The human carbonic anhydrase isoenzymes I and II (hCA I and II) inhibition effects of trimethoxyindane derivatives

References

• Supuran CT, Scozzafava A. Carbonic anhydrases as targets for medicinal chemistry. Bioorg Med Chem 2007;15:4336–50
   PubMed Web of Science ®Google Scholar
• Gülçin İ, Beydemir Ş, Büyükokuroğlu ME. In vitro and in vivo effects of dantrolene on carbonic anhydrase enzyme activities. Biol Pharm Bull 2004;27:613–16
   PubMed Web of Science ®Google Scholar
• Zo1nowska B, S1awinskia J, Pogorzelska A, et al. Carbonic anhydrase inhibitors. Synthesis, and molecular structure of novel series N-substituted N′-(2-arylmethylthio-4-chloro-5-methyl benzenesulfonyl) guanidines and their inhibition of human cytosolic isozymes I and II and the transmembrane tumor-associated isozymes IX and XII. Eur. J Med Chem 2014;71:135–47
   PubMed Web of Science ®Google Scholar
• Aksu K, Nar M, Tanç M, et al. The synthesis of sulfamide analogues of dopamine related compounds and their carbonic anhydrase inhibitory properties. Bioorg Med Chem 2013;21:2925–31
   PubMed Web of Science ®Google Scholar
• Akıncıoğlu A, Topal M, Gülçin İ, Göksu S. Novel sulfamides and sulfonamides incorporating tetralin scaffold as carbonic anhydrase and acetylcholine esterase inhibitors. Arch Pharm 2014;347:68–76
   PubMed Web of Science ®Google Scholar
• Çetinkaya Y, Göçer H, Göksu S, Gülçin İ. Synthesis and carbonic anhydrase isoenzymes inhibitory effects of novel benzylamine derivatives. J Enzyme Inhib Med Chem 2014;29:168–74
   PubMed Web of Science ®Google Scholar
• Supuran CT. Carbonic anhydrases: novel therapeutic applications for inhibitors and activators. Nat Rev Drug Disc 2008;7:168–81
   PubMed Web of Science ®Google Scholar
• Akbaba Y, Akıncıoğlu A, Göçer H, et al. Carbonic anhydrase inhibitory properties of novel sulfonamide derivatives of aminoindanes and aminotetralins. J Enzyme Inhib Med Chem 2014;29:35–42
   PubMed Web of Science ®Google Scholar
• Beydemir Ş, Gülçin İ. Effect of melatonin on carbonic anhydrase from human erythrocyte in vitro and from rat erythrocyte in vivo. J Enzyme Inhib Med Chem 2004;19:193–7
   PubMed Web of Science ®Google Scholar
• Gülçin İ, Beydemir S. Phenolic compounds as antioxidants: carbonic anhydrase isoenzymes inhibitors. Mini Rev Med Chem 2013;13:408–30
   PubMed Web of Science ®Google Scholar
• Del Pretea S, Vullo D, Fisher GM, et al. Discovery of a new family of carbonic anhydrases in the malaria pathogen Plasmodium falciparum – the η-carbonic anhydrases. Bioorg Med Chem Lett 2014;24:4389–96
   PubMed Web of Science ®Google Scholar
• Ceruso M, Antel S, Vullo D, et al. Inhibition studies of new ureido-substituted sulfonamides incorporating a GABA moiety against human carbonic anhydrase isoforms I–XIV. Bioorg Med Chem Lett 2014;22:6768–75
   Web of Science ®Google Scholar
• Boztaş M, Çetinkaya Y, Topal M et al. Synthesis and carbonic anhydrase isoenzymes I, II, IX, and XII inhibitory effects of dimethoxy-bromophenol derivatives incorporating cyclopropane moieties. J Med Chem, 2015;58:640–50
   PubMed Web of Science ®Google Scholar
• Sen E, Alim Z, Duran H, et al. Inhibitory effect of novel pyrazole carboxamide derivatives on human carbonic anhydrase enzyme. J Enzyme Inhib Med Chem 2013;28:328–36
   PubMed Web of Science ®Google Scholar
• Guney M, Coskun A, Topal F, et al. Oxidation of cyanobenzocycloheptatrienes: synthesis, photooxygenation reaction and carbonic anhydrase isoenzymes inhibition properties of some new benzotropone derivatives. Bioorg Med Chem 2014;22:3537–43
   PubMed Web of Science ®Google Scholar
