The structural comparison between membrane-associated human carbonic anhydrases provides insights into drug design of selective inhibitors

Biopolymers

Volumn 101, Issue 7, 2014, Pages 769-778

  Alterio, Vincenzo ^a   Pan, Peiwen ^b   Parkkila, Seppo ^b   Buonanno, Martina ^a   Supuran, Claudiu T ^c,d   Monti, Simona M ^a   De Simone, Giuseppina ^a  

^a CNR   (Italy)

^b TAMPERE UNIVERSITY OF TECHNOLOGY   (Finland)

^c UNIVERSITY OF FLORENCE   (Italy)

^d Section of Pharmaceutical Chemistry NEUROFARBA Department   (Italy)

Author keywords

carbonic anhydrase; drug design; inhibitors; X ray crystallography

Indexed keywords

CORROSION INHIBITORS; DESIGN; DRUG DELIVERY; ENZYME INHIBITION; X RAY CRYSTALLOGRAPHY;

CRYSTALLOGRAPHIC STRUCTURE; DRUG DESIGN; EXTRACELLULAR DOMAINS; HUMAN CARBONIC ANHYDRASES; MEMBRANE-ASSOCIATED PROTEINS; STRUCTURAL COMPARISON; STRUCTURAL DIFFERENCES; TRANSMEMBRANE REGIONS;

CARBONIC ANHYDRASE;

CARBONATE DEHYDRATASE; CARBONATE DEHYDRATASE INHIBITOR; CARBONATE DEHYDRATASE IV; CARBONATE DEHYDRATASE IX; CARBONATE DEHYDRATASE XII; CARBONATE DEHYDRATASE XIV; UNCLASSIFIED DRUG; CARBONIC ANHYDRASE XIV; ENZYME INHIBITOR; ISOENZYME; MEMBRANE PROTEIN; RECOMBINANT PROTEIN;

ARTICLE; CONTROLLED STUDY; CRYSTAL STRUCTURE; DRUG DESIGN; ENZYME PURIFICATION; ENZYME STRUCTURE; MOLECULE; PROTEIN EXPRESSION; SEQUENCE ALIGNMENT; AMINO ACID SEQUENCE; ANIMAL; ANTAGONISTS AND INHIBITORS; CHEMICAL STRUCTURE; CHEMISTRY; COMPARATIVE STUDY; ELECTROSPRAY MASS SPECTROMETRY; GENETICS; HUMAN; KINETICS; LIQUID CHROMATOGRAPHY; METABOLISM; MOLECULAR GENETICS; PROTEIN SECONDARY STRUCTURE; PROTEIN TERTIARY STRUCTURE; SEQUENCE HOMOLOGY; SF9 CELL LINE; SIZE EXCLUSION CHROMATOGRAPHY; X RAY CRYSTALLOGRAPHY;

AMINO ACID SEQUENCE; ANIMALS; CARBONIC ANHYDRASES; CHROMATOGRAPHY, GEL; CHROMATOGRAPHY, LIQUID; CRYSTALLOGRAPHY, X-RAY; DRUG DESIGN; ENZYME INHIBITORS; HUMANS; ISOENZYMES; KINETICS; MEMBRANE PROTEINS; MODELS, MOLECULAR; MOLECULAR SEQUENCE DATA; PROTEIN STRUCTURE, SECONDARY; PROTEIN STRUCTURE, TERTIARY; RECOMBINANT PROTEINS; SEQUENCE HOMOLOGY, AMINO ACID; SF9 CELLS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 84898981110     PISSN: 00063525     EISSN: 10970282     Source Type: Journal    
DOI: 10.1002/bip.22456     Document Type: Article

References (60)

