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Carbonic anhydrase inhibitors: inhibition of human, bacterial, and archaeal isozymes with benzene-1,3-disulfonamides--solution and crystallographic studies.

Alterio V, De Simone G, Monti SM, Scozzafava A, Supuran CT
Bioorg Med Chem Lett 17 4201-7 (2007)
Related entries: 2pou, 2pov

Cited: 28 times
EuropePMC logo PMID: 17540563

Abstract

Three benzene-1,3-disulfonamide derivatives were investigated for their interaction with 12 mammalian alpha-carbonic anhydrases (CAs, EC 4.2.1.1), and three bacterial/archaeal CAs belonging to the alpha-, beta-, and gamma-CA class, respectively. X-ray crystal structure of the three inhibitors in complex with the dominant human isozyme CA II revealed a particular binding mode within the cavity. The sulfonamide group in meta-position to the Zn(2+)-coordinated SO(2)NH(2) moiety was oriented toward the hydrophilic side of the active site cleft, establishing hydrogen bonds with His64, Asn67, Gln92, and Thr200. The plane of the phenyl moiety of the inhibitors was rotated by 45 degrees and tilted by 10 degrees with respect to its most recurrent orientation in other CA II-sulfonamide complexes.

Reviews - 2pow mentioned but not cited (1)

  1. Carbonic anhydrase as a model for biophysical and physical-organic studies of proteins and protein-ligand binding. Krishnamurthy VM, Kaufman GK, Urbach AR, Gitlin I, Gudiksen KL, Weibel DB, Whitesides GM. Chem Rev 108 946-1051 (2008)

Articles - 2pow mentioned but not cited (2)

  1. CSAR benchmark exercise of 2010: selection of the protein-ligand complexes. Dunbar JB, Smith RD, Yang CY, Ung PM, Lexa KW, Khazanov NA, Stuckey JA, Wang S, Carlson HA. J Chem Inf Model 51 2036-2046 (2011)
  2. High-resolution structure of human carbonic anhydrase II complexed with acetazolamide reveals insights into inhibitor drug design. Sippel KH, Robbins AH, Domsic J, Genis C, Agbandje-McKenna M, McKenna R. Acta Crystallogr Sect F Struct Biol Cryst Commun 65 992-995 (2009)


Reviews citing this publication (5)

  1. Structure-based drug discovery of carbonic anhydrase inhibitors. Supuran CT. J Enzyme Inhib Med Chem 27 759-772 (2012)
  2. How many carbonic anhydrase inhibition mechanisms exist? Supuran CT. J Enzyme Inhib Med Chem 31 345-360 (2016)
  3. Exploiting the hydrophobic and hydrophilic binding sites for designing carbonic anhydrase inhibitors. De Simone G, Alterio V, Supuran CT. Expert Opin Drug Discov 8 793-810 (2013)
  4. Thermodynamic, kinetic, and structural parameterization of human carbonic anhydrase interactions toward enhanced inhibitor design. Linkuvienė V, Zubrienė A, Manakova E, Petrauskas V, Baranauskienė L, Zakšauskas A, Smirnov A, Gražulis S, Ladbury JE, Matulis D. Q Rev Biophys 51 e10 (2018)
  5. α-CAs from Photosynthetic Organisms. Langella E, Di Fiore A, Alterio V, Monti SM, De Simone G, D'Ambrosio K. Int J Mol Sci 23 12045 (2022)

Articles citing this publication (20)

