2znc › Citations

Structures of murine carbonic anhydrase IV and human carbonic anhydrase II complexed with brinzolamide: molecular basis of isozyme-drug discrimination.

Stams T, Chen Y, Boriack-Sjodin PA, Hurt JD, Liao J, May JA, Dean T, Laipis P, Silverman DN, Christianson DW
Protein Sci 7 556-63 (1998)
Related entries: 1a42, 3znc

Cited: 44 times
EuropePMC logo PMID: 9541386

Abstract

Carbonic anhydrase IV (CAIV) is a membrane-associated enzyme anchored to plasma membrane surfaces by a phosphatidylinositol glycan linkage. We have determined the 2.8-angstroms resolution crystal structure of a truncated, soluble form of recombinant murine CAIV. We have also determined the structure of its complex with a drug used for glaucoma therapy, the sulfonamide inhibitor brinzolamide (Azopt). The overall structure of murine CAIV is generally similar to that of human CAIV; however, some local structural differences are found in the active site resulting from amino acid sequence differences in the "130's segment" and the residue-63 loop (these may affect the nearby catalytic proton shuttle, His-64). Similar to human CAIV, the C-terminus of murine CAIV is surrounded by a substantial electropositive surface potential that may stabilize the interaction with the phospholipid membrane. Binding interactions observed for brinzolamide rationalize the generally weaker affinity of inhibitors used in glaucoma therapy toward CAIV compared with CAII.

Reviews - 2znc mentioned but not cited (1)

  1. Carbonic anhydrase as a model for biophysical and physical-organic studies of proteins and protein-ligand binding. Krishnamurthy VM, Kaufman GK, Urbach AR, Gitlin I, Gudiksen KL, Weibel DB, Whitesides GM. Chem Rev 108 946-1051 (2008)

Articles - 2znc mentioned but not cited (2)

  1. Crystal structure of the dimeric extracellular domain of human carbonic anhydrase XII, a bitopic membrane protein overexpressed in certain cancer tumor cells. Whittington DA, Waheed A, Ulmasov B, Shah GN, Grubb JH, Sly WS, Christianson DW. Proc Natl Acad Sci U S A 98 9545-9550 (2001)
  2. From the similarity analysis of protein cavities to the functional classification of protein families using cavbase. Kuhn D, Weskamp N, Schmitt S, Hüllermeier E, Klebe G. J Mol Biol 359 1023-1044 (2006)


Reviews citing this publication (4)

  1. Pharmacological and ocular hypotensive properties of topical carbonic anhydrase inhibitors. Sugrue MF. Prog Retin Eye Res 19 87-112 (2000)
  2. Charting a Path to Success in Virtual Screening. Forli S. Molecules 20 18732-18758 (2015)
  3. 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)
  4. Topical carbonic anhydrase inhibitors and visual function in glaucoma and ocular hypertension. Gugleta K. Curr Med Res Opin 26 1255-1267 (2010)

Articles citing this publication (37)

