120243-02-9

Usage

Uses

Used in Pharmaceutical Applications:
Myxochelin A is used as an inhibitor of human 5-lipoxygenase (5-LO) for its potential therapeutic effects on conditions related to 5-LO activity, such as asthma and other inflammatory diseases. Its potent inhibition with an IC50 value of 1.9 μM for the recombinant human enzyme makes it a promising candidate for further research and development in this area.
Used in Anticancer Applications:
Myxochelin A is used as an antitumor agent for its potential to exhibit antitumor activity at non-cytotoxic concentrations. Studies suggest that it may be effective against various types of cancer, and its natural product status could offer advantages in terms of reduced side effects and increased patient compliance.
Used in Antimicrobial Applications:
Myxochelin A is used as an antimicrobial agent, particularly against certain Gram-positive bacteria such as B. cereus, S. aureus, and M. luteus. Its activity in an agar diffusion assay at a concentration of 80 μg/disc indicates its potential for development as a novel antimicrobial compound to combat bacterial infections.
Used in Drug Delivery Systems:
Considering the cytotoxicity of Myxochelin A to 26-L5 colon cancer cells at a concentration of 3 μg/ml, it may be utilized in the development of drug delivery systems specifically designed to target cancer cells while minimizing damage to healthy cells. This could involve the use of nanoparticles or other advanced delivery methods to improve the bioavailability and therapeutic outcomes of Myxochelin A in cancer treatment.

InChI:InChI=1/C20H24N2O7/c23-11-12(22-20(29)14-7-4-9-16(25)18(14)27)5-1-2-10-21-19(28)13-6-3-8-15(24)17(13)26/h3-4,6-9,12,23-27H,1-2,5,10-11H2,(H,21,28)(H,22,29)

Upstream product

• 56-87-1 L-lysine 
• 303-38-8 2,3-Dihydroxybenzoic acid 
• 1521-38-6 2,3-dimethoxybenzoic acid 
• 3844-53-9 L-lysine ethyl ester dihydrochloride 

Relevant academic research and scientific papers

Myxochelin biosynthesis: Direct evidence for two- and four-electron reduction of a carrier protein-bound thioester

Microorganisms produce small molecules known as siderophores to scavenge iron from the environment. Insight into iron acquisition in myxobacteria has been provided recently by the sequencing of the gene cluster for the catecholate myxochelins A and B, from the myxobacterium Stigmatella aurantiaca Sg a15. The gene cluster contains enzymes (MxcCDEF) for assembly of 2,3-dihydroxybenzoic acid (DHBA), an amino transferase, MxcL, and a nonribosomal peptide synthetase (NRPS) subunit, MxcG. In the proposed pathway to the myxochelins, two molecules of DHBA are condensed with the two amino groups of lysine, which is itself tethered to the peptidyl carrier protein domain (PCP) of MxcG. The resulting thioester is then reduced by the NADPH-dependent reductase (Red) domain of MxcG to generate an aldehyde intermediate; subsequent Red-catalyzed reduction yields myxochelin A, while transamination by MxcL produces myxochelin B. Although myxochelin A has been obtained successfully in vitro, it has not been possible to date to reconstitute the transamination reaction to give myxochelin B nor to unequivocally establish the intermediacy of the aldehyde. We report here the successful biosynthesis of myxochelin B in vitro. Furthermore, we demonstrate for the first time the existence of an aldehyde intermediate in the four-electron reduction of a PCP-bound thioester. Finally, we show that the relative levels of myxochelin A and B are likely to be controlled by the direct competition of MxcL and the MxcG Red domain for a free aldehyde intermediate. Copyright

A fast and efficient method for the preparation of the 5-lipoxygenase inhibitor myxochelin A

Previous studies revealed the natural product myxochelin A to possess potent antitumour activity at non-cytotoxic concentrations. While its antiinvasive properties are possibly due to an inhibition of matrix metalloproteinases, the antileukemic effects of myxochelin A could be traced to an inhibition of human 5-lipoxygenase. These findings make myxochelin A an interesting model compound for pharmacological investigations. Here, we present a concise synthetic route for the preparation of myxochelin A, which only involves three steps.