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Literature summary extracted from

  • Storz, M.P.; Maurer, C.K.; Zimmer, C.; Wagner, N.; Brengel, C.; de Jong, J.C.; Lucas, S.; Müsken, M.; Häussler, S.; Steinbach, A.; Hartmann, R.W.
    Validation of PqsD as an anti-biofilm target in Pseudomonas aeruginosa by development of small-molecule inhibitors (2012), J. Am. Chem. Soc., 134, 16143-16146.
    View publication on PubMed

Inhibitors

EC Number Inhibitors Comment Organism Structure
2.3.1.230 (2-nitrophenyl)(phenyl)methanol 0.05 mM, 99% inhibition Pseudomonas aeruginosa
2.3.1.230 (2R)-2,4-dihydroxy-3,3-dimethyl-N-(3-[[4-(2-nitrophenyl)-4-oxobutyl]amino]-3-oxopropyl)butanamide 0.05 mM, 18% inhibition Pseudomonas aeruginosa
2.3.1.230 (2R)-2,4-dihydroxy-N-(3-[[4-hydroxy-4-(2-nitrophenyl)butyl]amino]-3-oxopropyl)-3,3-dimethylbutanamide 0.05 mM, 95% inhibition Pseudomonas aeruginosa
2.3.1.230 1-benzyl-2-nitrobenzene 0.025 mM, 24% inhibition Pseudomonas aeruginosa
2.3.1.230 1-[methoxy(phenyl)methyl]-2-nitrobenzene 0.05 mM, 97% inhibition Pseudomonas aeruginosa
2.3.1.230 2-nitrophenyl phenyl sulfone 0.05 mM, 87% inhibition Pseudomonas aeruginosa
2.3.1.230 additional information 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 Pseudomonas aeruginosa
2.3.1.230 N-[2-[hydroxy(2-nitrophenyl)methyl]phenyl]acetamide 0.05 mM, 93% inhibition Pseudomonas aeruginosa
2.3.1.230 N-[3-[hydroxy(2-nitrophenyl)methyl]phenyl]acetamide 0.05 mM, 99% inhibition Pseudomonas aeruginosa
2.3.1.230 N-[4-(2-nitrophenyl)-4-oxobutyl]acetamide 0.05 mM, 98% inhibition Pseudomonas aeruginosa
2.3.1.230 N-[4-hydroxy-4-(2-nitrophenyl)butyl]acetamide 0.05 mM, 99% inhibition Pseudomonas aeruginosa
2.3.1.230 N-[4-[hydroxy(2-nitrophenyl)methyl]phenyl]acetamide 0.05 mM, 98% inhibition Pseudomonas aeruginosa
2.3.1.262 (2-nitrophenyl)(phenyl)methanol at a concentration of 250 microM, both the 2-heptyl-4-hydroxyquinoline and Pseudomonas quinolone signal levels are strongly reduced by 77 and 42%, respectively, in Pseudomonas aeruginosa PA14 cultures. The 2,4-dihydroxyquinoline level increases in the presence of the compound. Addition of the compound to a 24 h old biofilm reduces the biovolume of the biofilm by 38% within a 24 h incubation period Pseudomonas aeruginosa
2.3.1.262 N-[4-hydroxy-4-(2-nitrophenyl)butyl]acetamide
-
 Pseudomonas aeruginosa

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
2.3.1.230 malonyl-CoA + 2-aminobenzoyl-CoA Pseudomonas aeruginosa 2-aminobenzoyl-CoA i.e. anthraniloyl-CoA. PqsD is a key enzyme in the biosynthesis of the signal molecules 2-heptyl-4-hydroxyquinoline and 4-hydroxy-2(1H)-quinolone, that are involved in regulation of virulence factor production and biofilm formation 2 CoA + 4-hydroxy-2(1H)-quinolone + CO2 i.e. 2,4-dihydroxyquinoline ?

Organism

EC Number Organism UniProt Comment Textmining
2.3.1.230 Pseudomonas aeruginosa
-
-
-
2.3.1.262 Pseudomonas aeruginosa
-
-
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
2.3.1.230 malonyl-CoA + 2-aminobenzoyl-CoA 2-aminobenzoyl-CoA i.e. anthraniloyl-CoA Pseudomonas aeruginosa 2 CoA + 4-hydroxy-2(1H)-quinolone + CO2 i.e. 2,4-dihydroxyquinoline ?
2.3.1.230 malonyl-CoA + 2-aminobenzoyl-CoA 2-aminobenzoyl-CoA i.e. anthraniloyl-CoA. PqsD is a key enzyme in the biosynthesis of the signal molecules 2-heptyl-4-hydroxyquinoline and 4-hydroxy-2(1H)-quinolone, that are involved in regulation of virulence factor production and biofilm formation Pseudomonas aeruginosa 2 CoA + 4-hydroxy-2(1H)-quinolone + CO2 i.e. 2,4-dihydroxyquinoline ?

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
2.3.1.230 3.2
-
 pH and temperature not specified in the publication Pseudomonas aeruginosa (2-nitrophenyl)(phenyl)methanol
2.3.1.230 4.3
-
 pH and temperature not specified in the publication Pseudomonas aeruginosa N-[4-hydroxy-4-(2-nitrophenyl)butyl]acetamide
2.3.1.230 4.3
-
 pH and temperature not specified in the publication Pseudomonas aeruginosa 1-[methoxy(phenyl)methyl]-2-nitrobenzene
2.3.1.230 6.2
-
 pH and temperature not specified in the publication Pseudomonas aeruginosa N-[2-[hydroxy(2-nitrophenyl)methyl]phenyl]acetamide
2.3.1.230 6.4
-
 pH and temperature not specified in the publication Pseudomonas aeruginosa N-[4-[hydroxy(2-nitrophenyl)methyl]phenyl]acetamide
2.3.1.230 7.8
-
 pH and temperature not specified in the publication Pseudomonas aeruginosa N-[4-(2-nitrophenyl)-4-oxobutyl]acetamide
2.3.1.230 7.9
-
 pH and temperature not specified in the publication Pseudomonas aeruginosa (2R)-2,4-dihydroxy-N-(3-[[4-hydroxy-4-(2-nitrophenyl)butyl]amino]-3-oxopropyl)-3,3-dimethylbutanamide
2.3.1.230 9
-
 pH and temperature not specified in the publication Pseudomonas aeruginosa N-[3-[hydroxy(2-nitrophenyl)methyl]phenyl]acetamide
2.3.1.230 14.8
-
 pH and temperature not specified in the publication Pseudomonas aeruginosa 2-nitrophenyl phenyl sulfone
2.3.1.262 0.0032
-
 pH not specified in the publication, temperature not specified in the publication Pseudomonas aeruginosa (2-nitrophenyl)(phenyl)methanol
2.3.1.262 0.0043
-
 pH not specified in the publication, temperature not specified in the publication Pseudomonas aeruginosa N-[4-hydroxy-4-(2-nitrophenyl)butyl]acetamide