Carbonic anhydrase inhibitors: guaiacol and catechol derivatives effectively inhibit certain human carbonic anhydrase isoenzymes (hCA I, II, IX and XII)

References

• 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
• Capasso C, Supuran CT. Sulfa and trimethoprim-like drugs-antimetabolites acting as carbonic anhydrase, dihydropteroate synthase and dihydrofolate reductase inhibitors. J Enzyme Inhib Med Chem 2014;29:379–87
   PubMed 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
• 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
• Said HM, Hagemann C, Carta F, et al. Hypoxia induced CA9 inhibitory targeting by two different sulfonamide derivatives including acetazolamide in human Glioblastoma. Bioorg Med Chem 2013;21:3949–57
   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
• Monti SM, Supuran CT, De Simone G. Anticancer carbonic anhydrase inhibitors: a patent review (2008–2013). Expert Opin Ther Pat 2013;23:737–49
   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
• Rummer JL, McKenzie DJ, Innocenti A, et al. Root effect hemoglobin may have evolved to enhance general tissue oxygen delivery. Science 2013;340:1327–9
   PubMed Web of Science ®Google Scholar
• Nishimori I, Vullo D, Minakuchi T, et al. Sulfonamide inhibition studies of two β-carbonic anhydrases from the bacterial pathogen Legionella pneumophila. Bioorg Med Chem 2014;22:2939–46
   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
• Smith KS, Jakubzick C, Whittam TS, Ferry JG. Carbonic anhydrase is an ancient enzyme widespread in prokaryotes. Proc Natl Acad Sci USA 1999;96:15184–9
   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
• 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
• Pastorekova S, Parkkila S, Pastorek J, Supuran CT. Carbonic anhydrases: current state of the art, therapeutic applications and future prospects. J Enzyme Inhib Med Chem 2004;19:199–229
   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
• Durdagi S, Scozzafava G, Vullo D, et al. Inhibition of mammalian carbonic anhydrases I–XIV with grayanotoxin III: solution and in silico studies. J Enzyme Inhib Med Chem 2014;29:469–75
   PubMed Web of Science ®Google Scholar
• Bilginer S, Unluer E, Gul HI, et al. Carbonic anhydrase inhibitors. Phenols incorporating 2- or 3-pyridyl-ethenylcarbonyl and tertiary amine moieties strongly inhibit Saccharomyces cerevisiae β-carbonic anhydrase. J Enzyme Inhib Med Chem 2014;29:495–9
   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
• 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
• Pan J, Lau J, Mesak F, et al. Synthesis and evaluation of 18F-labeled carbonic anhydrase IX inhibitors for imaging with positron emission tomography. J Enzyme Inhib Med Chem 2014;29:249–55
   PubMed Web of Science ®Google Scholar
• Joseph P, Turtaut F, Ouahrani-Bettache S, et al. Cloning, Characterization, and inhibition studies of a β-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 β-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, 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
• Topal M, Gülçin İ. Rosmarinic acid: a potent carbonic anhydrase isoenzymes inhibitor. Turk J Chem 2014;38:894–902
   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
• Robbins RJ. Phenolic acids in foods: an overview of analytical methodology. J Agric Food Chem 2003;51:2866–87
   PubMed 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
• Gülçin İ. Antioxidant activity of food constituents – an overview. Arch Toxicol 2012;86:345–96
   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
• Lauraguaisa A, Coeur-Tourneur C, Cassez A, et al. Atmospheric reactivity of hydroxyl radicals with guaiacol (2-methoxyphenol), a biomass burning emitted compound: secondary organic aerosol formation and gas-phase oxidation products. Atmos Environ 2014;86:155–63
   Web of Science ®Google Scholar
• Mohan D, Pittman CU, Steele PH. Pyrolysis of wood/biomass for bio-oil: a critical review. Energy Fuels 2006;20:848–89
   Web of Science ®Google Scholar
• Elliott DC, Hart TR. Catalytic hydroprocessing of chemical models for bio-oil. Energy Fuels 2009;23:631–7
   Web of Science ®Google Scholar
• Chang SS, Kang DH. Alicyclobacillus spp. in the fruit juice industry: history, characteristics, and current isolation/detection procedures. Crit Rev Microbiol 2004;30:55–74
   PubMed Web of Science ®Google Scholar
• Bui VN, Toussaint G, Laurenti D, et al. Co-processing of pyrolisis bio oils and gas oil for new generation of bio-fuels: hydrodeoxygenation of guaïacol and SRGO mixed feed. Catal Today 2009;143:172–8