• Arabaci B, Gülçin İ, Alwasel S. Capsaicin: a potent inhibitor of carbonic anhydrase isoenzymes. Molecules 2014;19:10103–14
   PubMed Web of Science ®Google Scholar
• Scozzafava A, Passaponti M, Supuran CT, Gülçin İ. Carbonic anhydrase inhibitors: guaiacol and catechol derivatives effectively inhibit certain human carbonic anhydrase isoenzymes (hCA I, II, IX, and XII). J Enzyme Inhib Med Chem 2014. [Epub ahead of print]. DOI:10.3109/14756366.2014.956310
   Web of Science ®Google Scholar
• Scozzafava A, Kalın P, Supuran CT, et al. The impact of hydroquinone on acetylcholine esterase and certain human carbonic anhydrase isoenzymes (hCA I, II, IX, and XII). J Enzyme Inhib Med Chem 2015. [Epub ahead of print]. doi: 10.3109/14756366.2014.999236
   Web of Science ®Google Scholar
• Ram S, Ceruso M, Khloya P, et al. 4-Functionalized 1,3-diarylpyrazoles bearing 6-aminosulfonylbenzothiazole moiety as potent inhibitors of carbonic anhydrase isoforms hCA I, II, IX and XII. Bioorg Med Chem 2014;22:6945–52
   PubMed Web of Science ®Google Scholar
• Mincione F, Scozzafava A, Supuran CT. Antiglaucoma carbonic anhydrase inhibitors as ophthalomologic drugs. In: Supuran CT, Winum JY, eds. Drug design of zinc-enzyme inhibitors: functional, structural, and disease applications. Hoboken: Wiley; 2009:139
   Google Scholar
• De Simone G, Di Fiore A, Supuran CT. Are carbonic anhydrase inhibitors suitable for obtaining antiobesity drugs? Curr Pharm Des 2008;14:655–60
   PubMed Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• Sethi KK, Verma SM, Tanç M, et al. Carbonic anhydrase inhibitors: synthesis and inhibition of the human carbonic anhydrase isoforms I, II, IX and XII with benzene sulfonamides incorporating 4- and 3-nitrophthalimide moieties. Bioorg Med Chem 2014;22:1586–95
   PubMed Web of Science ®Google Scholar
• Franchi M, Vullo D, Gallori E, et al. Carbonic anhydrase inhibitors: inhibition of human and murine mitochondrial isozymes V with anions. Bioorg Med Chem Lett 2003;13:2857–61
   PubMed Web of Science ®Google Scholar
• Supuran CT, Scozzafava A. Carbonic anhydrase inhibitors and their therapeutic potential. Exp Opin Ther Patents 2000;10:575–600
   Web of Science ®Google Scholar
• Goodman CB, Soliman KFA. Altered brain cholinergic enzymes activity in the genetically obese rat. Cell Mol Life Sci 1991;47:833–5
   Web of Science ®Google Scholar
• Kouniniotou-Krontiri P, Tsakiris S. Time dependence of Li+ action on acetylcholinesterase activity in correlation with spontaneous quantal release of acetylcholine in rat diaphragm. Jpn J Physiol 1989;39:429–40
   PubMedGoogle Scholar
• Herholz K, Weisenbach S, Zundorf G, et al. In vivo study of acetylcholine esterase in basal forebrain, amygdala, and cortex in mild to moderate Alzheimer disease. Neuroimage 2004;21:136–43
   PubMed Web of Science ®Google Scholar
• Srividhya R, Gayathri R, Kalaiselvi P. Impact of epigallo catechin-3-gallate on acetylcholine-acetylcholine esterase cycle in aged rat brain. Neurochem Int 2012;60:517–22
   PubMed Web of Science ®Google Scholar
• Tucek S. Regulation of acetylcholine synthesis in the brain. J Neurochem 1985;44:11–24
   PubMed Web of Science ®Google Scholar
• Willis LM, Shukitt-Hale B, Joseph JA. Dietary polyunsaturated fatty acids improve cholinergic transmission in the aged brain. Genes Nutr 2009;4:309–14
   PubMed Web of Science ®Google Scholar
• Winum JY, Scozzafava A, Montero JL, Supuran CT. Therapeutic potential of sulfamides as enzyme inhibitors. Med Res Rev 2006;26:767–92
   PubMed Web of Science ®Google Scholar
• Akbaba Y, Bastem E, Topal F, et al. Synthesis and carbonic anhydrase inhibitory effects of novel sulfamides derived from 1-aminoindanes and anilines. Arch Pharm 2014;347:950–7
