Synthesis and characterisation of two novel proton transfer compounds and their inhibition studies on carbonic anhydrase isoenzymes

References

• Supuran CT, Casini A, Mastrolorenzo A, Scozzafava A. Carbonic anhydrase inhibitors. Synthesis and inhibition of cytosolic/tumor-associated carbonic anhydrase isozymes I, II, and IX with boron-containing sulfonamides, sulfamides, and sulfamates: Toward agents for boron neutron capture therapy of hypoxic tumors. Mini Rev Med Chem 2004;4:625–632
   PubMed Web of Science ®Google Scholar
• Owa T, Nagasu T. Novel sulphonamide derivatives for the treatment of cancer. Expert Opinion Therapeutic Patents 2000;10:1725–1740.
   Web of Science ®Google Scholar
• Scozzafava A, Owa T, Mastrolorenzo A, Supuran CT. Anticancer and Antiviral Sulfonamides. Curr Med Chem 2003;10:925–953
   PubMed Web of Science ®Google Scholar
• Choan ZH, Hassan M, Khan MK, Supuran CT. In-vitro antibacterial, antifungal and cytotoxic properties of sulfonamide-derived Schiff’s bases and their metal complexes. J Enzyme Inhib Med Chem 2005;20:183–188.
   PubMedGoogle Scholar
• Supuran CT. Carbonic anhydrases: novel therapeutic applications for inhibitors and activators. Nat Rev Drug Disc 2008;7:168–181.
   PubMed Web of Science ®Google Scholar
• Bülbül M, Saracoğlu N, Küfrevioğlu Öİ, Çiftci M. Bile acid derivatives of 5-amino-1,3,4-thiadiazole-2-sulfonamide as new carbonic anhydrase inhibitors: Synthesis and investigation of inhibition effects. Bioorg Med Chem 2002;10:2561–2567.
   PubMed Web of Science ®Google Scholar
• Bülbül M, Kasımoğulları R, Küfrevioğlu Öİ. Amide derivatives with pyrazole carboxylic acids of 5-amino-1,3, 4-thiadiazole 2-sulfonamide as new carbonic anhydrase inhibitors: Synthesis and investigation of inhibitory effects. J Enzyme Inhib Med Chem 2008;23:895–900.
   PubMed Web of Science ®Google Scholar
• Nuti E, Orlandini E, Nencetti S, Rossello A, Innocenti A, Scozzafava A, Supuran CT. Carbonic anhydrase and matrix metalloproteinase inhibitors. Inhibition of human tumor-associated isozymes IX and cytosolic isozyme I and II with sulfonylated hydroxamates. Bioorg Med Chem 2007;15:2298–2311.
   PubMed Web of Science ®Google Scholar
• Özensoy Ö,Koçkar F, Arslan O, Işık S, Supuran CT. An evaluation of cytosolic erythrocyte carbonic anhydrase and catalase in carcinoma patients: An elevation of carbonic anhydrase activity. Clin Biochem 2007;40:835.
   Web of Science ®Google Scholar
• Supuran CT, Scozzafava A. Carbonic anhydrases as targets for medicinal chemistry. Bioorg Med Chem 2007:15:4336–4350.
   PubMed Web of Science ®Google Scholar
• Di Fiore A, Scozzafava A, Winum JY, Montero JL, Pedone C, Supuran CT, Simone GD. Carbonic anhydrase inhibitors: Binding of an antiglaucoma glycosyl-sulfanilamide derivative to human isoform II and its consequences for the drug design of enzyme inhibitors incorporating sugar moieties. Bioorg Med Chem Lett 2007;17:1726–1731.
   PubMed Web of Science ®Google Scholar
• Innocenti A, Vullo D, Pastorek J, Scozzafava A, Pastorekova S, Nishimori I, Supuran CT. Carbonic anhydrase inhibitors. Inhibition of transmembrane isozymes XII (cancer-associated) and XIV with anions. Bioorg Med Chem Lett 2007;17:1532–1537.
   PubMed Web of Science ®Google Scholar
• Winum JY, Thiry A, Cheikh KE, Dogne JM, Montero JL, Vullo D, Scozzafava A, Masereel B, Supuran CT. Carbonic anhydrase inhibitors. Inhibition of isoforms I, II, IV, VA, VII, IX, and XIV with sulfonamides incorporating fructopyranose-thioureido tails. Bioorg Med Chem Lett 2007;17:2685–2691.
   PubMed Web of Science ®Google Scholar
• Scozzafava A, Banciu MD, Popescu A, Supuran CT. Carbonic anhydrase inhibitors: Inhibition of isozymes I, II and IV by sulfamide and sulfamic acid derivatives. J Enzyme Inhib Med Chem 2000;15:443–553.
