4kp8 › Citations

Benzenesulfonamides with pyrimidine moiety as inhibitors of human carbonic anhydrases I, II, VI, VII, XII, and XIII.

Čapkauskaitė E, Zubrienė A, Smirnov A, Torresan J, Kišonaitė M, Kazokaitė J, Gylytė J, Michailovienė V, Jogaitė V, Manakova E, Gražulis S, Tumkevičius S, Matulis D
Bioorg Med Chem 21 6937-47 (2013)
Related entries: 4kni, 4knj, 4knm, 4knn, 4kp5

Cited: 23 times
EuropePMC logo PMID: 24103428

Abstract

Two groups of benzenesulfonamide derivatives, bearing pyrimidine moieties, were designed and synthesized as inhibitors of carbonic anhydrases (CA). Their binding affinities to six recombinant human CA isoforms I, II, VI, VII, XII, and XIII were determined by the thermal shift assay (TSA). The binding of several inhibitors was measured by isothermal titration calorimetry (ITC). Direct demonstration of compound inhibition was achieved by determining the inhibition constant by stopped-flow CO2 hydration assay. The most potent compounds demonstrated selectivity towards isoform I and affinities of 0.5 nM. The crystal structures of selected compounds in complex with CA II, XII, and XIII were determined to atomic resolution. Compounds described here were compared with previously published pyrimidinebenzenesulfonamides.(1) Systematic structure-activity analysis of 40 compound interactions with six isoforms yields clues for the design of compounds with greater affinities and selectivities towards target CA isoforms.

Articles - 4kp8 mentioned but not cited (1)

  1. Intrinsic Thermodynamics and Structure Correlation of Benzenesulfonamides with a Pyrimidine Moiety Binding to Carbonic Anhydrases I, II, VII, XII, and XIII. Kišonaitė M, Zubrienė A, Capkauskaitė E, Smirnov A, Smirnovienė J, Kairys V, Michailovienė V, Manakova E, Gražulis S, Matulis D. PLoS One 9 e114106 (2014)


Reviews citing this publication (2)

  1. Applications of isothermal titration calorimetry - the research and technical developments from 2011 to 2015. Falconer RJ. J Mol Recognit 29 504-515 (2016)
  2. Thermodynamic, kinetic, and structural parameterization of human carbonic anhydrase interactions toward enhanced inhibitor design. Linkuvienė V, Zubrienė A, Manakova E, Petrauskas V, Baranauskienė L, Zakšauskas A, Smirnov A, Gražulis S, Ladbury JE, Matulis D. Q Rev Biophys 51 e10 (2018)

Articles citing this publication (20)

