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Selective hydrophobic pocket binding observed within the carbonic anhydrase II active site accommodate different 4-substituted-ureido-benzenesulfonamides and correlate to inhibitor potency.

Pacchiano F, Aggarwal M, Avvaru BS, Robbins AH, Scozzafava A, McKenna R, Supuran CT
Chem Commun (Camb) 46 8371-3 (2010)
Related entries: 3n0n, 3n2p, 3n3j, 3n4b

Cited: 96 times
EuropePMC logo PMID: 20922253

Abstract

4-Substituted-ureido benzenesulfonamides showing inhibitory activity against carbonic anhydrase (CA, EC 4.2.1.1) II between 3.3-226 nM were crystallized in complex with the enzyme. Hydrophobic interactions between the scaffold of the inhibitors in different hydrophobic pockets of the enzyme were observed, explaining the diverse inhibitory range of these derivatives.

Articles - 3mzc mentioned but not cited (1)

  1. Discovery of novel 1,3-diaryltriazene sulfonamides as carbonic anhydrase I, II, VII, and IX inhibitors. Akocak S, Lolak N, Bua S, Supuran CT. J Enzyme Inhib Med Chem 33 1575-1580 (2018)


Reviews citing this publication (18)

  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. Advances in structure-based drug discovery of carbonic anhydrase inhibitors. Supuran CT. Expert Opin Drug Discov 12 61-88 (2017)
  4. Anticancer carbonic anhydrase inhibitors: a patent review (2008 - 2013). Monti SM, Supuran CT, De Simone G. Expert Opin Ther Pat 23 737-749 (2013)
  5. Sulfonamides: a patent review (2008 - 2012). Carta F, Scozzafava A, Supuran CT. Expert Opin Ther Pat 22 747-758 (2012)
  6. Inhibition of carbonic anhydrase IX targets primary tumors, metastases, and cancer stem cells: Three for the price of one. Supuran CT, Alterio V, Di Fiore A, D' Ambrosio K, Carta F, Monti SM, De Simone G. Med Res Rev 38 1799-1836 (2018)
  7. 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)
  8. Carbonic anhydrase inhibitors as emerging agents for the treatment and imaging of hypoxic tumors. Supuran CT. Expert Opin Investig Drugs 27 963-970 (2018)
  9. Carbonic Anhydrase Inhibition and the Management of Hypoxic Tumors. Supuran CT. Metabolites 7 E48 (2017)
  10. Carbonic anhydrase inhibitors as antitumor/antimetastatic agents: a patent review (2008-2018). Nocentini A, Supuran CT. Expert Opin Ther Pat 28 729-740 (2018)
  11. Targeting tumour hypoxia to prevent cancer metastasis. From biology, biosensing and technology to drug development: the METOXIA consortium. Pettersen EO, Ebbesen P, Gieling RG, Williams KJ, Dubois L, Lambin P, Ward C, Meehan J, Kunkler IH, Langdon SP, Ree AH, Flatmark K, Lyng H, Calzada MJ, Peso LD, Landazuri MO, Görlach A, Flamm H, Kieninger J, Urban G, Weltin A, Singleton DC, Haider S, Buffa FM, Harris AL, Scozzafava A, Supuran CT, Moser I, Jobst G, Busk M, Toustrup K, Overgaard J, Alsner J, Pouyssegur J, Chiche J, Mazure N, Marchiq I, Parks S, Ahmed A, Ashcroft M, Pastorekova S, Cao Y, Rouschop KM, Wouters BG, Koritzinsky M, Mujcic H, Cojocari D. J Enzyme Inhib Med Chem 30 689-721 (2015)
  12. Update on carbonic anhydrase inhibitors: a patent review (2008 - 2011). Aggarwal M, McKenna R. Expert Opin Ther Pat 22 903-915 (2012)
