895
Views
13
CrossRef citations to date
0
Altmetric
Research Article

Inhibition of carbonic anhydrase isoforms I, II, IX and XII with Schiff’s bases incorporating iminoureido moieties

, , , &
Pages 901-907 | Received 09 Sep 2014, Accepted 03 Nov 2014, Published online: 06 Mar 2015

References

  • Supuran CT. Carbonic anhydrases: novel therapeutic applications for inhibitors and activators. Nat Rev Drug Disc 2008;7:168–81
  • Capasso C, Supuran CT. Sulfa and trimethoprim-like drugs-antimetabolites acting as carbonic anhydrase, dihydropteroate synthase and dihydrofolate reductase inhibitors. J Enzyme Inhib Med Chem 2014;29:379–87
  • Supuran CT. Structure-based drug discovery of carbonic anhydrase inhibitors. J Enzyme Inhib Med Chem 2012;27:759–72
  • Alterio V, Di Fiore A, D’Ambrosio K, et al. Multiple binding modes of inhibitors to carbonic anhydrases: how to design specific drugs targeting 15 different isoforms? Chem Rev 2012;112:4421–68
  • Monti SM, Supuran CT, De Simone G. Anticancer carbonic anhydrase inhibitors: a patent review (2008–2013). Expert Opin Ther Pat 2013;23:737–49
  • Supuran CT. Carbonic anhydrase inhibitors. Bioorg Med Chem Lett 2010;20:3467–74
  • Rummer JL, McKenzie DJ, Innocenti A, et al. Root effect hemoglobin may have evolved to enhance general tissue oxygen delivery. Science 2013;340:1327–9
  • Harju AK, Bootorabi F, Kuuslahti M, et al. Carbonic anhydrase III: a neglected isozyme is stepping into the limelight. J Enzyme Inhib Med Chem 2013;28:231–9
  • Supuran CT. Carbonic anhydrases: from biomedical applications of the inhibitors and activators to biotechnologic use for CO2 capture. J Enzyme Inhib Med Chem 2013;28:229–30
  • Çavdar H, Ekinci D, Talaz O, et al. α-Carbonic anhydrases are sulfatases with cyclic diol monosulfate esters. J Enzyme Inhib Med Chem 2012;27:148–54
  • De Simone G, Alterio V, Supuran CT. Exploiting the hydrophobic and hydrophilic binding sites for designing carbonic anhydrase inhibitors. Expert Opin Drug Discov 2013;8:793–810
  • Durdagi S, Scozzafava G, Vullo D, et al. Inhibition of mammalian carbonic anhydrases I-XIV with grayanotoxin III: solution and in silico studies. J Enzyme Inhib Med Chem 2014;29:469–75
  • Bilginer S, Unluer E, Gul HI, et al. Carbonic anhydrase inhibitors. Phenols incorporating 2- or 3-pyridyl-ethenylcarbonyl and tertiary amine moieties strongly inhibit Saccharomyces cerevisiae β-carbonic anhydrase. J Enzyme Inhib Med Chem 2014;29:495–9
  • Sharma A, Tiwari M, Supuran CT. Novel coumarins and benzocoumarins acting as isoform-selective inhibitors against the tumor-associated carbonic anhydrase IX. J Enzyme Inhib Med Chem 2014;29:292–6
  • Pan J, Lau J, Mesak F, et al. Synthesis and evaluation of 18F-labeled carbonic anhydrase IX inhibitors for imaging with positron emission tomography. J Enzyme Inhib Med Chem 2014;29:249–55
  • Supuran CT, Nicolae A, Popescu A. Carbonic anhydrase inhibitors. Part 35. Synthesis of Schiff bases derived from sulfanilamide and aromatic aldehydes: the first inhibitors with equally high affinity towards cytosolic and membrane-bound isozymes. Eur J Med Chem 1996;31:431–8
  • Supuran CT, Popescu A, Ilisiu M, et al. Carbonic anhydrase inhibitors. Part 36. Inhibition of isozymes I and II with Schiff bases derived from chalcones and aromatic/heterocyclic sulfonamides. Eur J Med Chem 1996;31:439–47
  • Puccetti L, Fasolis G, Vullo D, et al. Carbonic anhydrase inhibitors. Inhibition of cytosolic/tumor-associated carbonic anhydrase isozymes I, II, IX and XII with Schiff’s bases incorporating chromone and aromatic sulfonamide moieties, and their zinc complexes. Bioorg Med Chem Lett 2005;15:3096–101