  1. Coupling between catalytic site and collective dynamics: a requirement for mechanochemical activity of enzymes. Yang LW, Bahar I. Structure 13 893-904 (2005)
  2. Expression, assay, and structure of the extracellular domain of murine carbonic anhydrase XIV: implications for selective inhibition of membrane-associated isozymes. Whittington DA, Grubb JH, Waheed A, Shah GN, Sly WS, Christianson DW. J Biol Chem 279 7223-7228 (2004)
  3. Crystal structure of human carbonic anhydrase XIII and its complex with the inhibitor acetazolamide. Di Fiore A, Monti SM, Hilvo M, Parkkila S, Romano V, Scaloni A, Pedone C, Scozzafava A, Supuran CT, De Simone G. Proteins 74 164-175 (2009)
  4. The crystal structure of D-lactate dehydrogenase, a peripheral membrane respiratory enzyme. Dym O, Pratt EA, Ho C, Eisenberg D. Proc Natl Acad Sci U S A 97 9413-9418 (2000)
  5. The catalytic properties of human carbonic anhydrase IX. Wingo T, Tu C, Laipis PJ, Silverman DN. Biochem Biophys Res Commun 288 666-669 (2001)
  6. Purification and kinetic analysis of recombinant CA XII, a membrane carbonic anhydrase overexpressed in certain cancers. Ulmasov B, Waheed A, Shah GN, Grubb JH, Sly WS, Tu C, Silverman DN. Proc Natl Acad Sci U S A 97 14212-14217 (2000)
  7. Structural analysis of inhibitor binding to human carbonic anhydrase II. Boriack-Sjodin PA, Zeitlin S, Chen HH, Crenshaw L, Gross S, Dantanarayana A, Delgado P, May JA, Dean T, Christianson DW. Protein Sci 7 2483-2489 (1998)
  8. Ultrahigh resolution crystal structures of human carbonic anhydrases I and II complexed with "two-prong" inhibitors reveal the molecular basis of high affinity. Jude KM, Banerjee AL, Haldar MK, Manokaran S, Roy B, Mallik S, Srivastava DK, Christianson DW. J Am Chem Soc 128 3011-3018 (2006)
  9. A comparison of the long-term effects of dorzolamide 2% and brinzolamide 1%, each added to timolol 0.5%, on retrobulbar hemodynamics and intraocular pressure in open-angle glaucoma patients. Martínez A, Sánchez-Salorio M. J Ocul Pharmacol Ther 25 239-248 (2009)
  10. 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. Supuran CT, Scozzafava A, Menabuoni L, Mincione F, Briganti F, Mincione G. Eur J Pharm Sci 8 317-328 (1999)
  11. Carbonic anhydrase inhibitors: binding of an antiglaucoma glycosyl-sulfanilamide derivative to human isoform II and its consequences for the drug design of enzyme inhibitors incorporating sugar moieties. Di Fiore A, Scozzafava A, Winum JY, Montero JL, Pedone C, Supuran CT, De Simone G. Bioorg Med Chem Lett 17 1726-1731 (2007)
  12. Structural analysis of charge discrimination in the binding of inhibitors to human carbonic anhydrases I and II. Srivastava DK, Jude KM, Banerjee AL, Haldar M, Manokaran S, Kooren J, Mallik S, Christianson DW. J Am Chem Soc 129 5528-5537 (2007)
  13. Theoretical study of gas-phase acidity, pKa, lipophilicity, and solubility of some biologically active sulfonamides. Remko M, von der Lieth CW. Bioorg Med Chem 12 5395-5403 (2004)
  14. Carbonic anhydrase inhibitors. Schiff bases of some aromatic sulfonamides and their metal complexes: towards more selective inhibitors of carbonic anhydrase isozyme IV. Popescu A, Simion A, Scozzafava A, Briganti F, Supuran CT. J Enzyme Inhib 14 407-423 (1999)
  15. Carbonic anhydrase inhibitors: the X-ray crystal structure of ethoxzolamide complexed to human isoform II reveals the importance of thr200 and gln92 for obtaining tight-binding inhibitors. Di Fiore A, Pedone C, Antel J, Waldeck H, Witte A, Wurl M, Scozzafava A, Supuran CT, De Simone G. Bioorg Med Chem Lett 18 2669-2674 (2008)
  16. Computational modeling of laminin N-terminal domains using sparse distance constraints from disulfide bonds and chemical cross-linking. Kalkhof S, Haehn S, Paulsson M, Smyth N, Meiler J, Sinz A. Proteins 78 3409-3427 (2010)
  17. Carbonic anhydrase inhibitors. Inhibition of the membrane-bound human and bovine isozymes IV with sulfonamides. Innocenti A, Firnges MA, Antel J, Wurl M, Scozzafava A, Supuran CT. Bioorg Med Chem Lett 15 1149-1154 (2005)
  18. Carbonic anhydrase inhibitors: X-ray crystallographic studies for the binding of 5-amino-1,3,4-thiadiazole-2-sulfonamide and 5-(4-amino-3-chloro-5-fluorophenylsulfonamido)-1,3,4-thiadiazole-2-sulfonamide to human isoform II. Menchise V, De Simone G, Di Fiore A, Scozzafava A, Supuran CT. Bioorg Med Chem Lett 16 6204-6208 (2006)
  19. Predictors for visual field progression and the effects of treatment with dorzolamide 2% or brinzolamide 1% each added to timolol 0.5% in primary open-angle glaucoma. Martínez A, Sanchez-Salorio M. Acta Ophthalmol 88 541-552 (2010)