   Google Scholar
• Schuman JS. Antiglaucoma medications: A review of safety and tolerability issues related to their use. Clin Ther 2000;22:167–208.
   PubMed Web of Science ®Google Scholar
• Wilkinson BL, Bornaghi LF, Houston TA, Innocenti A, Vullo D, Supuran CT, Poulsen SA. Inhibition of membrane-associated carbonic anhydrase isozymes IX, XII and XIV with a library of glycoconjugate benzenesulfonamides. Bioorg Med Chem Lett 2007;17:987–992.
   PubMed Web of Science ®Google Scholar
• Santos MA, Marques S, Vullo D, Innocenti A, Scozzafava A, Supuran CT. Carbonic anhydrase inhibitors: Inhibition of cytosolic/tumor-associated isoforms I, II, and IX with iminodiacetic carboxylates/hydroxamates also incorporating benzene sulfonamide moieties. Bioorg Med Chem Lett 2007;17:1538–1543.
   PubMed Web of Science ®Google Scholar
• Glaser R, Lewis M. Single- and double-proton-transfer in the aggregate between cytosine and guaninediazonium ion. Org Lett 1999;1:273–276.
   PubMedGoogle Scholar
• Semo N, Osheroff MA, Koskl WS. Proton-transfer from the formyl and isoformyl positive-ions to acetylene. J Phys Chem 1983;87:2302–2303.
   Google Scholar
• He F, Ramirez J, Lebrilla CB. Evidence for an intermolecular proton-transfer reaction induced by collision in gas-phase noncovalently bound complexes. J Am Chem Soc 1999;121:4726–4727.
   Google Scholar
• Tarkka RM, Zhang X, Jenekhe SA. Electrically generated intramolecular proton transfer: Electroluminescence and stimulated emission from polymers. J Am Chem Soc 1996;118:9438–9439.
   Google Scholar
• Nogami M, Daiko V, Akai V, Kasuga V. Dynamics of proton transfer in the sol-gel-derived P2O5-SiO2 glasses. J Phys Chem 2001;105:4653–4656.
   Google Scholar
• Sharif MA, Aghabozorg A, Shokrollahi A, Kickelbick G, Moghimi A, Shamsipur M. Novel proton transfer compounds containing 2,6-pyridinedicarboxylic acid and melamine and their Pb-II complex: Synthesis, characterization, crystal structure and solution studies. Polish J Chem 2006;80:847–863.
   Google Scholar
• Moghimi A, Moosavi SM, Kordestani D, Maddah B, Shamsipur M, Aghabozorg H, Ramezanipour F, Kickelbick G. Pyridine-2,6-bis(monothiocarboxylic) acid and 2-aminopyridine as building blocks of a novel proton transfer compound: Solution and X-ray crystal structural studies. J Mol Struct 2007;828:38–45.
   Web of Science ®Google Scholar
• Zhang J, Zhu LG. Different supramolecular assemblies in two 1:1 proton-transfer compounds of sulfobenzoic acids with aromatic amines. Acta Cryst 2007;C63:o484–o486.
   Google Scholar
• Franklin S, Balasubramanian T. Salts of maleic and fumaric acids with oxine: the role of isomeric acids in hydrogen-bonding patterns. Acta Cryst 2009;C65:o58–o61.
   Google Scholar
• Soleimannejad J, Aghabozorg H, Morsali A, Hemmati F, Manteghi F. 4,4′-Bipyridinium bis(2-carboxypyridine-3-carboxylate). Acta Cryst 2009;E65:O153–U2591.
   Google Scholar
• Yenikaya C, Poyraz M, Sarı M, Demirci F, İlkimen H, Büyükgüngör O. Synthesis, characterization and biological evaluation of a novel Cu(II) complex with the mixed ligands 2,6-pyridinedicarboxylic acid and 2-aminopyridine. Polyhedron 2009;28:3526–3532
   Web of Science ®Google Scholar
• Moghimi A, Alizadeh R, Aghabozorgb H, Shockravib A, Aragonic MC, Demartind F, Isaiac F, Lippolisc V, Harrisone A, Shokrollahif A, Shamsipurf M. Ion pairing, H-bonding, and pi-pi interactions in copper(II) complex-organo-networks derived from a proton-transfer compound of the 1,10-phenanthroline-2,9-dicarboxylic acid. J Mol Struct 2005;750:166–173.
   Web of Science ®Google Scholar
• Ramezanipour F, Aghabozorg H, Shokrollahi A, Shamsipur M, Stoeckli-Evans H, Soleimannejad J, Sheshmani S. Different complexation behavior of a proton transfer compound obtained from 1,10-phenanthroline and pyridine-2,6-dicarboxylic acid with In-III and Ce-III: Synthesis, crystal structures and solution studies. J Mol Struct 2005;779:77–86.
