The synthesis of some β-lactams and investigation of their metal-chelating activity, carbonic anhydrase and acetylcholinesterase inhibition profiles

References

• Naumann K. How chlorine in molecules affects biological activity. Brussels: Science Dossier; 2003:1–37
   Google Scholar
• Holten KB, Onusko EM. Appropriate prescribing of oral beta-lactam antibiotics. Am Fam Phys 2000;62:611–20
   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. Effects of melatonin on carbonic anhydrase from human erythrocytes in vitro and from rat erythrocytes in vivo. J Enzyme Inhib Med Chem 2004;19:193–7
   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
• 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 2016;31:152–7
   PubMed Web of Science ®Google Scholar
• Scozzafava A, Kalin 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
• 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
• 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
• 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
• De Simone G, Alterio V, Supuran CT. Exploiting the hydrophobic and hydrophilic binding sites for designing carbonic anhydrase inhibitors. Expert Opin Drug Discov 2013;8:793–810
   PubMed 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
• Supuran CT. Carbonic anhydrase inhibitors. Bioorg Med Chem Lett 2010;20:3467–74
   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
• Supuran CT. Structure-based drug discovery of carbonic anhydrase inhibitors. J Enzyme Inhib Med Chem 2012;27:759–72
   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 2015;30:586–91
   PubMed Web of Science ®Google Scholar
• Supuran CT. Carbonic anhydrase inhibitors: an editorial. Expert Opin Ther Pat 2013;23:677–9
   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
• Supuran CT. Carbonic anhydrases. Bioorg Med Chem 2013;21:1377–8
   PubMed Web of Science ®Google Scholar
• Göçer 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: novel therapeutic applications for inhibitors and activators. Nat Rev Drug Discov 2008;7:168–81
   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
• 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
• 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
• Topal M, Gülçin İ. Rosmarinic acid: a potent carbonic anhydrase isoenzymes inhibitor. Turk J Chem 2014;38:894–902
   Web of Science ®Google Scholar
• Pinard MA, Boone CD, Rife BD, et al. Structural study of interaction between brinzolamide and dorzolamide inhibition of human carbonic anhydrases. Bioorg Med Chem 2013;21:7210–15
   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
• 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
• 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
• Capasso C, Supuran CT. An overview of the alpha-, beta- and gamma-carbonic anhydrases from bacteria: can bacterial carbonic anhydrases shed new light on evolution of bacteria? J Enzyme Inhib Med Chem 2015;30:325–32
   PubMed Web of Science ®Google Scholar
• Aksu K, Nar M, Tanç M, et al. Synthesis and carbonic anhydrase inhibitory properties of sulfamides structurally related to dopamine. Bioorg Med Chem 2013;21:2925–31
   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;21:1379–85
   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
• 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
• 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
• 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
   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
• 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
• 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
   PubMed Web of Science ®Google Scholar
• Mao F, Li J, Wei H, et al. Tacrine-propargylamine derivatives with improved acetylcholinesterase inhibitory activity and lower hepatotoxicity as a potential lead compound for the treatment of Alzheimer’s disease. J Enzyme Inhib Med Chem 2015;30:995–1001