  1. Synthesis and carbonic anhydrase inhibitory effects of novel sulfamides derived from 1-aminoindanes and anilines. Akbaba Y, Bastem E, Topal F, Gülçin I, Maraş A, Göksu S. Arch Pharm (Weinheim) 347 950-957 (2014)
  2. Intrinsic thermodynamics of 4-substituted-2,3,5,6-tetrafluorobenzenesulfonamide binding to carbonic anhydrases by isothermal titration calorimetry. Zubrienė A, Smirnovienė J, Smirnov A, Morkūnaitė V, Michailovienė V, Jachno J, Juozapaitienė V, Norvaišas P, Manakova E, Gražulis S, Matulis D. Biophys Chem 205 51-65 (2015)
  3. Isothermal titration calorimetry for drug design: Precision of the enthalpy and binding constant measurements and comparison of the instruments. Linkuvienė V, Krainer G, Chen WY, Matulis D. Anal Biochem 515 61-64 (2016)
  4. Picomolar inhibitors of carbonic anhydrase: Importance of inhibition and binding assays. Smirnovienė J, Smirnovas V, Matulis D. Anal Biochem 522 61-72 (2017)
  5. 4-amino-substituted benzenesulfonamides as inhibitors of human carbonic anhydrases. Rutkauskas K, Zubrienė A, Tumosienė I, Kantminienė K, Kažemėkaitė M, Smirnov A, Kazokaitė J, Morkūnaitė V, Čapkauskaitė E, Manakova E, Gražulis S, Beresnevičius ZJ, Matulis D. Molecules 19 17356-17380 (2014)
  6. Intrinsic Thermodynamics and Structures of 2,4- and 3,4-Substituted Fluorinated Benzenesulfonamides Binding to Carbonic Anhydrases. Zubrienė A, Smirnov A, Dudutienė V, Timm DD, Matulienė J, Michailovienė V, Zakšauskas A, Manakova E, Gražulis S, Matulis D. ChemMedChem 12 161-176 (2017)
  7. Intrinsic binding of 4-substituted-2,3,5,6-tetrafluorobenezenesulfonamides to native and recombinant human carbonic anhydrase VI. Kazokaitė J, Milinavičiūtė G, Smirnovienė J, Matulienė J, Matulis D. FEBS J 282 972-983 (2015)
  8. An update on anticancer drug development and delivery targeting carbonic anhydrase IX. Kazokaitė J, Aspatwar A, Parkkila S, Matulis D. PeerJ 5 e4068 (2017)
  9. Crystal structure correlations with the intrinsic thermodynamics of human carbonic anhydrase inhibitor binding. Smirnov A, Zubrienė A, Manakova E, Gražulis S, Matulis D. PeerJ 6 e4412 (2018)
  10. Inhibitory Monoclonal Antibodies and Their Recombinant Derivatives Targeting Surface-Exposed Carbonic Anhydrase XII on Cancer Cells. Stravinskiene D, Sliziene A, Baranauskiene L, Petrikaite V, Zvirbliene A. Int J Mol Sci 21 E9411 (2020)
  11. Intrinsic thermodynamics of trifluoromethanesulfonamide and ethoxzolamide binding to human carbonic anhydrase VII. Pilipuitytė V, Matulis D. J Mol Recognit 28 166-172 (2015)
  12. Methyl 2-Halo-4-Substituted-5-Sulfamoyl-Benzoates as High Affinity and Selective Inhibitors of Carbonic Anhydrase IX. Zakšauskas A, Čapkauskaitė E, Paketurytė-Latvė V, Smirnov A, Leitans J, Kazaks A, Dvinskis E, Stančaitis L, Mickevičiūtė A, Jachno J, Jezepčikas L, Linkuvienė V, Sakalauskas A, Manakova E, Gražulis S, Matulienė J, Tars K, Matulis D. Int J Mol Sci 23 130 (2021)
  13. Pyrimidine non-nucleoside analogs: A direct synthesis of a novel class of N-substituted amino and N-sulfonamide derivatives of pyrimidines. Elgemeie GH, Salah AM, Abbas NS, Hussein HA, Mohamed RA. Nucleosides Nucleotides Nucleic Acids 36 213-223 (2017)
  14. Terpenoids enriched ethanol extracts of aerial roots of Ceriops decandra (Griff.) and Ceriops tagal (Perr.) promote diuresis in mice. Biswas B, Golder M, Abid MA, Mazumder K, Sadhu SK. Heliyon 7 e07580 (2021)
  15. Aqueous acidities of primary benzenesulfonamides: Quantum chemical predictions based on density functional theory and SMD. Aidas K, Lanevskij K, Kubilius R, Juška L, Petkevičius D, Japertas P. J Comput Chem 36 2158-2167 (2015)
  16. Engineered Carbonic Anhydrase VI-Mimic Enzyme Switched the Structure and Affinities of Inhibitors. Kazokaitė J, Kairys V, Smirnovienė J, Smirnov A, Manakova E, Tolvanen M, Parkkila S, Matulis D. Sci Rep 9 12710 (2019)
  17. Herbicide oryzalin inhibits human carbonic anhydrases in vitro. Baranauskiene L, Matulis D. J Biochem Mol Toxicol 31 (2017)
  18. Intrinsic thermodynamics of high affinity inhibitor binding to recombinant human carbonic anhydrase IV. Mickevičiūtė A, Timm DD, Gedgaudas M, Linkuvienė V, Chen Z, Waheed A, Michailovienė V, Zubrienė A, Smirnov A, Čapkauskaitė E, Baranauskienė L, Jachno J, Revuckienė J, Manakova E, Gražulis S, Matulienė J, Di Cera E, Sly WS, Matulis D. Eur Biophys J 47 271-290 (2018)
  19. A novel proteochemometrics model for predicting the inhibition of nine carbonic anhydrase isoforms based on supervised Laplacian score and k-nearest neighbour regression. Nazarshodeh E, Sheikhpour R, Gharaghani S, Sarram MA. SAR QSAR Environ Res 29 419-437 (2018)
  20. Switching the Inhibitor-Enzyme Recognition Profile via Chimeric Carbonic Anhydrase XII. Smirnovienė J, Smirnov A, Zakšauskas A, Zubrienė A, Petrauskas V, Mickevičiūtė A, Michailovienė V, Čapkauskaitė E, Manakova E, Gražulis S, Baranauskienė L, Chen WY, Ladbury JE, Matulis D. ChemistryOpen 10 567-580 (2021)


Quick links