(Z)-2-decenoic acid - CAS 15790-91-7
Catalog number: 15790-91-7
Category: Inhibitor
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Molecular Formula:
C10H18O2
Molecular Weight:
170.25
COA:
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Targets:
Others
Description:
Microorganisms commonly accumulate at interfaces as part of biofilms held together by a matrix of hydrated extracellular polymeric substances. cis-2-Decenoic acid is an unsaturated short chain fatty acid that is secreted by P. aeruginosa and induces a dispersion response in biofilms formed by gram-negative and gram-positive bacteria, as well as by the yeast C. albicans. It effectively promotes dispersion of P. aeruginosa biofilms over a concentration range of 1.0 to 10 nM.
Purity:
>98%
Synonyms:
cis-2-Decenoic acid
MSDS:
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InChIKey:
WXBXVVIUZANZAU-HJWRWDBZSA-N
InChI:
InChI=1S/C10H18O2/c1-2-3-4-5-6-7-8-9-10(11)12/h8-9H,2-7H2,1H3,(H,11,12)/b9-8-
Canonical SMILES:
CCCCCCCC=CC(=O)O
1.Control of Biofilms with the Fatty Acid Signaling Molecule cis-2-Decenoic Acid.
Marques CN;Davies DG;Sauer K Pharmaceuticals (Basel). 2015 Nov 25;8(4):816-35. doi: 10.3390/ph8040816.
Biofilms are complex communities of microorganisms in organized structures attached to surfaces. Importantly, biofilms are a major cause of bacterial infections in humans, and remain one of the most significant challenges to modern medical practice. Unfortunately, conventional therapies have shown to be inadequate in the treatment of most chronic biofilm infections based on the extraordinary innate tolerance of biofilms to antibiotics. Antagonists of quorum sensing signaling molecules have been used as means to control biofilms. QS and other cell-cell communication molecules are able to revert biofilm tolerance, prevent biofilm formation and disrupt fully developed biofilms, albeit with restricted effectiveness. Recently however, it has been demonstrated that Pseudomonas aeruginosa produces a small messenger molecule cis-2-decenoic acid (cis-DA) that shows significant promise as an effective adjunctive to antimicrobial treatment of biofilms. This molecule is responsible for induction of the native biofilm dispersion response in a range of Gram-negative and Gram-positive bacteria and in yeast, and has been shown to reverse persistence, increase microbial metabolic activity and significantly enhance the cidal effects of conventional antimicrobial agents.
2.Structural characterization of a Δ
Liu L;Li T;Peng CT;Sun CZ;Li CC;Xiao QJ;He LH;Wang NY;Song YJ;Zhu YB;Li H;Kang M;Tang H;Xiong X;Bao R J Biomol Struct Dyn. 2018 Jul 27:1-22. doi: 10.1080/07391102.2018.1495102. [Epub ahead of print]
Gene PA4980 from Pseudomonas aeruginosa encodes a putative enoyl-coenzyme A hydratase/isomerase that is associated with the function of the biofilm dispersion-inducing signal molecule cis-2-decenoic acid. To elucidate the role of PA4980 in cis-2-decenoic acid biosynthesis, we reported the crystal structure of its protein product at 2.39 Å. The structural analysis and substrate binding prediction suggest that it acts as a monofunctional enoyl-coenzyme A isomerase, implicating an alternative pathway of the cis-2-decenoic acid synthesis.
3.A combination of cis-2-decenoic acid and chlorhexidine removes dental plaque.
Rahmani-Badi A;Sepehr S;Babaie-Naiej H Arch Oral Biol. 2015 Nov;60(11):1655-61. doi: 10.1016/j.archoralbio.2015.08.006. Epub 2015 Aug 12.
OBJECTIVES: ;To investigate the ability of cis-2-decenoic acid (C2DA) to induce dispersion in single-species biofilms formed by Streptococcus mutans and Candida albicans, as well as to remove their bacterial-fungal dual-species biofilms when combined with low concentrations of chlorhexidine (CHX).;METHODS: ;For biofilm dispersal bioassays, single-species biofilms of S. mutans and C. albicans were grown on the inside surface of petri dishes, using a semi-batch culture method in which the medium was replaced every 24h for 5 days. Biofilms were then treated with very low concentrations of C2DA (100 and 310 nM) for 1h to release cells into the bulk liquid and to evaluate dispersed cell number by measuring the optical density (OD). To assess the ability of C2DA combined CHX treatments to remove tested microorganisms' dual-species biofilms, they were grown on saliva-coated hydroxyapatite (sHA) discs for 48 h and then were treated with three different concentrations of CHX (0.08%, 0.06% and 0.04%) alone or in combination with indicated concentrations of C2DA for 1 min twice daily for 3 subsequent days. Biofilms were then either subjected to the field emission scanning electron microscopy (FESEM) analysis or harvested and colony forming units (CFUs) were counted after plating on agar.
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CAS 15790-91-7 (Z)-2-decenoic acid

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