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Short Communication

Screening of benzenesulfonamide in combination with chemically diverse fragments against carbonic anhydrase by differential scanning fluorimetry

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Pages 306-310 | Received 05 Nov 2019, Accepted 21 Nov 2019, Published online: 04 Dec 2019

References

  • Cummings MD, Farnum MA, Nelen MI. Universal screening methods and applications of thermofluor®. J Biomol Screen 2006;11:854–63.
  • Khalifah RG. Carbon dixoide hydration activity of carbonic anhydrase: paradoxical consequences of the unusually rapid catalysis. Proc Natl Acad Sci USA 1973;70:1986–9.
  • Maren TH. Carbonic anhydrase chemistry, physiology, and inhibition. Physiol Rev 1967;47:595–781.
  • Supuran CT. Carbonic anhydrsases: novel therapeutic applications for inhibitors and activators. Nat Rev Drug Discov 2008;7:168–81.
  • Supuran CT. Carbonic anhydrases: from biomedical applications of the inhibitors and activators to biotechnologic use for CO2 capture. J Enzyme Inhib Med Chem 2013;28:229–30.
  • Winum J-Y, Scozzafava A, Montero JL, Supuran CT. New zinc binding motifs in the design of selective carbonic anhydrase inhibitors. Mini-Rev Med Chem 2006;6:921–36.
  • Supuran CT, Casini A, Scozzafava A, Development of sulfonamide carbonic anhydrase inhibitors. In: Supuran CT, Scozzafava A, Conway J, ed. Carbonic anhydrase: its inhibitors and activators. Boca Raton (FL): CRC Press; 2004:67.
  • Khloya P, Celik G, SitaRam Vullo D, et al. 4-Functionalized 1,3-diarylpyrazoles bearing benzenesulfonamide moiety as selective potent inhibitors of the tumor associated carbonic anhydrase isoforms IX and XII. Eur J Med Chem 2014;76:284–90.
  • Suthar SK, Bansal S, Lohan S, et al. Design and synthesis of novel 4-(4-oxo-2-arylthiazolidin-3-yl) benzenesulfonamides as selective inhibitors of carbonic anhydrase IX over I and II with potential anticancer activity. Eur J Med Chem 2013;66:372–9.
  • Garaj V, Puccetti L, Fasolis G, Winum J-Y, Montero J-L, Scozzafava A, Vullo D, Innocenti A, Supuran CT. Carbonic anhydrase inhibitors: synthesis and inhibition of cytosolic/tumor-associated carbonic anhydrase isozymes I, II and IX with sulfonamides incorporating 1,2,4-triazine moieties. Bioorg Med Chem Lett 2004;14:5427–33.
  • Gitto R, Agnello S, Ferro S, et al. Identification of potent and selective human carbonic anhydrase VII (CA VII) inhibitors. ChemMedChem 2010;5:823–6.
  • Casu B, Arya T, Bessette B, Baron C. Fragment-based screening identifies novel targets for inhibitors of conjugative transfer of antimicrobial resistance by plasmid pKM101. Sci Rep 2017;7:14907.
  • Congreve M, Carr R, Murray C, Jhoti H. A ‘rule of three’ for fragment-based lead discovery? Drug Discov Today 2003;8:876–7.
  • Abadzapatero C, Metz J. Ligand efficiency indices as guideposts for drug discovery. Drug Discov Today 2005;10:464–9.
  • Schultes S, de Graaf C, Haaksma EEJ, et al. Ligand efficiency as a guide in fragment hit selection and optimization. Drug Discov Today Technol 2010;7:e157–e162.
  • The screening and the building block collection of Enamine, Ltd. Available from: https://www.enaminestore.com/catalog.
  • Krasavin M, Stavniichuk R, Zozulya S, et al. Discovery of Strecker-type alpha-aminonitriles as a new class of human carbonic anhydrase inhibitors using differential scanning fluorimetry. J Enzyme Inhib Med Chem 2016;31:1707–11.
  • Ghose AK, Viswanadhan VN, Wendoloski JJ. What is the theoretical basis used in the calculation of ALogP in Schrödinger software? J Phys Chem A 1998;102:3762–72.
  • Lo MC, Aulabaugh A, Jin G, et al. Evaluation of fluorescence-based thermal shift assays for hit identification in drug discovery. Anal Biochem 2004;332:153–9.
  • Matulis D, Kranz JK, Salemme FR, Todd MJ. Thermodynamic stability of carbonic anhydrase: measurements of binding affinity and stoichiometry using ThermoFluor. Biochemistry 2005;44:5258–66.
  • Niesen FH, Berglund H, Vedadi M. The use of differential scanning fluorimetry to detect ligand interactions that promote protein stability. Nat Protoc 2007;2:2212–4421.
  • 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.
  • Kabir A, Honda RP, Kamatari YO, et al. Effects of ligand binding on the stability of aldo-keto reductases: implications for stabilizer or destabilizer chaperones. Protein Sci 2016;25:2132–41.
  • Nocentini A, Ferraroni M, Carta F, et al. Benzenesulfonamides incorporating flexible triazole moieties are highly effective carbonic anhydrase inhibitors: synthesis and kinetic, crystallographic, computational, and intraocular pressure lowering investigations. J Med Chem 2016;59:10692–704.