterial behavior, which can ultimately lead to the discovery of novel targets for antibiotic development and other applications.
Used in Biotechnology:
N-CAPROYL-L-HOMOSERINE LACTONE can also be utilized in the biotechnology industry for the development of genetically engineered organisms with enhanced capabilities. By understanding the role of N-CAPROYL-L-HOMOSERINE LACTONE in bacterial communication, scientists can potentially manipulate the expression of specific genes to create organisms with improved characteristics, such as increased resistance to diseases or enhanced production of valuable compounds.

Biochem/physiol Actions

N-Hexanoyl-DL-homoserine lactone is a member of N-acyl-homoserine lactone family. N-acylhomoserine lactones (AHL) regulate gene expression in gram-negative bacteria, such as Echerichia and Salmonella and are involved in quorum sensing, cell to cell communication among bacteria. Some AHLs are potent chemoattractants for human immune cells such as neutrophils.

Upstream product

• 6305-38-0 α-amino-γ-butyrolactone hydrobromide 
• 142-62-1 hexanoic acid 
• 142-61-0 Hexanoyl chloride 

Downstream Products

• 21394-52-5 N-hexanoyl-methionine 

Relevant academic research and scientific papers

Synthesis and biological evaluation of new N-acyl-homoserine-lactone analogues, based on triazole and tetrazole scaffolds, acting as LuxR-dependent quorum sensing modulators

New analogues of N-acyl-homoserine-lactone (AHL), in which the amide was replaced by a triazole or tetrazole ring, were prepared and tested for their activity as LuxR-dependent QS modulators. Several compounds showed a level of antagonistic or agonistic activity, notably some 1,4-triazolic and 1,5-tetrazolic derivatives, whereas the 2,5-tetrazolic compounds were inactive. In 1,5-tetrazoles, substituted with butyrolactone and an alkyl chain, the activity was reversed, depending on the connection between the lactone and the tetrazole. The C-N connected compounds were agonists whereas the C-C connected ones were antagonists.

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.

Acyl-homoserine lactones from Erwinia psidii R. IBSBF 435T, a guava phytopathogen (Psidium guajava L.)

The phytopathogen Erwinia psidii R. IBSBF 435T causes rot in branches, flowers, and fruits of guava (Psidium guajava L.), being responsible for crop losses, and has no effective control. It was demonstrated that this strain produces two compounds [S-(-)-N-hexanoyl and N-heptanoyl-homoserine lactone], both belonging to the class of quorum-sensing signaling substances. A protocol using gas chromatography - flame ionization detection with chiral stationary phase is described for the absolute configuration determination of a natural acyl-homoserine lactone. Biological assays with specific reporter and synthesis of identified substances are also described. This is the first report on the N-heptanoyl-homoserine lactone occurrence in the Erwinia genus.