A bacterial quorum-sensing signaling molecule
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2-heptyl-3-hydroxy-4(1H)-Quinolone

Item No. 29186

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-heptyl-3-hydroxy-4(1H)-quinolinone
CAS Number
108985-27-9
Synonyms
  • PQS
  • Pseudomonas Quinolone Signal
Molecular Formula
C16H21NO2
Formula Weight
259.3
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Methanol: soluble
λmax
216, 251, 342 nm
SMILES
OC1=C(CCCCCCC)NC2=CC=CC=C2C1=O
InChi Code
InChI=1S/C16H21NO2/c1-2-3-4-5-6-11-14-16(19)15(18)12-9-7-8-10-13(12)17-14/h7-10,19H,2-6,11H2,1H3,(H,17,18)
InChi Key
CEIUIHOQDSVZJQ-UHFFFAOYSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $72

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    10 mg

    $134

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    25 mg

    $209

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    Cayman Chemical
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    Product Description

    2-heptyl-3-hydroxy-4(1H)-Quinolone is a quorum-sensing signaling molecule produced by P. aeruginosa in response to increasing cell density.1 It increases expression of the lasB gene, which encodes the virulence factor elastase, in P. aeruginosa (EC50 = ~30 µM in a reporter cell assay). 2-heptyl-3-hydroxy-4(1H)-Quinolone (60 µM) increases secretion of the metabolite pyocyanin (Item No. 10009594) and the lectin PA-IL, as well as increases biofilm production in P. aeruginosa populations.2 It also reduces iron levels in P. aeruginosa growth media when used at a concentration of 40 µM and acts as an iron chelator in a Fe(III)-sulfate solution.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Pesci, E.C., Milbank, J.B.J., Pearson, J.P., et al. Quinolone signaling in the cell-to-cell communication system of Pseudomonas aeruginosa. Proc. Natl. Acad. Sci. USA 96(20), 11229-11234 (1999).

    2. Diggle, S.P., Winzer, K., Chhabra, S.R., et al. The Pseudomonas aeruginosa quinolone signal molecule overcomes the cell density-dependency of the quorum sensing hierarchy, regulates rhl-dependent genes at the onset of stationary phase and can be produced in the absence of LasR. Mol. Microbiol. 50(1), 29-43 (2003).

    3. Bredenbruch, F., Geffers, R., Nimtz, M., et al. The Pseudomonas aeruginosa quinolone signal (PQS) has an iron-chelating activity. Environ. Microbiol. 8(8), 1318-1329 (2006).