   Web of Science ®Google Scholar
• Aghabozorg H, Derikvand Z, Olmstead MM, Gharamaleki JA. Hydroxonium hydrate tris(2,4,6-triamino-1,3,5-triazin-1-ium)bis[bis(pyridine-2,6-dicarboxylato)manganate (II/III)] hydroxide pyridine-2,6-dicarboxylic acid solvate pentahydrate. Acta Cryst 2008;C64:m372–m374.
   Google Scholar
• Aghabozorg H, Motyeian E, Soleimannejad J, Ghadermazi M, Gharamaleki JA. Aqua(4-hydroxypyridine-2,6-dicarboxylato)(1,10-phenanothroline)copper(II)4.5-hydrate. Acta Cryst 2008;E64:m252–u2372.
   Google Scholar
• Aghabozorg H, Derikvand Z, Nemati A, Bahrami Z, Gharamaleki JA. Poly[piperazinediium [aquabis(mu-pyridine-2,5-dicarboxylato)zincate] dihydrate] Acta Cryst 2008;E64:m111–u1098.
   Google Scholar
• Yenikaya C, Sarı M, Bülbül M, İlkimen H, Çelik H, Büyükgüngör O. Synthesis, characterization and antiglaucoma activity of a novel proton transfer compound and a mixed-ligand Zn(II) complex. Bioorg Med Chem 2010;18:930–938.
   PubMed Web of Science ®Google Scholar
• Sheldrick GM. SHELXS97 and SHEXL97. Program for Crystal Structure Solution and Refinement. University of Göttingen, Germany, 1997.
   Google Scholar
• Stoe & Cie, X-AREA (Version 1.18) and X-RED32 (Version 1.04). Stoe & Cie, Darmstadt, Germany, 2002.
   Google Scholar
• Farrugia LJ. ORTEP-3 for Windows - a version of ORTEP-III with a Graphical User Interface (GUI) J Appl Cryst 1997;30:565.
   Web of Science ®Google Scholar
• Arslan O, Nalbantoğlu B, Demir N, Özdemir H, Küfrevioğlu Öİ. A new method for the purification of carbonic anhydrase isozymes by affinity chromatography. Trop J Med Sci 1996;26:163–166.
   Google Scholar
• Rickli EE, Ghazanfar SA, Gibbson BH, Edsall JT. Carbonic Anhydrases from Human Erythrocytes: Preparation and properties of two enzymes. J Biol Chem 1964;239:1065–1068.
   PubMed Web of Science ®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;72:248–254.
   PubMed Web of Science ®Google Scholar
• Laemmli UK. Cleavage of Structural Proteins during the Assembly of the Head of Bacteriophage T4. Nature 1970;227:680–685.
   PubMed Web of Science ®Google Scholar
• Wilbur KM, Anderson NG. Electrometric and colorimetric determination of carbonic anhydrase. J Biol Chem 1948;176:147–154.
   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;242:4221–4229.
   PubMed Web of Science ®Google Scholar
• Innocenti A, Scozzafava A, Parkkila S, Pucceti L, De Simone G, Supuran CT. Investigations of the esterase, phosphatase, and sulfatase activities of the cytosolic mammalian carbonic anhydrase isoforms I, II, and XIII with 4-nitrophenyl esters as substrates. Bioorg Med Chem Lett 2008;18:2267–2271.
   PubMed Web of Science ®Google Scholar
• Landolfi C, Marchetti M, Ciocci G, Milanese C. Development and pharmacological characterization of a modified procedure for the measurement of carbonic anhydrase activity. J Pharmacol Toxicol Methods 1998;38:169–172.
   Web of Science ®Google Scholar
• Bülbül M, Hisar O, Beydemir S, Ciftci M, Küfrevioğlu Öİ. The in vitro and in vivo inhibitory effects of some sulfonamide derivatives on rainbow trout (Oncorhynchus mykiss) erythrocyte carbonic anhydrase activity. J Enzyme Inhib Med Chem 2003:18;371–375.
   PubMed Web of Science ®Google Scholar
• Ciftci M, Bülbül M, Gül M, Gümüştekin K, Dane Ş, Süleyman H. Effects of nicotine and Vitamin E on carbonic anhydrase activity in some rat tissues in vivo and in vitro. J Enzyme Inhib Med Chem 2005:20;103–109.
   PubMed Web of Science ®Google Scholar
• Hisar O, Beydemir Ş, Bülbül M, Yanık T. Kinetic properties of carbonic anhydrase purified from gills of rainbow trout (Oncorhynchus mykiss). J Appl Anim Res 2006;30:185–188.