1. Alterio, V.; Di Fiore, A.; D'Ambrosio, K.; Supuran, C. T.; De Simone, G., Chem Rev 2012, 112, 4421-4468.
2. Supuran, C. T.; Di Fiore, A.; Alterio, V.; Monti, S. M.; De Simone, G., Curr Pharm Des 2010, 16, 3246-3254.
3. Supuran, C. T., Nat Rev Drug Discov 2008, 7, 168-181.
4. Supuran, C. T.; Scozzafava, A., Bioorg Med Chem 2007, 15, 4336-4350.
5. Supuran, C. T.; Scozzafava, A.; Conway, J., Carbonic Anhydrase. Its Inhibitors and Activators; CRC Press: Boca Raton, FL, 2004; p 363.
6. Datta, R.; Waheed, A.; Bonapace, G.; Shah, G. N.; Sly, W. S., Proc Natl Acad Sci USA 2009, 106, 3437-3442.
7. Guler, O. O.; De Simone, G.; Supuran, C. T., Curr Med Chem 2010, 17, 1516-1526.
8. Ogilvie, J. M.; Ohlemiller, K. K.; Shah, G. N.; Ulmasov, B.; Becker, T. A.; Waheed, A.; Hennig, A. K.; Lukasiewicz, P. D.; Sly, W. S., Proc Natl Acad Sci USA 2007, 104, 8514-8519.
9. Parkkila, S.; Parkkila, A. K.; Rajaniemi, H.; Shah, G. N.; Grubb, J. H.; Waheed, A.; Sly, W. S., Proc Natl Acad Sci USA 2001, 98, 1918-1923.
10. Pastorekova, S.; Zatovicova, M.; Pastorek, J., Curr Pharm Des 2008, 14, 685-698.
11. Pastorekova, S.; Parkkila, S.; Zavada, J., Adv Clin Chem 2006, 42, 167-216.
12. Riihonen, R.; Supuran, C. T.; Parkkila, S.; Pastorekova, S.; Väänänen, H. K.; Laitala-Leinonen, T., Bone 2007, 40, 1021-1031.
13. Scheibe, R. J.; Gros, G.; Parkkila, S.; Waheed, A.; Grubb, J. H.; Shah, G. N.; Sly, W. S.; Wetzel, P., J. Histochem Cytochem 2006, 54, 1379-1391.
14. Matsui, H.; Murakami, M.; Wynns, G. C.; Conroy, C. W.; Mead, A.; Maren, T. H.; Sears, M. L., Exp Eye Res 1996, 62, 409-417.
15. Ochrietor, J. D.; Clamp, M. F.; Moroz, T. P.; Grubb, J. H.; Shah, G. N.; Waheed, A.; Sly, W. S.; Linser, P., J. Exp Eye Res 2005, 81, 492-500.
16. Tang, Y.; Xu, H.; Du, X.; Lit, L.; Walker, W.; Lu, A.; Ran, R.; Gregg, J. P.; Reilly, M.; Pancioli, A.; Khoury, J. C.; Sauerbeck, L. R.; Carrozzella, J. A.; Spilker, J.; Clark, J.; Wagner, K. R.; Jauch, E. C.; Chang, D. J.; Verro, P.; Broderick, J. P.; Sharp, F. R., J. Cereb Blood Flow Metab 2006, 26, 1089-1102.
17. Battke, C.; Kremmer, E.; Mysliwietz, J.; Gondi, G.; Dumitru, C.; Brandau, S.; Lang, S.; Vullo, D.; Supuran, C. T.; Zeidler, R., Cancer Immunol Immunother 2011, 60, 649-658.
18. De Simone, G.; Supuran, C. T., Biochim Biophys Acta 2010, 1804, 404-409.
19. Hen, N.; Bialer, M.; Yagen, B.; Maresca, A.; Aggarwal, M.; Robbins, A. H.; McKenna, R.; Scozzafava, A.; Supuran, C. T., J Med Chem 2011, 54, 3977-3981.
20. Shah, G. N.; Ulmasov, B.; Waheed, A.; Becker, T.; Makani, S.; Svichar, N.; Chesler, M.; Sly, W. S., Proc Natl Acad Sci USA 2005, 102, 16771-16776.