   Web of Science ®Google Scholar
• Gutierrez A, Kaila RK, Honkela ML, et al. Hydrodeoxygenation of guaiacol on noble metal catalysts. Catal Today 2009;147:239–46
   Web of Science ®Google Scholar
• Bykova MV, Ermakov DY, Kaichev VV, et al. Ni-based sol–gel catalysts as promising systems for crude bio-oil upgrading: guaiacol hydrodeoxygenation study. Appl Catal B 2012;113–114:296–307
   Web of Science ®Google Scholar
• Nava B, Pawelec P, Castano MC, et al. Upgrading of bio-liquids on different mesoporous silica-supported CoMo catalysts. Appl Catal B 2009;92:154–67
   Web of Science ®Google Scholar
• He W, Li Y, Si H, et al. Molecular modeling and spectroscopic studies on the binding of guaiacol to human serum albumin. J Photochem Photobiol A Chem 2006;182:158–67
   Web of Science ®Google Scholar
• Bolton JL, Pisha E, Li S, et al. The reactivity of o-quinones which do not isomerize to quinone methods correlates with alkylcatechol-induced toxicity in human melanoma cells Chem Biol Interact 1997;106:133–48
   Google Scholar
• Shirai K. Screening of microorganisms for catechol production from benzene Agric Biol Chem 1986;50:2875–80
   Google Scholar
• Dignum MJW, Kerler J, Verpoorte R. Vanilla production: technological, chemical, and biosynthetic aspects. Food Rev Int 2001;17:119–20
   Google Scholar
• Held M, Schmid A, Kohler HPE, et al. An integrated process for the production of toxic catechols from toxic phenols based on a designer biocatalyst. Biotechnol Bioeng 1999;62:641–8
   PubMed Web of Science ®Google Scholar
• Kauffman ME, Keener WK, Clingenpeel SR, et al. Use of 3-hydroxyphenylacetylene for activity-dependent, fluorescent labeling of bacteria that degrade toluene via 3-methylcatechol. J Microbiol Meth 2003;55:801–5
   PubMed Web of Science ®Google Scholar
• Husken LE, Oomes M, Schroen K, et al. Membrane-facilitated bioproduction of 3-methylcatechol in an octanol/water two-phase system. J Biotechnol 2002;96:281–9
   PubMed Web of Science ®Google Scholar
• Callizot N, Warter JM, Poindron P. Pyridoxine-induced neuropathy in rats: a sensory neuropathy that responds to 4-methylcatechol. Neurobiol Dis 2001;8:626–35
   PubMed Web of Science ®Google Scholar
• Liu C, Zhang Y, Huang X. Study of guaiacol pyrolysis mechanism based on density function theory. Fuel Proces Technol 2014;123:159–65
   Web of Science ®Google Scholar
• Öztürk Sarikaya 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
• 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
• 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, Ozturk Sarikaya SB, Gulcin I, 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
• 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, 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. Antioxidant activity of caffeic acid (3,4-dihydroxycinnamic acid). Toxicology 2006;217:213–20
   PubMed Web of Science ®Google Scholar
• Gülçin İ. Antioxidant and antiradical activities of l-carnitine. Life Sci 2006;78:803–11
   PubMed 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. 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
• Supuran CT. Diuretics: from classical carbonic anhydrase inhibitors to novel applications of the sulfonamides. Curr Pharm Des 2008;14:641–8
   PubMed Web of Science ®Google Scholar
• Ilkimen H, Yenikaya C, Sarı M, et al. Synthesis and characterization of a proton transfer salt between 2,6-pyridinedicarboxylic acid and 2-aminobenzothiazole, and its complexes and their inhibition studies on carbonic anhydrase isoenzymes. J Enzyme Inhib Med Chem 2014;29:353–61
   PubMed Web of Science ®Google Scholar
• Scozzafava A, Mastrolorenzo A, Supuran CT. Carbonic anhydrase inhibitors and activators and their use in therapy. Expert Opin Ther Pat 2006;16:1627–64
   Web of Science ®Google Scholar
• Innocenti A, Vullo D, Scozzafava A, Supuran CT. Carbonic anhydrase inhibitors: interactions of phenols with the 12 catalytically active mammalian isoforms (CA I–XIV). Bioorg Med Chem Lett 2008;18:1583–7
   PubMed Web of Science ®Google Scholar
• Steele RM, Batugo MR, Benedini F, et al. Nitric oxide-donating carbonic anhydrase inhibitors for the treatment of open-angle glaucoma. Bioorg Med Chem Lett 2009;19:6565–70
   PubMed Web of Science ®Google Scholar
• Alterio V, Hilvo M, Di Fiore A, et al. Crystal structure of the catalytic domain of the tumor-associated human carbonic anhydrase IX. Proc Natl Acad Sci USA 2009;106:16233–8
