3k34 Citations

Atomic resolution studies of carbonic anhydrase II.

Acta Crystallogr D Biol Crystallogr 66 616-27 (2010)
Cited: 31 times
EuropePMC logo PMID: 20445237

Abstract

Carbonic anhydrase has been well studied structurally and functionally owing to its importance in respiration. A large number of X-ray crystallographic structures of carbonic anhydrase and its inhibitor complexes have been determined, some at atomic resolution. Structure determination of a sulfonamide-containing inhibitor complex has been carried out and the structure was refined at 0.9 A resolution with anisotropic atomic displacement parameters to an R value of 0.141. The structure is similar to those of other carbonic anhydrase complexes, with the inhibitor providing a fourth nonprotein ligand to the active-site zinc. Comparison of this structure with 13 other atomic resolution (higher than 1.25 A) isomorphous carbonic anhydrase structures provides a view of the structural similarity and variability in a series of crystal structures. At the center of the protein the structures superpose very well. The metal complexes superpose (with only two exceptions) with standard deviations of 0.01 A in some zinc-protein and zinc-ligand bond lengths. In contrast, regions of structural variability are found on the protein surface, possibly owing to flexibility and disorder in the individual structures, differences in the chemical and crystalline environments or the different approaches used by different investigators to model weak or complicated electron-density maps. These findings suggest that care must be taken in interpreting structural details on protein surfaces on the basis of individual X-ray structures, even if atomic resolution data are available.

Articles - 3k34 mentioned but not cited (22)