  13. Reconsidering anion inhibitors in the general context of drug design studies of modulators of activity of the classical enzyme carbonic anhydrase. Nocentini A, Angeli A, Carta F, Winum JY, Zalubovskis R, Carradori S, Capasso C, Donald WA, Supuran CT. J Enzyme Inhib Med Chem 36 561-580 (2021)
  14. Carbonic Anhydrase Inhibitors Targeting Metabolism and Tumor Microenvironment. Angeli A, Carta F, Nocentini A, Winum JY, Zalubovskis R, Akdemir A, Onnis V, Eldehna WM, Capasso C, Simone G, Monti SM, Carradori S, Donald WA, Dedhar S, Supuran CT. Metabolites 10 E412 (2020)
  15. Experimental Carbonic Anhydrase Inhibitors for the Treatment of Hypoxic Tumors. Supuran CT. J Exp Pharmacol 12 603-617 (2020)
  16. Crystallography and Its Impact on Carbonic Anhydrase Research. Lomelino CL, Andring JT, McKenna R. Int J Med Chem 2018 9419521 (2018)
  17. 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)
  18. Immunogenicity of necrotic cell death. Gamrekelashvili J, Greten TF, Korangy F. Cell Mol Life Sci 72 273-283 (2015)

Articles citing this publication (77)

  1. Dithiocarbamates strongly inhibit carbonic anhydrases and show antiglaucoma action in vivo. Carta F, Aggarwal M, Maresca A, Scozzafava A, McKenna R, Masini E, Supuran CT. J Med Chem 55 1721-1730 (2012)
  2. Dithiocarbamates: a new class of carbonic anhydrase inhibitors. Crystallographic and kinetic investigations. Carta F, Aggarwal M, Maresca A, Scozzafava A, McKenna R, Supuran CT. Chem Commun (Camb) 48 1868-1870 (2012)
  3. Editorial Carbonic Anhydrases and Metabolism. Supuran CT. Metabolites 8 E25 (2018)
  4. Kinetic and docking studies of phenol-based inhibitors of carbonic anhydrase isoforms I, II, IX and XII evidence a new binding mode within the enzyme active site. Durdagi S, Şentürk M, Ekinci D, Balaydın HT, Göksu S, Küfrevioğlu Öİ, Innocenti A, Scozzafava A, Supuran CT. Bioorg Med Chem 19 1381-1389 (2011)
  5. Insights towards sulfonamide drug specificity in α-carbonic anhydrases. Aggarwal M, Kondeti B, McKenna R. Bioorg Med Chem 21 1526-1533 (2013)
  6. Sulfonamides incorporating 1,3,5-triazine moieties selectively and potently inhibit carbonic anhydrase transmembrane isoforms IX, XII and XIV over cytosolic isoforms I and II: Solution and X-ray crystallographic studies. Carta F, Garaj V, Maresca A, Wagner J, Avvaru BS, Robbins AH, Scozzafava A, McKenna R, Supuran CT. Bioorg Med Chem 19 3105-3119 (2011)
  7. Combining the tail and the ring approaches for obtaining potent and isoform-selective carbonic anhydrase inhibitors: solution and X-ray crystallographic studies. Bozdag M, Ferraroni M, Nuti E, Vullo D, Rossello A, Carta F, Scozzafava A, Supuran CT. Bioorg Med Chem 22 334-340 (2014)
  8. An α-carbonic anhydrase from the thermophilic bacterium Sulphurihydrogenibium azorense is the fastest enzyme known for the CO2 hydration reaction. Luca VD, Vullo D, Scozzafava A, Carginale V, Rossi M, Supuran CT, Capasso C. Bioorg Med Chem 21 1465-1469 (2013)
  9. 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)
  10. Inhibition of carbonic anhydrases from the extremophilic bacteria Sulfurihydrogenibium yellostonense (SspCA) and S. azorense (SazCA) with a new series of sulfonamides incorporating aroylhydrazone-, [1,2,4]triazolo[3,4-b][1,3,4]thiadiazinyl- or 2-(cyanophenylmethylene)-1,3,4-thiadiazol-3(2H)-yl moieties. Alafeefy AM, Abdel-Aziz HA, Vullo D, Al-Tamimi AM, Al-Jaber NA, Capasso C, Supuran CT. Bioorg Med Chem 22 141-147 (2014)
