BRENDA - Enzyme Database show

Carbonic anhydrase inhibitors: inhibition of the beta-class enzyme from the yeast Saccharomyces cerevisiae with sulfonamides and sulfamates

Isik, S.; Kockar, F.; Aydin, M.; Arslan, O.; Guler, O.O.; Innocenti, A.; Scozzafava, A.; Supuran, C.T.; Bioorg. Med. Chem. 17, 1158-1163 (2009)

Data extracted from this reference:

Cloned(Commentary)
EC Number
Commentary
Organism
4.2.1.1
expressed in Escherichia coli BL21 (DE3) cells
Saccharomyces cerevisiae
Inhibitors
EC Number
Inhibitors
Commentary
Organism
Structure
4.2.1.1
1-[(aminooxy)sulfinyl]-4-methylbenzene
-
Saccharomyces cerevisiae
4.2.1.1
1-[4-[(aminooxy)sulfinyl]phenyl]methanamine
-
Saccharomyces cerevisiae
4.2.1.1
2,4-bis[(aminooxy)sulfinyl]-5-(trifluoromethyl)aniline
-
Saccharomyces cerevisiae
4.2.1.1
2,4-bis[(aminooxy)sulfinyl]-5-chloroaniline
-
Saccharomyces cerevisiae
4.2.1.1
2-[(aminooxy)sulfinyl]-5-(2-chlorophenyl)-1,3,4-thiadiazole
-
Saccharomyces cerevisiae
4.2.1.1
2-[(aminooxy)sulfinyl]aniline
-
Saccharomyces cerevisiae
4.2.1.1
2-[4-[(aminooxy)sulfinyl]phenyl]ethanamine
-
Saccharomyces cerevisiae
4.2.1.1
2-[4-[(aminooxy)sulfinyl]phenyl]ethanol
-
Saccharomyces cerevisiae
4.2.1.1
3-[4-[(aminooxy)sulfinyl]phenyl]propanoic acid
-
Saccharomyces cerevisiae
4.2.1.1
4,5-dichloro-benzene-1,3-disulfonamide
shows effective carbonic anhydrase inhibitory activity
Saccharomyces cerevisiae
4.2.1.1
4-(2-amino-pyrimidin-4-yl)-benzenesulfonamide
best inhibitor
Saccharomyces cerevisiae
4.2.1.1
4-amino-N-[2-(4-sulfamoylphenyl)ethyl]benzenesulfonamide
-
Saccharomyces cerevisiae
4.2.1.1
4-amino-N-[4-[(aminooxy)sulfinyl]benzyl]benzenesulfonamide
-
Saccharomyces cerevisiae
4.2.1.1
4-[(aminooxy)sulfinyl]-2-bromoaniline
-
Saccharomyces cerevisiae
4.2.1.1
4-[(aminooxy)sulfinyl]-2-chloroaniline
-
Saccharomyces cerevisiae
4.2.1.1
4-[(aminooxy)sulfinyl]-2-fluoroaniline
-
Saccharomyces cerevisiae
4.2.1.1
4-[(aminooxy)sulfinyl]-2-iodoaniline
-
Saccharomyces cerevisiae
4.2.1.1
4-[(aminooxy)sulfinyl]aniline
-
Saccharomyces cerevisiae
4.2.1.1
4-[(aminooxy)sulfinyl]benzoic acid
-
Saccharomyces cerevisiae
4.2.1.1
5-[(aminooxy)sulfinyl]-1,3,4-thiadiazol-2-amine
-
Saccharomyces cerevisiae
4.2.1.1
5-[(aminooxy)sulfinyl]-3-methyl-1,3,4-thiadiazol-2(3H)-imine
-
Saccharomyces cerevisiae
4.2.1.1
5-[[(4-aminophenyl)sulfonyl]amino]-1,3,4-thiadiazole-2-sulfonamide
-
Saccharomyces cerevisiae
4.2.1.1
acetazolamide
shows effective carbonic anhydrase inhibitory activity
Saccharomyces cerevisiae
4.2.1.1
benzolamide
