Inhibition of human carbonic anhydrase isozymes I, II and VI with a series of bisphenol, methoxy and bromophenol compounds

References

• Maren TH. The kinetics of HCO3- synthesis related to fluid secretion, pH control, and CO2 elimination. Annu Rev Physiol 1988;50:695–717.
   PubMed Web of Science ®Google Scholar
• Supuran CT. Carbonic anhydrases: novel therapeutic applications for inhibitors and activators. Nat Rev Drug Discov 2008;7:168–181.
   PubMed Web of Science ®Google Scholar
• 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.
   PubMed Web of Science ®Google Scholar
• Kivelä J, Parkkila S, Waheed A, Parkkila AK, Sly WS, Rajaniemi H. Secretory carbonic anhydrase isoenzyme (CA VI) in human serum. Clin Chem 1997;43:2318–2322.
   PubMed Web of Science ®Google Scholar
• Karhumaa P, Leinonen J, Parkkila S, Kaunisto K, Tapanainen J, Rajaniemi H. The identification of secreted carbonic anhydrase VI as a constitutive glycoprotein of human and rat milk. Proc Natl Acad Sci USA 2001;98:11604–11608.
   PubMed Web of Science ®Google Scholar
• Supuran CT, Scozzafava A. Carbonic anhydrases as targets for medicinal chemistry. Bioorg Med Chem 2007;15:4336–4350.
   PubMed Web of Science ®Google Scholar
• Murakami H, Sly WS. Purification and characterization of human salivary carbonic anhydrase. J Biol Chem 1987;262:1382–1388.
   PubMed Web of Science ®Google Scholar
• Sly WS, Hu PY. Human carbonic anhydrases and carbonic anhydrase deficiencies. Annu Rev Biochem 1995;64:375–401.
   PubMed Web of Science ®Google Scholar
• 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.
   PubMed Web of Science ®Google Scholar
• 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.
   PubMed Web of Science ®Google Scholar
• 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.
   PubMed Web of Science ®Google Scholar
• Innocenti A, Beyza Oztürk Sarikaya S, Gülçin I, Supuran CT. Carbonic anhydrase inhibitors. Inhibition of mammalian isoforms I-XIV with a series of natural product polyphenols and phenolic acids. Bioorg Med Chem 2010;18:2159–2164.
   PubMed Web of Science ®Google Scholar
• 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.
   PubMed Web of Science ®Google Scholar
• Gribble GW. Naturally occurring organohalogen compounds-a survey. J Nat Prod 1992;55:1353–1395.
   Web of Science ®Google Scholar
• Gribble GW. The diversity of naturally occuring organobromine compounds. Chem Soc Rev 1999;28:335–346.
   Web of Science ®Google Scholar
• Balaydin HT, Gülçin Í, Menzek A, Göksu S, Sahin E. Synthesis and antioxidant properties of diphenylmethane derivative bromophenols including a natural product. J Enzyme Inhib Med Chem 2010;25:685–695.
   PubMed Web of Science ®Google Scholar
• 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 (In Press).
   Google Scholar
• Talaz O, Gülçin I, Göksu S, Saracoglu N. Antioxidant activity of 5,10-dihydroindeno[1,2-b]indoles containing substituents on dihydroindeno part. Bioorg Med Chem 2009;17:6583–6589.
   PubMed Web of Science ®Google Scholar
• Akbaba Y, Balaydin HT, Goksu S, Sahin E, Menzek A. Total synthesis of the biologically active, naturally occurring 3,4-dibromo-5-[2-bromo-3,4-dihydroxy-6-(methoxymethyl) benzyl]benzene-1,2-diol and regioselective o-demethylation of aryl methyl ethers. Helv Chim Acta 2010;93:1127–1135.
   Web of Science ®Google Scholar
• Balaydin HT, Akbaba Y, Menzek A, Sahin E, Goksu S. First and short syntheses of biologically active, naturally occurring brominated mono- and dibenzyl phenols. Arkivoc 2009;XIV:75–87.
   Google Scholar
• Pearl IA. Reactions of vanillin and its derived compounds. XXIII. The synthesis of 4,4′-dihydroxy-3,3′-dimethoxybenzophenone. J Am Chem Soc 1954;76:3635–3637.
   Web of Science ®Google Scholar
• Cabaton N, Zalko D, Rathahao E, Canlet C, Delous G, Chagnon MC et al. Biotransformation of bisphenol F by human and rat liver subcellular fractions. Toxicol in Vitro 2008;22:1697–1704.
   PubMed Web of Science ®Google Scholar
• Verpoorte JA, Mehta S, Edsall JT. Esterase activities of human carbonic anhydrases B and C. J Biol Chem 1967;242:4221–4229.
   PubMed Web of Science ®Google Scholar
• Lineweaver H, Burk D. The determination of enzyme dissocation constants. J Am Chem Soc 1934;56:658–666.
   Web of Science ®Google Scholar
• 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.
   PubMed Web of Science ®Google Scholar
• Schrodinger Suite, Schrodinger, LLC, New York, USA 2007 (web page: www.schrodinger.com).
   Google Scholar
• 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.
   PubMed Web of Science ®Google Scholar
• 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.
   PubMed Web of Science ®Google Scholar
• 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.
   Web of Science ®Google Scholar
• 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.
   PubMed Web of Science ®Google Scholar
• 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.
   PubMed Web of Science ®Google Scholar
• Ceyhun SB, Senturk M, Yerlikaya E, Erdogan O, Kufrevioglu 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 Phar 2010;32:69–74.
   Google Scholar
• Laemmli UK. Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature 1970;227:680–685.
