2.3.1.230: 2-heptyl-4(1H)-quinolone synthase
This is an abbreviated version!
For detailed information about 2-heptyl-4(1H)-quinolone synthase, go to the full flat file.
Word Map on EC 2.3.1.230
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2.3.1.230
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arachidonic
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20-hydroxyeicosatetraenoic
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omega-hydroxylase
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constrictor
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phenylephrine
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microcirculation
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cyp4a2
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clofibrate
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ppars
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lauric
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omega-hydroxylation
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interlobar
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20-hydroxyeicosa-6z,15z-dienoic
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myogenic
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n-methylsulfonyl-12,12-dibromododec-11-enamide
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proliferators
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nafenopin
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arterioles
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vasoconstrictor
- 2.3.1.230
-
arachidonic
-
20-hydroxyeicosatetraenoic
-
omega-hydroxylase
-
constrictor
- phenylephrine
-
microcirculation
- cyp4a2
- clofibrate
-
ppars
-
lauric
-
omega-hydroxylation
-
interlobar
-
20-hydroxyeicosa-6z,15z-dienoic
-
myogenic
- n-methylsulfonyl-12,12-dibromododec-11-enamide
-
proliferators
-
nafenopin
-
arterioles
-
vasoconstrictor
Reaction
Synonyms
2,4-dihydroxyquinoline synthase, PqsBC, PqsD, PsqD
ECTree
2.3.1.230 2-heptyl-4(1H)-quinolone synthaseAdvanced search results
results (
results (Inhibitors
Inhibitors on EC 2.3.1.230 - 2-heptyl-4(1H)-quinolone synthase
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INHIBITOR 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
IMAGE
(2-nitrophenyl)(thiophen-3-yl)methanol
inhibitor shows almost no time-dependency of PqsD inhibition
(2R)-2,4-dihydroxy-3,3-dimethyl-N-(3-[[4-(2-nitrophenyl)-4-oxobutyl]amino]-3-oxopropyl)butanamide
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0.05 mM, 18% inhibition
(2R)-2,4-dihydroxy-N-(3-[[4-hydroxy-4-(2-nitrophenyl)butyl]amino]-3-oxopropyl)-3,3-dimethylbutanamide
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0.05 mM, 95% inhibition
(S)-(2-nitrophenyl)(phenyl)methanol
most active compound of the series, capable of reducing the HHQ and PQS levels as well as the biofilm volume in Pseudomonas aeruginosa PA14 without affecting cell viability. The (S)-enantiomer has a pronounced entropic binding profile. Docking results show a short hydrogen bond between NO2 and NH of Ser317. The hydroxyl group is involved in different interactions, either facing toward Asn287 or His256/Cys112
1-(2-nitrophenyl)propan-1-ol
best inhibitor in the cellular test
2-[[3-(diethylsulfamoyl)-4-ethylbenzoyl]amino]benzoic acid
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0.05 mM, 39% inhibition
2-[[3-(diethylsulfamoyl)benzoyl]amino]-5-(trifluoromethyl)benzoic acid
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2-[[3-(diethylsulfamoyl)benzoyl]amino]-6-methoxybenzoic acid
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0.05 mM, 44% inhibition
2-[[3-(dimethylsulfamoyl)benzoyl]amino]benzoic acid
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0.05 mM, 35% inhibition
2-[[3-(morpholin-4-ylsulfonyl)benzoyl]amino]benzoic acid
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0.05 mM, 16% inhibition
2-[[3-(pyrrolidin-1-ylsulfonyl)benzoyl]amino]benzoic acid
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0.05 mM, 47% inhibition
2-[[4-bromo-3-(diethylsulfamoyl)benzoyl]amino]-5-fluorobenzoic acid
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3'-carbamoyl-4-[[3-(diethylsulfamoyl)benzoyl]amino]biphenyl-3-carboxylic acid
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3-(3,4-dihydroxyphenyl)-N-methylpropanamide
potent inhibitor, completely inactive in the cell-based assay
4'-carbamoyl-4-[[3-(diethylsulfamoyl)benzoyl]amino]biphenyl-3-carboxylic acid
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4-[[3-(diethylsulfamoyl)benzoyl]amino]biphenyl-3,3'-dicarboxylic acid
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4-[[3-(diethylsulfamoyl)benzoyl]amino]biphenyl-3,4'-dicarboxylic acid
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5-bromo-2-[[4-bromo-3-(diethylsulfamoyl)benzoyl]amino]benzoic acid
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N-(2-chloro-6-methylphenyl)biphenyl-4-carboxamide
strong inhibition of enzyme, without inhibition of RNA polymerase
N-[2-[hydroxy(2-nitrophenyl)methyl]phenyl]acetamide
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0.05 mM, 93% inhibition
N-[3-[hydroxy(2-nitrophenyl)methyl]phenyl]acetamide
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0.05 mM, 99% inhibition
N-[4-hydroxy-4-(2-nitrophenyl)butyl]acetamide
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0.05 mM, 99% inhibition
N-[4-[hydroxy(2-nitrophenyl)methyl]phenyl]acetamide
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0.05 mM, 98% inhibition
additional information
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identification of a class of PqsD inhibitors using a ligand-based approach. Simplification and rigidization leads to fragments with high ligand efficiencies. These small molecules repress HHQ and PQS production and biofilm formation in Pseudomonas aeruginosa. This validates PqsD as a target for the development of anti-infectives. No inhibition by 0.05 mM (3-[[4-(2-aminophenyl)-4-oxobutyl]amino]-3-oxopropyl)-2,4-dihydroxy-3,3-dimethylbutanamide, (2R)-N-(3-[[4-(2-aminophenyl)-4-hydroxybutyl]amino]-3-oxopropyl)-2,4-dihydroxy-3,3-dimethylbutanamide, (2-nitrophenyl)(phenyl)methanone, 1-(2-nitrophenyl)-1-phenylethanol and 2,2,2-trifluoro-1-(2-nitrophenyl)-1-phenylethanol
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additional information
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optimization and characterization of 2-benzamidobenzoic acids as PqsD inhibitors. Structural modifications show that both the carboxylic acid ortho to the amide and 3'-sulfonamide are essential for binding. Introduction of substituents in the anthranilic part of the molecule results in compounds with IC50 values in the low micromolar range. This class of inhibitors does not bind into the active center of PqsD but in the ACoA channel, preventing the substrate from accessing the active site
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additional information
evaluation of selected substrates of the Medicago sativa chalcone synthase CHS2 as potential inhibitors of PqsD. Catechol derivatives possessing an ester moiety are able to reduce the production of 2-heptyl-4(1H)-quinolone in the bacterial cultures without affecting cellular growth
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