   PubMed Web of Science ®Google Scholar
• Öztaşkin 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
• Polat Köse L, Gülçin İ, Gören AC, et al. LC-MS/MS analysis, antioxidant and anticholinergic properties of galanga (Alpinia officinarum Hance) rhizomes. Ind Crops Prod 2015;74:712–21
   Web of Science ®Google Scholar
• Topal M, Gocer H, Topal F, et al. Antioxidant, antiradical and anticholinergic properties of cynarin purified from the illyrian thistle (Onopordum illyricum L.). J Enzyme Inhib Med Chem 2016;31:266–75
   PubMed Web of Science ®Google Scholar
• Iqbal K, del C, Alonso A, Chen S, et al. Tau pathology in Alzheimer disease and other tauopathies. Biochim Biophys Acta 2005;1739:198–210
   PubMed Web of Science ®Google Scholar
• Pratico D. Oxidative stress hypothesis in Alzheimer’s disease: a reappraisal. Trends Pharmacol Sci 2008;29:609–15
   PubMed 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
• 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
• 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 2016;31:441–7
   PubMed Web of Science ®Google Scholar
• Gülçin İ, Scozzafava A, Supuran CT, et al. The effect of caffeic acid phenethyl ester (CAPE) metabolic enzymes including acetylcholinesterase, butyrylcholinesterase, glutathione s-transferase, lactoperoxidase and carbonic anhydrase ısoenzymes I, II, IX and XII. J Enzyme Inhib Med Chem 2015;9:1–7
   Web of Science ®Google Scholar
• Tidwell TT. Hugo (Ugo) Schiff, Schiff Bases, and a century of β-lactam synthesis. Angewandte Chemie 2008;47:1016–20
   Google Scholar
• Jia Y, Li J. Molecular assembly of schiff base interactions: construction and application. Chem Rev 2015;115:1597–621
   PubMed Web of Science ®Google Scholar
• Naka H, Koseki D, Kondo Y. Catalytic deprotonative functionalization of propargyl silyl ethers with imines. Adv Synth Catal 2008;350:1901–6
   Web of Science ®Google Scholar
• Orita A, Uehara G, Miwa K, Otera J. Rate acceleration of organic reaction by immediate solvent evaporation. Chem Commun 2006;7:4729–31
   Web of Science ®Google Scholar
• Artunç T, Çetinkaya Y, Göçer H, et al. Synthesis of 4-[2-(3,4-dimethoxybenzyl)cyclopentyl]-1,2-dimethoxybenzene derivatives and evaluations of their carbonic anhydrase isoenzymes inhibitory effects. Chem Biol Drug Des 2016;87:594–607
   PubMed Web of Science ®Google Scholar
• Atasever 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
• Beydemir Ş, Gülçin İ, Küfrevioğlu Öİ, Çiftçi M. Glucose 6-phosphate dehydrogenase: in vitro and in vivo effects of dantrolene sodium. Pol J Pharmacol 2003;55:787–92
   PubMedGoogle Scholar
• Gülçin İ, Küfrevioğlu Öİ, Oktay M. Purification and characterization of polyphenol oxidase from nettle (Urtica dioica L.) and inhibitory effects of some chemicals on enzyme activity. J Enzyme Inhib Med Chem 2005;20:297–302
   PubMed Web of Science ®Google Scholar
• Gülçin İ, Yıldırım A. Purification and characterization of peroxidase from Brassica oleracea var. Acephala. Asian J Chem 2005;17:2175–83
   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
• 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
• 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
• Çoban TA, Beydemir Ş, Gülçin İ, Ekinci D. The effect of ethanol on erythrocyte carbonic anhydrase isoenzymes activity: an in vitro and in vivo study. J Enzyme Inhib Med Chem 2008;23:266–70
   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
• Göcer H, Akıncıoğlu A, Göksu S, İ Gülçin I. Carbonic anhydrase inhibitory properties of phenolic sulfonamides derived from dopamine related compounds. Arab J Chem 2016. [Epub ahead of print]. http://dx.doi:10.1016/j.arabjc.2014.08.005
   Web of Science ®Google Scholar