  11. 4-Substituted-2,3,5,6-tetrafluorobenzenesulfonamides as inhibitors of carbonic anhydrases I, II, VII, XII, and XIII. Dudutienė V, Zubrienė A, Smirnov A, Gylytė J, Timm D, Manakova E, Gražulis S, Matulis D. Bioorg Med Chem 21 2093-2106 (2013)
  12. 7-Substituted-sulfocoumarins are isoform-selective, potent carbonic anhydrase II inhibitors. Tanc M, Carta F, Bozdag M, Scozzafava A, Supuran CT. Bioorg Med Chem 21 4502-4510 (2013)
  13. Carbonic anhydrase inhibitors: inhibition of the β-class enzyme from the pathogenic yeast Candida glabrata with sulfonamides, sulfamates and sulfamides. Vullo D, Leewattanapasuk W, Mühlschlegel FA, Mastrolorenzo A, Capasso C, Supuran CT. Bioorg Med Chem Lett 23 2647-2652 (2013)
  14. Polypharmacology of sulfonamides: pazopanib, a multitargeted receptor tyrosine kinase inhibitor in clinical use, potently inhibits several mammalian carbonic anhydrases. Winum JY, Maresca A, Carta F, Scozzafava A, Supuran CT. Chem Commun (Camb) 48 8177-8179 (2012)
  15. Synthesis and biological evaluation of histamine Schiff bases as carbonic anhydrase I, II, IV, VII, and IX activators. Akocak S, Lolak N, Vullo D, Durgun M, Supuran CT. J Enzyme Inhib Med Chem 32 1305-1312 (2017)
  16. Carbonic anhydrase inhibitors: benzenesulfonamides incorporating cyanoacrylamide moieties are low nanomolar/subnanomolar inhibitors of the tumor-associated isoforms IX and XII. Alafeefy AM, Isik S, Abdel-Aziz HA, Ashour AE, Vullo D, Al-Jaber NA, Supuran CT. Bioorg Med Chem 21 1396-1403 (2013)
  17. Inhibition of mammalian carbonic anhydrases I-XIV with grayanotoxin III: solution and in silico studies. Durdagi S, Scozzafava G, Vullo D, Sahin H, Kolayli S, Supuran CT. J Enzyme Inhib Med Chem 29 469-475 (2014)
  18. Mono-/dihydroxybenzoic acid esters and phenol pyridinium derivatives as inhibitors of the mammalian carbonic anhydrase isoforms I, II, VII, IX, XII and XIV. Carta F, Vullo D, Maresca A, Scozzafava A, Supuran CT. Bioorg Med Chem 21 1564-1569 (2013)
  19. Synthesis and carbonic anhydrase I, II, VII, and IX inhibition studies with a series of benzo[d]thiazole-5- and 6-sulfonamides. Abdoli M, Angeli A, Bozdag M, Carta F, Kakanejadifard A, Saeidian H, Supuran CT. J Enzyme Inhib Med Chem 32 1071-1078 (2017)
  20. 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)
  21. Probing the 'bipolar' nature of the carbonic anhydrase active site: aromatic sulfonamides containing 1,3-oxazol-5-yl moiety as picomolar inhibitors of cytosolic CA I and CA II isoforms. Krasavin M, Korsakov M, Dorogov M, Tuccinardi T, Dedeoglu N, Supuran CT. Eur J Med Chem 101 334-347 (2015)
  22. A class of 4-sulfamoylphenyl-ω-aminoalkyl ethers with effective carbonic anhydrase inhibitory action and antiglaucoma effects. Bozdag M, Pinard M, Carta F, Masini E, Scozzafava A, McKenna R, Supuran CT. J Med Chem 57 9673-9686 (2014)
  23. IM Special Issue: Sulfonamides. Supuran CT. Molecules 22 E1642 (2017)
  24. New pyrazolo[4,3-e][1,2,4]triazine sulfonamides as carbonic anhydrase inhibitors. Mojzych M, Ceruso M, Bielawska A, Bielawski K, Fornal E, Supuran CT. Bioorg Med Chem 23 3674-3680 (2015)
