A class of sulfonamides as carbonic anhydrase I and II inhibitors

References

• 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 from rainbow trout (Oncorhynchus mykiss) erythrocytes in vitro and in vivo. Acta Vet Hung 2004;52:413–22
   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
• Rahman TU, Khattrak KF, Liaqat W, Zaman K. Characterization of one novel flavone and four new source compounds from the bark of Milletia ovalifolia and in vitro inhibition of carbonic anhydrase-II by the novel flavonoid. Rec Nat Prod 2015;9:553–60
   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
• Innocenti A, Gülçin İ, Scozzafava A, Supuran CT. Carbonic anhydrase inhibitors. Antioxidant polyphenols effectively inhibit mammalian isoforms I-XV. Bioorg Med Chem Lett 2010;20:5050–3
   PubMed Web of Science ®Google Scholar
• ÖztürkSarikaya 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
• 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
• Zimmerman SA, Ferry JG, Supuran CT. Inhibition of the archaeal beta-class (Cab) and gamma-class (Cam) carbonic anhydrases. Curr Top Med Chem 2007;7:901–8
   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
• 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
• 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
• 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
• Hisar O, Beydemir Ş, Gülçin İ, 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
• 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
• Çankaya 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
• 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
• Montgomery JC, Venta PJ, Eddy RL, et al. Characterization of the human gene for a newly discovered carbonic anhydrase, CA VII, and its localization to chromosome 16. Genomics 1991;11:835–48
   PubMed Web of Science ®Google Scholar
• Lehtonen J, Shen B, Vihinen M, et al. Characterization of CA XIII, a novel member of the carbonic anhydrase isozyme family. J Biol Chem 2004;279:2719–27
   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
• 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 (Weinheim) 2014;347:950–7
   PubMed Web of Science ®Google Scholar
• FujikawaAdachi K, Nishimori I, Taguchi T, Onishi S. Human mitochondrial carbonic anhydrase VB. cDNA cloning, mRNA expression, subcellular localization, and mapping to chromosome x. J Biol Chem 1999;274:21228–33
   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
• FujikawaAdachi K, Nishimori I, Taguchi T, Onishi S. Human carbonic anhydrase XIV (CA14): cDNA cloning, mRNA expression, and mapping to chromosome 1. Genomics 1999;61:74–81
   PubMed Web of Science ®Google Scholar
• Ratto F, Witort E, Tatini F, et al. Plasmonic particles that hit hypoxic cells. Adv Funct Mater 2015;25:316–23
   Web of Science ®Google Scholar
• Hilvo M, Salzano AM, Innocenti A, et al. Cloning, expression, post-translational modifications and inhibition studies on the latest mammalian carbonic anhydrase isoform, CA XV. J Med Chem 2009;52:646–54
   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 (Weinheim) 2013;346:783–92
   PubMed Web of Science ®Google Scholar
• Göçer H, Çetinkaya Y, 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
• 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
• 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
• Clare BW, Supuran CT. A perspective on quantitative structure–activity relationships and carbonic anhydrase inhibitors. Expert Opin Drug Metab Toxicol 2006;2:113–37
   PubMed Web of Science ®Google Scholar
• Thiry A, Dogne’ JM, Supuran CT, Masereel B. Anticonvulsant sulfonamides/sulfamates/sulfamides with carbonic anhydrase inhibitory activity: drug design and mechanism of action. Curr Pharm Des 2008;14:661–71
