Simple methanesulfonates are hydrolyzed by the sulfatase carbonic anhydrase activity

References

• 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
• Innocenti A, Scozzafava A, Parkkila S, Puccetti L, De Simone G, Supuran CT. Investigations of the esterase, phosphatase, and sulfatase activities of the cytosolic mammalian carbonic anhydrase isoforms I, II, and XIII with 4-nitrophenyl esters as substrates. Bioorg Med Chem Lett 2008;18:2267–2271.
   PubMed Web of Science ®Google Scholar
• Neri D, Supuran CT. Interfering with pH regulation in tumours as a therapeutic strategy. Nat Rev Drug Discov 2011;10:767–777.
   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
• Parkkila S, Parkkila AK. Carbonic anhydrase in the alimentary tract. Roles of the different isozymes and salivary factors in the maintenance of optimal conditions in the gastrointestinal canal. Scand J Gastroenterol 1996;31:305–317.
   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
• Mercan L, Okumus A, Sentürk M, Ekinci D. In vitro enzymatic response of Turkish native chicken “Gerze” to heavy metal exposure. J Enzyme Inhib Med Chem 2011. (In Press).
   PubMed Web of Science ®Google Scholar
• 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 2011. (In Press).
   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
• 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
• 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
• Burri J, Graf M, Lambelet P, Loliger J., Vanillin. More than a flavouring agent-a potent antioxidant. J Sci Food Agric 1989;48:49–56.
   Web of Science ®Google Scholar
• Supuran CT, Conroy CW, Maren TH. Is cyanate a carbonic anhydrase substrate? Proteins 1997;27:272–278.
   PubMed Web of Science ®Google Scholar
• Briganti F, Mangani S, Scozzafava A, Vernaglione G, Supuran CT. Carbonic anhydrase catalyzes cyanamide hydration to urea: Is it mimicking the physiological reaction? J Biol Inorg Chem 1999;4:528–536.
   PubMed Web of Science ®Google Scholar
• Pocker Y, Dickerson DG. The catalytic versatility of erythrocyte carbonic anhydrase. V. Kinetic studies of enzyme-catalyzed hydrations of aliphatic aldehydes. Biochemistry 1968;7:1995–2004.
   PubMed Web of Science ®Google Scholar
• Pocker Y, Meany JE. The catalytic versatility of erythrocyte carbonic anhydrase. II. Kinetic studies of the enzyme-catalyzed hydration of pyridine aldehydes. Biochemistry 1967;6:239–246.
   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
• Innocenti A, Supuran CT. Paraoxon, 4-nitrophenyl phosphate and acetate are substrates of a- but not of β-, γ- and ζ-carbonic anhydrases. Bioorg Med Chem Lett 2010;20:6208–6212.
   PubMed Web of Science ®Google Scholar
• Kaiser ET, Lo KW. The Carbonic anhydrase catalyzed hydrolysis of 2-hydroxy-5-nitro-α-toluenesuIfonic acid sultone. J Am Chem Soc 1969;91:4912–4918.
   Web of Science ®Google Scholar
• Henkart P, Guidotti G, Edsall JT. Catalysis of the hydrolysis of 1-fluoro-2,4-dinitrobenzene by carbonic anhydrase. J Biol Chem 1968;243:2447–2449.
   PubMed Web of Science ®Google Scholar
• Register AM, Koester MK, Noltmann EA. Identification of pseudo-isoenzymic subforms of muscle carbonic anhydrase. J Biol Chem 1978;253:4143–4152.
   PubMed Web of Science ®Google Scholar
• Kim G, Selengut J, Levine RL. Carbonic anhydrase III: The phosphatase activity is extrinsic. Arch Biochem Biophys 2000;377:334–340.
   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
• Ekinci D, al-Rashida M, Abbas G, Senturk M, Supuran CT. Chromone containing sulfonamides as potent carbonic anhydrase inhibitors. J Enzyme Inhib Med Chem 2011. DOI: 10.3109/14756366.2011.614607.
   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
• Laemmli DK. Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature 1970;227:680–685.
   PubMed Web of Science ®Google Scholar
• Morita J, Nakatsuji H, Misaki T, Tanabe Y. Green Chem 2005;7:711–715.
   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
• Ekinci D, Kurbanoglu NI, Salamci E, Senturk M, Supuran CT. Carbonic anhydrase inhibitors: Inhibition of human and bovine isoenzymes by benzenesulfonamides, cyclitols and phenolic compounds. J Enzyme Inhib Med Chem 2011. DOI: 10.3109/14756366.2011.621122.
