Inhibitory effects of some phenolic compounds on the activities of carbonic anhydrase: from in vivo to ex vivo

References

• Singh S, Supuran CT. 3D-QSAR CoMFA studies on sulfonamide inhibitors of the Rv3588c β-carbonic anhydrase from Mycobacterium tuberculosis and design of not yet synthesized new molecules. J Enzyme Inhib Med Chem 2014;29:449–55
   PubMed Web of Science ®Google Scholar
• Akbaba Y, Bastem E, Topal F, et al. Synthesis and carbonic anhydrase inhibitory effects of novel sulfonamides derived from 1-aminoaindanes and anilines. Arch Pharm (Weinheim) 2014;347:950–7
   PubMed Web of Science ®Google Scholar
• Çetinkaya Y, Göçer H, Göksu S, Gülçin İ. Synthesis and carbonic anhydrase isoenzymes I and II inhibitory effects of novel benzylamine derivatives. J Enzyme Inhib Med Chem 2014;29:168–74
   PubMed Web of Science ®Google Scholar
• Akıncıoğlu A, Topal M, Gülçin İ, Göksu S. Novel sulphamides and sulphonamides incorporating the tetralin scaffold as carbonic anhydrase and acetylcholine esterase inhibitors. Arch Pharm (Weinheim) 2014;347:68–76
   PubMed Web of Science ®Google Scholar
• Güney M, Coşkun A, Topal F, et al. Oxidation of cyanobenzocycloheptatrienes: synthesis, photooxygenation reaction and carbonic anhydrase isoenzymes inhibition properties of some new benzotropone derivates. Bioorg Med Chem 2014;22:3537–43
   PubMed Web of Science ®Google Scholar
• Chegaev K, Lazzarato L, Tamboli Y, et al. Furazan and furoxan sulfonamides are strong α-carbonic anhydrase inhibitors and potential antiglaucoma agents. Bioorg Med Chem 2014;22:3913–21
   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 (Weinheim) 2014;347:354–9
   PubMed Web of Science ®Google Scholar
• Nar M, Çetinkaya Y, Gülçin İ, Menzek A. (3,4-Dihydroxyphenyl)(2,3,4-trihydroxphenyl)methanone and its derivatives as carbonic anhydrase isoenzymes inhibitors. J Enzyme Inhib Med Chem 2013;28:402–6
   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 2015;23:2598–605
   PubMed Web of Science ®Google Scholar
• Ż  olnowska B, Slawiński J, Pogorzelska A, et al. Carbonic anhydrase inhibitors. Synthesis, and molecular structure of novel series N-substitued N'-(2-arylmethylthio-4-chloro-5-methylbenzenesulfonyl) 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
• Slawiński J, Pogorzelska A, Ż  olnowska B, et al. Carbonic anhydrase inhibitors. Synthesis of novel series of 5-substituted 2,4-dichlorobenzenesulfonamides and their inhibition of human cytosolic isozymes I and II and the transmembrane tumor-associated isozymes IX and XII. Eur J Med Chem 2014;82:47–55
   PubMed Web of Science ®Google Scholar
• Göksu S, Naderi A, Akbaba Y, Kalın P, 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
• Gocer H, Akıncıoğlu A, Göksu S, et al. Carbonic anhydrase and acetylcholinesterase inhibitory effects of carbamates and sulfamoylcarbamates. J Enzyme Inhib Med Chem 2015;30:316–20
   PubMed Web of Science ®Google Scholar
• Supuran CT. Carbonic anhydrases: from biomedical applications of the inhibitors and activators to biotechnological use for CO2 capture. J Enzyme Inhib Med Chem 2013;28:229–30
   PubMed Web of Science ®Google Scholar
• Gülçin İ, Beydemir Ş. Phenolic compounds as antioxidants: carbonic anhydrase isoenzymes inhibitors. Mini Rev Med Chem 2013;13:408–30
   PubMed Web of Science ®Google Scholar
• Öztürk Sarikaya 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
• Marinelli S, Di Marzo V, Florenzano F, et al. N-aranhydonoyl-dopamine tunes synaptic transmission onto dopaminergic neurons by activating both cannabinoid and vanilloid receptors. Neuropsychopharmacology 2007;32:298–308
   PubMed Web of Science ®Google Scholar
• Sharkey KA, Cristino L, Oland LD, et al. Arvanil, anandamide and N-arachidonoyl-dopamine (NADA) inhibit emesis through cannabinoid CB1 and vanilloid TRPV1 receptors in the ferret. Eur J Neurosci 2007;25:2773–82
   PubMed Web of Science ®Google Scholar
• O’Sullivan SE, Kendall DA, Randall MD. Characterisation of the vasorelaxant properties of the novel endocannabinoid N-arachidonoyl-dopamine (NADA). Br J Pharmacol 2004;141:803–12
   PubMed Web of Science ®Google Scholar
• Gülçin İ, Daştan A. Synthesis of dimeric phenol derivatives and determination of in vitro antioxidant and radical scavenging activities. J Enzyme Inhib Med Chem 2007;22:685–95
   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
• Sarıkaya SB, Gülçin İ, 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, Öztürk Sarikaya SB, Gülçin İ, 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;18:2159–64
   PubMed 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
• Boztaş M, Çetinkaya Y, Topal M, et al. Synthesis and carbonic anhydrase isoenzymes I, II, IX, and XII inhibitory effects of dimethoxybromophenol derivatives incorporating cyclopropane moieties. J Med Chem 2015;58:640–50
   PubMed Web of Science ®Google Scholar
• Balaydın HT, Gülçin İ, Menzek A, et al. Synthesis and antioxidant properties of diphenylmethane derivative bromophenols including a natural product. J Enzyme Inhib Med Chem 2010;25:685–95