  25. Psychoactive substances belonging to the amphetamine class potently activate brain carbonic anhydrase isoforms VA, VB, VII, and XII. Angeli A, Vaiano F, Mari F, Bertol E, Supuran CT. J Enzyme Inhib Med Chem 32 1253-1259 (2017)
  26. Synthesis and crystallographic analysis of new sulfonamides incorporating NO-donating moieties with potent antiglaucoma action. Mincione F, Benedini F, Biondi S, Cecchi A, Temperini C, Formicola G, Pacileo I, Scozzafava A, Masini E, Supuran CT. Bioorg Med Chem Lett 21 3216-3221 (2011)
  27. Structure activity study of carbonic anhydrase IX: Selective inhibition with ureido-substituted benzenesulfonamides. Mboge MY, Mahon BP, Lamas N, Socorro L, Carta F, Supuran CT, Frost SC, McKenna R. Eur J Med Chem 132 184-191 (2017)
  28. Inhibition of the α-carbonic anhydrase from Vibrio cholerae with amides and sulfonamides incorporating imidazole moieties. De Vita D, Angeli A, Pandolfi F, Bortolami M, Costi R, Di Santo R, Suffredini E, Ceruso M, Del Prete S, Capasso C, Scipione L, Supuran CT. J Enzyme Inhib Med Chem 32 798-804 (2017)
  29. Inhibition of β-carbonic anhydrases with ureido-substituted benzenesulfonamides. Pacchiano F, Carta F, Vullo D, Scozzafava A, Supuran CT. Bioorg Med Chem Lett 21 102-105 (2011)
  30. X-ray crystallography-promoted drug design of carbonic anhydrase inhibitors. Ivanova J, Leitans J, Tanc M, Kazaks A, Zalubovskis R, Supuran CT, Tars K. Chem Commun (Camb) 51 7108-7111 (2015)
  31. Discovery of New Selenoureido Analogues of 4-(4-Fluorophenylureido)benzenesulfonamide as Carbonic Anhydrase Inhibitors. Angeli A, Tanini D, Peat TS, Di Cesare Mannelli L, Bartolucci G, Capperucci A, Ghelardini C, Supuran CT, Carta F. ACS Med Chem Lett 8 963-968 (2017)
  32. Selective inhibition of carbonic anhydrase IX over carbonic anhydrase XII in breast cancer cells using benzene sulfonamides: Disconnect between activity and growth inhibition. Mboge MY, Chen Z, Wolff A, Mathias JV, Tu C, Brown KD, Bozdag M, Carta F, Supuran CT, McKenna R, Frost SC. PLoS One 13 e0207417 (2018)
  33. Synthesis and biological evaluation of novel aromatic and heterocyclic bis-sulfonamide Schiff bases as carbonic anhydrase I, II, VII and IX inhibitors. Akocak S, Lolak N, Nocentini A, Karakoc G, Tufan A, Supuran CT. Bioorg Med Chem 25 3093-3097 (2017)
  34. Furazan and furoxan sulfonamides are strong α-carbonic anhydrase inhibitors and potential antiglaucoma agents. Chegaev K, Lazzarato L, Tamboli Y, Boschi D, Blangetti M, Scozzafava A, Carta F, Masini E, Fruttero R, Supuran CT, Gasco A. Bioorg Med Chem 22 3913-3921 (2014)
  35. 5-Substituted-(1,2,3-triazol-4-yl)thiophene-2-sulfonamides strongly inhibit human carbonic anhydrases I, II, IX and XII: solution and X-ray crystallographic studies. Leitans J, Sprudza A, Tanc M, Vozny I, Zalubovskis R, Tars K, Supuran CT. Bioorg Med Chem 21 5130-5138 (2013)
  36. In vitro inhibition effect and structure-activity relationships of some saccharin derivatives on erythrocyte carbonic anhydrase I and II. Sonmez F, Bilen C, Sumersan S, Gencer N, Isik S, Arslan O, Kucukislamoglu M. J Enzyme Inhib Med Chem 29 118-123 (2014)