• Taslimi P, Gülçin İ, Öztaşkin N, et al. The effects of some bromophenol derivatives on human carbonic anhydrase isoenzymes. J Enzyme Inhib Med Chem 2016;31:603–7
   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
• 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 2016;31:568–73
   PubMed Web of Science ®Google Scholar
• Gocer H, Aslan A, Gülçin İ, Supuran CT. Spirobisnaphthalenes effectively inhibit carbonic anhydrase. J Enzyme Inhib Med Chem 2016;31:503–7
   PubMed Web of Science ®Google Scholar
• Bradford MM. A rapid and sensitive method for the quantitation of protein utilizing the principle of protein dye binding. Anal Biochem 1976;72:248–54
   PubMed Web of Science ®Google Scholar
• Ayık O, Hisar O, Gülçin İ, et al. Effects of light on trace elements and thriiodothyronine levels in plasma of mirror carp. Biol Trace Elem Res 2005;108:147–54
   PubMed Web of Science ®Google Scholar
• Birdane FM, Cemek M, Birdane YO, et al. Beneficial effects of Foeniculum vulgare on ethanol-induced acute gastric mucosal injury in rats. World J Gastroenterol 2007;13:607–11
   PubMed Web of Science ®Google Scholar
• Cankaya M, Hernandez AM, Ciftci M, et al. An analysis of expression patterns of genes encoding proteins with catalytic activities. BMC Genomics 2007;8:232
   PubMed 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
• 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
• Koksal Z, Kalın R, Gülçin İ, et al. The impact of some avermectins on lactoperoxidase from bovine milk. Int J Food Propert 2016;19:1207–16
   Web of Science ®Google Scholar
• Şişecioğlu M, Kireçci E, Çankaya M, et al. The prohibitive effect of lactoperoxidase system (LPS) on some pathogen fungi and bacteria. Afr J Pharm Pharmacol 2010;4:671–7
   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 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
• 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 2015;30:479–83
   PubMed Web of Science ®Google Scholar
• Aydin B, Gülcin I, Alwasel SH. Purification and characterization of polyphenol oxidase from Hemşin apple (Malus communis L.). Int J Food Propert 2015;18:2735–45
   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. J Am Chem Soc 1934;56:658–66
   Web of Science ®Google Scholar
• Dinis TCP, Madeira VMC, Almeida LM. Action of phenolic derivates (acetoaminophen, salycilate, and 5-aminosalycilate) as inhibitors of membrane lipid peroxidation and as peroxyl radical scavengers. Arch Biochem Biophys 1994;315:161–9
   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
• 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
• Talaz O, Gülçin İ, Göksu S, Saracoglu N. Antioxidant activity of 5,10-dihydroindeno[1,2-b]indoles containing substituents on dihydroindeno part. Bioorg Med Chem 2009;17:6583–9
   PubMed Web of Science ®Google Scholar
• Gülçin İ, Elias R, Gepdiremen A, et al. Antioxidant activity of bisbenzylisoquinoline alkaloids from Stephania rotunda: cepharanthine and fangchinoline. J Enzyme Inhib Med Chem 2010;25:44–53
   PubMed Web of Science ®Google Scholar
• Kalın P, Gülçin İ, Gören AC. Antioxidant activity and polyphenol content of Vaccinium macrocarpon. Rec Nat Prod 2015;9:496–502
   Google Scholar
• Sehitoglu MH, Han H, Kalin P, et al. Pistachio (Pistacia vera L.) Gum: a potent inhibitor of reactive oxygen species. J Enzyme Inhib Med Chem 2015;30:264–9
   PubMed Web of Science ®Google Scholar
• Bursal E, Köksal E, Gülçin İ, et al. Antioxidant activity and polyphenol content of cherry stem (Cerasus avium L.) determined by LC-MS/MS. Food Res Int 2013;51:66–74
   Web of Science ®Google Scholar
• Gülçin İ, Elmastaş M, Aboul-Enein HY. Antioxidant activity of clove oil – a powerful antioxidant source. Arab J Chem 2012;5:489–99
   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
• Gülçin İ, Beydemir S, Topal F, et al. Apoptotic, antioxidant and antiradical effects of majdine and isomajdine from Vinca herbacea Waldst. and kit. J Enzyme Inhib Med Chem 2012;27:587–94