   PubMed Web of Science ®Google Scholar
• Taslimi P, Gülçin İ, Öztaşkın N, et al. The effects of some bromophenol derivatives on human carbonic anhydrase isoenzymes. J Enzyme Inhib Med Chem. doi: 10.3109/14756366.2015.1054820
   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 2015;30:586–91
   PubMed Web of Science ®Google Scholar
• Gocer H, Topal F, Topal M, et al. Acetylcholinesterase and carbonic anhydrase isoenzymes I and II inhibition profiles of taxifolin. J Enzyme Inhib Med Chem. doi: 10.3109/14756366.2015.1036051
   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;30:941–6
   PubMed Web of Science ®Google Scholar
• Gocer H, Gülçin İ. Caffeic acid phenethyl ester (CAPE): correlation of structure and antioxidant properties. Int J Food Sci Nutr 2011;62:821–5
   PubMed 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
• Gülçin İ, Beydemir Ş, Büyükokuroğlu ME. In vitro and in vivo effects of dantrolene on carbonic anhydrase enzyme activities. Biol Pharm Bull 2004;27:613–6
   PubMed Web of Science ®Google Scholar
• Laemmli UK. Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature 1970;227:680–5
   PubMed Web of Science ®Google Scholar
• Segel IH. Biochemical calculations: enzyme kinetics. New York: John Wiley and Sons, Inc; 1968: 213
   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;72:248–54
   PubMed Web of Science ®Google Scholar
• Akıncıoğlu A, Akıncıoğlu H, Gülçin I, et al. Discovery of potent carbonic anhydrase and acetylcholine esterase inhibitors: novel sulfamoylcarbamates and sulfamides derived from acetophenones. Bioorg Med Chem 2015;23:3592–602
   PubMed Web of Science ®Google Scholar
• Hisar O, Beydemir Ş, Gulcin I, et al. The effects 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
• Ekinci D, Beydemir Ş. Purification of PON1 from human serum and assessment of enzyme kinetics against metal toxicity. Biol Trace Elem Res 2010;135:112–20
   PubMed Web of Science ®Google Scholar
• Rickly EE, Ghazanfar SA, Gibbons BH, Edsall JT. Carbonic anhydrases from human erythrocytes. Preparation and properties of two enzymes. J Biol Chem 1964;239:1065–78
   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;242:4221–9
   PubMed Web of Science ®Google Scholar
• Soyut H, Beydemir Ş, Hisar O. Effects of some metals on carbonic anhydrase from brains of rainbow trout. Biol Trace Elem Res 2008;123:179–90
   PubMed Web of Science ®Google Scholar
• Beydemir Ş, Ciftci M, Ozmen I, et al. Effects of some medical drugs on enzyme activities of carbonic anhydrase from human erythrocytes in vitro and from rat erythrocytes in vivo. Pharmacol Res 2000;42:187–91
   PubMed Web of Science ®Google Scholar
• Lineweaver H, Burk D. The determination of enzyme dissociation constants. J Am Chem Soc 1934;56:658–66
   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
• Supuran CT. Carbonic anhydrase inhibitors. Bioorg Med Chem Lett 2010;20:3467–74
   PubMed Web of Science ®Google Scholar
• Carta F, Vullo D, Maresca A, et al. Mono-/dihydroxybenzoic acid esters and phenol pyridinium derivatives as inhibitors of the mammalian carbonic anhydrase isoforms I, II, VII, IX, XII and XIV. Bioorg Med Chem 2013;21:1564–9
   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
• Atasaver A, Özdemir H, Gülçin İ, Irfan Küfrevioğlu O. One-step purification of lactoperoxidase from bovine milk by affinity chromatography. Food Chem 2013;136:864–70
   PubMed Web of Science ®Google Scholar
• Ekinci D, Beydemir Ş, Alım Ş. Some drugs inhibit in vitro hydratase and esterase activities of human carbonic anhydrase-I and II. Pharmacol Rep 2007;59:580–7
   PubMed Web of Science ®Google Scholar
• Gülçin I, Beydemir Ş, Çoban TA, Ekinci D. The inhibitory effect of dantrolene sodium and propofol on 6-phosphogluconate dehydrogenase from rat erythrocyte. Fresen Environ Bull 2008;17:1283–7
   Web of Science ®Google Scholar
• Şişecioğlu M, Çankaya M, Gülçin I, Özdemir M. The inhibitory effect of propofol on lactoperoxidase. Protein Peptide Lett 2009;16:46–9
   PubMed Web of Science ®Google Scholar
• Şentürk M, Gülçin I, Çiftci M, Küfreviolu OI. Dantrolene inhibits human erythrocyte glutathione reductase. Biol Pharm Bull 2008;31:2036–9
   PubMed Web of Science ®Google Scholar
• Beydemir Ş, Gülçin I, Küfreviolu OI, Çiftçi M. Glucose 6-phosphate dehydrogenase: in vitro and in vivo effects of dantrolene sodium. Pol J Pharmacol 2003;55:787–92
   PubMedGoogle 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
• Arabaci B, Gülçin İ, Alwasel S. Capsaicin: a potent inhibitor of carbonic anhydrase isoenzymes. Molecules 2015;19:10103–14
   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
• 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
• Beydemir Ş, Çiftçi M, Küfrevioğlu Öİ, Büyükokuroğlu ME. Effects of gentamicin sulfate on enzyme activities of carbonic anhydrase from human erythrocytes in vitro and from rat erythrocytes in vivo. Biol Pharm Bull 2002;25:966–69
   PubMed Web of Science ®Google Scholar