21. Casey, J. R.; Morgan, P. E.; Vullo, D.; Scozzafava, A.; Mastrolorenzo, A.; Supuran, C. T., J Med Chem 2004, 47, 2337-2347.
22. Monti, S. M.; Supuran, C. T.; De Simone, G., Expert Opin Ther Pat 2013, 23, 737-749.
23. Pastorekova, S.; Casini, A.; Scozzafava, A.; Vullo, D.; Pastorek, J.; Supuran, C. T., Bioorg Med Chem Lett 2004, 14, 869-873.
24. Scozzafava, A.; Briganti, F.; Ilies, M. A.; Supuran, C. T., J Med Chem 2000, 43, 292-300.
25. Supuran, C. T.; Scozzafava, A.; Ilies, M. A.; Briganti, F., J Enzyme Inhib 2000, 15, 381-401.
26. Menchise, V.; De Simone, G.; Alterio, V.; Di Fiore, A.; Pedone, C.; Scozzafava, A.; Supuran, C. T., J Med Chem 2005, 48, 5721-5727.
27. Supuran, C. T.; Scozzafava, A.; Ilies, M. A.; Iorga, B.; Cristea, T.; Briganti, F.; Chiraleu, F.; Banciu, M. D., Eur J Med Chem 1998, 33, 577-594.
28. Stams, T.; Nair, S. K.; Okuyama, T.; Waheed, A.; Sly, W. S.; Christianson, D. W., Proc Natl Acad Sci USA 1996, 93, 13589-13594.
29. Alterio, V.; Hilvo, M.; Di Fiore, A.; Supuran, C. T.; Pan, P.; Parkkila, S.; Scaloni, A.; Pastorek, J.; Pastorekova, S.; Pedone, C.; Scozzafava, A.; Monti, S. M.; De Simone, G., Proc Natl Acad Sci USA 2009, 106, 16233-16238.
30. Whittington, D. A.; Waheed, A.; Ulmasov, B.; Shah, G. N.; Grubb, J. H.; Sly, W. S.; Christianson, D. W., Proc Natl Acad Sci USA 2001, 98, 9545-9550.
31. Whittington, D. A.; Grubb, J. H.; Waheed, A.; Shah, G. N.; Sly, W. S.; Christianson, D. W., J Biol Chem 2004, 279, 7223-7228.
32. Fujikawa-Adachi, K.; Nishimori, I.; Taguchi, T.; Onishi, S., Genomics 1999, 61, 74-81.
33. Hilvo, M.; Baranauskiene, L.; Salzano, A. M.; Scaloni, A.; Matulis, D.; Innocenti, A.; Scozzafava, A.; Monti, S. M.; Di Fiore, A.; De Simone, G.; Lindfors, M.; Jänis, J.; Valjakka, J.; Pastoreková, S.; Pastorek, J.; Kulomaa, M. S.; Nordlund, H. R.; Supuran, C. T.; Parkkila, S., J Biol Chem 2008, 283, 27799-27809.
34. Nishimori, I.; Vullo, D.; Innocenti, A.; Scozzafava, A.; Mastrolorenzo, A.; Supuran, C. T., Bioorg Med Chem Lett 2005, 15, 3828-3833.
35. Ashida, S.; Nishimori, I.; Tanimura, M.; Onishi, S.; Shuin, T., J. Cancer Res Clin Oncol 2002, 128, 561-568.
36. Kaunisto, K.; Parkkila, S.; Rajaniemi, H.; Waheed, A.; Grubb, J.; Sly, W. S., Kidney Int 2002, 61, 2111-2118.
37. Nishimori, I.; Onishi, S., Dig Liver Dis 2001, 33, 68-74.
38. Parkkila, S.; Kivela, A. J.; Kaunisto, K.; Parkkila, A. K.; Hakkola, J.; Rajaniemi, H.; Waheed, A.; Sly, W. S., BMC Gastroenterol 2002, 2, 13-20.
39. Hilvo, M.; Salzano, A. M.; Innocenti, A.; Kulomaa, M. S.; Scozzafava, A.; Scaloni, A.; Parkkila, S.; Supuran, C. T., J Med Chem 2009, 52, 646-654.