shows effective carbonic anhydrase inhibitory activity
Saccharomyces cerevisiae
4.2.1.1
brinzolamide
shows effective carbonic anhydrase inhibitory activity
Saccharomyces cerevisiae
4.2.1.1
celecoxib
shows effective carbonic anhydrase inhibitory activity
Saccharomyces cerevisiae
4.2.1.1
dorzolamide
shows effective carbonic anhydrase inhibitory activity
Saccharomyces cerevisiae
4.2.1.1
ethoxzolamide
shows effective carbonic anhydrase inhibitory activity
Saccharomyces cerevisiae
4.2.1.1
indisulam
shows effective carbonic anhydrase inhibitory activity
Saccharomyces cerevisiae
4.2.1.1
methazolamide
shows effective carbonic anhydrase inhibitory activity
Saccharomyces cerevisiae
4.2.1.1
saccharin
shows effective carbonic anhydrase inhibitory activity
Saccharomyces cerevisiae
4.2.1.1
sulpiride
shows effective carbonic anhydrase inhibitory activity
Saccharomyces cerevisiae
4.2.1.1
sulthiame
shows effective carbonic anhydrase inhibitory activity
Saccharomyces cerevisiae
4.2.1.1
topiramate
shows effective carbonic anhydrase inhibitory activity
Saccharomyces cerevisiae
4.2.1.1
valdecoxib
shows effective carbonic anhydrase inhibitory activity
Saccharomyces cerevisiae
4.2.1.1
zonisamide
shows effective carbonic anhydrase inhibitory activity
Saccharomyces cerevisiae
4.2.1.1
[4-[(aminooxy)sulfinyl]phenyl]methanol
-
Saccharomyces cerevisiae
Natural Substrates/ Products (Substrates)
EC Number
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
4.2.1.1
CO2 + H2O
Saccharomyces cerevisiae
-
H2CO3
-
-
r
Organism
EC Number
Organism
Primary Accession No. (UniProt)
Commentary
Textmining
4.2.1.1
Saccharomyces cerevisiae
-
-
-
Purification (Commentary)
EC Number
Commentary
Organism
4.2.1.1
ammonium sulfate precipitation and Sephadex G-100 gel filtration
Saccharomyces cerevisiae
Substrates and Products (Substrate)
EC Number
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
4.2.1.1
CO2 + H2O
-
696740
Saccharomyces cerevisiae
H2CO3
-
-
-
r
Turnover Number [1/s]
EC Number
Turnover Number Minimum [1/s]
Turnover Number Maximum [1/s]
Substrate
Commentary
Organism
Structure
4.2.1.1
940000
-
CO2
-
Saccharomyces cerevisiae
Ki Value [mM]
EC Number
Ki Value [mM]
Ki Value maximum [mM]
Inhibitor
Commentary
Organism
Structure
4.2.1.1
0.0000151
-
4-(2-amino-pyrimidin-4-yl)-benzenesulfonamide
-
Saccharomyces cerevisiae
4.2.1.1
0.0000826
-
acetazolamide
-
Saccharomyces cerevisiae
4.2.1.1
0.0000984
-
ethoxzolamide
-
Saccharomyces cerevisiae
4.2.1.1
0.000103
-
4,5-dichloro-benzene-1,3-disulfonamide
-
Saccharomyces cerevisiae
4.2.1.1
0.000106
