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Literature summary for 4.2.1.1 extracted from
- Phenylethynylbenzenesulfonamide regioisomers strongly and selectively inhibit the transmembrane, tumor-associated carbonic anhydrase isoforms IX and XII over the cytosolic isoforms I and II (2011), Bioorg. Med. Chem. Lett., 21, 5892-5896.
Inhibitors
| Inhibitors | Comment | Organism | Structure |
|---|---|---|---|
| 2-(phenylethynyl)benzenesulfonamide | - |
Homo sapiens |  |
| 3-(phenylethynyl)benzenesulfonamide | - |
Homo sapiens | |
| 3-phenylpropanenitrile | - |
Homo sapiens | |
| 3-[(3-fluorophenyl)ethynyl]benzenesulfonamide | - |
Homo sapiens | |
| 3-[(3-methoxyphenyl)ethynyl]benzenesulfonamide | - |
Homo sapiens | |
| 3-[(4-methylphenyl)ethynyl]benzenesulfonamide | - |
Homo sapiens | |
| 4,5-dichlorobenzene-1,3-disulfonamide | - |
Homo sapiens | |
| 4-(phenylethynyl)benzenesulfonamide | - |
Homo sapiens | |
| 4-Aminobenzenesulfonamide | - |
Homo sapiens | |
| 4-[(3-fluorophenyl)ethynyl]benzenesulfonamide | - |
Homo sapiens | |
| 4-[(3-hydroxyphenyl)ethynyl]benzenesulfonamide | - |
Homo sapiens | |
| 4-[(3-methoxyphenyl)ethynyl]benzenesulfonamide | - |
Homo sapiens | |
| 4-[(4-methylphenyl)ethynyl]benzenesulfonamide | - |
Homo sapiens | |
| 4-[4-(methylsulfonyl)phenyl]-3-phenyldihydrofuran-2(3H)-one | - |
Homo sapiens | |
| acetazolamide | - |
Homo sapiens | |
| celecoxib | - |
Homo sapiens | |
| dichlorophenamide | - |
Homo sapiens | |
| additional information | development and synthesis of a series of compounds incorporating regioisomeric phenylethynylbenzenesulfonamide moieties, analysis of potential as inhibitors of the four human isozymes, hCA I, hCA II, hCA IX, and hCA XII. The position of the sulfamoyl group with respect to the alkyne functionality, and the nature of the moieties substituting the second aromatic ring are the principal structural features influencing CA inhibition. The para-sulfamoyl-substituted derivatives are effective inhibitors of CA IX and XII, the meta-substituted regioisomers of CA I, X and XII, whereas the ortho-substituted sulfonamides ae weak inhibitors of CA I, II and IX, but inhibit ignificantly CA XII, structure-activity relationship study, overview | Homo sapiens | |
| N-(5-sulfamoyl-1,3,4-thiadiazol-2-yl)acetamide | - |
Homo sapiens | |
| phenylacetonitrile | - |
Homo sapiens | |
| rofecoxib | - |
Homo sapiens | |
| sulfanilamide | - |
Homo sapiens | |
| valdecoxib | - |
Homo sapiens | |
Localization
| Localization | Comment | Organism | GeneOntology No. | Textmining |
|---|---|---|---|---|
| cytosol | isozymes CA I and CA II | Homo sapiens | 5829 | - |
| membrane | transmembrane isozymes CA IX and CA XI | Homo sapiens | 16020 | - |
Organism
| Organism | UniProt | Comment | Textmining |
|---|---|---|---|
| Homo sapiens | - |
isozymes, hCA I, hCA II, hCA IX, and hCA XII | - |
Synonyms
| Synonyms | Comment | Organism |
|---|---|---|
| carbonic anhydrase | - |
Homo sapiens |
Ki Value [mM]
| Ki Value [mM] | Ki Value maximum [mM] | Inhibitor | Comment | Organism | Structure |
|---|---|---|---|---|---|
| 0.000001 | - |
3-[(3-fluorophenyl)ethynyl]benzenesulfonamide | isozyme CA IX, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | |
| 0.0000011 | - |
3-[(4-methylphenyl)ethynyl]benzenesulfonamide | isozyme CA IX, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | |
| 0.0000012 | - |
4-[(3-methoxyphenyl)ethynyl]benzenesulfonamide | isozyme CA XII, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | |
| 0.0000013 | - |
3-(phenylethynyl)benzenesulfonamide | isozyme CA XII, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | |
| 0.0000016 | - |
4-[(3-hydroxyphenyl)ethynyl]benzenesulfonamide | isozyme CA IX, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | |
| 0.0000017 | - |
3-[(3-methoxyphenyl)ethynyl]benzenesulfonamide | isozyme CA IX, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | |
| 0.0000057 | - |
N-(5-sulfamoyl-1,3,4-thiadiazol-2-yl)acetamide | isozyme CA XII, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | |
| 0.0000058 | - |
4-[(3-fluorophenyl)ethynyl]benzenesulfonamide | isozyme CA IX, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | |
| 0.0000065 | - |
4-[(3-methoxyphenyl)ethynyl]benzenesulfonamide | isozyme CA IX, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | |
| 0.0000069 | - |
3-(phenylethynyl)benzenesulfonamide | isozyme CA IX, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | |
| 0.0000092 | - |
3-[(3-methoxyphenyl)ethynyl]benzenesulfonamide | isozyme CA XII, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | |
| 0.0000094 | - |
4-(phenylethynyl)benzenesulfonamide | isozyme CA XII, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | |
| 0.00001 | - |
2-(phenylethynyl)benzenesulfonamide | isozyme CA XII, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | |
| 0.000012 | - |
N-(5-sulfamoyl-1,3,4-thiadiazol-2-yl)acetamide | isozyme CA II, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | |
| 0.000012 | - |
3-phenylpropanenitrile | isozyme CA XII, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | |
| 0.000013 | - |
valdecoxib | isozyme CA XII, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | |
| 0.000016 | - |
celecoxib | isozyme CA IX, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | |
| 0.000018 | - |
celecoxib | isozyme CA XII, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | |
| 0.000021 | - |
celecoxib | isozyme CA II, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | |
| 0.000025 | - |
N-(5-sulfamoyl-1,3,4-thiadiazol-2-yl)acetamide | isozyme CA IX, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | |
| 0.000027 | - |
valdecoxib | isozyme CA IX, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | |
| 0.000037 | - |
4-Aminobenzenesulfonamide | isozyme CA XII, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | |
| 0.000038 | - |
4,5-dichlorobenzene-1,3-disulfonamide | isozyme CA II, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | |
| 0.000043 | - |
valdecoxib | isozyme CA II, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | |
| 0.00005 | - |
4,5-dichlorobenzene-1,3-disulfonamide | isozyme CA IX, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | |
| 0.00005 | - |
4,5-dichlorobenzene-1,3-disulfonamide | isozyme CA XII, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | |
| 0.000057 | - |
4-[(3-fluorophenyl)ethynyl]benzenesulfonamide | isozyme CA II, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | |
| 0.000057 | - |
3-[(3-fluorophenyl)ethynyl]benzenesulfonamide | isozyme CA XII, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | |
| 0.000059 | - |
3-(phenylethynyl)benzenesulfonamide | isozyme CA I, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | |
| 0.000059 | - |
4-[(3-hydroxyphenyl)ethynyl]benzenesulfonamide | isozyme CA XII, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | |
| 0.000062 | - |
4-[(3-fluorophenyl)ethynyl]benzenesulfonamide | isozyme CA I, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | |
| 0.000068 | - |
4-[(4-methylphenyl)ethynyl]benzenesulfonamide | isozyme CA IX, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | |
| 0.000069 | - |
4-(phenylethynyl)benzenesulfonamide | isozyme CA IX, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | |
| 0.000076 | - |
3-[(3-methoxyphenyl)ethynyl]benzenesulfonamide | isozyme CA I, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | |
| 0.000076 | - |
4-[(3-fluorophenyl)ethynyl]benzenesulfonamide | isozyme CA XII, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | |
| 0.000078 | - |
4-[(3-methoxyphenyl)ethynyl]benzenesulfonamide | isozyme CA I, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | |
| 0.000078 | - |