  37. Synthesis and biological evaluation of novel 3-(quinolin-4-ylamino)benzenesulfonamidesAQ3 as carbonic anhydrase isoforms I and II inhibitors. Al-Sanea MM, Elkamhawy A, Paik S, Bua S, Ha Lee S, Abdelgawad MA, Roh EJ, Eldehna WM, Supuran CT. J Enzyme Inhib Med Chem 34 1457-1464 (2019)
  38. Benzamide-4-Sulfonamides Are Effective Human Carbonic Anhydrase I, II, VII, and IX Inhibitors. Abdoli M, Bozdag M, Angeli A, Supuran CT. Metabolites 8 E37 (2018)
  39. Inhibition of Carbonic Anhydrase Using SLC-149: Support for a Noncatalytic Function of CAIX in Breast Cancer. Mboge MY, Combs J, Singh S, Andring J, Wolff A, Tu C, Zhang Z, McKenna R, Frost SC. J Med Chem 64 1713-1724 (2021)
  40. Phenyl(thio)phosphon(amid)ate Benzenesulfonamides as Potent and Selective Inhibitors of Human Carbonic Anhydrases II and VII Counteract Allodynia in a Mouse Model of Oxaliplatin-Induced Neuropathy. Nocentini A, Alterio V, Bua S, Micheli L, Esposito D, Buonanno M, Bartolucci G, Osman SM, ALOthman ZA, Cirilli R, Pierini M, Monti SM, Di Cesare Mannelli L, Gratteri P, Ghelardini C, De Simone G, Supuran CT. J Med Chem 63 5185-5200 (2020)
  41. Structural effect of phenyl ring compared to thiadiazole based adamantyl-sulfonamides on carbonic anhydrase inhibition. Biswas S, Carta F, Scozzafava A, McKenna R, Supuran CT. Bioorg Med Chem 21 2314-2318 (2013)
  42. Sulphonamide inhibition studies of the β-carbonic anhydrase from the bacterial pathogen Clostridium perfringens. Vullo D, Kumar RSS, Scozzafava A, Ferry JG, Supuran CT. J Enzyme Inhib Med Chem 33 31-36 (2018)
  43. Synthesis of novel acridine and bis acridine sulfonamides with effective inhibitory activity against the cytosolic carbonic anhydrase isoforms II and VII. Ulus R, Yeşildağ I, Tanç M, Bülbül M, Kaya M, Supuran CT. Bioorg Med Chem 21 5799-5805 (2013)
  44. The first activation study of a δ-carbonic anhydrase: TweCAδ from the diatom Thalassiosira weissflogii is effectively activated by amines and amino acids. Angeli A, Alasmary FAS, Del Prete S, Osman SM, AlOthman Z, Donald WA, Capasso C, Supuran CT. J Enzyme Inhib Med Chem 33 680-685 (2018)
  45. Dioxygen, an unexpected carbonic anhydrase ligand. Ferraroni M, Gaspari R, Scozzafava A, Cavalli A, Supuran CT. J Enzyme Inhib Med Chem 33 999-1005 (2018)
  46. Isoform-selective inhibitory profile of 2-imidazoline-substituted benzene sulfonamides against a panel of human carbonic anhydrases. Supuran CT, Kalinin S, Tanç M, Sarnpitak P, Mujumdar P, Poulsen SA, Krasavin M. J Enzyme Inhib Med Chem 31 197-202 (2016)
  47. Novel thiazolidinone-containing compounds, without the well-known sulphonamide zinc-binding group acting as human carbonic anhydrase IX inhibitors. Güzel-Akdemir Ö, Angeli A, Demir K, Supuran CT, Akdemir A. J Enzyme Inhib Med Chem 33 1299-1308 (2018)
  48. Intramolecular oxidative deselenization of acylselenoureas: a facile synthesis of benzoxazole amides and carbonic anhydrase inhibitors. Angeli A, Peat TS, Bartolucci G, Nocentini A, Supuran CT, Carta F. Org Biomol Chem 14 11353-11356 (2016)
  49. Quantitative Characterization of the Interaction Space of the Mammalian Carbonic Anhydrase Isoforms I, II, VII, IX, XII, and XIV and their Inhibitors, Using the Proteochemometric Approach. Rasti B, Karimi-Jafari MH, Ghasemi JB. Chem Biol Drug Des 88 341-353 (2016)