   PubMed Web of Science ®Google Scholar
• Göksu S, Naderi A, Akbaba Y, et al. Carbonic anhydrase inhibitory properties of novel benzylsulfamides using molecular modeling and experimental studies. Bioorg Chem 2014;56:75–82
   PubMed Web of Science ®Google Scholar
• Christianson DW, Fierke CA. Carbonic anhydrase: evolution of the zinc binding site by nature and by design. Acc Chem Res 1996;29:331–9
   Web of Science ®Google Scholar
• Topal, M, Gülçin İ. Rosmarinic acid: a potent carbonic anhydrase isoenzymes inhibitor. Turk J Chem 2014;38:894–902
   Web of Science ®Google Scholar
• Gitto R, Damiano FM, Mader P, et al. Synthesis, structure-activity relationship studies, and x-ray crystallographic analysis of arylsulfonamides as potent carbonic anhydrase inhibitors. J Med Chem 2012;55:3891–9
   PubMed Web of Science ®Google Scholar
• Pecina A, Lepsik M, Rezac C, et al. QM/MM Calculations reveal the different nature of the interaction of two carborane-based sulfamide inhibitors of human carbonic anhydrase II. J Phys Chem B 2013;117:16096–104
   PubMed Web of Science ®Google Scholar
• Özgeriş B, Aksu K, Tümer F, Göksu S. The synthesis of dopamine, rotigotin, ladostigil, rasagiline analogues 2-amino-4,5,6-trımethoxyindane, 1-amino-5,6,7-trımethoxyindane and their sulfamide derivatives. Synthetic Commun 2015;45:78–85
   Web of Science ®Google Scholar
• Gülçin İ, Beydemir Ş, Büyükokuroğlu ME. In vitro and in vivo effects of dantrolene on carbonic anhydrase enzyme activities. Biol Pharm Bull 2004;27:613–16
   PubMed Web of Science ®Google Scholar
• Kaya ED, Soyut H, Beydemir S. Carbonic anhydrase activity from the gilthead sea bream (Sparus aurata) liver: the toxicological effects of heavy metals. Environ Toxicol Pharmacol 2013;36:514–21
   PubMed Web of Science ®Google Scholar
• Çoban TA, Beydemir Ş, Gülçin İ, Ekinci D. Morphine inhibits erythrocyte carbonic anhydrase in vitro and in vivo. Biol Pharm Bull 2007;30:2257–61
   PubMed Web of Science ®Google Scholar
• ArasHisar Ş, Hisar O, Beydemir Ş, et al. Effect of vitamin E on carbonic anhydrase enzyme activity in rainbow trout (Oncorhynchus mykiss) erythrocytes in vitro and in vivo. Acta Vet Hung 2004;52:413–22
   PubMed Web of Science ®Google Scholar
• Göcer H, Akıncıoğlu A, Göksu S, Gülçin I. Carbonic anhydrase inhibitory properties of phenolic sulfonamides derived from dopamine related compounds. Arab J Chem 2014. [Epub ahead of print]. doi:10.1016/j.arabjc.2014.08.005
   Google Scholar
• Köksal E, Ağgül AG, Bursal E, Gülçin İ. Purification and characterization of peroxidase from sweet gourd (Cucurbita Moschata Lam. Poiret). Int J Food Propert 2012;15:1110–19
   Web of Science ®Google Scholar
• Şişecioğlu M, Gülçin İ, Çankaya M, Özdemir H. The inhibitory effects of l-Adrenaline on lactoperoxidase enzyme (LPO) purified from buffalo milk. Int J Food Propert 2012;15:1182–9
   Web of Science ®Google Scholar
• Gülçin İ, Küfrevioğlu Öİ, Oktay M. Purification and characterization of polyphenol oxidase from nettle (Urtica dioica L.) and inhibition effects of some chemicals on the enzyme activity. J Enzyme Inhib Med Chem 2005;20:297–302
   PubMed Web of Science ®Google Scholar
• Beydemir Ş, Gülçin İ, Hisar O, et al. Effect of melatonin on glucose-6-phospate dehydrogenase from rainbow trout (Oncorhynchus mykiss) erythrocytes in vitro and in vivo. J Appl Anim Res 2005;28:65–8
   Web of Science ®Google Scholar
• Atasaver A, Özdemir H, Gülçin İ, Küfrevioğlu Öİ. One-step purification of lactoperoxidase from bovine milk by affinity chromatography. Food Chem 2013;136:864–70
