Any feedback?
Literature summary for 2.3.1.230 extracted from
- Structure optimization of 2-benzamidobenzoic acids as PqsD inhibitors for Pseudomonas aeruginosa infections and elucidation of binding mode by SPR, STD NMR, and molecular docking (2013), J. Med. Chem., 56, 6146-6155.
Cloned(Commentary)
| Cloned (Comment) | Organism |
|---|---|
| expression in Escherichia coli | Pseudomonas aeruginosa |
Protein Variants
| Protein Variants | Comment | Organism |
|---|---|---|
| C112A | binding behavior towards inhibitors is different from wild-type enzyme | Pseudomonas aeruginosa |
| H257F | binding behavior towards inhibitors is different from wild-type enzyme | Pseudomonas aeruginosa |
| S317F | binding behavior towards inhibitors is different from wild-type enzyme | Pseudomonas aeruginosa |
Inhibitors
| Inhibitors | Comment | Organism | Structure |
|---|---|---|---|
| 2-([3-[benzyl(ethyl)sulfamoyl]benzoyl]amino)benzoic acid | - |
Pseudomonas aeruginosa |  |
| 2-chloro-6-[[3-(diethylsulfamoyl)benzoyl]amino]benzoic acid | - |
Pseudomonas aeruginosa | |
| 2-[(3-sulfamoylbenzoyl)amino]benzoic acid | - |
Pseudomonas aeruginosa | |
| 2-[[3-(azepan-1-ylsulfonyl)benzoyl]amino]benzoic acid | - |
Pseudomonas aeruginosa | |
| 2-[[3-(diethylsulfamoyl)-4-ethylbenzoyl]amino]benzoic acid | 0.05 mM, 39% inhibition | Pseudomonas aeruginosa | |
| 2-[[3-(diethylsulfamoyl)-4-methylbenzoyl]amino]benzoic acid | - |
Pseudomonas aeruginosa | |
| 2-[[3-(diethylsulfamoyl)benzoyl]amino]-4-fluorobenzoic acid | - |
Pseudomonas aeruginosa | |
| 2-[[3-(diethylsulfamoyl)benzoyl]amino]-4-nitrobenzoic acid | - |
Pseudomonas aeruginosa | |
| 2-[[3-(diethylsulfamoyl)benzoyl]amino]-5-(trifluoromethyl)benzoic acid | - |
Pseudomonas aeruginosa | |
| 2-[[3-(diethylsulfamoyl)benzoyl]amino]-5-fluorobenzoic acid | - |
Pseudomonas aeruginosa | |
| 2-[[3-(diethylsulfamoyl)benzoyl]amino]-5-methylbenzoic acid | - |
Pseudomonas aeruginosa | |
| 2-[[3-(diethylsulfamoyl)benzoyl]amino]-5-nitrobenzoic acid | - |
Pseudomonas aeruginosa | |
| 2-[[3-(diethylsulfamoyl)benzoyl]amino]-6-fluorobenzoic acid | - |
Pseudomonas aeruginosa | |
| 2-[[3-(diethylsulfamoyl)benzoyl]amino]-6-hydroxybenzoic acid | - |
Pseudomonas aeruginosa | |
| 2-[[3-(diethylsulfamoyl)benzoyl]amino]-6-methoxybenzoic acid | 0.05 mM, 44% inhibition | Pseudomonas aeruginosa | |
| 2-[[3-(diethylsulfamoyl)benzoyl]amino]benzoic acid | - |
Pseudomonas aeruginosa | |
| 2-[[3-(dimethylsulfamoyl)benzoyl]amino]benzoic acid | 0.05 mM, 35% inhibition | Pseudomonas aeruginosa | |
| 2-[[3-(dipropylsulfamoyl)benzoyl]amino]benzoic acid | - |
Pseudomonas aeruginosa | |
| 2-[[3-(morpholin-4-ylsulfonyl)benzoyl]amino]benzoic acid | 0.05 mM, 16% inhibition | Pseudomonas aeruginosa | |
| 2-[[3-(piperidin-1-ylsulfonyl)benzoyl]amino]benzoic acid | - |
Pseudomonas aeruginosa | |
| 2-[[3-(pyrrolidin-1-ylsulfonyl)benzoyl]amino]benzoic acid | 0.05 mM, 47% inhibition | Pseudomonas aeruginosa | |
| 2-[[4-bromo-3-(diethylsulfamoyl)benzoyl]amino]-5-fluorobenzoic acid | - |
Pseudomonas aeruginosa | |
| 2-[[4-bromo-3-(diethylsulfamoyl)benzoyl]amino]benzoic acid | - |
Pseudomonas aeruginosa | |
| 3'-carbamoyl-4-[[3-(diethylsulfamoyl)benzoyl]amino]biphenyl-3-carboxylic acid | - |
Pseudomonas aeruginosa | |