  50. Resolution of co-eluting isomers of anti-inflammatory drugs conjugated to carbonic anhydrase inhibitors from plasma in liquid chromatography by energy-resolved tandem mass spectrometry. Menicatti M, Pallecchi M, Bua S, Vullo D, Di Cesare Mannelli L, Ghelardini C, Carta F, Supuran CT, Bartolucci G. J Enzyme Inhib Med Chem 33 671-679 (2018)
  51. Serendipitous fragment-based drug discovery: ketogenic diet metabolites and statins effectively inhibit several carbonic anhydrases. Parkkila S, Vullo D, Maresca A, Carta F, Scozzafava A, Supuran CT. Chem Commun (Camb) 48 3551-3553 (2012)
  52. The three-tails approach as a new strategy to improve selectivity of action of sulphonamide inhibitors against tumour-associated carbonic anhydrase IX and XII. Bonardi A, Bua S, Combs J, Lomelino C, Andring J, Osman SM, Toti A, Di Cesare Mannelli L, Gratteri P, Ghelardini C, McKenna R, Nocentini A, Supuran CT. J Enzyme Inhib Med Chem 37 930-939 (2022)
  53. Novel 6- and 7-Substituted Coumarins with Inhibitory Action against Lipoxygenase and Tumor-Associated Carbonic Anhydrase IX. Peperidou A, Bua S, Bozdag M, Hadjipavlou-Litina D, Supuran CT. Molecules 23 E153 (2018)
  54. Synthesis, antioxidant and carbonic anhydrase I and II inhibitory activities of novel sulphonamide-substituted coumarylthiazole derivatives. Kurt BZ, Sönmez F, Bilen Ç, Ergun A, Gençer N, Arslan O, Kucukislamoglu M. J Enzyme Inhib Med Chem 31 991-998 (2016)
  55. Benzylaminoethyureido-Tailed Benzenesulfonamides: Design, Synthesis, Kinetic and X-ray Investigations on Human Carbonic Anhydrases. Ali M, Bozdag M, Farooq U, Angeli A, Carta F, Berto P, Zanotti G, Supuran CT. Int J Mol Sci 21 E2560 (2020)
  56. Carbonic anhydrase I, II, IV and IX inhibition with a series of 7-amino-3,4-dihydroquinolin-2(1H)-one derivatives. Bozdag M, Bua S, Osman SM, AlOthman Z, Supuran CT. J Enzyme Inhib Med Chem 32 885-892 (2017)
  57. Synthesis and in vitro inhibition effect of new pyrido[2,3-d]pyrimidine derivatives on erythrocyte carbonic anhydrase I and II. Kuday H, Sonmez F, Bilen C, Yavuz E, Gençer N, Kucukislamoglu M. Biomed Res Int 2014 594879 (2014)
  58. Synthesis of an acridine orange sulfonamide derivative with potent carbonic anhydrase IX inhibitory action. Bragagni M, Carta F, Osman SM, AlOthman Z, Supuran CT. J Enzyme Inhib Med Chem 32 701-706 (2017)
  59. The first activation study of the β-carbonic anhydrases from the pathogenic bacteria Brucella suis and Francisella tularensis with amines and amino acids. Angeli A, Del Prete S, Pinteala M, Maier SS, Donald WA, Simionescu BC, Capasso C, Supuran CT. J Enzyme Inhib Med Chem 34 1178-1185 (2019)
  60. Hydrophobic substituents of the phenylmethylsulfamide moiety can be used for the development of new selective carbonic anhydrase inhibitors. De Simone G, Pizika G, Monti SM, Di Fiore A, Ivanova J, Vozny I, Trapencieris P, Zalubovskis R, Supuran CT, Alterio V. Biomed Res Int 2014 523210 (2014)
  61. Thiol-ene click chemistry for the synthesis of highly effective glycosyl sulfonamide carbonic anhydrase inhibitors. Saada MC, Ombouma J, Montero JL, Supuran CT, Winum JY. Chem Commun (Camb) 49 5699-5701 (2013)