   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
• Winum JY, Monter JL, Scozzafava A, Supuran CT. Functional, structural, and disease applications. In: Supuran CT, Winum JY, Wang B, eds. Drug design of zinc-enzyme inhibitors. Hoboken (NJ): Wiley; 2009:39
   Google Scholar
• Alterio V, Di Fiore A, D’Ambrosio K, et al. Functional, structural, and disease applications. In: Supuran CT, Winum JY, Wang B, eds. Drug design of zinc-enzyme inhibitors. Hoboken (NJ): Wiley; 2009:73
   Google Scholar
• Di Fiore A, Monti SM, Hilvo M, et al. Crystal structure of human carbonic anhydrase XIII and its complex with the inhibitor acetazolamide. Proteins 2008;74:164–75
   Web of Science ®Google Scholar
• King RW, Burgen AS. Sulphonamide complexes of human carbonic anhydrases. Ultraviolet difference spectroscopy. Biochim Biophys Acta 1970;207:278–85
   PubMed Web of Science ®Google Scholar
• Supuran CT, Scozzafava A, Casini A. Carbonic anhydrase inhibitors. Med Res Rev 2003;23:146–89
   PubMed Web of Science ®Google Scholar
• Abbate F, Supuran CT, Scozzafava A, et al. Nonaromatic sulfonamide group as an ideal anchor for potent human carbonic anhydrase inhibitors: role of hydrogen-bonding networks in ligand binding and drug design. J Med Chem 2002;45:3583–7
   PubMed Web of Science ®Google Scholar
• Innocenti A, ÖztürkSarıkaya SB, Gülçin İ, Supuran CT. Carbonic anhydrase inhibitors. Inhibition of mammalian isoforms I-XIV with a series of natural product polyphenols and phenolic acids. Synthesis and carbonic anhydrase inhibitory properties of sulfamides structurally related to dopamine. Bioorg Med Chem 2010;18:2159–64
   PubMed Web of Science ®Google Scholar
• Marini AM, Maresca A, Aggarwal M, et al. Tricyclic sulfonamides incorporating benzothiopyrano[4,3-c]pyrazole and pyridothiopyrano[4,3-c]pyrazole effectively inhibit α- and β-carbonic anhydrase: x-ray crystallography and solution investigations on 15 Isoforms. J Med Chem 2012;55:9619–29
   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. Synthesis and carbonic anhydrase inhibitory properties of sulfamides structurally related to dopamine. Bioorg Med Chem 2014;22:6768–75
   PubMed Web of Science ®Google Scholar
• Maresca A, Temperini C, Pochet L, et al. Deciphering the mechanism of carbonic anhydrase inhibition with coumarins and thiocoumarins. J Med Chem 2010;53:335–44
   PubMed Web of Science ®Google Scholar
• ÖztürkSarikaya 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
• Chen H-M, Wu Y-C, Chia Y-C, et al. Gallic acid, a major component of Toona sinensis leaf extracts, contains a ROS-mediated anti-cancer activity in human prostate cancer cells. Cancer Lett 2009;286:161–71
   PubMed Web of Science ®Google Scholar
• Hsu C-L, Lo W-H, Yen G-C. Gallic acid induces apoptosis in 3T3-L1 pre-adipocytes via a Fas- and mitochondrial-mediated pathway. J Agric Food Chem 2007;55:7359–65
   PubMed Web of Science ®Google Scholar
• Manuja R, Sachdeva S, Jain A, Chaudhary J. A comprehensive review on biological activities of P-hydroxy benzoic acid and its derivatives. Int J Pharm Sci Rev Res 2013;22:109–15
   Google Scholar
• Gülçin İ, Scozzafava A, Supuran CT, et al. The effect of caffeic acid phenethyl ester (CAPE) on metabolic enzymes including acetylcholinesterase, butyrylcholinesterase, glutathione S-transferase, lactoperoxidase, and carbonic anhydrase isoenzymes I, II, IX, and XII. J Enzyme Inhib Med Chem 2015. [Epub ahead of print]. DOI: 10.3109/14756366.2015.1094470
   Web of Science ®Google Scholar
• Wang P, Liu C, Sanches T, et al. Design and synthesis of novel nitrogen-containing polyhydroxylated aromatics as HIV-1 integrase inhibitors from caffeic acid phenethyl ester. Bioorg Med Chem Lett 2009;19:4574–8
