626
Views
8
CrossRef citations to date
0
Altmetric
Research Article

Chromatographic evaluation and QSAR optimization for benzoic acid analogues against carbonic anhydrase III

, &
Pages 420-429 | Received 07 Jun 2014, Accepted 28 Jun 2014, Published online: 28 Jul 2014

References

  • Supuran CT, Scozzafava A, Casini A. Carbonic anhydrase inhibitors. Med Res Rev 2003;23:146–89
  • Migliardini F, De Luca V, Carginale V, et al. Biomimetic CO2 capture using a highly thermostable bacterial α-carbonic anhydrase immobilized on a polyurethane foam. J Enzyme Inhib Med Chem 2014;29:146–50
  • Supuran CT. Carbonic anhydrases: novel therapeutic applications for inhibitors and activators. Nat Rev Drug Discov 2008;7:168–81
  • Neri D, Supuran CT. Interfering with pH regulation in tumours as a therapeutic strategy. Nat Rev Drug Discov 2011;10:767–77
  • Supuran CT, Scozzafava A. Carbonic anhydrases as targets for medicinal chemistry. Bioorg Med Chem 2007;15:4336–50
  • Gilmour KM. Perspectives on carbonic anhydrase. Comp Biochem Physiol A Mol Integr Physiol 2010;157:193–7
  • Imtaiyaz Hassan M, Shajee B, Waheed A, et al. Structure, function and applications of carbonic anhydrase isozymes. Bioorg Med Chem 2012;21:1570–82
  • Thiry A, Rolin S, Vullo D, et al. Indanesulfonamides as carbonic anhydrase inhibitors and anticonvulsant agents: structure-activity relationship and pharmacological evaluation. Eur J Med Chem 2008;43:2853–60
  • Supuran CT, Scozzafava A, Menabuoni L, et al. Carbonic anhydrase inhibitors. Part 71: Synthesis and ocular pharmacology of a new class of water-soluble, topically effective intraocular pressure lowering sulfonamides incorporating picolinoyl moieties. Eur J Pharm Sci 1999;8:317–28
  • Vuotikka P, Uusimaa P, Niemelä M, et al. Serum myoglobin/carbonic anhydrase III ratio as a marker of reperfusion after myocardial infarction. Int J Cardiol 2003;91:137–44
  • Nishita T, Igarashi S-I, Asari M. Determination of carbonic anhydrase-III by enzyme-immunoassay in liver, muscle and serum of male rats with streptozotocin-induced diabetes mellitus. Int J Biochem Cell Biol 1995;27:359–64
  • Mitterberger MC, Kim G, Rostek U, et al. Carbonic anhydrase III regulates peroxisome proliferator-activated receptor-γ2. Exp Cell Res 2012;318:877–86
  • 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
  • Innocenti A, Vullo D, Scozzafava A, Supuran CT. Carbonic anhydrase inhibitors: inhibition of mammalian isoforms I-XIV with a series of substituted phenols including paracetamol and salicylic acid. Bioorg Med Chem Lett 2008;16:7424–8
  • Carta F, Vullo D, Maresca A, Scozzafava A, Supuran CT. Mono-/dihydroxybenzoic acid esters and phenol pyridinium derivatives as inhibitors of the mammalian carbonic anhydrase isoforms I, II, VII, IX, XII and XIV. Bioorg Med Chem 2012;21:1564–9
  • Davis RA, Innocenti A, Poulsen S-A, 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
  • Alzweiri M, Al-Hiari Y. Evaluation of vanillic acid as inhibitor of carbonic anhydrase isozyme III by using a modified Hummel-Dreyer method: approach for drug discovery. Biomed Chromatogr 2013;27:1157–61
  • Rengel Z. Carbonic anhydrase activity in leaves of wheat genotypes differing in Zn efficiency. J Plant Physiol 1995;147:251–6
  • Conroy CW, Buck RH, Maren TH. The microchemical detection of carbonic anhydrase in corneal epithelia. Exp Eye Res 1992;55:637–40
  • Elder I, Fisher Z, Laipis PJ, et al. Structural and kinetic analysis of proton shuttle residues in the active site of human carbonic anhydrase III. Proteins: Struct Funct Bioinform 2007;68:337–43
  • Al-Balas Q, Hassan M, Al-Oudat B, et al. Generation of the first structure-based pharmacophore model containing a selective “zinc binding group” feature to identify potential glyoxalase-1 inhibitors. Molecules 2012;17:13740–58
  • Clark RD, Strizhev A, Leonard JM, et al. Consensus scoring for ligand/protein interactions. J Mol Graph Model 2002;20:281–95
  • Wu G, Robertson DH, Brooks CL, Vieth M. Detailed analysis of grid-based molecular docking: a case study of CDOCKER-A CHARMm-based MD docking algorithm. J Comput Chem 2003;24:1549–62
  • Rao SN, Head MS, Kulkarni A, LaLonde JM. Validation studies of the site-directed docking program LibDock. J Chem Inf Model 2007;47:2159–71
  • Muegge I. PMF scoring revisited. J Med Chem 2006;49:5895–902
  • Böhm H-J. Prediction of binding constants of protein ligands: a fast method for the prioritization of hits obtained from de novo design or 3D database search programs. J Comput Aided Mol Des 1998;12:309
  • Verdonk ML, Cole JC, Hartshorn MJ, et al. Improved protein-ligand docking using GOLD. Proteins: Struct Funct Bioinform 2003;52:609–23
  • Flood KG, Reynolds ER, Snow NH. Determination of apparent association constants of steroid-cyclodextrin inclusion complexes using a modification of the Hummel-Dreyer method. J Chromatogr A 2001;913:261–8
  • Alzweiri M, Watson DG, Parkinson JA. Metabonomics as a clinical tool of analysis: LC-MS approaches. J Liquid Chromatogr Relat Technol 2012;36:94–115
  • Alzweiri M, Sills GJ, Leach JP, et al. Response to drug treatment in newly diagnosed epilepsy: A pilot study of 1H NMR-and MS-based metabonomic analysis. Epilepsy Res 2010;88:189–95
  • Hothorn T, Bretz F, Westfall P. Simultaneous inference in general parametric models. Biometrical J 2008;50:346–63
  • Martens H, Høy M, Westad F, et al. Analysis of designed experiments by stabilised PLS regression and jack-knifing. Chemometr Intell Lab 2001;58:151–70
  • Shiyab S, Shatnawi M, Shibli R, et al. Influence of developmental stage on yield and composition of Origanum syriacum L. oil by multivariate analysis. J Med Plants Res 2012;6:2985–94
  • Li X, Lu X, Tian J, et al. Application of fuzzy c-means clustering in data analysis of metabolomics. Anal Chem 2009;81:4468–75
  • Gilbody S, Bower P, Whitty P. Costs and consequences of enhanced primary care for depression: systematic review of randomised economic evaluations. Br J Psychiatry 2006;189:297–308
  • Kawai K, Nagata N. Metal-ligand interactions: an analysis of zinc binding groups using the Protein Data Bank. Eur J Med Chem 2012;51:271–6

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.