Carbonic anhydrase inhibitors: the X-ray crystal structure of ethoxzolamide complexed to human isoform II reveals the importance of thr200 and gln92 for obtaining tight-binding inhibitors.

Article Details

Citation

Di Fiore A, Pedone C, Antel J, Waldeck H, Witte A, Wurl M, Scozzafava A, Supuran CT, De Simone G

Carbonic anhydrase inhibitors: the X-ray crystal structure of ethoxzolamide complexed to human isoform II reveals the importance of thr200 and gln92 for obtaining tight-binding inhibitors.

Bioorg Med Chem Lett. 2008 Apr 15;18(8):2669-74. doi: 10.1016/j.bmcl.2008.03.023. Epub 2008 Mar 18.

PubMed ID
18359629 [ View in PubMed
]
Abstract

Ethoxzolamide, an almost forgotten inhibitor of the metalloenzyme carbonic anhydrase (CA, EC 4.2.1.1), is the only classical inhibitor whose structure in adduct with any isoform was not reported yet. We report here the inhibition data of this molecule with the 12 catalytically active mammalian isozymes (CA I-CA XIV) and the X-ray crystal structure with the cytosolic, ubiquitous isoform CA II. These data are presumably useful for the design of novel CA inhibitors, targeting various CA isozymes, considering that ethoxzolamide was already the lead molecule to obtain the second generation inhibitors, dorzolamide and brinzolamide, clinically used antiglaucoma agents with topical action, as well as various other investigational agents.

DrugBank Data that Cites this Article

Polypeptides
NameUniProt ID
Carbonic anhydrase 2P00918Details
Binding Properties
DrugTargetPropertyMeasurementpHTemperature (°C)
2-(hydrazinocarbonyl)-3-phenyl-1H-indole-5-sulfonamideCarbonic anhydrase 2Ki (nM)7.2N/AN/ADetails
AcetazolamideCarbonic anhydrase 1Ki (nM)250N/AN/ADetails
AcetazolamideCarbonic anhydrase 12Ki (nM)5.7N/AN/ADetails
AcetazolamideCarbonic anhydrase 14Ki (nM)41N/AN/ADetails
AcetazolamideCarbonic anhydrase 2Ki (nM)12N/AN/ADetails
AcetazolamideCarbonic anhydrase 3Ki (nM)200000N/AN/ADetails
AcetazolamideCarbonic anhydrase 4Ki (nM)74N/AN/ADetails
AcetazolamideCarbonic anhydrase 7Ki (nM)2.5N/AN/ADetails
BrinzolamideCarbonic anhydrase 1Ki (nM)45000N/AN/ADetails
BrinzolamideCarbonic anhydrase 2Ki (nM)3N/AN/ADetails
BrinzolamideCarbonic anhydrase 3Ki (nM)110000N/AN/ADetails
BrinzolamideCarbonic anhydrase 4Ki (nM)3950N/AN/ADetails
BrinzolamideCarbonic anhydrase 5A, mitochondrialKi (nM)50N/AN/ADetails
DiclofenamideCarbonic anhydrase 1Ki (nM)374N/AN/ADetails
DiclofenamideCarbonic anhydrase 2Ki (nM)9N/AN/ADetails
DiclofenamideCarbonic anhydrase 3Ki (nM)630000N/AN/ADetails
DiclofenamideCarbonic anhydrase 4Ki (nM)95N/AN/ADetails
DiclofenamideCarbonic anhydrase 7Ki (nM)6N/AN/ADetails
DorzolamideCarbonic anhydrase 1Ki (nM)50000N/AN/ADetails
DorzolamideCarbonic anhydrase 2Ki (nM)9N/AN/ADetails
DorzolamideCarbonic anhydrase 3Ki (nM)770000N/AN/ADetails
DorzolamideCarbonic anhydrase 4Ki (nM)8500N/AN/ADetails
EthoxzolamideCarbonic anhydrase 1Ki (nM)25N/AN/ADetails
EthoxzolamideCarbonic anhydrase 2Ki (nM)8N/AN/ADetails
EthoxzolamideCarbonic anhydrase 3Ki (nM)1000000N/AN/ADetails
EthoxzolamideCarbonic anhydrase 4Ki (nM)93N/AN/ADetails
EthoxzolamideCarbonic anhydrase 7Ki (nM)0.8N/AN/ADetails