   PubMed Web of Science ®Google Scholar
• Parkkila S, Kaunisto K, Rajaniemi L, Kumpulainen T, Jokinen K, Rajaniemi H. Immunohistochemical localization of carbonic anhydrase isoenzymes VI, II, and I in human parotid and submandibular glands. J Histochem Cytochem 1990;38:941–947.
   PubMed Web of Science ®Google Scholar
• Wilbur KM, Anderson NG. Electrometric and colorimetric determination of carbonic anhydrase. J Biol Chem 1948;176:147–154.
   PubMed Web of Science ®Google Scholar
• Supuran CT, Scozzafava A, Casini A. Carbonic anhydrase inhibitors. Med Res Rev 2003;23:146–189.
   PubMed Web of Science ®Google Scholar
• Scozzafava A, Mastrolorenzo A, Supuran CT. Carbonic anhydrase inhibitors and activators and their use in therapy. Expert Opin Ther Pat 2006;16:1627–1664.
   Web of Science ®Google Scholar
• Thiry A, Dogné JM, Supuran CT, Masereel B. Carbonic anhydrase inhibitors as anticonvulsant agents. Curr Top Med Chem 2007;7:855–864.
   PubMed Web of Science ®Google Scholar
• 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.
   PubMed Web of Science ®Google Scholar
• Ekinci D, Beydemir S, Küfrevioglu OI. In vitro inhibitory effects of some heavy metals on human erythrocyte carbonic anhydrases. J Enzyme Inhib Med Chem 2007;22:745–750.
   PubMed Web of Science ®Google Scholar
• Sentürk M, Talaz O, Ekinci D, Cavdar H, Küfrevioglu OI. In vitro inhibition of human erythrocyte glutathione reductase by some new organic nitrates. Bioorg Med Chem Lett 2009;19:3661–3663.
   PubMed Web of Science ®Google Scholar
• Abdülkadir Coban T, Beydemir S, Gülcin I, Gücin I, Ekinci D, Innocenti A et al. Sildenafil is a strong activator of mammalian carbonic anhydrase isoforms I-XIV. Bioorg Med Chem 2009;17:5791–5795.
   PubMed Web of Science ®Google Scholar
• Supuran CT. Carbonic anhydrases–an overview. Curr Pharm Des 2008;14:603–614.
   PubMed Web of Science ®Google Scholar
• 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.
   PubMed Web of Science ®Google Scholar
• 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.
   PubMed Web of Science ®Google Scholar
• Ceyhun SB, Senturk M, Erdogan O, Kufrevioglu OI. In vitro and in vivo effects of some pesticides on carbonic anhydrase enzyme from rainbow trout (Oncorhynchus mykiss) gills. Pestic Biochem Physiol 2010;97:177–181.
   Web of Science ®Google Scholar
• Nishimori I, Minakuchi T, Onishi S, Vullo D, Scozzafava A, Supuran CT. Carbonic anhydrase inhibitors. DNA cloning, characterization, and inhibition studies of the human secretory isoform VI, a new target for sulfonamide and sulfamate inhibitors. J Med Chem 2007;50:381–388.
   PubMed Web of Science ®Google Scholar
• Supuran CT, Mincione F, Scozzafava A, Briganti F, Mincione G, Ilies MA. 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;33:247–254.
   Web of Science ®Google Scholar
• Supuran CT, Scozzafava A. Novel aromatic/heterocyclic sulfonamides and their metal complexes as inhibitors of carbonic anhydrase isozymes I, II and IV. J Enzym Inhib 1997;12:37–51.
   PubMed Web of Science ®Google Scholar
• Abbate F, Winum JY, Potter BV, Casini A, Montero JL, Scozzafava A et al. Carbonic anhydrase inhibitors: X-ray crystallographic structure of the adduct of human isozyme II with EMATE, a dual inhibitor of carbonic anhydrases and steroid sulfatase. Bioorg Med Chem Lett 2004;14:231–234.
   PubMed Web of Science ®Google Scholar
• Barrese AA 3rd, Genis C, Fisher SZ, Orwenyo JN, Kumara MT, Dutta SK et al. Inhibition of carbonic anhydrase II by thioxolone: a mechanistic and structural study. Biochemistry 2008;47:3174–3184.
   PubMed Web of Science ®Google Scholar
• Innocenti A, Maresca A, Scozzafava A, Supuran CT. Carbonic anhydrase inhibitors: thioxolone versus sulfonamides for obtaining isozyme-selective inhibitors? Bioorg Med Chem Lett 2008;18:3938–3941.
   PubMed Web of Science ®Google Scholar
• Senturk M, Irfan Kufrevioglu O, Ciftci M. Effects of some analgesic anaesthetic drugs on human erythrocyte glutathione reductase: an in vitro study. J Enzyme Inhib Med Chem 2009;24:420–424.
   PubMed Web of Science ®Google Scholar
• Sahin A, Senturk M, Ciftci M, Varoglu E, Kufrevioglu OI. The effects of chemical and radioactive properties of Tl-201 on human erythrocyte glucose 6-phosphate dehydrogenase activity. Nucl Med Biol 2010;37:389–394.
   PubMed Web of Science ®Google Scholar
• Ceyhun SB, Sentürk M, Ekinci D, Erdogan O, Ciltas A, Kocaman EM. Deltamethrin attenuates antioxidant defense system and induces the expression of heat shock protein 70 in rainbow trout. Comp Biochem Physiol C 2010;152:215–223.
   PubMed Web of Science ®Google Scholar
• Akkemik E, Senturk M, Ozgeris FB, Taser P, Ciftci M. In vitro eff ects of some drugs on human erythrocyte glutathione reductase. Turk J Med Sci 2011;41:235–241.
   Web of Science ®Google Scholar
• 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.
   PubMed Web of Science ®Google Scholar
• 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 (In Press).
   Google Scholar