  • Supuran CT, Scozzafava A, Popescu A, et al. Carbonic anhydrase inhibitors. Part 43. Schiff bases derived from aromatic sulfonamides: towards more specific inhibitors for membrane-bound versus cytosolic isozymes. Eur J Med Chem 1997;32:445–52
  • Popescu A, Simion A, Scozzafava A, et al. Carbonic anhydrase inhibitors. Schiff bases of some aromatic sulfonamides and their metal complexes: towards more selective inhibitors of carbonic anhydrase isozyme IV. J Enzyme Inhib 1999;14:407–23
  • Scozzafava A, Banciu MD, Popescu A, Supuran CT. Carbonic anhydrase inhibitors. Synthesis of Schiff bases of hydroxybenzaldehydes with aromatic sulfonamides, and their reactions with arylsulfonyl isocyanates. J Enzyme Inhib 2000;15:533–46
  • Nasr G, Petit E, Supuran CT, et al. Dynamic combinatorial libraries in the presence of human carbonic anhydrase: towards hCA II isozyme-specific inhibitors. Bioorg Med Chem Lett 2009;19:6014–17
  • Nasr G, Petit E, Vullo D, et al. Carbonic anhydrase-encoded dynamic constitutional libraries: towards the discovery of isozyme-specific inhibitors. J Med Chem 2009;52:4853–9
  • Supuran CT, Mincione F, Scozzafava A, et al. Carbonic anhydrase inhibitors. Part 52. Metal complexes of heterocyclic sulfonamides: a new class of strong topical intraocular pressure-lowering agents with potential use as antiglaucoma drugs. Eur J Med Chem 1998;33:247–54
  • Nasr G, Cristian A, Barboiu M, et al. Carbonic anhydrase inhibitors. Inhibition of human cytosolic isoforms I and II with (reduced) Schiff’s bases incorporating sulfonamide, carboxylate and carboxymethyl moieties. Bioorg Med Chem 2014;22:2867–74
  • Abdelrahim MY, Tanc M, Winum JY, et al. Dominant behaviours in the expression of human of carbonic anhydrase hCA I activity. Chem Commun 2014;50:8043–6
  • Pichake J, Kharkar PS, Ceruso M, et al. Carbonic anhydrase inhibitors: design, synthesis and biological evaluation of novel sulfonyl semicarbazide derivatives. ACS Med Chem Lett 2014;5:793–6
  • Fabrizi F, Mincione F, Somma T, et al. A new approach to antiglaucoma drugs: carbonic anhydrase inhibitors with or without NO donating moieties. Mechanism of action and preliminary pharmacology. J Enzyme Inhib Med Chem 2012;27:138–47
  • Ekinci D, Karagoz L, Ekinci D, et al. Carbonic anhydrase inhibitors: in vitro inhibition of α isoforms (hCA I, hCA II, bCA III, hCA IV) by flavonoids. J Enzyme Inhib Med Chem 2013;28:283–8
  • Carta F, Supuran CT, Scozzafava A. Novel therapies for glaucoma: a patent review 2007–2011. Expert Opin Ther Pat 2012;22:79–88
  • Masini E, Carta F, Scozzafava A, Supuran CT. Antiglaucoma carbonic anhydrase inhibitors: a patent review. Expert Opin Ther Pat 2013;23:705–16
  • Supuran CT, Maresca A, Gregáň F, Remko M. Three new aromatic sulfonamide inhibitors of carbonic anhydrases I, II, IV and XII. J Enzyme Inhib Med Chem 2013;28:289–93
  • Alp C, Maresca A, Alp NA, et al. Secondary/tertiary benzenesulfonamides with inhibitory action against the cytosolic human carbonic anhydrase isoforms I and II. J Enzyme Inhib Med Chem 2013;28:294–8
  • Carta F, Scozzafava A, Supuran CT. Sulfonamides (RSO2NH2): a patent review 2008–2012. Expert Opin Ther Pat 2012;22:747–58
  • Supuran CT. Carbonic anhydrase inhibitors: an Editorial. Expert Opin Ther Pat 2013;23:677–9
  • Wilkinson BL, Bornaghi LF, Houston TA, et al. Carbonic anhydrase inhibitors: inhibition of isozymes I, II and IX with triazole-linked O-glycosides of benzene sulfonamides. J Med Chem 2007;50:1651–7