  20. Carbonic Anhydrase Inhibitors. Synthesis of Topically Effective Intraocular Pressure Lowering Agents Derived from 5-(omega-Amino- alkylcarboxamido)-1,3,4-Thia- diazole-2-Sulfonamide. Barboiu M, Supuran CT, Menabuoni L, Scozzafava A, Mincione F, Briganti F, Mincione G. J Enzyme Inhib 15 23-46 (1999)
  21. Carbonic anhydrase inhibitors. Water-soluble, topically effective intraocular pressure lowering agents derived from isonicotinic acid and aromatic/heterocyclic sulfonamides: is the tail more important than the ring? Menabuoni L, Scozzafava A, Mincione F, Briganti F, Mincione G, Supuran CT. J Enzyme Inhib 14 457-474 (1999)
  22. Creation of nano eye-drops and effective drug delivery to the interior of the eye. Ikuta Y, Aoyagi S, Tanaka Y, Sato K, Inada S, Koseki Y, Onodera T, Oikawa H, Kasai H. Sci Rep 7 44229 (2017)
  23. Hepatitis C virus NS4B carboxy terminal domain is a membrane binding domain. Liefhebber JM, Brandt BW, Broer R, Spaan WJ, van Leeuwen HC. Virol J 6 62 (2009)
  24. Synergistic Structural Information from Covalent Labeling and Hydrogen-Deuterium Exchange Mass Spectrometry for Protein-Ligand Interactions. Liu T, Limpikirati P, Vachet RW. Anal Chem 91 15248-15254 (2019)
  25. Exploration of the binding mode of indanesulfonamides as selective inhibitors of human carbonic anhydrase type VII by targeting Lys 91. Thiry A, Masereel B, Dogné JM, Supuran CT, Wouters J, Michaux C. ChemMedChem 2 1273-1280 (2007)
  26. Carbonic anhydrase inhibitors - part 78(#). Synthesis of water-soluble sulfonamides incorporating beta-alanyl moieties, possessing long lasting-intraocular pressure lowering properties via the topical route. Supuran CT, Briganti F, Menabuoni L, Mincione G, Mincione F, Scozzafava A. Eur J Med Chem 35 309-321 (2000)
  27. Carbonic anhydrase inhibitors. Part 79. Synthesis of topically acting sulfonamides incorporating GABA moieties in their molecule, with long-lasting intraocular pressure-lowering properties. Mincione G, Menabuoni L, Briganti F, Mincione F, Scozzafava A, Supuran CT. Eur J Pharm Sci 9 185-199 (1999)
  28. 2H-Thieno[3,2-e]- and [2,3-e]-1,2-thiazine-6-sulfonamide 1,1-dioxides as ocular hypotensive agents: synthesis, carbonic anhydrase inhibition and evaluation in the rabbit. Chen HH, Gross S, Liao J, McLaughlin M, Dean T, Sly WS, May JA. Bioorg Med Chem 8 957-975 (2000)
  29. Analysis of evolution of carbonic anhydrases IV and XV reveals a rich history of gene duplications and a new group of isozymes. Tolvanen ME, Ortutay C, Barker HR, Aspatwar A, Patrikainen M, Parkkila S. Bioorg Med Chem 21 1503-1510 (2013)
  30. Carbonic anhydrase inhibitors. Interaction of the antitumor sulfamate EMD 486019 with twelve mammalian carbonic anhydrase isoforms: Kinetic and X-ray crystallographic studies. Temperini C, Innocenti A, Scozzafava A, Supuran CT. Bioorg Med Chem Lett 18 4282-4286 (2008)
  31. Carbonic anhydrase inhibitors: binding of indanesulfonamides to the human isoform II. D'Ambrosio K, Masereel B, Thiry A, Scozzafava A, Supuran CT, De Simone G. ChemMedChem 3 473-477 (2008)
  32. Update and critical appraisal of combined timolol and carbonic anhydrase inhibitors and the effect on ocular blood flow in glaucoma patients. Moss AM, Harris A, Siesky B, Rusia D, Williamson KM, Shoshani Y. Clin Ophthalmol 4 233-241 (2010)
  33. Synthesis and biological evaluation of a new family of anti-benzylanilinosulfonamides as CA IX inhibitors. Thiry A, Delayen A, Goossens L, Houssin R, Ledecq M, Frankart A, Dogné JM, Wouters J, Supuran CT, Hénichart JP, Masereel B. Eur J Med Chem 44 511-518 (2009)
  34. A dynamic C-terminal segment in the Mycobacterium tuberculosis Mn/Fe R2lox protein can adopt a helical structure with possible functional consequences. Andersson CS, Berthold CL, Högbom M. Chem Biodivers 9 1981-1988 (2012)
  35. Head-to-tail and side-by-side oligomerization of human carbonic anhydrase II: a small angle X-ray scattering study. Ceolín M, Colombo US, Frate MC, Clérico E, Antón E, Ermácora MR. Int J Biol Macromol 28 143-150 (2001)
  36. Primate-conserved carbonic anhydrase IV and murine-restricted LY6C1 enable blood-brain barrier crossing by engineered viral vectors. Shay TF, Sullivan EE, Ding X, Chen X, Ravindra Kumar S, Goertsen D, Brown D, Crosby A, Vielmetter J, Borsos M, Wolfe DA, Lam AW, Gradinaru V. Sci Adv 9 eadg6618 (2023)
  37. Therapeutic potential of a novel combination of Curcumin with Sulfamethoxazole against carbon tetrachloride-induced acute liver injury in Swiss albino mice. Zahran RF, Geba ZM, Tabll AA, Mashaly MM. J Genet Eng Biotechnol 18 13 (2020)


Related citations provided by authors (1)

  1. Crystal Structure of the Secretory Form of Membrane-Associated Human Carbonic Anhydrase Iv at 2.8-A Resolution. Stams T, Nair SK, Okuyama T, Waheed A, Sly WS, Christianson DW Proc. Natl. Acad. Sci. U.S.A. 93 13589- (1996)

Quick links