  1. Insights towards sulfonamide drug specificity in α-carbonic anhydrases. Aggarwal M, Kondeti B, McKenna R. Bioorg Med Chem 21 1526-1533 (2013)
  2. Atomic resolution studies of carbonic anhydrase II. Behnke CA, Le Trong I, Godden JW, Merritt EA, Teller DC, Bajorath J, Stenkamp RE. Acta Crystallogr D Biol Crystallogr 66 616-627 (2010)
  3. Novel 2-substituted-benzimidazole-6-sulfonamides as carbonic anhydrase inhibitors: synthesis, biological evaluation against isoforms I, II, IX and XII and molecular docking studies. Milite C, Amendola G, Nocentini A, Bua S, Cipriano A, Barresi E, Feoli A, Novellino E, Da Settimo F, Supuran CT, Castellano S, Cosconati S, Taliani S. J Enzyme Inhib Med Chem 34 1697-1710 (2019)
  4. Selective inhibition of carbonic anhydrase IX and XII by coumarin and psoralen derivatives. Meleddu R, Deplano S, Maccioni E, Ortuso F, Cottiglia F, Secci D, Onali A, Sanna E, Angeli A, Angius R, Alcaro S, Supuran CT, Distinto S. J Enzyme Inhib Med Chem 36 685-692 (2021)
  5. Discovery of a Potent and Highly Selective Dipeptidyl Peptidase IV and Carbonic Anhydrase Inhibitor as "Antidiabesity" Agents Based on Repurposing and Morphing of WB-4101. Artasensi A, Angeli A, Lammi C, Bollati C, Gervasoni S, Baron G, Matucci R, Supuran CT, Vistoli G, Fumagalli L. J Med Chem 65 13946-13966 (2022)
  6. New Carbonic Anhydrase-II Inhibitors from Marine Macro Brown Alga Dictyopteris hoytii Supported by In Silico Studies. Rafiq K, Khan A, Ur Rehman N, Halim SA, Khan M, Ali L, Hilal Al-Balushi A, Al-Busaidi HK, Al-Harrasi A. Molecules 26 7074 (2021)
  7. Sulfa drugs as inhibitors of carbonic anhydrase: new targets for the old drugs. al-Rashida M, Hussain S, Hamayoun M, Altaf A, Iqbal J. Biomed Res Int 2014 162928 (2014)
  8. Synthetic Strategies and Computational Inhibition Activity Study for Triazinyl-Substituted Benzenesulfonamide Conjugates with Polar and Hydrophobic Amino Acids as Inhibitors of Carbonic Anhydrases. Mikulová MB, Kružlicová D, Pecher D, Supuran CT, Mikuš P. Int J Mol Sci 21 E3661 (2020)
  9. Acipimox inhibits human carbonic anhydrases. Mori M, Supuran CT. J Enzyme Inhib Med Chem 37 672-679 (2022)
  10. The Shapes of Sulfonamides: A Rotational Spectroscopy Study. Vigorito A, Calabrese C, Maris A, Loru D, Peña I, Sanz ME, Melandri S. Molecules 27 2820 (2022)
  11. Carbonic anhydrase activation profile of indole-based derivatives. Barresi E, Ravichandran R, Germelli L, Angeli A, Baglini E, Salerno S, Marini AM, Costa B, Da Pozzo E, Martini C, Da Settimo F, Supuran C, Cosconati S, Taliani S. J Enzyme Inhib Med Chem 36 1783-1797 (2021)
  12. New Dihydrothiazole Benzensulfonamides: Looking for Selectivity toward Carbonic Anhydrase Isoforms I, II, IX, and XII. Meleddu R, Distinto S, Cottiglia F, Angius R, Caboni P, Angeli A, Melis C, Deplano S, Alcaro S, Ortuso F, Supuran CT, Maccioni E. ACS Med Chem Lett 11 852-856 (2020)
  13. Synthesis, Carbonic Anhydrase II/IX/XII Inhibition, DFT, and Molecular Docking Studies of Hydrazide-Sulfonamide Hybrids of 4-Methylsalicyl- and Acyl-Substituted Hydrazide. Khushal A, Mumtaz A, Shadoul WA, Zaidi SHM, Rafique H, Munir A, Maalik A, Shah SJA, Baig A, Khawaja W, Al-Rashida M, Hashmi MA, Iqbal J. Biomed Res Int 2022 5293349 (2022)
  14. Benzenesulfonamide derivatives as Vibrio cholerae carbonic anhydrases inhibitors: a computational-aided insight in the structural rigidity-activity relationships. Fantacuzzi M, D'Agostino I, Carradori S, Liguori F, Carta F, Agamennone M, Angeli A, Sannio F, Docquier JD, Capasso C, Supuran CT. J Enzyme Inhib Med Chem 38 2201402 (2023)
  15. Discovery of the first-in-class potent and isoform-selective human carbonic anhydrase III inhibitors. Giovannuzzi S, Bonardi A, Gratteri P, Nocentini A, Supuran CT. J Enzyme Inhib Med Chem 38 2202360 (2023)
  16. Identification of new 4-(6-oxopyridazin-1-yl)benzenesulfonamides as multi-target anti-inflammatory agents targeting carbonic anhydrase, COX-2 and 5-LOX enzymes: synthesis, biological evaluations and modelling insights. Badawi WA, Rashed M, Nocentini A, Bonardi A, Abd-Alhaseeb MM, Al-Rashood ST, Veerakanellore GB, Majrashi TA, Elkaeed EB, Elgendy B, Gratteri P, Supuran CT, Eldehna WM, Elagawany M. J Enzyme Inhib Med Chem 38 2201407 (2023)
  17. Inhibition Studies on Human and Mycobacterial Carbonic Anhydrases with N-((4-Sulfamoylphenyl)carbamothioyl) Amides. Abdoli M, Bonardi A, Paoletti N, Aspatwar A, Parkkila S, Gratteri P, Supuran CT, Žalubovskis R. Molecules 28 4020 (2023)
  18. Selenium-analogs based on natural sources as cancer-associated carbonic anhydrase isoforms IX and XII inhibitors. Astrain-Redin N, Paoletti N, Plano D, Bonardi A, Gratteri P, Angeli A, Sanmartin C, Supuran CT. J Enzyme Inhib Med Chem 38 2191165 (2023)
  19. Synthesis and Inhibition Activity Study of Triazinyl-Substituted Amino(alkyl)-benzenesulfonamide Conjugates with Polar and Hydrophobic Amino Acids as Inhibitors of Human Carbonic Anhydrases I, II, IV, IX, and XII. Mikulová MB, Kružlicová D, Pecher D, Petreni A, Supuran CT, Mikuš P. Int J Mol Sci 22 11283 (2021)
  20. Tetrahydroquinazole-based secondary sulphonamides as carbonic anhydrase inhibitors: synthesis, biological evaluation against isoforms I, II, IV, and IX, and computational studies. Baglini E, Ravichandran R, Berrino E, Salerno S, Barresi E, Marini AM, Viviano M, Castellano S, Da Settimo F, Supuran CT, Cosconati S, Taliani S. J Enzyme Inhib Med Chem 36 1874-1883 (2021)
  21. The oxygen-oxygen distance of water in crystallographic data sets. Palese LL. Data Brief 28 105076 (2020)
  22. [1, 8]-Naphthyridine derivatives as dual inhibitor of alkaline phosphatase and carbonic anhydrase. Alrokayan S, Hussain T, Alamery S, Mohammed AA, Mahmood A, Ejaz SA, Langer P, Iqbal J. BMC Chem 17 142 (2023)


