978
Views
4
CrossRef citations to date
0
Altmetric
Research Paper

Further validation of strecker-type α-aminonitriles as a new class of potent human carbonic anhydrase II inhibitors: hit expansion within the public domain using differential scanning fluorimetry leads to chemotype refinement

, , , , , ORCID Icon & ORCID Icon show all
Pages 165-171 | Received 16 Oct 2019, Accepted 11 Nov 2019, Published online: 22 Nov 2019

References

  • Cummings MD, Farnum MA, Nelen MI. Universal screening methods and applications of ThermoFluor®. J Biomol Screen 2006;11:854–63.
  • The screening and the building block collection of Enamine, Ltd. can be obtained at https://www.enaminestore.com/catalog
  • Krasavin M, Stavniichuk R, Zozulya S, et al. Discovery of strecker-type α-aminonitriles as a new class of human carbonic anhydrase inhibitors using differential scanning fluorimetry. J Enzyme Inhib Med Chem 2016;31:1707–11.
  • Supuran CT, Scozzafava A, Briganti F. Carbonic anhydrase inhibitors: N-cyanosulfonamides, a new class of high affinity isozyme II and IV inhibitors. J Enzyme Inh 1999;14:289–306.
  • Krasavin M, Korsakov M, Dorogov M, et al. Probing the ‘bipolar nature of the carbonic anhydrase active site: aromatic sulfonamides containing 1,3-oxazol-5-yl moiety as picomolar inhibitors of cytosolic CA I and CA II isoforms. Eur J Med Chem 2015;101:334–47.
  • 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;2:2212–21.
  • 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.
  • Khalifah RG, Edsall JT. Carbon dioxide hydration activity of carbonic anhydrase: kinetics of alkylated anhydrases B and C from humans. Proc Natl Acad Sci USA 1972;69:172–6.
  • 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.
  • Temperini C, Innocenti A, Scozzafava A, et al. The coumarin-binding site in carbonic anhydrase accommodates structurally diverse inhibitors: the antiepileptic lacosamide as an example and lead molecule for novel classes of carbonic anhydrase inhibitors. J Med Chem 2010;53:850–4.
  • 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.
  • Casey JR, Morgan PE, Vullo D, et al. Carbonic anhydrase inhibitors. Design of selective, membrane-impermeant inhibitors targeting the human tumor-associated isozyme IX. J Med Chem 2004; 47:2337–47.
  • Casini A, Scozzafava A, Mincione F, et al. Carbonic anhydrase inhibitors: water-soluble 4-sulfamoylphenylthioureas as topical intraocular pressure-lowering agents with long-lasting effects. J Med Chem 2000;43:4884–92.
  • Winum JY, Scozzafava A, Montero JL, Supuran CT. Design of zinc binding functions for carbonic anhydrase inhibitors. Curr Pharm Des 2008;14:615–21.