   PubMed Web of Science ®Google Scholar
• Ahlskog JKJ, Dumelin CE, Trüssel S, et al. In vivo targeting of tumor-associated carbonic anhydrases using acetazolamide derivatives. Bioorg Med Chem Lett 2009;19:4851–6
   PubMed Web of Science ®Google Scholar
• Dubois L, Lieuwes NG, Maresca A, et al. Imaging of CA IX with fluorescent labelled sulfonamides distinguishes hypoxic and (re)-oxygenated cells in a xenograft tumour model. Radiother Oncol 2009;92:423–8
   PubMed Web of Science ®Google Scholar
• Nair SK, Ludwig PA, Christianson DW. Two-site binding of phenol in the active side of human carbonic anhydrase II: Structural implications for substrate association. J Am Chem Soc 1994;116:3659–60
   Web of Science ®Google Scholar
• Maresca A, Temperini C, Vu H, et al. Non-zinc mediated inhibition of carbonic anhydrases: coumarins are a new class of suicide inhibitors. J Am Chem Soc 2009;131:3057–62
   PubMed Web of Science ®Google Scholar
• Davis RA, Innocenti A, Poulsen SA, Supuran CT. Carbonic anhydrase inhibitors. Identification of selective inhibitors of the human mitochondrial isozymes VA and VB over the cytosolic isozymes I and II from a natural product-based phenolic library. Bioorg Med Chem 2010;18:14–18
   PubMed Web of Science ®Google Scholar
• Senturk M, Gulcin I, Dastan 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
• 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
• Akincioglu A, Akbaba Y, Goçer H, et al. Novel sulfamides as potential carbonic anhydrase isoenzymes inhibitors. Bioorg Med Chem 2013;21:1379–85
   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
• Barclay LRC, Vinqvist MR, Mukai K, et al. Chain-breaking phenolic antioxidants: steric and electronic effects in polyalkylchromanols, tocopherol analogs, hydroquinones, and superior antioxidants of the polyalkylbenzochromanol and naphthofuran class. J Org Chem 1993;58:7416–20
   Web of Science ®Google Scholar
• Tomiyama S, Sakai S, Nishiyama T, Yamada F. Factors influencing the antioxidant activities of phenols by an ab initio study. Bull Chem Soc Jpn 1993;66:299–304
   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
• Winum JY, Maresca A, Carta F, et al. Polypharmacology of sulfonamides: pazopanib, a multitargeted receptor tyrosine kinase inhibitor in clinical use, potently inhibits several mammalian carbonic anhydrases. Chem Commun 2012;48:8177–9
   PubMed Web of Science ®Google Scholar
• Supuran CT, Scozzafava A. Carbonic anhydrase inhibitors and their therapeutic potential. Expert Opin Ther Pat 2000;10:575–600
   Web of Science ®Google Scholar
• Supuran CT. Carbonic anhydrase inhibitors and activators for novel therapeutic applications. Fut Med Chem 2011;3:1165–80
   PubMed Web of Science ®Google Scholar
• Chohan ZH, Supuran CT, Scozzafava A. Metal binding and antibacterial activity of ciprofloxacin complexes. J Enzyme Inhib Med Chem 2005;20:303–7
   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
• Supuran CT, Scozzafava A. Carbonic anhydrases as targets for medicinal chemistry. Bioorg Med Chem 2007;15:4336–50
   PubMed Web of Science ®Google Scholar
• Ghorab MM, Alsaid MS, Ceruso M, et al. Carbonic anhydrase inhibitors: synthesis, molecular docking, cytotoxic and inhibition of the human carbonic anhydrase isoforms I, II, IX, XII with novel benzenesulfonamides incorporating pyrrole, pyrrolopyrimidine and fused pyrrolopyrimidine moieties. Bioorg Med Chem 2014;22:3684–95
   PubMed Web of Science ®Google Scholar
• Lou Y, McDonald PC, Oloumi A, et al. Targeting tumor hypoxia: suppression of breast tumor growth and metastasis by novel carbonic anhydrase IX inhibitors. Cancer Res 2011;71:3364–76
   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-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
• Rice-Evans CA, Miller NJ, Paganga G. Structure–antioxidant activity relationships of flavonoids and phenolic acids. Free Radical Biol Med 1996;20:933–56
   PubMed Web of Science ®Google Scholar
• Sroka Z, Cisowski W. Hydrogen peroxide scavenging, antioxidant and anti-radical activity of some phenolic acids. Food Chem Toxicol 2003;41:753–8
   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. (in press) doi:10.3109/14756366.2014.928704
   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
• Khalifah RG. The carbon dioxide hydration activity of carbonic anhydrase. I. Stop-flow kinetic studies on the native human isoenzymes B and C. J Biol Chem 1971;246:2561–73
   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