   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
• Ekinci D, Senturk M. Assesment of metal inhibition of antioxidant enzyme glutathione reductase from rainbow trout liver. J Enzyme Inhib Med Chem 2011. DOI: 10.3109/14756366.2011.615745.
   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
• 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.
   PubMed Web of Science ®Google Scholar
• Wistrand PJ, Carter ND, Conroy CW, Mahieu I. Carbonic anhydrase IV activity is localized on the exterior surface of human erythrocytes. Acta Physiol Scand 1999;165:211–218.
   PubMedGoogle Scholar
• Whitney PL, Briggle TV. Membrane-associated carbonic anhydrase purified from bovine lung. J Biol Chem 1982;257:12056–12059.
   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
• Kornprobst JM, Sallenave C, Barnathan G. Sulfated compounds from marine organisms. Comp Biochem Physiol B, Biochem Mol Biol 1998;119:1–51.
   PubMed Web of Science ®Google Scholar
• McKee TC, Cardellina JH 2nd, Riccio R, D’Auria MV, Iorizzi M, Minale L et al. HIV-inhibitory natural products. 11. Comparative studies of sulfated sterols from marine invertebrates. J Med Chem 1994;37:793–797.
   PubMed Web of Science ®Google Scholar
• Anderson CJ, Lucas LJH, Widlanski TS. Molecular recognition in biological systems: Phosphate esters vs. sulfate esters and the mechanism of action of steroid sulfatases. J Am Chem Soc 1995;117:3889–3890.
   Web of Science ®Google Scholar
• Senturk M, Ekinci D, Goksu 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.
   Google Scholar
• Balaydin HT, Durdagi 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 2011. DOI:10.3109/14756366.2011.596836.
   Web of Science ®Google Scholar
• Balaydin HT, Soyut H, Ekinci D, Goksu S, Beydemir S, Menzek A, Sahin E. Synthesis and carbonic anhydrase inhibitory properties of novel bromophenols including natural products. J Enzyme Inhib Med Chem 2011. DOI: 10.3109/14756366.2011.574131.
   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 Toxicol Pharmacol 2010;152:215–223.
   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, Ceyhun SB, Aksakal E, Erdogan O. IGF and GH mRNA levels are suppressed upon exposure to micromolar concentrations of cobalt and zinc in rainbow trout white muscle. Comp Biochem Physiol C Toxicol Pharmacol 2011;153:336–341.
   PubMed Web of Science ®Google Scholar
• Erdogan O, Ceyhun SB, Ekinci D, Aksakal E. Impact of deltamethrin exposure on mRNA expression levels of metallothionein A, B and cytochrome P450 1A in rainbow trout muscles. Gene 2011;484:13–17.
   PubMed Web of Science ®Google Scholar
• Cakmak R, Durdagi S, Ekinci D, Sentürk M, Topal G. Design, synthesis and biological evaluation of novel nitroaromatic compounds as potent glutathione reductase inhibitors. Bioorg Med Chem Lett 2011;21:5398–5402.
   PubMed Web of Science ®Google Scholar
• Ceyhun SB, Aksakal E, Ekinci D, Erdogan O, Beydemir S. Influence of cobalt and zinc exposure on mRNA expression profiles of metallothionein and cytocrome P450 in rainbow trout. Biol Trace Elem Res 2011. DOI: 10.1007/s12011-011-9068-z.
   PubMed Web of Science ®Google Scholar
• Aksakal E, Ekinci D, Erdogan O, Beydemir S, Alim Z, Ceyhun SB. Increasing stocking density causes inhibition of metabolic-antioxidant enzymes and elevates mRNA levels of heat shock protein 70 in rainbow trout. Livest Sci 2011;141:69–75.
   Web of Science ®Google Scholar
• Siktar E, Ekinci D, Siktar E, Beydemir S, Gülçin I, Günay M. Protective role of l-carnitine supplementation against exhaustive exercise induced oxidative stress in rats. Eur J Pharmacol 2011;668:407–413.
   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
• Senturk M, Ekinci D, Alici HA, Beydemir S. Paraoxonase-1, an organophosphate detoxifier and cardioprotective enzyme, is inhibited by anesthetics: An in vitro and in vivo insight. Pestic Biochem Physiol 2011. DOI:10.1016/j.pestbp.2011.09.007.
   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
• Aksakal E, Ceyhun SB, Erdogan O, Ekinci D. Acute and long-term genotoxicity of deltamethrin to insulin-like growth factors and growth hormone in rainbow trout. Comp Biochem Physiol C Toxicol Pharmacol 2010;152:451–455.
   PubMed Web of Science ®Google Scholar