2-Heptyl-3-hydroxy-4-quinolone
2-Alkyl-4(1H)-quinolones (AQs) are produced by higher plants of the Rutaceae family as well as by some microorganisms including Alteromonas, Burkholderia and Pseudomonas species. Representatvive of 2-alkyl-3-hydroxy-4(1H)-quinolone (PQS Pseudomonas quinolone signal). PQS which is exclusively used in the complex quorum sensing (QS) system of Pseudomonas aeruginosa, an opportunistic pathogen employing QS to regulate virulence and biofilm development. It is degraded by 2-alkyl-3-hydroxy-4(1H)-quinolone 2,4-dioxygenase HodC. Degradation of PQS by exogenous addition of HodC to planktonic cells of P. aeruginosa attenuated production of virulence factors, and reduced virulence. Pseudomonas aeruginosa is an important opportunistic human pathogens, causing infections in patients immunocompromised or suffering from cystic fibrosis
General
Chemical_Nomenclature : 2-heptyl-3-hydroxy-1H-quinolin-4-one
Canonical SMILES : CCCCCCCC1=C(C(=O)C2=CC=CC=C2N1)O
InChI : 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)
InChIKey : CEIUIHOQDSVZJQ-UHFFFAOYSA-N
Other name(s) : 2-heptyl-3-hydroxy-4(1H)-quinolone || 2-Heptyl-3-hydroxy-quinolone || Pseudomonas quinolone signal || 2-heptyl-3-hydroxy-1H-quinolin-4-one || CHEMBL2426244 || PQS
MW : 259.34
Formula : C16H21NO2
CAS_number :
PubChem : 2763159
UniChem : CEIUIHOQDSVZJQ-UHFFFAOYSA-N
Target
Structures : 6RB3
Families : HOD-cofactorfree-dioxygenase
References (8)
| Title : Enzyme-Mediated Quenching of the Pseudomonas Quinolone Signal (PQS): A Comparison between Naturally Occurring and Engineered PQS-Cleaving Dioxygenases - Arranz San Martin_2022_Biomolecules_12_170 |
| Author(s) : Arranz San Martin A , Vogel J , Wullich SC , Quax WJ , Fetzner S |
| Ref : Biomolecules , 12 :170 , 2021 |
| Abstract : |
| PubMedSearch : Arranz San Martin_2022_Biomolecules_12_170 |
| PubMedID: |
| Gene_locus related to this paper: artsp-hod , strbb-d7bw96 , mycab-x8en65 , nocfa-q5yp20 |
| Title : Structural basis for recognition and ring-cleavage of the Pseudomonas quinolone signal (PQS) by AqdC, a mycobacterial dioxygenase of the alpha\/beta-hydrolase fold family - Wullich_2019_J.Struct.Biol_207_287 |
| Author(s) : Wullich SC , Kobus S , Wienhold M , Hennecke U , Smits SHJ , Fetzner S |
| Ref : J Struct Biol , 207 :287 , 2019 |
| Abstract : |
| PubMedSearch : Wullich_2019_J.Struct.Biol_207_287 |
| PubMedID: 31228546 |
| Gene_locus related to this paper: mycab-x8en65 |
| Title : Mycobacterium abscessus subsp. abscessus Is Capable of Degrading Pseudomonas aeruginosa Quinolone Signals - Birmes_2017_Front.Microbiol_8_339 |
| Author(s) : Birmes FS , Wolf T , Kohl TA , Ruger K , Bange F , Kalinowski J , Fetzner S |
| Ref : Front Microbiol , 8 :339 , 2017 |
| Abstract : |
| PubMedSearch : Birmes_2017_Front.Microbiol_8_339 |
| PubMedID: 28303132 |
| Gene_locus related to this paper: rhoer-aqdC1 , rhoer-aqdC2 |
| Title : Enzyme-Mediated Quenching of the Pseudomonas Quinolone Signal (PQS) Promotes Biofilm Formation of Pseudomonas aeruginosa by Increasing Iron Availability - Tettmann_2016_Front.Microbiol_7_1978 |
| Author(s) : Tettmann B , Niewerth C , Kirschhofer F , Neidig A , Dotsch A , Brenner-Weiss G , Fetzner S , Overhage J |
| Ref : Front Microbiol , 7 :1978 , 2016 |
| Abstract : |
| PubMedSearch : Tettmann_2016_Front.Microbiol_7_1978 |
| PubMedID: 28018312 |
| Title : Rhodococcus erythropolis BG43 Genes Mediating Pseudomonas aeruginosa Quinolone Signal Degradation and Virulence Factor Attenuation - Muller_2015_Appl.Environ.Microbiol_81_7720 |
| Author(s) : Muller C , Birmes FS , Ruckert C , Kalinowski J , Fetzner S |
| Ref : Applied Environmental Microbiology , 81 :7720 , 2015 |
| Abstract : |
| PubMedSearch : Muller_2015_Appl.Environ.Microbiol_81_7720 |
| PubMedID: 26319870 |
| Gene_locus related to this paper: rhoer-aqdC1 , rhoer-aqdC2 , rhoer-aqda1 |
| Title : Conversion of the Pseudomonas aeruginosa Quinolone Signal and Related Alkylhydroxyquinolines by Rhodococcus sp. Strain BG43 - Muller_2014_Appl.Environ.Microbiol_80_7266 |
| Author(s) : Muller C , Birmes FS , Niewerth H , Fetzner S |
| Ref : Applied Environmental Microbiology , 80 :7266 , 2014 |
| Abstract : |
| PubMedSearch : Muller_2014_Appl.Environ.Microbiol_80_7266 |
| PubMedID: 25239889 |
| Gene_locus related to this paper: rhoer-aqdC1 , rhoer-aqdC2 |
| Title : Validation of PqsD as an anti-biofilm target in Pseudomonas aeruginosa by development of small-molecule inhibitors - Storz_2012_J.Am.Chem.Soc_134_16143 |
| Author(s) : Storz MP , Maurer CK , Zimmer C , Wagner N , Brengel C , de Jong JC , Lucas S , Musken M , Haussler S , Steinbach A , Hartmann RW |
| Ref : Journal of the American Chemical Society , 134 :16143 , 2012 |
| Abstract : |
| PubMedSearch : Storz_2012_J.Am.Chem.Soc_134_16143 |
| PubMedID: 22992202 |
| Title : Quorum sensing by 2-alkyl-4-quinolones in Pseudomonas aeruginosa and other bacterial species - Dubern_2008_Mol.Biosyst_4_882 |
| Author(s) : Dubern JF , Diggle SP |
| Ref : Mol Biosyst , 4 :882 , 2008 |
| Abstract : |
| PubMedSearch : Dubern_2008_Mol.Biosyst_4_882 |
| PubMedID: 18704225 |