   PubMed Web of Science ®Google Scholar
• Yıldırım A, Atmaca U, Keskin A et al. N-acylsulfonamides strongly inhibit human carbonic anhydrase isoenzymes I and II. Bioorg Med Chem 2014. [Epub ahead of print]. doi:10.1016/j.bmc.2014.12.054
   Web of Science ®Google Scholar
• Akıncıoğlu A, Akbaba Y, Göçer H, et al. Novel sulfamides as potential carbonic anhydrase isoenzymes inhibitors. Bioorg Med Chem 2013;21:1379–85
   PubMed Web of Science ®Google Scholar
• Şişecioğlu M, Uguz MT, Çankaya M, et al. Effects of Ceftazidime Pentahydrate, Prednisolone, Amikacin Sulfate, Ceftriaxone Sodium and Teicoplanin on bovine milk lactoperoxidase activity. Int J Pharmacol 2011;7:79–83
   Web of Science ®Google Scholar
• Şişecioğlu M, Gülçin İ, Çankaya M, et al. The effects of norepinephrine on lactoperoxidase enzyme (LPO). Sci Res Essays 2010;5:1351–6
   Web of Science ®Google Scholar
• Şentürk M, Gülçin İ, Beydemir Ş, et al. In vitro inhibition of human carbonic anhydrase I and II isozymes with natural phenolic compounds. Chem Biol Drug Des 2011;77:494–9
   PubMed Web of Science ®Google Scholar
• Şişecioğlu M, Gülçin İ, Çankaya M, et al. Purification and characterization of peroxidase from Turkish black radish (Raphanus sativus L.). J Med Plants Res 2010;4:1187–96
   Web of Science ®Google Scholar
• Verpoorte JA, Mehta S, Edsall JT. Esterase activities of human carbonic anhydrases B and C. J Biol Chem 1967;242:4221–9
   PubMed Web of Science ®Google Scholar
• Şentürk M, Gülçin İ, Daştan A, et al. Carbonic anhydrase inhibitors. Inhibition of human erythrocyte isozymes I and II with a series of antioxidant phenols. Bioorg Med Chem 2009;17:3207–11
   PubMed Web of Science ®Google Scholar
• Coban TA, Beydemir S, Gücin İ, et al. Sildenafil is a strong activator of mammalian carbonic anhydrase isoforms I-XIV. Bioorg Med Chem 2009;17:5791–5
   PubMed Web of Science ®Google Scholar
• Göçer H, Akıncıoğlu A, Öztaşkın N, et al. Synthesis, antioxidant and antiacetylcholinesterase activities of sulfonamide derivatives of dopamine related compounds. Arch Pharm 2013;346:783–92
   PubMed 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;72:248–51
   PubMed Web of Science ®Google Scholar
• Ozturk Sarikaya SB, Sisecioglu M, Cankaya M, et al. Inhibition profile of a series of phenolic acids on bovine lactoperoxidase enzyme. J Enzyme Inhib Med Chem 2014. [Epub ahead of print]. DOI: 10.3109/14756366.2014.949254
   Web of Science ®Google Scholar
• Köksal E, Gülçin İ. Purification and characterization of peroxidase from cauliflower (Brassica oleracea L.) buds. Protein Peptide Lett 2008;15:320–6
   PubMed Web of Science ®Google Scholar
• Şentürk M, Gülçin İ, Çiftci M, Küfrevioğlu Öİ. Dantrolene inhibits human erythrocyte glutathione reductase. Biol Pharm Bull 2008;31:2036–9
   PubMed Web of Science ®Google Scholar
• Çetinkaya Y, Göçer H, Gülçin İ, Menzek A. Synthesis and carbonic anhydrase isoenzymes inhibitory effects of brominated diphenylmethanone and its derivatives. Arch Pharm 2014;347:354–9
   PubMed Web of Science ®Google Scholar
• Beydemir Ş, Gülçin İ, Ekinci D. The inhibitory effect of ethanol on carbonic anhydrase isoenzymes: in vivo and in vitro studies. J Enzyme Inhib Med Chem 2008;23:266–70
   PubMed Web of Science ®Google Scholar
• Ellman GL, Courtney KD, Andres V, Featherston RM. A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem Pharmacol 1961;7:88–95
   PubMed Web of Science ®Google Scholar
• Lineweaver H, Burk D. The determination of enzyme dissociation constants. Am Chem Soc 1934;56:658–66
   Web of Science ®Google Scholar
