The effects of some bromophenols on human carbonic anhydrase isoenzymes

References

• 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
• Aras Hisar 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
• 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
• Ward C, Langdon SP, Mullen P, et al. New strategies for targeting the hypoxic tumour microenvironment in breast cancer. Cancer Treat Rev 2013;39:171–9
   PubMed Web of Science ®Google Scholar
• Tanpure RP, Ren B, Peat TS, et al. Carbonic anhydrase inhibitors with dual-tail moieties to match the hydrophobic and hydrophilic halves of the carbonic anhydrase active site. J Med Chem 2015;58:1494–501
   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;10:767–77
   PubMed Web of Science ®Google Scholar
• Çoban TA, 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
• Vullo D, De Luca V, Del Prete S, et al. Sulfonamide inhibition studies of the c-carbonic anhydrase from the Antarctic cyanobacterium Nostoc commune. Bioorg Med Chem 2015;23:1728–34
   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 dimethoxy-bromophenol derivatives incorporating cyclopropane moieties. J Med Chem 2015;58:640–50
   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
• Carta F, Mannelli LDC, Pinard M, et al. A class of sulfonamide carbonic anhydrase inhibitors with neuropathic pain modulating effects. Bioorg Med Chem 2015;23:1828–40
   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
   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
• Güney M, Coşkun 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
• Supuran CT. Carbonic anhydrases: novel therapeutic applications for inhibitors and activators. Nat Rev Drug Discov 2008;7:168–81
   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
• 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
• 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
• Sethi KK, Verma SM, Tanç M, et al. Carbonic anhydrase inhibitors: synthesis and inhibition of the cytosolic mammalian carbonic anhydrase isoforms I, II and VII with benzene sulfonamides incorporating 4,5,6,7-tetrachlorophthalimide moiety. Bioorg Med Chem 2013;21:5168–74
   PubMed Web of Science ®Google Scholar
• Öztürk 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
   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
• Sharma A, Tiwari M, Supuran CT. Novel coumarins and benzocoumarins acting as isoform-selective inhibitors against the tumor-associated carbonic anhydrase IX. J Enzyme Inhib Med Chem 2014;29:292–6
   PubMed Web of Science ®Google Scholar
• Joseph P, Turtaut F, Ouahrani-Bettache S, et al. Cloning, characterization, and inhibition studies of a b-carbonic anhydrase from Brucella suis. J Med Chem 2010;53:2277–85
   PubMed Web of Science ®Google Scholar
• Burghout P, Vullo D, Scozzafava A, et al. Inhibition of the b-carbonic anhydrase from Streptococcus pneumoniae by inorganic anions and small molecules: toward innovative drug design of antiinfectives? Bioorg Med Chem 2011;19:243–8
   PubMed Web of Science ®Google Scholar
• Aksu K, Nar M, Tanc 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
• Akbaba Y, Balaydın HT, Menzek A, et al. Synthesis and biological evaluation of novel bromophenolderivatives as carbonic anhydrase inhibitors. Arch Pharm 2013;346:447–54
   PubMed Web of Science ®Google Scholar
• Balaydin HT, Durdagi S, Ekinci D, et al. Inhibition of human carbonic anhydrase isozymes I, II and VI with a series of bisphenol, methoxy and bromophenol compounds. J Enzyme Inhib Med Chem 2012;27:467–75
   PubMed Web of Science ®Google Scholar
• Balaydin HT, Senturk M, Menzek A. Synthesis and carbonic anhydrase inhibitory properties of novel cyclohexanonyl bromophenol derivatives. Bioorg Med Chem Lett 2012;22:1352–7
   PubMed Web of Science ®Google Scholar
• Atasever A, Ozdemir H, Gulcin I, Kufrevioglu OI. One-step purification of lactoperoxidase from bovine milk by affinity chromatography. Food Chem 2013;136:864–70
   PubMed Web of Science ®Google Scholar
• Gribble GW. The diversity of naturally occurring organobromine compounds. Chem Soc Rev 1999;28:335–46
   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
• Gocer H, Aslan A, Gülçin İ, Supuran CT. Spirobisnaphthalenes effectively inhibit carbonic anhydrase. J Enzyme Inhib Med Chem 2015. [Epub ahead of print]. http://dx.doi.org/10.3109/14756366.2015.1047359
   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
• Uhlen M. Affinity as a tool in life science. Biotechniques 2008;44:649–54
   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
• Gül Hİ, Kucukoglu K, Yamali C, et al. Synthesis of 4-(2-substitutedhydrazinyl)benzenesulfonamides and their carbonic anhydrase inhibitory effects. J Enzyme Inhib Med Chem 2015. [Epub ahead of print]. http://dx.doi.org/10.3109/14756366.2015.1047359
   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
• 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
• 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
• Laemmli DK. Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature 1970;227:680–5
   PubMed 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
• 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
• Aksu K, Topal F, Gülçin I, et al. Acetylcholinesterase inhibitory and antioxidant activities of novel symmetric sulfamides derived from phenethylamines. Arch Pharm 2015;348:446–55
   PubMed Web of Science ®Google Scholar
• Gülçin İ, 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
• 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
• 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