  62. Cloning, characterization and sulfonamide inhibition studies of an α-carbonic anhydrase from the living fossil sponge Astrosclera willeyana. Ohradanova A, Vullo D, Pastorekova S, Pastorek J, Jackson DJ, Wörheide G, Supuran CT. Bioorg Med Chem 20 1403-1410 (2012)
  63. Proteochemometric Modeling of the Interaction Space of Carbonic Anhydrase and its Inhibitors: An Assessment of Structure-based and Sequence-based Descriptors. Rasti B, Namazi M, Karimi-Jafari MH, Ghasemi JB. Mol Inform 36 (2017)
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  65. Anion inhibition studies of a beta carbonic anhydrase from the malaria mosquito Anopheles gambiae. Vullo D, Syrjänen L, Kuuslahti M, Parkkila S, Supuran CT. J Enzyme Inhib Med Chem 33 359-363 (2018)
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  67. Design and synthesis of some new benzoylthioureido phenyl derivatives targeting carbonic anhydrase enzymes. Najm MAA, Mahmoud WR, Taher AT, Abbas SE, Awadallah FM, Allam HA, Vullo D, Supuran CT. J Enzyme Inhib Med Chem 37 2702-2709 (2022)
  68. Synthesis and evaluation of N-heteroarylsubstituted triazolosulfonamides as carbonic anhydrase inhibitors. Balci A, Arslan M, Nixha AR, Bilen C, Ergun A, Gençer N. J Enzyme Inhib Med Chem 30 377-382 (2015)
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  70. The effects of bronchodilator drugs and antibiotics used for respiratory infection on human erythrocyte carbonic anhydrase I and II isozymes. Sarioglu N, Bilen C, Sackes Z, Gencer N. Arch Physiol Biochem 121 56-61 (2015)
  71. Biochemical profiling of anti-HIV prodrug Elsulfavirine (Elpida®) and its active form VM1500A against a panel of twelve human carbonic anhydrase isoforms. Supuran CT, Nocentini A, Yakubova E, Savchuk N, Kalinin S, Krasavin M. J Enzyme Inhib Med Chem 36 1056-1060 (2021)
  72. New Insights into Conformationally Restricted Carbonic Anhydrase Inhibitors. Combs J, Bozdag M, Cravey LD, Kota A, McKenna R, Angeli A, Carta F, Supuran CT. Molecules 28 890 (2023)
  73. Computational Prediction of the Binding Pose of Metal-Binding Pharmacophores. Karges J, Stokes RW, Cohen SM. ACS Med Chem Lett 13 428-435 (2022)
  74. Iodine-mediated one-pot intramolecular decarboxylation domino reaction for accessing functionalised 2-(1,3,4-oxadiazol-2-yl)anilines with carbonic anhydrase inhibitory action. Angapelly S, Ramya PVS, Sodhi R, Angeli A, Rangan K, Nagesh N, Supuran CT, Arifuddin M. J Enzyme Inhib Med Chem 33 615-628 (2018)
  75. MM/GBSA prediction of relative binding affinities of carbonic anhydrase inhibitors: effect of atomic charges and comparison with Autodock4Zn. Taylor M, Ho J. J Comput Aided Mol Des 37 167-182 (2023)
  76. Potent carbonic anhydrase I, II, IX and XII inhibition activity of novel primary benzenesulfonamides incorporating bis-ureido moieties. Tekeli T, Akocak S, Petreni A, Lolak N, Çete S, Supuran CT. J Enzyme Inhib Med Chem 38 2185762 (2023)
  77. Sulfonamide-Based Azaheterocyclic Schiff Base Derivatives as Potential Carbonic Anhydrase Inhibitors: Synthesis, Cytotoxicity, and Enzyme Inhibitory Kinetics. Abas M, Rafique H, Shamas S, Roshan S, Ashraf Z, Iqbal Z, Raza H, Hassan M, Afzal K, Rizvanov AA, Asad MHHB. Biomed Res Int 2020 8104107 (2020)


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