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Research Article

Kinetic and in silico analysis of thiazolidin-based inhibitors of α-carbonic anhydrase isoenzymes

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Pages 370-374 | Received 28 Aug 2012, Accepted 17 Sep 2012, Published online: 23 Nov 2012

References

  • Supuran CT. Carbonic anhydrases: novel therapeutic applications for inhibitors and activators. Nat Rev Drug Discov 2008;7:168–181.
  • Supuran CT, Scozzafava A. Carbonic anhydrases as targets for medicinal chemistry. Bioorg Med Chem 2007;15:4336–4350.
  • Hilvo M, Baranauskiene L, Salzano AM, Scaloni A, Matulis D, Innocenti A et al. Biochemical characterization of CA IX, one of the most active carbonic anhydrase isozymes. J Biol Chem 2008;283:27799–27809.
  • Pastorekova S, Parkkila S, Pastorek J, Supuran CT. Carbonic anhydrases: current state of the art, therapeutic applications and future prospects. J Enzyme Inhib Med Chem 2004;19:199–229.
  • Durdagi S, Sentürk M, Ekinci D, Balaydin HT, Göksu S, Küfrevioglu ÖI et al. 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. Bioorg Med Chem 2011;19:1381–1389.
  • Alp C, Ekinci D, Gültekin MS, Sentürk M, Sahin E, Küfrevioglu OI. A novel and one-pot synthesis of new 1-tosyl pyrrol-2-one derivatives and analysis of carbonic anhydrase inhibitory potencies. Bioorg Med Chem 2010;18:4468–4474.
  • Ekinci D, Cavdar H, Talaz O, Sentürk M, Supuran CT. NO-releasing esters show carbonic anhydrase inhibitory action against human isoforms I and II. Bioorg Med Chem 2010;18:3559–3563.
  • Ceyhun SB, Sentürk M, Yerlikaya E, Erdogan O, Küfrevioglu OI, Ekinci D. Purification and characterization of carbonic anhydrase from the teleost fish Dicentrarchus labrax (European seabass) liver and toxicological effects of metals on enzyme activity. Environ Toxicol Pharmacol 2011;32:69–74.
  • Sentürk M, Ekinci D, Göksu S, Supuran CT. Effects of dopaminergic compounds on carbonic anhydrase isozymes I, II, and VI. J Enzyme Inhib Med Chem 2012;27:365–369.
  • Ekinci D, Cavdar H, Durdagi S, Talaz O, Sentürk M, Supuran CT. Structure-activity relationships for the interaction of 5,10-dihydroindeno[1,2-b]indole derivatives with human and bovine carbonic anhydrase isoforms I, II, III, IV and VI. Eur J Med Chem 2012;49:68–73.
  • Cavdar H, Talaz O, Ekinci D. Synthesis of novel mono and bis-indoleconduritol derivatives and their α/β-glycosidase inhibitory effects. Bioorg Med ChemLett 2012 (In Press).
  • Balaydin HT, Durdagi S, Ekinci D, Sentürk M, Göksu S, Menzek A. Inhibition of human carbonic anhydrase isozymes I, II and VI with a series of bisphenol, methoxy and bromophenol compounds. J Enzyme Inhib Med Chem 2012;27:467–475.
  • Andres CJ, Bronson JJ, D’Andrea SV, Deshpande MS, Falk PJ, Grant-Young KA et al. 4-Thiazolidinones: novel inhibitors of the bacterial enzyme MurB. Bioorg Med Chem Lett 2000;10:715–717.
  • Grasso S, Chimirri A, Monforte P, Fenech G, Zappalà M, Monforte AM. Compounds with potential antitumor activity. VI–2-Alkyl-3-[2-(1,3,4-thiadiazolyl)]-4-thiazolidinones. Farmaco Sci 1988;43:851–856.
  • Look GC, Schullek JR, Holmes CP, Chinn JP, Gordon EM, Gallop MA. The identification of cyclooxygenase-1 inhibitors from 4-thiazolidinone combinatorial libraries. Bioorg Med Chem Lett 1996;6:707–712.
  • Fidan I, Kazaz C, Sahin E, Kaban S. Synthesis and spectral investigation of some methyl-substituted 3-(2-pyridyl)-2-(2-thienyl)thiazolidin-4-one derivatives. J Chem Res 2010;5:296–300.
  • Ekinci D, Ceyhun SB, Sentürk M, Erdem D, Küfrevioglu OI, Supuran CT. Characterization and anions inhibition studies of an a-carbonic anhydrase from the teleost fish Dicentrarchus labrax. Bioorg Med Chem 2011;19:744–748.
  • Bradford MM. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem 1976;72:248–254.
  • Laemmli UK. Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature 1970;227:680–685.
  • Verpoorte JA, Mehta S, Edsall JT. Esterase activities of human carbonic anhydrases B and C. J Biol Chem 1967;242:4221–4229.
  • Lineweaver H, Burk D. The determination of enzyme dissocation constants. J Am Chem Soc 1934;56:658–666.
