920
Views
21
CrossRef citations to date
0
Altmetric
Research Article

Inhibitory effect of novel pyrazole carboxamide derivatives on human carbonic anhydrase enzyme

, , , , , & show all
Pages 328-336 | Received 14 Nov 2011, Accepted 16 Dec 2011, Published online: 03 Feb 2012

References

  • Wilkinson BL, Bornaghi LF, Houston TA, Innocenti A, Vullo D, Supuran CT et al. Carbonic anhydrase inhibitors: inhibition of isozymes I, II, and IX with triazole-linked O-glycosides of benzene sulfonamides. J Med Chem 2007;50:1651–1657.
  • Yin Y, Cameron MD, Lin L, Khan S, Schroter T, Grant W, Pocas J et al. Discovery of potent and selective urea-based ROCK inhibitors and their effects on intraocular pressure in rats. ACS Med Chem Lett 2010;1:175–179.
  • Kim CY, Whittington DA, Chang JS, Liao J, May JA, Christianson DW. Structural aspects of isozyme selectivity in the binding of inhibitors to carbonic anhydrases II and IV. J Med Chem 2002;45:888–893.
  • Tarongoy P, Ho CL, Walton DS. Angle-closure glaucoma: the role of the lens in the pathogenesis, prevention, and treatment. Surv Ophthalmol 2009;54:211–225.
  • Gokhale NH, Bradford S, Cowan JA. Catalytic inactivation of human carbonic anhydrase I by a metallopeptide-sulfonamide conjugate is mediated by oxidation of active site residues. J Am Chem Soc 2008;130:2388–2389.
  • Hen N, Bialer M, Yagen B, Maresca A, Aggarwal M, Robbins AH et al. Anticonvulsant 4-aminobenzenesulfonamide derivatives with branched-alkylamide moieties: X-ray crystallography and inhibition studies of human carbonic anhydrase isoforms I, II, VII, and XIV. J Med Chem 2011;54:3977–3981.
  • Neri D, Supuran CT. Interfering with pH regulation in tumours as a therapeutic strategy. Nat Rev Drug Discov 2011;10:767–777.
  • Chegwidden WR, Carter ND, Edwards YH (eds.) The Carbonic Anhydrases-New Horizons. Basel: Birkhauser Verlag 2000.
  • Supuran CT. Carbonic anhydrases: novel therapeutic applications for inhibitors and activators. Nat Rev Drug Discov 2008;7:168–181.
  • Koike T, Kimura E, Nakamura I, Hashimoto Y, Shiro M. The first anionic sulfonamide-binding zinc(II) complexes with a macrocyclic triamine: chemical verification of the sulfonamide inhibition of carbonic anhydrase. J Am Chem Soc 1992;114:7388–7345.
  • 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.
  • Maren TH, Carbonic anhydrase: general perspective and advances in glaucoma research. Drug Dev Res 1987;10:255–276.
  • Lindskog S. Structure and mechanism of carbonic anhydrase. Pharmacol Ther 1997;74:1–20.
  • Supuran CT, Scozzafava A. Carbonic anhydrase inhibitors. Curr Med Chem 2001;1:61–97.
  • Bülbül M, Hisar O, Beydemir S, Ciftçi M, Küfrevioglu OI. 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.
  • Kasimogullari R, Bülbül M, Arslan BS, Gökçe B. Synthesis, characterization and antiglaucoma activity of some novel pyrazole derivatives of 5-amino-1,3,4-thiadiazole-2-sulfonamide. Eur J Med Chem 2010;45:4769–4773.
  • Kasimogullari R, Bülbül M, Günhan H, Güleryüz H. Effects of new 5-amino-1,3,4-thiadiazole-2-sulfonamide derivatives on human carbonic anhydrase isozymes. Bioorg Med Chem 2009;17:3295–3301.
  • Sener A, Kasımogullari R, Sener MK, Bildirici I, Akcamur Y. Studies on the reactions of cyclic oxalyl compounds with hydrazines or hydrazones: synthesis and reactions of 4-benzoyl-1-(3-nitrophenyl)-5-phenyl-1H-pyrazole-3-carboxylic acid. J Heterocycl Chem 2002;39:869–875.
  • Beydemir S, CIftçi M, Ozmen I, Buyukokuroglu ME, Ozdemir H, Küfrevioglu OI. Effects of some medical drugs on enzyme activities of carbonic anhydrase from human erythrocytes in vitro and from rat erythrocytes in vivo. Pharmacol Res 2000;42:187–191.
  • Wilbur KM, Anderson NG. Electrometric and colorimetric determination of carbonic anhydrase. J Biol Chem 1948;176:147–154.
  • Rickli EE, Ghazanfar SA, Gibbons BH, Edsall JT. Carbonic anhydrases from human erythrocytes. preparation and properties of two enzymes. J Biol Chem 1964;239:1065–1078.
  • Shah GN, Hewett-Emmett D, Grubb JH, Migas MC, Fleming RE, Waheed A et al. Mitochondrial carbonic anhydrase CA VB: differences in tissue distribution and pattern of evolution from those of CA VA suggest distinct physiological roles. Proc Natl Acad Sci USA 2000;97:1677–1682.
  • Verpoorte JA, Mehta S, Edsall JT. Esterase activities of human carbonic anhydrases B and C. J Biol Chem 1967;242:4221–4229.
  • 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.
  • Lineweaver H, Burk D. The determination of enzyme dissociation constants. J Am Chem Soc 1934;56:658–666.
  • Kim H-D, Ishida H. Model compounds study on the network structure of polybenzoxazines. Macromolecules 2003;36:8320–8329.
  • Cheuk KKL, Lam JWY, Chen J, Lai LM, Tang BZ. Amino acid-containing polyacetylenes: synthesis, hydrogen bonding, chirality transcription, and chain helicity of amphiphilic poly(phenylacetylene)s carrying l-leucine pendants. Macromolecules 2003;36:5947–5959.
  • Syud FA, Stanger HE, Gellman SH. Interstrand side chain–side chain interactions in a designed beta-hairpin: significance of both lateral and diagonal pairings. J Am Chem Soc 2001;123:8667–8677.
  • Nishimura N, Banno M, Maki A, Nishiyama Y, Maeba I. Synthesis of 3-β-d-ribofuranosylpyrazole-1-carboxamide. Carbohydr Res 1998;307:211–215.
  • Kaushal AM, Chakraborti AK, Bansal AK. FTIR studies on differential intermolecular association in crystalline and amorphous states of structurally related non-steroidal anti-inflammatory drugs. Mol Pharm 2008;5:937–945.
  • Stauffer SR, Katzenellenbogen JA. Solid-phase synthesis of tetrasubstituted pyrazoles, novel ligands for the estrogen receptor. J Comb Chem 2000;2:318–329.
  • Travers MJ, Eldenburg EL, Gilbert JV. Low-temperature matrix isolation studies of BCl(N3)2: infrared spectra and photolysis processes. J Phys Chem A 1999;103:9661–9668.
  • Unterberg C, Gerlach A, Schrader T, Gerhards M. Clusters of a protected amino acid with pyrazole derivatives: β-sheet model systems in the gas phase. Eur Phys J 2002;20:543–550.
  • Beydemir S, Gülçin I. Effects of melatonin on carbonic anhydrase from human erythrocytes in vitro and from rat erythrocytes in vivo. J Enzyme Inhib Med Chem 2004;19:193–197.
  • 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 Enzym Inhib 2000;15:443–453.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.