2-Heptyl-4-quinolone
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| Category | Enzyme inhibitors |
| Catalog number | BBF-01817 |
| CAS | 40522-46-1 |
| Molecular Weight | 243.34 |
| Molecular Formula | C16H21NO |
| Purity | 95% |
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Description
It is produced by the strain of Pseudomonas pyocyanea, P. aeruginosa, P. methanica. It has weak anti-gram-positive bacterial activity. It can inhibit the microsomal respiratory chain and 5-lipoxygenase of cytochrome BC1 complex, and antagonize the antibacterial activity of dihydrostreptomycin.
Specification
| Synonyms | 2-Heptyl-4-hydroxyquinolinone; Antibiotic MY 12-62a; 2-Heptyl-4-(1H)-quinolinone; 2-heptylquinolin-4(1H)-one; 2-heptyl-4-quinolone; HHQ; 4(1H)-Quinolone, 2-heptyl-; 2-n-Heptyl-4-quinolone; 4-Hydroxy-2-heptylquinolone; Dihydroakutine; Pseudane VII |
| Storage | Store at 2-8°C |
| IUPAC Name | 2-heptyl-1H-quinolin-4-one |
| Canonical SMILES | CCCCCCCC1=CC(=O)C2=CC=CC=C2N1 |
| InChI | InChI=1S/C16H21NO/c1-2-3-4-5-6-9-13-12-16(18)14-10-7-8-11-15(14)17-13/h7-8,10-12H,2-6,9H2,1H3,(H,17,18) |
| InChI Key | UYRHHBXYXSYGHA-UHFFFAOYSA-N |
Properties
| Appearance | Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Boiling Point | 361.5±42.0°C at 760 mmHg |
| Melting Point | 122-126°C |
| Density | 1.013±0.06 g/cm3 |
| Solubility | Soluble in Ethanol, DMSO (5 mg/mL) |
Reference Reading
1.The role of 2,4-dihydroxyquinoline (DHQ) in Pseudomonas aeruginosa pathogenicity.
Gruber JD1, Chen W1, Parnham S1, Beauchesne K2, Moeller P2, Flume PA3, Zhang YM1. PeerJ. 2016 Jan 7;4:e1495. doi: 10.7717/peerj.1495. eCollection 2016.
Bacteria synchronize group behaviors using quorum sensing, which is advantageous during an infection to thwart immune cell attack and resist deleterious changes in the environment. In Pseudomonas aeruginosa, the Pseudomonas quinolone signal (Pqs) quorum-sensing system is an important component of an interconnected intercellular communication network. Two alkylquinolones, 2-heptyl-4-quinolone (HHQ) and 2-heptyl-3-hydroxy-4-quinolone (PQS), activate transcriptional regulator PqsR to promote the production of quinolone signals and virulence factors. Our work focused on the most abundant quinolone produced from the Pqs system, 2,4-dihydroxyquinoline (DHQ), which was shown previously to sustain pyocyanin production and antifungal activity of P. aeruginosa. However, little is known about how DHQ affects P. aeruginosa pathogenicity. Using C. elegans as a model for P. aeruginosa infection, we found pqs mutants only able to produce DHQ maintained virulence towards the nematodes similar to wild-type.
2.A Bacterial Quorum-Sensing Precursor Induces Mortality in the Marine Coccolithophore, Emiliania huxleyi.
Harvey EL1, Deering RW2, Rowley DC2, El Gamal A3, Schorn M3, Moore BS3, Johnson MD4, Mincer TJ5, Whalen KE5. Front Microbiol. 2016 Feb 3;7:59. doi: 10.3389/fmicb.2016.00059. eCollection 2016.
Interactions between phytoplankton and bacteria play a central role in mediating biogeochemical cycling and food web structure in the ocean. However, deciphering the chemical drivers of these interspecies interactions remains challenging. Here, we report the isolation of 2-heptyl-4-quinolone (HHQ), released by Pseudoalteromonas piscicida, a marine gamma-proteobacteria previously reported to induce phytoplankton mortality through a hitherto unknown algicidal mechanism. HHQ functions as both an antibiotic and a bacterial signaling molecule in cell-cell communication in clinical infection models. Co-culture of the bloom-forming coccolithophore, Emiliania huxleyi with both live P. piscicida and cell-free filtrates caused a significant decrease in algal growth. Investigations of the P. piscicida exometabolome revealed HHQ, at nanomolar concentrations, induced mortality in three strains of E. huxleyi. Mortality of E. huxleyi in response to HHQ occurred slowly, implying static growth rather than a singular loss event (e.
3.A structure activity-relationship study of the bacterial signal molecule HHQ reveals swarming motility inhibition in Bacillus atrophaeus.
Reen FJ1, Shanahan R, Cano R, O'Gara F, McGlacken GP. Org Biomol Chem. 2015 May 21;13(19):5537-41. doi: 10.1039/c5ob00315f.
The sharp rise in antimicrobial resistance has been matched by a decline in the identification and clinical introduction of new classes of drugs to target microbial infections. Thus new approaches are being sought to counter the pending threat of a post-antibiotic era. In that context, the use of non-growth limiting small molecules, that target virulence behaviour in pathogens, has emerged as a solution with real clinical potential. We have previously shown that two signal molecules (HHQ and PQS) from the nosocomial pathogen Pseudomonas aeruginosa have modulatory activity towards other microorganisms. This current study involves the synthesis and evaluation of analogues of HHQ towards swarming and biofilm virulence behaviour in Bacillus atrophaeus, a soil bacterium and co-inhibitor with P. aeruginosa. Compounds with altered C6-C8 positions on the anthranilate-derived ring of HHQ, display a surprising degree of biological specificity, with certain candidates displaying complete motility inhibition.
4.From in vitro to in cellulo: structure-activity relationship of (2-nitrophenyl)methanol derivatives as inhibitors of PqsD in Pseudomonas aeruginosa.
Storz MP1, Allegretta G, Kirsch B, Empting M, Hartmann RW. Org Biomol Chem. 2014 Aug 28;12(32):6094-104. doi: 10.1039/c4ob00707g. Epub 2014 Jun 9.
Recent studies have shown that compounds based on a (2-nitrophenyl)methanol scaffold are promising inhibitors of PqsD, a key enzyme of signal molecule biosynthesis in the cell-to-cell communication of Pseudomonas aeruginosa. The most promising molecule displayed anti-biofilm activity and a tight-binding mode of action. Herein, we report on the convenient synthesis and biochemical evaluation of a comprehensive series of (2-nitrophenyl)methanol derivatives. The in vitro potency of these inhibitors against recombinant PqsD as well as the effect of selected compounds on the production of the signal molecules HHQ and PQS in P. aeruginosa were examined. The gathered data allowed the establishment of a structure-activity relationship, which was used to design fluorescent inhibitors, and finally, led to the discovery of (2-nitrophenyl)methanol derivatives with improved in cellulo efficacy providing new perspectives towards the application of PqsD inhibitors as anti-infectives.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
