Cloning, characterization, and sulfonamide and thiol inhibition studies of an alpha-carbonic anhydrase from Trypanosoma cruzi, the causative agent of Chagas disease.

Article Details

Citation

Pan P, Vermelho AB, Capaci Rodrigues G, Scozzafava A, Tolvanen ME, Parkkila S, Capasso C, Supuran CT

Cloning, characterization, and sulfonamide and thiol inhibition studies of an alpha-carbonic anhydrase from Trypanosoma cruzi, the causative agent of Chagas disease.

J Med Chem. 2013 Feb 28;56(4):1761-71. doi: 10.1021/jm4000616. Epub 2013 Feb 19.

PubMed ID
23391336 [ View in PubMed
]
Abstract

An alpha-carbonic anhydrase (CA, EC 4.2.1.1) has been identified, cloned, and characterized from the unicellular protozoan Trypanosoma cruzi, the causative agent of Chagas disease. The enzyme (TcCA) has a very high catalytic activity for the CO2 hydration reaction, being similar kinetically to the human (h) isoform hCA II, although it is devoid of the His64 proton shuttle. A large number of aromatic/heterocyclic sulfonamides and some 5-mercapto-1,3,4-thiadiazoles were investigated as TcCA inhibitors. The aromatic sulfonamides were weak inhibitors (K(I) values of 192 nM to 84 muM), whereas some heterocyclic compounds inhibited the enzyme with K(I) values in the range 61.6-93.6 nM. The thiols were the most potent in vitro inhibitors (K(I) values of 21.1-79.0 nM), and some of them also inhibited the epimastigotes growth of two T. cruzi strains in vivo.

DrugBank Data that Cites this Article

Binding Properties
DrugTargetPropertyMeasurementpHTemperature (°C)
4-(2-AMINOETHYL)BENZENESULFONAMIDECarbonic anhydrase 2Ki (nM)160N/AN/ADetails
5-[(phenylsulfonyl)amino]-1,3,4-thiadiazole-2-sulfonamideCarbonic anhydrase 2Ki (nM)9N/AN/ADetails
AcetazolamideCarbonic anhydrase 1Ki (nM)250N/AN/ADetails
AcetazolamideCarbonic anhydrase 2Ki (nM)12N/AN/ADetails
BrinzolamideCarbonic anhydrase 1Ki (nM)45000N/AN/ADetails
BrinzolamideCarbonic anhydrase 2Ki (nM)3N/AN/ADetails
CelecoxibCarbonic anhydrase 2Ki (nM)21N/AN/ADetails
DiclofenamideCarbonic anhydrase 1Ki (nM)1200N/AN/ADetails
DiclofenamideCarbonic anhydrase 2Ki (nM)38N/AN/ADetails
DorzolamideCarbonic anhydrase 1Ki (nM)50000N/AN/ADetails
DorzolamideCarbonic anhydrase 2Ki (nM)9N/AN/ADetails
EthoxzolamideCarbonic anhydrase 1Ki (nM)25N/AN/ADetails
EthoxzolamideCarbonic anhydrase 2Ki (nM)8N/AN/ADetails
SulpirideCarbonic anhydrase 2Ki (nM)40N/AN/ADetails
SulthiameCarbonic anhydrase 2Ki (nM)9N/AN/ADetails
TopiramateCarbonic anhydrase 1Ki (nM)250N/AN/ADetails
TopiramateCarbonic anhydrase 2Ki (nM)10N/AN/ADetails
ValdecoxibCarbonic anhydrase 2Ki (nM)43N/AN/ADetails
ZonisamideCarbonic anhydrase 1Ki (nM)56N/AN/ADetails
ZonisamideCarbonic anhydrase 2Ki (nM)35N/AN/ADetails