   PubMed Web of Science ®Google Scholar
• Moeker J, Peat TS, Bornaghi LF, et al. Cyclic secondary sulfonamides: unusually good inhibitors of cancer-related carbonic anhydrase enzymes. J Med Chem 2014;57:3522–31
   PubMed Web of Science ®Google Scholar
• Di Fiore A, Maresca A, Alterio V, et al. Carbonic anhydrase inhibitors: X-ray crystallographic studies for the binding of N-substituted benzenesulfonamides to human isoform II. Chem Commun 2011;47:11636–8
   PubMed Web of Science ®Google Scholar
• Métayer B, Mingot A, Vullo D, et al. New superacid synthesized (fluorinated) tertiary benzenesulfonamides acting as selective hCA IX inhibitors: toward a new mode of carbonic anhydrase inhibition by sulfonamides. Chem Commun 2013;49:6015–17
   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
• Ahmed M, Azam F, Gbaj A, et al. Ester prodrugs of ketoprofen: synthesis, in vitro stability, in vivo biological evaluation and in silico comparative docking studies against COX-1 and COX-2. Curr Drug Discov Technol 2016;13:41–57
   PubMedGoogle Scholar
• Carroux CJ, Rankin GM, Moeker J, et al. A prodrug approach toward cancer-related carbonic anhydrase inhibition. J Med Chem 2013;56:9623–34
   PubMed Web of Science ®Google Scholar
• Müller CE. Prodrug approaches for enhancing the bioavailability of drugs with low solubility. Chem Biodivers 2009;6:2071–83
   PubMed Web of Science ®Google Scholar
• Lv P-C, Elsayed MSA, Agama K, et al. Design, synthesis, and biological evaluation of potential prodrugs related to the experimental anticancer agent indotecan (LMP400). J Med Chem 2016;59:4890–9
   PubMed Web of Science ®Google Scholar
• Farhat MB, Landoulsi A, Chaouch-Hamada R, et al. Profiling of essential oils and polyphenolics of Salvia argentea and evaluation of its by-products antioxidant activity. Ind Crops Prod 2013;47:106–12
   Web of Science ®Google Scholar
• Smeriglio A, Mandalari G, Bisignano C, et al. Polyphenolic content and biological properties of Avola almond (Prunus dulcis Mill. D.A. Webb) skin and its industrial byproducts. Ind Crops Prod 2016;83:283–93
   Web of Science ®Google Scholar
• Kıvrak İ, Kıvrak Ş, Harmandar M, Çetintaş Y. Phenolic compounds of Pinus brutia Ten.: chemical investigation and quantitative analysis using an ultra-performance liquid chromatography tandem mass spectrometry with electrospray ionization source. Rec Nat Prod 2013;7:313–19
   Google Scholar
• Kalın P, Gülçin İ, Gören AC. Antioxidant activity and polyphenol content of Cranberries (Vaccinium macrocarpon). Rec Nat Prod 2015;9:496–502
   Google Scholar
• Patki VM, Shirsat MV. Chemotherapy of intestinal infections. I. Synthesis of N4-acyl derivatives of N1-substituted sulfanilamides. J Sci Ind Res 1959;18C:113–16
   Google Scholar
• Lin C, Lin X, Liu B, et al. Preparation of 3,4,5-trihydroxygallic acid amide containing benzene sulphonamide derivatives for treating osteoarthritis. Fam Zhuanli Shenqing 2014; CN 104193690 A 20141210
   Google Scholar
• Lin X, Zheng L, Liu Q, et al. In vitro effect of a synthesized sulfonamido-based gallate on articular chondrocyte metabolism. Bioorg Med Chem Lett 2014;24:2497–503
   PubMed Web of Science ®Google Scholar
• Ye J, Abiman P, Crossley A, et al. Building block syntheses of gallic acid monomers and tris-(o-gallyl)-gallic acid dendrimers chemically attached to graphite powder: a comparative study of their uptake of Al(III) ions. Langmuir 2010;26:1776–85
   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
• 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
• 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, 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