-
zonisamide
-
Saccharomyces cerevisiae
4.2.1.1
0.000108
-
celecoxib
-
Saccharomyces cerevisiae
4.2.1.1
0.00011
-
dorzolamide
-
Saccharomyces cerevisiae
4.2.1.1
0.00011
-
topiramate
-
Saccharomyces cerevisiae
4.2.1.1
0.000111
-
benzolamide
-
Saccharomyces cerevisiae
4.2.1.1
0.000114
-
brinzolamide
-
Saccharomyces cerevisiae
4.2.1.1
0.000119
-
methazolamide
-
Saccharomyces cerevisiae
4.2.1.1
0.000124
-
sulpiride
-
Saccharomyces cerevisiae
4.2.1.1
0.000133
-
indisulam
-
Saccharomyces cerevisiae
4.2.1.1
0.000654
-
valdecoxib
-
Saccharomyces cerevisiae
4.2.1.1
0.00102
-
sulthiame
-
Saccharomyces cerevisiae
4.2.1.1
12.5
-
saccharin
-
Saccharomyces cerevisiae
IC50 Value
EC Number
IC50 Value
IC50 Value Maximum
Commentary
Organism
Inhibitor
Structure
4.2.1.1
0.0000151
-
-
Saccharomyces cerevisiae
2-[(aminooxy)sulfinyl]-5-(2-chlorophenyl)-1,3,4-thiadiazole
4.2.1.1
0.000124
-
-
Saccharomyces cerevisiae
4-amino-N-[5-[(aminooxy)sulfinyl]-1,3,4-thiadiazol-2-yl]benzenesulfonamide
4.2.1.1
0.000154
-
-
Saccharomyces cerevisiae
4-amino-N-(2-[4-[(aminooxy)sulfinyl]phenyl]ethyl)benzenesulfonamide
4.2.1.1
0.000163
-
-
Saccharomyces cerevisiae
2-[4-[(aminooxy)sulfinyl]phenyl]ethanamine
4.2.1.1
0.000165
-
-
Saccharomyces cerevisiae
3-[4-[(aminooxy)sulfinyl]phenyl]propanoic acid
4.2.1.1
0.000166
-
-
Saccharomyces cerevisiae
4-amino-N-[4-[(aminooxy)sulfinyl]benzyl]benzenesulfonamide
4.2.1.1
0.000169
-
-
Saccharomyces cerevisiae
2,4-bis[(aminooxy)sulfinyl]-5-chloroaniline
4.2.1.1
0.000223
-
-
Saccharomyces cerevisiae
2,4-bis[(aminooxy)sulfinyl]-5-(trifluoromethyl)aniline
4.2.1.1
0.000248
-
-
Saccharomyces cerevisiae
4-[(aminooxy)sulfinyl]-2-bromoaniline
4.2.1.1
0.00036
-
-
Saccharomyces cerevisiae
5-[(aminooxy)sulfinyl]-3-methyl-1,3,4-thiadiazol-2(3H)-imine
4.2.1.1
0.000389
-
-
Saccharomyces cerevisiae
4-[(aminooxy)sulfinyl]-2-fluoroaniline
4.2.1.1
0.000433
-
-
Saccharomyces cerevisiae
1-[4-[(aminooxy)sulfinyl]phenyl]methanamine
4.2.1.1
0.000447
-
-
Saccharomyces cerevisiae
5-[(aminooxy)sulfinyl]-1,3,4-thiadiazol-2-amine
4.2.1.1
0.000457
-
-
Saccharomyces cerevisiae
4-[(aminooxy)sulfinyl]-2-chloroaniline
4.2.1.1
0.000565
-
-
Saccharomyces cerevisiae
[4-[(aminooxy)sulfinyl]phenyl]methanol
4.2.1.1
0.000976
-
-
Saccharomyces cerevisiae
4-[(aminooxy)sulfinyl]-2-iodoaniline
4.2.1.1
0.00754
-
-
Saccharomyces cerevisiae
4-[(aminooxy)sulfinyl]benzoic acid
4.2.1.1
0.00897
-
-
Saccharomyces cerevisiae
2-[4-[(aminooxy)sulfinyl]phenyl]ethanol
4.2.1.1
0.0123
-
-
Saccharomyces cerevisiae
2-[(aminooxy)sulfinyl]aniline