• Akıncıoğlu A, Akbaba Y, Göçer H, et al. Novel sulfamides as potential carbonic anhydrase isoenzymes inhibitors. Bioorg Med Chem 2013;21:379–85
   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. 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
• 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
• Lineweaver H, Burk D. The determination of enzyme dissociation constants. J Am Chem Soc 1934;56:658–66
   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 2015. [Epub ahead of print]. doi.org/10.3109/14756366.2015.1036051
   Web of Science ®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 Prop 2012;15:1110–19
   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
• Öztaşkın N, Çetinkaya Y, Taslimi P, et al. Antioxidant and acetylcholinesterase inhibition properties of novel bromophenol derivatives. Bioorg Chem 2015;60:49–57
   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
• 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 Ş, Hisar O. The effect of α-tocopherol on the antioxidant enzymes activities and lipid peroxidation of rainbow trout (Oncorhynchus mykiss). Acta Vet Hung 2005;53:425–33
   PubMed Web of Science ®Google Scholar
• Innocenti A, Öztürk Sarıkaya 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
   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
• 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
• Taslimi P, Gulcin İ, Ozgeris B, et al. The human carbonic anhydrase isoenzymes I and II (hCA I and II) inhibition effects of trimethoxyindane derivatives. J Enzyme Inhib Med Chem 2015. [Epub ahead of print]. doi:10.3109/14756366.2015.1014476
   Web of Science ®Google Scholar
• Büyükokuroğlu ME, Gülçin İ, Oktay M, Küfrevioğlu Öİ. In vitro antioxidant properties of dantrolene sodium. Pharmacol Res 2001;44:491–5
   PubMed Web of Science ®Google Scholar
• Gülçin İ, Beydemir Ş, Alici HA, et al. In vitro antioxidant properties of morphine. Pharmacol Res 2004;49:59–66
   PubMed Web of Science ®Google Scholar
• Gülçin İ, Alici HA, Cesur M. Determination of in vitro antioxidant and radical scavenging activities of propofol. Chem Pharm Bull 2005;53:281–5
   PubMed Web of Science ®Google Scholar
• Gülçin İ, Berashvili D, Gepdiremen A. Antiradical and antioxidant activity of total anthocyanins from Perilla pankinensis decne. J Ethnopharmacol 2005;101:287–93
   PubMed Web of Science ®Google Scholar
• Gülçin İ, Mshvildadze V, Gepdiremen A, Elias R. Antioxidant activity of a triterpenoid glycoside isolated from the berries of Hedera colchica: 3-O-(β-d-glucopyranosyl)-hederagenin. Phytother Res 2006;20:130–4
   PubMed Web of Science ®Google Scholar
• Gülçin İ. Antioxidant activity of caffeic acid (3,4-dihydroxycinnamic acid). Toxicology 2006;217:213–20
   PubMed Web of Science ®Google Scholar
• Gülçin İ, Elias R, Gepdiremen A, Boyer L. Antioxidant activity of lignans from fringe tree (Chionanthus virginicus L.). Eur Food Res Technol 2006;223:759–67
   Web of Science ®Google Scholar
• Gülçin İ. Comparison of in vitro antioxidant and antiradical activities of l-tyrosine and l-dopa. Amino Acids 2007;32:431–8
   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
• Gülçin İ. Measurement of antioxidant ability of melatonin and serotonin by the DMPD and CUPRAC methods as trolox equivalent. J Enzyme Inhib Med Chem 2008;23:871–6
   PubMed Web of Science ®Google Scholar
• Ak T, Gülçin İ. Antioxidant and radical scavenging properties of curcumin. Chem Biol Interact 2008;174:27–37
   PubMed Web of Science ®Google Scholar
• Köksal E, Gülçin İ, Öztürk Sarıkaya SB, Bursal E. On the in vitro antioxidant activity of silymarin. J Enzyme Inhib Med Chem 2009;24:395–405
   PubMed Web of Science ®Google Scholar
• Gülçin İ, Elias R, Gepdiremen A, et al. Antioxidant secoiridoids from fringe tree (Chionanthus virginicus L.). Wood Sci Technol 2009;43:195–212
   Web of Science ®Google Scholar
• Gülçin İ. Antioxidant activity of l-adrenaline: an activity–structure insight. Chem Biol Interact 2009;179:71–80
   PubMed Web of Science ®Google Scholar
• Gülçin İ. Antioxidant properties of resveratrol: a structure–activity insight. Innov Food Sci Emerg 2010;11:210–18
   Web of Science ®Google Scholar
• Gülçin İ, Huyut Z, Elmastaş M, Aboul-Enein HY. Radical scavenging and antioxidant activity of tannic acid. Arab J Chem 2010;3:43–53
   Web of Science ®Google Scholar
• Gülçin İ. Antioxidant activity of eugenol – a structure and activity relationship study. J Med Food 2011;14:975–85
   PubMed Web of Science ®Google Scholar
• Göçer 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
• Şişecioğlu M, Çankaya M, Gülçin İ, Özdemir M. The inhibitory effect of propofol on lactoperoxidase. Protein Peptide Lett 2009;16:46–9
   PubMed Web of Science ®Google Scholar
• Gülçin İ, Beydemir Ş, Hisar O, et al. Melatonin administration increases antioxidant enzymes activities and reduce lipid peroxidation in the rainbow trout (Oncorhynchus mykiss, Walbaum) erythrocytes. Turk J Vet Anim Sci 2009;33:241–5
   Web of Science ®Google Scholar
• Şişecioğlu M, Çankaya M, Gülçin İ, Özdemir M. Interactions of melatonin and serotonin to lactoperoxidase enzyme. J Enzyme Inhib Med Chem 2010;25:779–83
   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
• Gülçin İ, Beydemir Ş, Hisar O. The effect of α-tocopherol on the antioxidant enzymes activities and lipid peroxidation of rainbow trout (Oncorhynchus mykiss). Acta Vet Hung 2005;53:425–33
   PubMed Web of Science ®Google Scholar
• Şentürk M, Gülçin İ, Çiftci M, Küfrevioğlu Öİ. Dantrolene inhibits human erythrocyte glutathione reductase. Biol Pharmacol Bull 2008;31:2036–9
   PubMed Web of Science ®Google Scholar