| 4'-carbamoyl-4-[[3-(diethylsulfamoyl)benzoyl]amino]biphenyl-3-carboxylic acid | - |
Pseudomonas aeruginosa | |
| 4-chloro-2-[[3-(diethylsulfamoyl)benzoyl]amino]benzoic acid | - |
Pseudomonas aeruginosa | |
| 4-[[3-(diethylsulfamoyl)benzoyl]amino]biphenyl-3,3'-dicarboxylic acid | - |
Pseudomonas aeruginosa | |
| 4-[[3-(diethylsulfamoyl)benzoyl]amino]biphenyl-3,4'-dicarboxylic acid | - |
Pseudomonas aeruginosa | |
| 4-[[3-(diethylsulfamoyl)benzoyl]amino]biphenyl-3-carboxylic acid | - |
Pseudomonas aeruginosa | |
| 5-bromo-2-[[3-(diethylcarbamoyl)benzoyl]amino]benzoic acid | - |
Pseudomonas aeruginosa | |
| 5-bromo-2-[[3-(diethylsulfamoyl)benzoyl]amino]benzoic acid | - |
Pseudomonas aeruginosa | |
| 5-bromo-2-[[4-(diethylsulfamoyl)benzoyl]amino]benzoic acid | - |
Pseudomonas aeruginosa | |
| 5-bromo-2-[[4-bromo-3-(diethylsulfamoyl)benzoyl]amino]benzoic acid | - |
Pseudomonas aeruginosa | |
| 5-cyano-2-[[3-(diethylsulfamoyl)benzoyl]amino]benzoic acid | - |
Pseudomonas aeruginosa | |
| additional information | 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 | Pseudomonas aeruginosa |
Organism
| Organism | UniProt | Comment | Textmining |
|---|---|---|---|
| Pseudomonas aeruginosa | - |
- |
- |
Purification (Commentary)
| Purification (Comment) | Organism |
|---|---|
- |
Pseudomonas aeruginosa |
Substrates and Products (Substrate)
| Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
|---|---|---|---|---|---|---|
| 3-oxodecanoate + 2-aminobenzoyl-CoA | - |
Pseudomonas aeruginosa | CoA + 2-heptyl-4(1H)-quinolone + CO2 + H2O | - |
? | |
IC50 Value
| IC50 Value | IC50 Value Maximum | Comment | Organism | Inhibitor | Structure |
|---|---|---|---|---|---|
| 0.0012 | - |
pH and temperature not specified in the publication | Pseudomonas aeruginosa | 2-[[3-(diethylsulfamoyl)benzoyl]amino]-6-hydroxybenzoic acid | |
| 0.0015 | - |
pH and temperature not specified in the publication | Pseudomonas aeruginosa | 4-[[3-(diethylsulfamoyl)benzoyl]amino]biphenyl-3,3'-dicarboxylic acid | |
| 0.0019 | - |
pH and temperature not specified in the publication | Pseudomonas aeruginosa | 4'-carbamoyl-4-[[3-(diethylsulfamoyl)benzoyl]amino]biphenyl-3-carboxylic acid | |
| 0.0027 | - |
pH and temperature not specified in the publication | Pseudomonas aeruginosa | 4-[[3-(diethylsulfamoyl)benzoyl]amino]biphenyl-3,4'-dicarboxylic acid | |
| 0.003 | - |
pH and temperature not specified in the publication | Pseudomonas aeruginosa | 4-[[3-(diethylsulfamoyl)benzoyl]amino]biphenyl-3-carboxylic acid | |
| 0.0038 | - |
pH and temperature not specified in the publication | Pseudomonas aeruginosa | 5-bromo-2-[[4-bromo-3-(diethylsulfamoyl)benzoyl]amino]benzoic acid | |
| 0.0038 | - |
pH and temperature not specified in the publication | Pseudomonas aeruginosa | 3'-carbamoyl-4-[[3-(diethylsulfamoyl)benzoyl]amino]biphenyl-3-carboxylic acid | |
| 0.0054 | - |
pH and temperature not specified in the publication | Pseudomonas aeruginosa | 2-[[3-(dipropylsulfamoyl)benzoyl]amino]benzoic acid | |
| 0.0063 | - |
pH and temperature not specified in the publication | Pseudomonas aeruginosa | 2-[[3-(diethylsulfamoyl)benzoyl]amino]-4-nitrobenzoic acid | |
| 0.0066 | - |