  • Cheng Y, Prusoff WH. Relationship between the inhibition constant (K1) and the concentration of inhibitor which causes 50 per cent inhibition (I50) of an enzymatic reaction. Biochem Pharmacol 1973;22:3099–3108.
  • Schrodinger Suite, Schrodinger, LLC, New York, USA. 2007. (web page: www.schrodinger.com). Accessed on 10/7/2012.
  • Sherman W, Day T, Jacobson MP, Friesner RA, Farid R. Novel procedure for modeling ligand/receptor induced fit effects. J Med Chem 2006;49:534–553.
  • Friesner RA, Murphy RB, Repasky MP, Frye LL, Greenwood JR, Halgren TA et al. Extra precision glide: docking and scoring incorporating a model of hydrophobic enclosure for protein-ligand complexes. J Med Chem 2006;49:6177–6196.
  • Talaz O, Cavdar H, Azak H, Durdagi S, Ekinci D. Synthesis of 1,4-bis(indolin-1-ylmethyl) benzene derivatives and their structure-activity relationships for the interaction of human carbonic anhydrase isoforms I and II. Bioorg Med Chem 2012, DOI: 10.1016/j.bmc.2012.09.027.
  • Demirdag R, Comakli V, Senturk M, Ekinci D, IrfanKüfrevioglu O, Supuran CT. Purification and characterization of carbonic anhydrase from sheep kidney and effects of sulfonamides on enzyme activity. Bioorg Med Chem 2012, DOI: 10.1016/j.bmc.2012.08.018.
  • Alp C, Maresca A, Alp NA, Gültekin MS, Ekinci D, Scozzafava A et al. Secondary/tertiary benzenesulfonamides with inhibitory action against the cytosolic human carbonic anhydrase isoforms I and II. J Enzyme Inhib Med Chem 2012, DOI: 10.3109/14756366.2012.658788.
  • Cavdar H, Ekinci D, Talaz O, Saraçoglu N, Sentürk M, Supuran CT. a-Carbonic anhydrases are sulfatases with cyclic diol monosulfate esters. J Enzyme Inhib Med Chem 2012;27:148–154.
  • Balaydin HT, Sentürk M, Menzek A. Synthesis and carbonic anhydrase inhibitory properties of novel cyclohexanonyl bromophenol derivatives. Bioorg Med Chem Lett 2012;22:1352–1357.
  • Nair SK, Ludwig PA, Christianson DW. Two-site binding of phenol in the active site of human carbonic anhydrase II: structural implications for substrate association. J Am Chem Soc 1994;116:3659–3660.
  • Ekinci D, Sentürk M, Küfrevioglu ÖI. Salicylic acid derivatives: synthesis, features and usage as therapeutic tools. Expert Opin Ther Pat 2011;21:1831–1841.
  • Ekinci D, Sentürk M, Beydemir S, Küfrevioglu OI, Supuran CT. An alternative purification method for human serum paraoxonase 1 and its interactions with sulfonamides. Chem Biol Drug Des 2010;76:552–558.
  • Innocenti A, Casini A, Alcaro MC, Papini AM, Scozzafava A, Supuran CT. Carbonic anhydrase inhibitors: the first on-resin screening of a 4-sulfamoylphenylthiourea library. J Med Chem 2004;47:5224–5229.
  • Balaydin HT, Durdagı S, Ekinci D, Senturk M, Goksu S, Menzek A. Inhibition of human carbonic anhydrase isozymes I, II and VI with a series of bisphenol, metoxy and bromophenol compounds. J Enzyme Inhib Med Chem 2012, doi:10.3109/14756366.2011.596836.
  • Ekinci D, Al-Rashida M, Abbas G, Sentürk M, Supuran CT. Chromone containing sulfonamides as potent carbonic anhydrase inhibitors. J Enzyme Inhib Med Chem 2012;27:744–747.
  • Ekinci D, Kurbanoglu NI, Salamci E, Sentürk M, Supuran CT. Carbonic anhydrase inhibitors: inhibition of human and bovine isoenzymes by benzenesulphonamides, cyclitols and phenolic compounds. J Enzyme Inhib Med Chem 2011, DOI: 10.3109/14756366.2011.621122.
  • Ozdemir ZO, Sentürk M, Ekinci D. Inhibition of mammalian carbonic anhydrase isoforms I, II and VI with thiamine and thiamine-like molecules. J Enzyme Inhib Med Chem 2011, DOI: 10.3109/14756366.2011.637200.
  • Ekinci D, Karagoz L, Ekinci D, Senturk M, Supuran CT. Carbonic anhydrase inhibitors: in vitro inhibition of a isoforms (hCA I, hCA II, bCA III, hCA IV) by flavonoids. J Enzyme Inhib Med Chem 2011, DOI: 10.3109/14756366.2011.643303.
  • Koz O, Ekinci D, Perrone A, Piacente S, Alankus-Caliskan O, Bedir E, Supuran CT. Analysis of saponins and phenolic compounds as inhibitors of α-carbonic anhydrase isoenzymes. J Enzyme Inhib Med Chem 2012, doi:10.3109/14756366.2011.651464.

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