4.2.1.1
0.0161
-
-
Saccharomyces cerevisiae
1-[(aminooxy)sulfinyl]-4-methylbenzene
4.2.1.1
0.0185
-
-
Saccharomyces cerevisiae
4-[(aminooxy)sulfinyl]aniline
Cloned(Commentary) (protein specific)
EC Number
Commentary
Organism
4.2.1.1
expressed in Escherichia coli BL21 (DE3) cells
Saccharomyces cerevisiae
IC50 Value (protein specific)
EC Number
IC50 Value
IC50 Value Maximum
Commentary
Organism
Inhibitor
Structure
4.2.1.1
0.0000151
-
-
Saccharomyces cerevisiae
2-[(aminooxy)sulfinyl]-5-(2-chlorophenyl)-1,3,4-thiadiazole
4.2.1.1
0.000124
-
-
Saccharomyces cerevisiae
4-amino-N-[5-[(aminooxy)sulfinyl]-1,3,4-thiadiazol-2-yl]benzenesulfonamide
4.2.1.1
0.000154
-
-
Saccharomyces cerevisiae
4-amino-N-(2-[4-[(aminooxy)sulfinyl]phenyl]ethyl)benzenesulfonamide
4.2.1.1
0.000163
-
-
Saccharomyces cerevisiae
2-[4-[(aminooxy)sulfinyl]phenyl]ethanamine
4.2.1.1
0.000165
-
-
Saccharomyces cerevisiae
3-[4-[(aminooxy)sulfinyl]phenyl]propanoic acid
4.2.1.1
0.000166
-
-
Saccharomyces cerevisiae
4-amino-N-[4-[(aminooxy)sulfinyl]benzyl]benzenesulfonamide
4.2.1.1
0.000169
-
-
Saccharomyces cerevisiae
2,4-bis[(aminooxy)sulfinyl]-5-chloroaniline
4.2.1.1
0.000223
-
-
Saccharomyces cerevisiae
2,4-bis[(aminooxy)sulfinyl]-5-(trifluoromethyl)aniline
4.2.1.1
0.000248
-
-
Saccharomyces cerevisiae
4-[(aminooxy)sulfinyl]-2-bromoaniline
4.2.1.1
0.00036
-
-
Saccharomyces cerevisiae
5-[(aminooxy)sulfinyl]-3-methyl-1,3,4-thiadiazol-2(3H)-imine
4.2.1.1
0.000389
-
-
Saccharomyces cerevisiae
4-[(aminooxy)sulfinyl]-2-fluoroaniline
4.2.1.1
0.000433
-
-
Saccharomyces cerevisiae
1-[4-[(aminooxy)sulfinyl]phenyl]methanamine
4.2.1.1
0.000447
-
-
Saccharomyces cerevisiae
5-[(aminooxy)sulfinyl]-1,3,4-thiadiazol-2-amine
4.2.1.1
0.000457
-
-
Saccharomyces cerevisiae
4-[(aminooxy)sulfinyl]-2-chloroaniline
4.2.1.1
0.000565
-
-
Saccharomyces cerevisiae
[4-[(aminooxy)sulfinyl]phenyl]methanol
4.2.1.1
0.000976
-
-
Saccharomyces cerevisiae
4-[(aminooxy)sulfinyl]-2-iodoaniline
4.2.1.1
0.00754
-
-
Saccharomyces cerevisiae
4-[(aminooxy)sulfinyl]benzoic acid
4.2.1.1
0.00897
-
-
Saccharomyces cerevisiae
2-[4-[(aminooxy)sulfinyl]phenyl]ethanol
4.2.1.1
0.0123
-
-
Saccharomyces cerevisiae
2-[(aminooxy)sulfinyl]aniline
4.2.1.1
0.0161
-
-
Saccharomyces cerevisiae
1-[(aminooxy)sulfinyl]-4-methylbenzene
4.2.1.1
0.0185
-
-
Saccharomyces cerevisiae
4-[(aminooxy)sulfinyl]aniline
Inhibitors (protein specific)
EC Number
Inhibitors
Commentary
Organism
Structure
4.2.1.1
1-[(aminooxy)sulfinyl]-4-methylbenzene
-
Saccharomyces cerevisiae
4.2.1.1