   PubMed Web of Science ®Google Scholar
• Bursal E, Gülçin İ. Polyphenol contents and in vitro antioxidant activities of lyophilized aqueous extract of kiwifruit (Actinidia deliciosa). Food Res Int 2011;44:1482–9
   Web of Science ®Google Scholar
• Supuran CT. How many carbonic anhydrase inhibition mechanisms exist? J Enzyme Inhib Med Chem 2016;31:345–60
   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
• Ferraroni M, Carta F, Scozzafava A, Supuran CT. Thioxocoumarins show an alternative carbonic anhydrase inhibition mechanism compared to coumarins. J Med Chem 2016;59:462–73
   PubMed Web of Science ®Google Scholar
• Isik S, Vullo D, Bozdag M, et al. 7-Amino-3,4-dihydro-1H-quinolin-2-one, a compound similar to the substituted coumarins, inhibits α-carbonic anhydrases without hydrolysis of the lactam ring. J Enzyme Inhib Med Chem 2015;30:773–7
   PubMed Web of Science ®Google Scholar
• Küçükbay FZ, Küçükbay H, Tanc M, Supuran CT. Synthesis and carbonic anhydrase I, II, IV and XII inhibitory properties of N-protected amino acid-sulfonamide conjugates. J Enzyme Inhib Med Chem. [Epub ahead of print]. http://dx.doi.org/10.3109/14756366.2016.1147438
   Google Scholar
• Durdagi S, Vullo D, Pan P, et al. Protein-protein interactions: inhibition of mammalian carbonic anhydrases I-XV by the murine inhibitor of carbonic anhydrase and other members of the transferrin family. J Med Chem 2012;55:5529–35
   PubMed Web of Science ®Google Scholar
• Grover S, Apushkin M, Fishman G. Topical dorzolamide for the treatment of cystoid macular edema in patients with retinitis pigmentosa. Am J Ophthalmol 2006;141:850–8
   PubMed Web of Science ®Google Scholar
• Stepankova S, Komers K. Cholinesterases and cholinesterase inhibitors. Curr Enzyme Inhib 2008;4:160–71
   Google Scholar
• Gülçin İ, Topal F, Çakmakçı R, et al. Pomological features, nutritional quality, polyphenol content analysis and antioxidant properties of domesticated and three wild ecotype forms of raspberries (Rubus idaeus L.). J Food Sci 2011;76:C585–93
   PubMed Web of Science ®Google Scholar
• Gülçin İ, Topal F, Oztürk Sarikaya SB, et al. Polyphenol contents and antioxidant properties of medlar (Mespilus germanica L.). Rec Nat Prod 2011;5:158–75
   Google Scholar
• Gülçin İ. Antioxidant activity of eugenol: a structure-activity relationship study. J Med Food 2011;14:975–85
   PubMed Web of Science ®Google Scholar
• Köksal E, Bursal E, Dikici E, et al. Antioxidant activity of Melissa officinalis leaves. J Med Plants Res 2011;5:217–22
   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, Bursal E, Şehitoğlu HM, et al. Polyphenol contents and antioxidant activity of lyophilized aqueous extract of propolis from Erzurum, Turkey. Food Chem Toxicol 2010;48:2227–38
   PubMed Web of Science ®Google Scholar
• Şerbetçi Tohma H, Gülçin İ. Antioxidant and radical scavenging activity of aerial parts and roots of Turkish liquorice (Glycyrrhiza glabra L.). Int J Food Propert 2010;13:657–71
   Web of Science ®Google Scholar
• Gülçin İ, Kirecci E, Akkemik E, et al. Antioxidant and antimicrobial activities of an aquatic plant: Duckweed (Lemna minor L.). Turk J Biol 2010;34:175–88
   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
• 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. Antioxidant activity of L-adrenaline: a structure-activity insight. Chem Biol Interact 2009;179:71–80
   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. In vitro prooxidant effect of caffeine. J Enzyme Inhib Med Chem 2008;23:149–52
   PubMed Web of Science ®Google Scholar
• Köksal E, Gülçin İ. Antioxidant activity of cauliflower (Brassica oleracea L.). Turk J Agric For 2008;32:65–78
   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