  1. Investigations of the esterase, phosphatase, and sulfatase activities of the cytosolic mammalian carbonic anhydrase isoforms I, II, and XIII with 4-nitrophenyl esters as substrates. Innocenti A, Scozzafava A, Parkkila S, Puccetti L, De Simone G, Supuran CT. Bioorg Med Chem Lett 18 2267-2271 (2008)
  2. Crystal structure of human carbonic anhydrase XIII and its complex with the inhibitor acetazolamide. Di Fiore A, Monti SM, Hilvo M, Parkkila S, Romano V, Scaloni A, Pedone C, Scozzafava A, Supuran CT, De Simone G. Proteins 74 164-175 (2009)
  3. Out of the active site binding pocket for carbonic anhydrase inhibitors. D'Ambrosio K, Carradori S, Monti SM, Buonanno M, Secci D, Vullo D, Supuran CT, De Simone G. Chem Commun (Camb) 51 302-305 (2015)
  4. Crystal structure of the most catalytically effective carbonic anhydrase enzyme known, SazCA from the thermophilic bacterium Sulfurihydrogenibium azorense. De Simone G, Monti SM, Alterio V, Buonanno M, De Luca V, Rossi M, Carginale V, Supuran CT, Capasso C, Di Fiore A. Bioorg Med Chem Lett 25 2002-2006 (2015)
  5. Carbonic anhydrase inhibitors. Sulfonamide diuretics revisited--old leads for new applications? Temperini C, Cecchi A, Scozzafava A, Supuran CT. Org Biomol Chem 6 2499-2506 (2008)
  6. Synthesis and carbonic anhydrase isoenzymes I and II inhibitory effects of novel benzylamine derivatives. Çetinkaya Y, Göçer H, Göksu S, Gülçin İ. J Enzyme Inhib Med Chem 29 168-174 (2014)
  7. Conformational variability of different sulfonamide inhibitors with thienyl-acetamido moieties attributes to differential binding in the active site of cytosolic human carbonic anhydrase isoforms. Biswas S, Aggarwal M, Güzel Ö, Scozzafava A, McKenna R, Supuran CT. Bioorg Med Chem 19 3732-3738 (2011)
  8. Carbonic anhydrase inhibitors. Interaction of indapamide and related diuretics with 12 mammalian isozymes and X-ray crystallographic studies for the indapamide-isozyme II adduct. Temperini C, Cecchi A, Scozzafava A, Supuran CT. Bioorg Med Chem Lett 18 2567-2573 (2008)
  9. Sulfonamide inhibition studies of the γ-carbonic anhydrase from the Antarctic cyanobacterium Nostoc commune. Vullo D, De Luca V, Del Prete S, Carginale V, Scozzafava A, Capasso C, Supuran CT. Bioorg Med Chem 23 1728-1734 (2015)
  10. A class of carbonic anhydrase I - selective activators. Licsandru E, Tanc M, Kocsis I, Barboiu M, Supuran CT. J Enzyme Inhib Med Chem 32 37-46 (2017)
  11. Synthesis of 4-(2-substituted hydrazinyl)benzenesulfonamides and their carbonic anhydrase inhibitory effects. Gul HI, Kucukoglu K, Yamali C, Bilginer S, Yuca H, Ozturk I, Taslimi P, Gulcin I, Supuran CT. J Enzyme Inhib Med Chem 31 568-573 (2016)
  12. Carbonic anhydrase inhibitors: X-ray crystallographic studies for the binding of N-substituted benzenesulfonamides to human isoform II. Di Fiore A, Maresca A, Alterio V, Supuran CT, De Simone G. Chem Commun (Camb) 47 11636-11638 (2011)
  13. 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. Di Fiore A, Pedone C, Antel J, Waldeck H, Witte A, Wurl M, Scozzafava A, Supuran CT, De Simone G. Bioorg Med Chem Lett 18 2669-2674 (2008)
  14. X-ray crystallographic and kinetic investigations of 6-sulfamoyl-saccharin as a carbonic anhydrase inhibitor. Alterio V, Tanc M, Ivanova J, Zalubovskis R, Vozny I, Monti SM, Di Fiore A, De Simone G, Supuran CT. Org Biomol Chem 13 4064-4069 (2015)
  15. A thiabendazole sulfonamide shows potent inhibitory activity against mammalian and nematode alpha-carbonic anhydrases. Crocetti L, Maresca A, Temperini C, Hall RA, Scozzafava A, Mühlschlegel FA, Supuran CT. Bioorg Med Chem Lett 19 1371-1375 (2009)
  16. Inhibition of human carbonic anhydrase isoforms I-XIV with sulfonamides incorporating fluorine and 1,3,5-triazine moieties. Ceruso M, Vullo D, Scozzafava A, Supuran CT. Bioorg Med Chem 21 6929-6936 (2013)
  17. Carbonic anhydrase inhibitors: design of spin-labeled sulfonamides incorporating TEMPO moieties as probes for cytosolic or transmembrane isozymes. Cecchi A, Ciani L, Winum JY, Montero JL, Scozzafava A, Ristori S, Supuran CT. Bioorg Med Chem Lett 18 3475-3480 (2008)
  18. Graphlet signature-based scoring method to estimate protein-ligand binding affinity. Singh O, Sawariya K, Aparoy P. R Soc Open Sci 1 140306 (2014)
  19. Biochemical, structural, and computational studies of a γ-carbonic anhydrase from the pathogenic bacterium Burkholderia pseudomallei. Di Fiore A, De Luca V, Langella E, Nocentini A, Buonanno M, Monti SM, Supuran CT, Capasso C, De Simone G. Comput Struct Biotechnol J 20 4185-4194 (2022)
  20. A Combined in Silico and Structural Study Opens New Perspectives on Aliphatic Sulfonamides, a Still Poorly Investigated Class of CA Inhibitors. Langella E, Esposito D, Monti SM, Supuran CT, De Simone G, Alterio V. Biology (Basel) 12 281 (2023)


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