• Çetinkaya Y, Göçer H, Menzek A, Gülçin İ. Synthesis and antioxidant properties of (3,4-dihydroxyphenyl)(2,3,4-trihydroxyphenyl)methanone and its derivatives. Arch Pharm 2012;345:323–34
   PubMed Web of Science ®Google Scholar
• Innocenti A, Gülçin İ, Scozzafava A, Supuran CT. Carbonic anhydrase inhibitors. Antioxidant polyphenol natural products effectively inhibit mammalian isoforms I-XV. Bioorg Med Chem Lett 2010;20:5050–3
   PubMed Web of Science ®Google Scholar
• Öztürk Sarıkaya SB, Topal F, Şentürk M, et al. In vitro inhibition of α-carbonic anhydrase isozymes by some phenolic compounds. Bioorg Med Chem Lett 2011;21:4259–62
   PubMed Web of Science ®Google Scholar
• Akbaba Y, Balaydın HT, Menzek A, et al. Synthesis and biological evaluation of novel bromophenol derivatives as carbonic anhydrase inhibitors. Arch Pharm 2013;346:447–54
   PubMed Web of Science ®Google Scholar
• Supuran CT. Carbonic anhydrase inhibitors. Bioorg Med Chem Lett 2010;20:3467–74
   PubMed Web of Science ®Google Scholar
• Nar M, Çetinkaya Y, Gülçin İ, Menzek A. (3,4-Dihydroxyphenyl)(2,3,4-trihydroxyphenyl)methanone and its derivatives as carbonic anhydrase isoenzymes inhibitors. J Enzyme Inhib Med Chem 2013;28:402–6
   PubMed Web of Science ®Google Scholar
• Hisar O, Beydemir Ş, Gülçin İ, et al. The effect of melatonin hormone on carbonic anhydrase enzyme activity in rainbow trout (Oncorhynchus mykiss) erythrocytes in vitro and in vivo. Turk J Vet Anim Sci 2005;29:841–5
   Web of Science ®Google Scholar
• Hisar O, Beydemir Ş, Gülçin İ, et al. Effect of low molecular weight plasma inhibitors of rainbow trout (Oncorhyncytes mykiss) on human erythrocytes carbonic anhydrase-II isozyme activity in vitro and rat erythrocytes in vivo. J Enzyme Inhib Med Chem 2005;20:35–9
   PubMed Web of Science ®Google Scholar
• Ogilvie JM, Ohlemiller KK, Shah GN, et al. Carbonic anhydrase XIV deficiency produces a functional defect in the retinal light response. Proc Natl Acad Sci USA 2007;104:8514–19
   PubMed Web of Science ®Google Scholar
• Avvaru BS, Busby SA, Chalmers MJ, et al. Apo-human carbonic anhydrase II revisited: implications of the loss of a metal in protein structure, stability, and solvent network. Biochemistry 2009;48:7365–72
   PubMed Web of Science ®Google Scholar
• Göçer H, Gülçin İ. Caffeic acid phenethyl ester (CAPE): a potent carbonic anhydrase isoenzymes inhibitor. Int J Acad Res 2013;5:150–5
   Google Scholar
• Ozturk Sarikaya SB, Guülçin I, Supuran CT. Carbonic anhydrase inhibitors. Inhibition of human erythrocyte isozymes I and II with a series of phenolic acids. Chem Biol Drug Des 2010;75:515–20
   PubMed Web of Science ®Google Scholar
• Innocenti A, Ozturk Sarıkaya SB, et al. Carbonic anhydrase inhibitors. Inhibition of mammalian isoforms I-XIV with a series of natural product polyphenols and phenolic acids. Bioorg Med Chem 2010;18:2159–64
   PubMed Web of Science ®Google Scholar
• Balaydın HT, Senturk M, Goksu S, Menzek A. Synthesis and carbonic anhydrase inhibitory properties of novel bromophenols and their derivatives including natural products: vidalol B. Eur J Med Chem 2012;54:423–8
   PubMed Web of Science ®Google Scholar
• Göçer H, Çetinkaya Y, Göksu S, et al. Carbonic anhydrase and acetylcholine esterase inhibitory effects of carbamates and sulfamoylcarbamates. J Enzyme Inhib Med Chem 2014;1–5. [Epub ahead of print]
   Google Scholar
• Pohanka M. Acetylcholinesterase inhibitors: a patent review (2008-present). Expert Opin Ther Pat 2012;22:871–86
   PubMed Web of Science ®Google Scholar
• Pohanka M. Alpha7 nicotinic acetylcholine receptor is a target in pharmacology and toxicology. Int J Mol Sci 2012;13:2219–38
   PubMed Web of Science ®Google Scholar