794
Views
17
CrossRef citations to date
0
Altmetric
Research Article

Dithiocarbamates with potent inhibitory activity against the Saccharomyces cerevisiaeβ-carbonic anhydrase

, , , , , , & show all
Pages 132-136 | Received 16 Dec 2014, Accepted 15 Jan 2015, Published online: 11 Feb 2015

References

  • 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
  • Supuran CT. Carbonic anhydrases: novel therapeutic applications for inhibitors and activators. Nat Rev Drug Discov 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
  • 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;20:3467–3474
  • 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
  • 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;17:11–5
  • 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
  • D'Ascenzio M, Carradori S, Secci D, et al. Selective inhibition of human carbonic anhydrases by novel amide derivatives of probenecid: synthesis, biological evaluation and molecular modelling studies. Bioorg Med Chem 2014;22:3982–8
  • 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
  • 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
  • Maresca A, Vullo D, Scozzafava A, Supuran CT. Inhibition of the alpha- and beta-carbonic anhydrases from the gastric pathogen Helycobacter 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;28:412–7
  • Ebbesen P, Pettersen EO, Gorr TA, et al. Taking advantage of tumor cell adaptations to hypoxia for developing new tumor markers and treatment strategies. J Enzyme Inhib Med Chem 2009;24(S1):1–39
  • Carta F, Aggarwal M, Maresca A, et al. Dithiocarbamates: a new class of carbonic anhydrase inhibitors. Crystallographic and kinetic investigations. Chem Commun (Cambridge) 2012;48:1868–70
  • Carta F, Aggarwal M, Maresca A, et al. Dithiocarbamates strongly inhibit carbonic anhydrases and show antiglaucoma action in vivo. J Med Chem 2012;55:1721–30
  • Monti SM, Maresca A, Viparelli F, et al. Dithiocarbamates strongly inhibit the beta-class fungal carbonic anhydrases from Cryptococcus neoformans, Candida albicans and Candida glabrata. Bioorg Med Chem Lett 2012;22:859–62
  • Maresca A, Carta F, Vullo D, Supuran CT. Dithiocarbamates strongly inhibit the beta-class carbonic anhydrases from Mycobacterium tuberculosis. J Enzyme Inhib Med Chem 2013;28:407–11
  • Avram S, Milac AL, Carta F, Supuran CT. More effective dithiocarbamate derivatives inhibiting carbonic anhydrases, generated by QSAR and computational design. J Enzyme Inhib Med Chem 2013;28:350–9
  • Temperini C, Scozzafava A, Supuran CT. Carbonic anhydrase inhibitors. X-ray crystal studies of the carbonic anhydrase II – trithiocarbonate adduct – an inhibitor mimicking the sulfonamide and urea binding to the enzyme. Bioorg Med Chem Lett 2010;20:474–8
  • Isik S, Kockar F, Arslan O, et al. Carbonic anhydrase inhibitors. Inhibition of the β-class enzyme from the yeast Saccharomyces cerevisiae with anions. Bioorg Med Chem Lett 2008;18:6327–31
  • Isik S, Kockar F, Aydin M, et al. Carbonic anhydrase inhibitors. Inhibition of the β-class enzyme from the yeast Saccharomyces cerevisiae with sulfonamides and sulfamates. Bioorg Med Chem 2009;17:1158–63
  • Isik S, Guler OO, Kockar F, et al. Saccharomyces cerevisiae β-carbonic anhydrase inhibition and activation studies. Curr Pharm Des 2010;16:3327–36
  • Hall RA, Mühlschlegel FA. Fungal and nematode carbonic anhydrases: their inhibition in drug design. In: Supuran CT, Winum JY, eds. Drug design of zinc-enzyme inhibitors: functional, structural, and disease applications. Hoboken: John Wiley & Sons; 2009:301–22
  • Ohndorf UM, Schlicker C, Steegborn C. Crystallographic studies on carbonic anhydrases from fungal pathogens for structure-assisted drug development. In: Supuran CT, Winum JY, eds. Drug design of zinc-enzyme inhibitors: functional, structural, and disease applications. Hoboken: John Wiley & Sons; 2009:323–34
  • Carta F, Innocenti A, Hall RA, et al. Carbonic anhydrase inhibitors. Inhibition of the β-class enzymes from the fungal pathogens Candida albicans and Cryptococcus neoformans with branched aliphatic-/aromatic carboxylates and their derivatives. Bioorg Med Chem Lett 2011;21:2521–6
  • Bozdag M, Carta F, Vullo D, et al. New dithiocarbamates with effective carbonic anhydrase inhibitory activity. J Med Chem, submitted
  • 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
  • Pacchiano F, Carta F, McDonald PC, et al. Ureido-substituted benzenesulfonamides potently inhibit carbonic anhydrase IX and show antimetastatic activity in a model of breast cancer metastasis. J Med Chem 2011;54:1896–902

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.