   Web of Science ®Google Scholar
• Winum JY, Cecchi A, Montero JL, Innocenti A, Scozzafava A, Supuran CT. Carbonic anhydrase inhibitors. Synthesis and inhibition of cytosolic/tumor-associated carbonic anhydrase isozymes I, II, and IX with boron-containing sulfonamides, sulfamides, and sulfamates: Toward agents for boron neutron capture therapy of hypoxic tumors. Bioorg Med Chem Lett 2005;15:3302–3306.
   PubMed Web of Science ®Google Scholar
• Lineweaver H, Burk D. The determination of enzyme dissociation contants. J Am Chem Soc 1934;56:658–666.
   Web of Science ®Google Scholar
• Siddiqui WA, Ahmad S, Siddiqui HL, Tariq MI, Parvez M. o-sulfamoylbenzoic acid. Acta Cryst 2007;E63:o4117–u3678.
   Google Scholar
• Yeşilel OZ, Büyükgüngör O. The novel monomeric bis(orotate-N,O) supramolecular complex of manganese(II): Synthesis, spectrothermal properties and crystal structures of (enH)2[Mn(HOr)2(H2O)2].2.5H2O. Solid State Science 2007;9:485–490.
   Google Scholar
• Aghabozorg H, Saei AA, Ramezanipour F. 2,6-Diaminopyridinium pyridinium-2,6-dicarboxylate: a redetermination. Acta Cryst 2005;E61:o3242–o3244.
   Google Scholar
• Nolan SJ, Shiels JC, Tuite JB, Cecere KL, Baranger AM. Recognition of an essential adenine at a protein-RNA interface: Comparison of the contributions of hydrogen bonds and a stacking interaction. J Am Chem Soc 1999;121:8951–8952.
   Web of Science ®Google Scholar
• Madalan AM, Kravtsov VC, Simonov YA, Voronkova V, Korobchenko L, Avarvari N, Andruh M. A unique diamondoid network resulting from the convolution of pi-pi stacking and lipophilic interactions. Cryst Growth Des 2005;5:45–47.
   Web of Science ®Google Scholar
• Bergman SD, Reshef D, Frish L, Cohen Y, Goldberg I, Kol M. From eilatin to isoeilatin: A skeletal rearrangement strongly influences pi-stacking of Ru(II) complex. Inorg Chem 2004;43;3792–3794.
   PubMedGoogle Scholar
• Rathore R, Abdelwahed SH, Guzei IA. Synthesis, structure, and evaluation of the effect of multiple stacking on the electron-donor properties of pi-stacked polyfluorenes. J Am Chem Soc 2003;125:8712–8713.
   PubMedGoogle Scholar
• Nakamoto K. Infrared And Raman Spectra of Inorganic and Coordination Compounds, 5th Edition, Interscience-Wiley, NewYork, 1997:16.
   Google Scholar
• Cooks, D. Vibrational spectra of pyridinium salts. Canadian J Chem 1961;39(10):2009–2024.
   Google Scholar
• Gowda BT, Jyothi K, Souza JDD. Infrared and NMR spectra of arylsulphonamides, 4-X-C6H4SO2NH2 and i-X, j-YC6H3SO2NH2 (X = H; CH3; C2H5; F; Cl; Br; I or NO2 and i-X, j-Y = 2,3-(CH3)(2); 2,4-(CH3)(2); 2,5(CH3)(2); 2-CH3, 4-Cl; 2-CH3, 5-Cl; 3-CH3, 4-Cl; 2,4-Cl-2 or 3,4-Cl-2). Z Naturforsch 2002;57:967–973.
   Google Scholar
• Nakamoto K. Infrared and Raman Spectra of Inorganic and Coordination Compounds. 5th Edition, NewYork: Interscience-Wiley, 1997:59.
   Google Scholar
• Mao L, Wang Y, Qi Y, Cao M, Hu C. A novel three-dimensional supramolecular framework with one-dimensional channels: synthesis and crystal structure of [Cu(DPC)(H2O)3] (H2DPC=Pyridine-2,6-dicarboxylic acid). J Mol Struct 2004;688:197–201.
   Web of Science ®Google Scholar
• Uçar İ,Karabulut B, Bulut A, Büyükgüngör O. Synthesis, structure, spectroscopic and electrochemical properties of (2-amino-4-methylpyrimidine)-(pyridine-2,6-dicarboxylato) copper(II) monohydrate. J Mol Struct 2007;834:336–344.
   Google Scholar
• Kirillova MV, Da Silva MFCG, Kirillov AM, Da Silva JJRF, Pombeiro AJL. 3D hydrogen bonded heteronuclear Co-II, Ni-II, Cu-II and Zn-II aqua complexes derived from dipicolinic acid. Inorg Chim Acta 2007;360:506–512.
   Web of Science ®Google Scholar
• Lindskog S. Structure and mechanism of carbonic anhydrase. Pharmacol Ther 1997;74:1–20.
   PubMed Web of Science ®Google Scholar