  • Capasso C, Supuran CT. Antiinfective carbonic anhydrase inhibitors: a patent and literature review. Expert Opin Ther Pat 2013;23:693–704
  • Supuran CT. Carbonic anhydrase inhibitors as emerging drugs for the treatment of obesity. Expert Opin Emerg Drugs 2012;17:11–15
  • Carta F, Supuran CT. Diuretics with carbonic anhydrase inhibitory action: a patent and literature review (2005–2013). Expert Opin Ther Pat 2013;23:681–91
  • Scozzafava A, Supuran CT, Carta F. Antiobesity carbonic anhydrase inhibitors: a literature and patent review. Expert Opin Ther Pat 2013;23:725–35
  • Neri D, Supuran CT. Interfering with pH regulation in tumours as a therapeutic strategy. Nat Rev Drug Discov 2011;10:767–77
  • Bonneau A, Maresca A, Winum JY, Supuran CT. Metronidazole-coumarin conjugates and 3-cyano-7-hydroxy-coumarin act as isoform-selective carbonic anhydrase inhibitors. J Enzyme Inhib Med Chem 2013;28:397–401
  • Allouche F, Chabchoub F, Carta F, Supuran CT. Synthesis of aminocyanopyrazoles via a multi-component reaction and anti-carbonic anhydrase inhibitory activity of their sulfamide derivatives against cytosolic and transmembrane isoforms. J Enzyme Inhib Med Chem 2013;28:343–9
  • Del Prete S, De Luca V, Scozzafava A, et al. Biochemical properties of a new α-carbonic anhydrase from the human pathogenic bacterium Vibrio cholerae. J Enzyme Inhib Med Chem 2014;29:23–7
  • Supuran CT, Casini A, Scozzafava A. In Supuran CT, Scozzafava A, Conway J, eds. Carbonic anhydrase: its inhibitors and activators. Boca Raton, FL: CRC Press; 2004:67–147
  • Singh S, Supuran CT. 3D-QSAR CoMFA studies on sulfonamide inhibitors of the Rv3588c β-carbonic anhydrase from Mycobacterium tuberculosis and design of not yet synthesized new molecules. J Enzyme Inhib Med Chem 2014;29:449–55
  • Gieling RG, Parker CA, De Costa LA, et al. Inhibition of carbonic anhydrase activity modifies the toxicity of doxorubicin and melphalan in tumour cells in vitro. J Enzyme Inhib Med Chem 2013;28:360–9
  • Yogeeswari P, Thirumurugan R, Kavya R, et al. 3-Chloro-2-methyl phenyl-substituted semicarbazones: synthesis and anticonvulsant activity. Eur J Med Chem 2004;39:729–34
  • Scozzafava A, Supuran CT. Carbonic anhydrase inhibitors: ureido and thioureido derivatives of aromatic sulphonamides possessing increased affinities for isoenzyme I.A novel route to 2,5-disubstituted-1,3,4-thiadiazoles via thioureas and their interaction with isozymes I, II and IV. J Enzyme Inhib Med Chem 1998;13:103–23
  • Pandeya SN, Yogeeswari P, Sausville E, et al. Synthesis and antitumour activity of some aryl semicarbazones. Sci Pharm 2000;68:369–77
  • Khalifah RG. The carbon dioxide hydration activity of carbonic anhydrase. I. Stop-flow kinetic studies on the native human isoenzymes B and C. J Biol Chem 1971;246:2561–73
  • Maresca A, Vullo D, Scozzafava A, Supuran CT. Inhibition of the alpha- and beta-carbonic anhydrases from the gastric pathogen Helicobacter pylori with anions. J Enzyme Inhib Med Chem 2013;28:388–91
  • Alp C, Özsoy S, Alp NA, et al. Sulfapyridine-like benzenesulfonamide derivatives as inhibitors of carbonic anhydrase isoenzymes I, II and VI. J Enzyme Inhib Med Chem 2012;27:818–24
  • Maresca A, Scozzafava A, Vullo D, Supuran CT. Dihalogenated sulfanilamides and benzolamides are effective inhibitors of the three β-class carbonic anhydrases from Mycobacterium tuberculosis. J Enzyme Inhib Med Chem 2013;28:384–7
  • Koz O, Ekinci D, Perrone A, et al. Analysis of saponins and phenolic compounds as inhibitors of α-carbonic anhydrase isoenzymes. J Enzyme Inhib Med Chem 2013;28:412–17

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.