1-[4-[(aminooxy)sulfinyl]phenyl]methanamine
-
Saccharomyces cerevisiae
4.2.1.1
2,4-bis[(aminooxy)sulfinyl]-5-(trifluoromethyl)aniline
-
Saccharomyces cerevisiae
4.2.1.1
2,4-bis[(aminooxy)sulfinyl]-5-chloroaniline
-
Saccharomyces cerevisiae
4.2.1.1
2-[(aminooxy)sulfinyl]-5-(2-chlorophenyl)-1,3,4-thiadiazole
-
Saccharomyces cerevisiae
4.2.1.1
2-[(aminooxy)sulfinyl]aniline
-
Saccharomyces cerevisiae
4.2.1.1
2-[4-[(aminooxy)sulfinyl]phenyl]ethanamine
-
Saccharomyces cerevisiae
4.2.1.1
2-[4-[(aminooxy)sulfinyl]phenyl]ethanol
-
Saccharomyces cerevisiae
4.2.1.1
3-[4-[(aminooxy)sulfinyl]phenyl]propanoic acid
-
Saccharomyces cerevisiae
4.2.1.1
4,5-dichloro-benzene-1,3-disulfonamide
shows effective carbonic anhydrase inhibitory activity
Saccharomyces cerevisiae
4.2.1.1
4-(2-amino-pyrimidin-4-yl)-benzenesulfonamide
best inhibitor
Saccharomyces cerevisiae
4.2.1.1
4-amino-N-[2-(4-sulfamoylphenyl)ethyl]benzenesulfonamide
-
Saccharomyces cerevisiae
4.2.1.1
4-amino-N-[4-[(aminooxy)sulfinyl]benzyl]benzenesulfonamide
-
Saccharomyces cerevisiae
4.2.1.1
4-[(aminooxy)sulfinyl]-2-bromoaniline
-
Saccharomyces cerevisiae
4.2.1.1
4-[(aminooxy)sulfinyl]-2-chloroaniline
-
Saccharomyces cerevisiae
4.2.1.1
4-[(aminooxy)sulfinyl]-2-fluoroaniline
-
Saccharomyces cerevisiae
4.2.1.1
4-[(aminooxy)sulfinyl]-2-iodoaniline
-
Saccharomyces cerevisiae
4.2.1.1
4-[(aminooxy)sulfinyl]aniline
-
Saccharomyces cerevisiae
4.2.1.1
4-[(aminooxy)sulfinyl]benzoic acid
-
Saccharomyces cerevisiae
4.2.1.1
5-[(aminooxy)sulfinyl]-1,3,4-thiadiazol-2-amine
-
Saccharomyces cerevisiae
4.2.1.1
5-[(aminooxy)sulfinyl]-3-methyl-1,3,4-thiadiazol-2(3H)-imine
-
Saccharomyces cerevisiae
4.2.1.1
5-[[(4-aminophenyl)sulfonyl]amino]-1,3,4-thiadiazole-2-sulfonamide
-
Saccharomyces cerevisiae
4.2.1.1
acetazolamide
shows effective carbonic anhydrase inhibitory activity
Saccharomyces cerevisiae
4.2.1.1
benzolamide
shows effective carbonic anhydrase inhibitory activity
Saccharomyces cerevisiae
4.2.1.1
brinzolamide
shows effective carbonic anhydrase inhibitory activity
Saccharomyces cerevisiae
4.2.1.1
celecoxib
shows effective carbonic anhydrase inhibitory activity
Saccharomyces cerevisiae
4.2.1.1
dorzolamide
shows effective carbonic anhydrase inhibitory activity
Saccharomyces cerevisiae
4.2.1.1
ethoxzolamide
shows effective carbonic anhydrase inhibitory activity
Saccharomyces cerevisiae
4.2.1.1
indisulam
shows effective carbonic anhydrase inhibitory activity
Saccharomyces cerevisiae
4.2.1.1
methazolamide
shows effective carbonic anhydrase inhibitory activity
