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Research Article

Carbonic anhydrase inhibitors: in vitro inhibition of α isoforms (hCA I, hCA II, bCA III, hCA IV) by flavonoids

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Pages 283-288 | Received 16 Oct 2011, Accepted 18 Nov 2011, Published online: 14 Dec 2011

References

  • Rhodes MJC, Price KR. Analytical problems in the study of flavonoid compounds in onions. Food Chem 1996;57:113–117.
  • Teillet F, Boumendjel A, Boutonnat J, Ronot X. Flavonoids as RTK inhibitors and potential anticancer agents. Med Res Rev 2008;28:715–745.
  • Kühnau J. The flavonoids. A class of semi-essential food components: Their role in human nutrition. World Rev Nutr Diet 1976;24:117–191.
  • Manach C, Williamson G, Morand C, Scalbert A, Rémésy C. Bioavailability and bioefficacy of polyphenols in humans. I. Review of 97 bioavailability studies. Am J Clin Nutr 2005;81:230S–242S.
  • Pick A, Müller H, Mayer R, Haenisch B, Pajeva IK, Weigt M et al. Structure-activity relationships of flavonoids as inhibitors of breast cancer resistance protein (BCRP). Bioorg Med Chem 2011;19:2090–2102.
  • Havsteen BH. The biochemistry and medical significance of the flavonoids. Pharmacol Ther 2002;96:67–202.
  • 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.
  • Temperini C, Innocenti A, Scozzafava A, Parkkila S, Supuran CT. The coumarin-binding site in carbonic anhydrase accommodates structurally diverse inhibitors: The antiepileptic lacosamide as an example and lead molecule for novel classes of carbonic anhydrase inhibitors. J Med Chem 2010;53:850–854.
  • Maresca A, Temperini C, Vu H, Pham NB, Poulsen SA, Scozzafava A et al. Non-zinc mediated inhibition of carbonic anhydrases: Coumarins are a new class of suicide inhibitors. J Am Chem Soc 2009;131:3057–3062.
  • Maresca A, Temperini C, Pochet L, Masereel B, Scozzafava A, Supuran CT. Deciphering the mechanism of carbonic anhydrase inhibition with coumarins and thiocoumarins. J Med Chem 2010;53:335–344.
  • Stams T, Christianson DW. X-ray Crystallographic Studies of Mammalian Carbonic Anhydrase Isozymes. In The Carbonic Anhydrases—New Horizons; Chegwidden, WR, Edwards, Y, Carter, N, Eds.; Birkha¨user Verlag: Basel, 2000; pp 159–174.
  • 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.
  • Neri D, Supuran CT. Interfering with pH regulation in tumours as a therapeutic strategy. Nat Rev Drug Discov 2011;10:767–777.
  • Innocenti A, Durdagi S, Doostdar N, Strom TA, Barron AR, Supuran CT. Nanoscale enzyme inhibitors: Fullerenes inhibit carbonic anhydrase by occluding the active site entrance. Bioorg Med Chem 2010;18:2822–2828.
  • 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.
  • 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.
  • Bayram E, Senturk M, Kufrevioglu OI, Supuran CT. In vitro inhibition of salicylic acid derivatives on human cytosolic carbonic anhydrase isozymes I and II. Bioorg Med Chem 2008;16:9101–9105.
  • Sentürk M, Gülçin I, Dastan A, Küfrevioglu OI, Supuran CT. Carbonic anhydrase inhibitors. Inhibition of human erythrocyte isozymes I and II with a series of antioxidant phenols. Bioorg Med Chem 2009;17:3207–3211.
  • Oztürk Sarikaya SB, Topal F, Sentürk M, Gülçin I, Supuran CT. In vitro inhibition of a-carbonic anhydrase isozymes by some phenolic compounds. Bioorg Med Chem Lett 2011;21:4259–4262.
  • 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 2011. DOI: 10.3109/14756366.2011.591290.
  • Zhu XL, Sly WS. Carbonic anhydrase IV from human lung. Purification, characterization, and comparison with membrane carbonic anhydrase from human kidney. J Biol Chem 1990;265:8795–8801.
  • Tu CK, Thomas HG, Wynns GC, Silverman DN. Hydrolysis of 4-nitrophenyl acetate catalyzed by carbonic anhydrase III from bovine skeletal muscle. J Biol Chem 1986;261:10100–10103.
  • 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.
  • 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 DK. Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature 1970;227:680–685.
  • Innocenti A, Vullo D, Scozzafava A, Supuran CT. Carbonic anhydrase inhibitors: Interactions of phenols with the 12 catalytically active mammalian isoforms (CA I-XIV). Bioorg Med Chem Lett 2008;18:1583–1587.
  • Sentürk M, Gülçin I, Beydemir S, Küfrevioglu OI, Supuran CT. In Vitro Inhibition of Human Carbonic Anhydrase I and II Isozymes with Natural Phenolic Compounds. Chem Biol Drug Des 2011;77:494–499.
  • 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, 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.
  • 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.
  • Carta F, Temperini C, Innocenti A, Scozzafava A, Kaila K, Supuran CT. Polyamines inhibit carbonic anhydrases by anchoring to the zinc-coordinated water molecule. J Med Chem 2010;53:5511–5522.

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