Reviews citing this publication (1)

  1. 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 (8)

  1. Mechanism of Action of Non-Synonymous Single Nucleotide Variations Associated with α-Carbonic Anhydrase II Deficiency. Sanyanga TA, Nizami B, Bishop ÖT. Molecules 24 E3987 (2019)
  2. Tuning the Dual Inhibition of Carbonic Anhydrase and Cyclooxygenase by Dihydrothiazole Benzensulfonamides. Meleddu R, Distinto S, Cottiglia F, Angius R, Gaspari M, Taverna D, Melis C, Angeli A, Bianco G, Deplano S, Fois B, Del Prete S, Capasso C, Alcaro S, Ortuso F, Yanez M, Supuran CT, Maccioni E. ACS Med Chem Lett 9 1045-1050 (2018)
  3. Flow synthesis and biological activity of aryl sulfonamides as selective carbonic anhydrase IX and XII inhibitors. Rosatelli E, Carotti A, Ceruso M, Supuran CT, Gioiello A. Bioorg Med Chem Lett 24 3422-3425 (2014)
  4. Targeted Covalent Inhibitors Allosterically Deactivate the DEDDh Lassa Fever Virus NP Exonuclease from Alternative Distal Sites. Huang KW, Chen JW, Hua TY, Chu YY, Chiu TY, Liu JY, Tu CI, Hsu KC, Kao YT, Chu JW, Hsiao YY. JACS Au 1 2315-2327 (2021)
  5. Computational Prediction of the Binding Pose of Metal-Binding Pharmacophores. Karges J, Stokes RW, Cohen SM. ACS Med Chem Lett 13 428-435 (2022)
  6. Discovery of Novel Hydroxyimine-Tethered Benzenesulfonamides as Potential Human Carbonic Anhydrase IX/XII Inhibitors. Peerzada MN, Vullo D, Paoletti N, Bonardi A, Gratteri P, Supuran CT, Azam A. ACS Med Chem Lett 14 810-819 (2023)
  7. Inhibition Profiles of Some Novel Sulfonamide-Incorporated α-Aminophosphonates on Human Carbonic Anhydrases. Sobati M, Abdoli M, Bonardi A, Gratteri P, Supuran CT, Žalubovskis R. ACS Med Chem Lett 14 1067-1072 (2023)
  8. MM/GBSA prediction of relative binding affinities of carbonic anhydrase inhibitors: effect of atomic charges and comparison with Autodock4Zn. Taylor M, Ho J. J Comput Aided Mol Des 37 167-182 (2023)