pH and temperature not specified in the publication | Pseudomonas aeruginosa | 2-[[4-bromo-3-(diethylsulfamoyl)benzoyl]amino]-5-fluorobenzoic acid | |
| 0.0069 | - |
pH and temperature not specified in the publication | Pseudomonas aeruginosa | 2-[[4-bromo-3-(diethylsulfamoyl)benzoyl]amino]benzoic acid | |
| 0.008 | - |
pH and temperature not specified in the publication | Pseudomonas aeruginosa | 2-[[3-(diethylsulfamoyl)benzoyl]amino]-4-fluorobenzoic acid | |
| 0.0089 | - |
pH and temperature not specified in the publication | Pseudomonas aeruginosa | 2-[[3-(diethylsulfamoyl)benzoyl]amino]-5-nitrobenzoic acid | |
| 0.009 | - |
pH and temperature not specified in the publication | Pseudomonas aeruginosa | 5-bromo-2-[[3-(diethylsulfamoyl)benzoyl]amino]benzoic acid | |
| 0.0094 | - |
pH and temperature not specified in the publication | Pseudomonas aeruginosa | 4-chloro-2-[[3-(diethylsulfamoyl)benzoyl]amino]benzoic acid | |
| 0.0114 | - |
pH and temperature not specified in the publication | Pseudomonas aeruginosa | 2-[[3-(diethylsulfamoyl)benzoyl]amino]-5-fluorobenzoic acid | |
| 0.0124 | - |
pH and temperature not specified in the publication | Pseudomonas aeruginosa | 2-[[3-(diethylsulfamoyl)benzoyl]amino]-5-(trifluoromethyl)benzoic acid | |
| 0.013 | - |
pH and temperature not specified in the publication | Pseudomonas aeruginosa | 5-bromo-2-[[4-(diethylsulfamoyl)benzoyl]amino]benzoic acid | |
| 0.0144 | - |
pH and temperature not specified in the publication | Pseudomonas aeruginosa | 2-[[3-(piperidin-1-ylsulfonyl)benzoyl]amino]benzoic acid | |
| 0.0148 | - |
pH and temperature not specified in the publication | Pseudomonas aeruginosa | 2-[[3-(azepan-1-ylsulfonyl)benzoyl]amino]benzoic acid | |
| 0.0165 | - |
pH and temperature not specified in the publication | Pseudomonas aeruginosa | 2-([3-[benzyl(ethyl)sulfamoyl]benzoyl]amino)benzoic acid | |
| 0.0184 | - |
pH and temperature not specified in the publication | Pseudomonas aeruginosa | 2-[[3-(diethylsulfamoyl)benzoyl]amino]-5-methylbenzoic acid | |
| 0.0198 | - |
pH and temperature not specified in the publication | Pseudomonas aeruginosa | 2-[[3-(diethylsulfamoyl)benzoyl]amino]benzoic acid | |
| 0.025 | - |
pH and temperature not specified in the publication | Pseudomonas aeruginosa | 2-[[3-(diethylsulfamoyl)benzoyl]amino]-6-fluorobenzoic acid | |
| 0.0255 | - |
pH and temperature not specified in the publication | Pseudomonas aeruginosa | 5-bromo-2-[[3-(diethylcarbamoyl)benzoyl]amino]benzoic acid | |
| 0.026 | - |
pH and temperature not specified in the publication | Pseudomonas aeruginosa | 5-cyano-2-[[3-(diethylsulfamoyl)benzoyl]amino]benzoic acid | |
| 0.0273 | - |
pH and temperature not specified in the publication | Pseudomonas aeruginosa | 2-[[3-(diethylsulfamoyl)-4-methylbenzoyl]amino]benzoic acid | |
| 0.039 | - |
pH and temperature not specified in the publication | Pseudomonas aeruginosa | 2-chloro-6-[[3-(diethylsulfamoyl)benzoyl]amino]benzoic acid | |
| 0.044 | - |
pH and temperature not specified in the publication | Pseudomonas aeruginosa | 2-[(3-sulfamoylbenzoyl)amino]benzoic acid | |
Use of this online version of BRENDA is free under the CC BY 4.0 license. See terms of use for full details.
Release 2023.1 (January 2023)
Legal
Curated at
Member of