3-[(3-fluorophenyl)ethynyl]benzenesulfonamide | isozyme CA I, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | |
| 0.000086 | - |
phenylacetonitrile | isozyme CA XII, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | |
| 0.000087 | - |
4-[(3-hydroxyphenyl)ethynyl]benzenesulfonamide | isozyme CA I, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | |
| 0.000087 | - |
3-(phenylethynyl)benzenesulfonamide | isozyme CA II, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | |
| 0.000102 | - |
3-[(4-methylphenyl)ethynyl]benzenesulfonamide | isozyme CA I, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | |
| 0.000104 | - |
4-[(4-methylphenyl)ethynyl]benzenesulfonamide | isozyme CA XII, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | |
| 0.00024 | - |
4-Aminobenzenesulfonamide | isozyme CA II, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | |
| 0.00025 | - |
acetazolamide | isozyme CA I, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | |
| 0.000294 | - |
4-Aminobenzenesulfonamide | isozyme CA IX, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | |
| 0.00041 | - |
3-[(4-methylphenyl)ethynyl]benzenesulfonamide | isozyme CA XII, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | |
| 0.0012 | - |
dichlorophenamide | isozyme CA I, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | |
| 0.00171 | - |
3-[(4-methylphenyl)ethynyl]benzenesulfonamide | isozyme CA II, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | |
| 0.00214 | - |
3-[(3-fluorophenyl)ethynyl]benzenesulfonamide | isozyme CA II, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | |
| 0.004125 | - |
3-phenylpropanenitrile | isozyme CA II, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | |
| 0.00461 | - |
phenylacetonitrile | isozyme CA II, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | |
| 0.00489 | - |
4-[(3-methoxyphenyl)ethynyl]benzenesulfonamide | isozyme CA II, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | |
| 0.00495 | - |
2-(phenylethynyl)benzenesulfonamide | isozyme CA II, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | |
| 0.0052 | - |
4-(phenylethynyl)benzenesulfonamide | isozyme CA II, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | |
| 0.00522 | - |
4-[(4-methylphenyl)ethynyl]benzenesulfonamide | isozyme CA II, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | |
| 0.00529 | - |
4-[(3-hydroxyphenyl)ethynyl]benzenesulfonamide | isozyme CA II, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | |
| 0.00559 | - |
4-[(4-methylphenyl)ethynyl]benzenesulfonamide | isozyme CA I, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | |
| 0.00565 | - |
4-(phenylethynyl)benzenesulfonamide | isozyme CA I, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | |
| 0.006315 | - |
3-[(3-methoxyphenyl)ethynyl]benzenesulfonamide | isozyme CA II, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | |
| 0.00637 | - |
2-(phenylethynyl)benzenesulfonamide | isozyme CA IX, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | |
| 0.00845 | - |
3-phenylpropanenitrile | isozyme CA IX, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | |
| 0.0086 | - |
phenylacetonitrile | isozyme CA IX, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | |
| 0.025 | - |
sulfanilamide | isozyme CA I, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | |
| 0.05 | - |
celecoxib | isozyme CA I, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | |
| 0.054 | - |
valdecoxib | isozyme CA I, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | |
| 0.416 | - |
3-phenylpropanenitrile | isozyme CA I, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | |
| 0.674 | - |
phenylacetonitrile | isozyme CA I, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | |
| 0.806 | - |
2-(phenylethynyl)benzenesulfonamide | isozyme CA I, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | |
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