Saccharomyces cerevisiae
4.2.1.1
saccharin
shows effective carbonic anhydrase inhibitory activity
Saccharomyces cerevisiae
4.2.1.1
sulpiride
shows effective carbonic anhydrase inhibitory activity
Saccharomyces cerevisiae
4.2.1.1
sulthiame
shows effective carbonic anhydrase inhibitory activity
Saccharomyces cerevisiae
4.2.1.1
topiramate
shows effective carbonic anhydrase inhibitory activity
Saccharomyces cerevisiae
4.2.1.1
valdecoxib
shows effective carbonic anhydrase inhibitory activity
Saccharomyces cerevisiae
4.2.1.1
zonisamide
shows effective carbonic anhydrase inhibitory activity
Saccharomyces cerevisiae
4.2.1.1
[4-[(aminooxy)sulfinyl]phenyl]methanol
-
Saccharomyces cerevisiae
Ki Value [mM] (protein specific)
EC Number
Ki Value [mM]
Ki Value maximum [mM]
Inhibitor
Commentary
Organism
Structure
4.2.1.1
0.0000151
-
4-(2-amino-pyrimidin-4-yl)-benzenesulfonamide
-
Saccharomyces cerevisiae
4.2.1.1
0.0000826
-
acetazolamide
-
Saccharomyces cerevisiae
4.2.1.1
0.0000984
-
ethoxzolamide
-
Saccharomyces cerevisiae
4.2.1.1
0.000103
-
4,5-dichloro-benzene-1,3-disulfonamide
-
Saccharomyces cerevisiae
4.2.1.1
0.000106
-
zonisamide
-
Saccharomyces cerevisiae
4.2.1.1
0.000108
-
celecoxib
-
Saccharomyces cerevisiae
4.2.1.1
0.00011
-
dorzolamide
-
Saccharomyces cerevisiae
4.2.1.1
0.00011
-
topiramate
-
Saccharomyces cerevisiae
4.2.1.1
0.000111
-
benzolamide
-
Saccharomyces cerevisiae
4.2.1.1
0.000114
-
brinzolamide
-
Saccharomyces cerevisiae
4.2.1.1
0.000119
-
methazolamide
-
Saccharomyces cerevisiae
4.2.1.1
0.000124
-
sulpiride
-
Saccharomyces cerevisiae
4.2.1.1
0.000133
-
indisulam
-
Saccharomyces cerevisiae
4.2.1.1
0.000654
-
valdecoxib
-
Saccharomyces cerevisiae
4.2.1.1
0.00102
-
sulthiame
-
Saccharomyces cerevisiae
4.2.1.1
12.5
-
saccharin
-
Saccharomyces cerevisiae
Natural Substrates/ Products (Substrates) (protein specific)
EC Number
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
4.2.1.1
CO2 + H2O
Saccharomyces cerevisiae
-
H2CO3
-
-
r
Purification (Commentary) (protein specific)
EC Number
Commentary
Organism
4.2.1.1
ammonium sulfate precipitation and Sephadex G-100 gel filtration
Saccharomyces cerevisiae
Substrates and Products (Substrate) (protein specific)
EC Number
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
4.2.1.1
CO2 + H2O
-
696740
Saccharomyces cerevisiae
H2CO3
-
-
-
r
Turnover Number [1/s] (protein specific)
EC Number
Turnover Number Minimum [1/s]
Turnover Number Maximum [1/s]
Substrate
Commentary
Organism
Structure
4.2.1.1
940000
-
CO2
-
Saccharomyces cerevisiae