40. Tornatore, L.; Marasco, D.; Dathan, N.; Vitale, R. M.; Benedetti, E.; Papa, S.; Franzoso, G.; Ruvo, M.; Monti, S. M., J Mol Biol 2008, 378, 97-111.
41. Dathan, N. A.; Alterio, V.; Troiano, E.; Vullo, D.; Ludwig, M.; De Simone, G.; Supuran, C. T.; Monti, S. M., J Enzyme Inhib Med Chem, 2013, doi: 10.3109/14756366.2013.813942.
42. Otwinowski, Z.; Minor, W., In Methods in Enzymology, Macromolecular Crystallography, Part A,;, Carter, R. M., Jr,.; Sweet, C. W., Eds.; Academic Press: New York, 1997; Vol. 276, pp 307-326.
43. Navaza, J., Acta Crystallogr Sect A 1994, 50, 157-163.
44. Brünger, A. T.; Adams, P. D.; Clore, G. M.; De Lano, W. L.; Gros, P.; Grosse-Kunstleve, R. W.; Jiang, J. S.; Kuszewski, J.; Nilges, N.; Pannu, N. S.; Read, R. J.; Rice, L. M.; Simonson, T.; Warren, G. L., Acta Crystallogr Sect D 1998, 54, 905-921.
45. Jones, T. A.; Zou, J. Y.; Cowan, S. W.; Kjeldgaard, M., Acta Crystallogr Sect A 1991, 47, 110-119.
46. Pilka, E. S.; Kochan, G.; Oppermann, U.; Yue, W. W., Biochem Biophys Res Commun 2012, 419, 485-489.
47. Huang, S.; Xue, Y.; Sauer-Eriksson, E.; Chirica, L.; Lindskog, S.; Jonsson, B. H., J Mol Biol 1998, 283, 301-310.
48. Premkumar, L.; Greenblatt, H. M.; Bageshwar, U. K.; Savchenko, T.; Gokhman, I.; Sussman, J. L.; Zamir, A., Proc Natl Acad Sci USA 2005, 102, 7493-7498.
49. Suzuki, K.; Yang, S. Y.; Shimizu, S.; Morishita, E. C.; Jiang, J.; Zhang, F.; Hoque, M. M.; Sato, Y.; Tsunoda, M.; Sekiguchi, T.; Takénaka, A., Acta Crystallogr Sect D 2011, 67, 894-901.
50. Cuesta-Seijo, J. A.; Borchert, M. S.; Navarro-Poulsen, J. C.; Schnorr, K. M.; Mortensen, S. B.; Lo Leggio, L., FEBS Lett 2011, 585, 1042-1048.
51. Di Fiore, A.; Capasso, C.; De Luca, V.; Monti, S. M.; Carginale, V.; Supuran, C. T.; Scozzafava, A.; Pedone, C.; Rossi, M., De Simone, G., Acta Crystallogr Sect D 2013, 69, 1150-1159.
52. De Simone, G.; Alterio, V.; Supuran, C. T., Expert Opin Drug Discov 2013, 8, 793-810.
53. Domsic, J. F.; Avvaru, B. S.; Kim, C. U.; Gruner, S. M.; Agbandje-McKenna, M.; Silverman, D. N.; McKenna, R., J Biol Chem 2008, 283, 30766-30771.
54. Sjöblom, B.; Polentarutti, M.; Djinovic-Carugo, K., Proc Natl Acad Sci USA 2009, 106, 10609-10613.
55. Mikulski, R. L.; Silverman, D. N., Biochim Biophys Acta 2010, 1804, 422-426.
56. Krissinel, E.; Henrick, K., J Mol Biol 2007, 372, 774-797.
57. Russ, W. P.; Engelman, D. M., J Mol Biol 2000, 296, 911-919.
58. Senes, A.; Gerstein, M.; Engelman, D. M., J Mol Biol 2000, 296, 921-936.
59. Eriksson, A. E.; Jones, T. A.; Liljas, A., Proteins 1988, 4, 274-282.
60. Alterio, V.; Vitale, R. M.; Monti, S. M.; Pedone, C.; Scozzafava, A.; Cecchi, A.; De Simone, G.; Supuran, C. T., J Am Chem Soc 2006, 128, 8329-8335.