Carbonic anhydrase activators: Activation of the human cytosolic isozyme III and membrane-associated isoform IV with amino acids and amines

Bioorganic and Medicinal Chemistry Letters

Volumn 18, Issue 15, 2008, Pages 4303-4307

  Vullo, Daniela ^a   Nishimori, Isao ^b   Scozzafava, Andrea ^a   Supuran, Claudiu T ^a  

^a UNIVERSITY OF FLORENCE   (Italy)

^b KOCHI MEDICAL SCHOOL   (Japan)

Author keywords

Amine; Amino acid; Carbonic anhydrase; Enzyme activator; Isoform III; Isoform IV

Indexed keywords

AMINO ACID DERIVATIVE; AROMATIC AMINE; CARBONATE DEHYDRATASE; HETEROCYCLIC AMINE; HISTIDINE; HUMAN CYTOSOLIC ISOZYME 3; HUMAN CYTOSOLIC ISOZYME 4; MORPHOLINE; SEROTONIN; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVATION; PROTON TRANSPORT; STRUCTURE ACTIVITY RELATION; X RAY CRYSTALLOGRAPHY;

AMINES; AMINO ACIDS; BINDING SITES; CARBONIC ANHYDRASE III; CARBONIC ANHYDRASE IV; CELL MEMBRANE; CYTOSOL; ENZYME ACTIVATION; HISTIDINE; HUMANS; ISOENZYMES; MOLECULAR STRUCTURE; MORPHOLINES; SEROTONIN; STEREOISOMERISM;

MAMMALIA;

EID: 47749106027     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2008.06.075     Document Type: Article

References (61)

1. Supuran C.T. Nat. Rev. Drug. Discov. 7 (2008) 161
2. Supuran C.T. Curr. Pharm. Des. 14 (2008) 603
3. Pastorekova S., Parkkila S., Pastorek J., and Supuran C.T. J. Enzyme Inhib. Med. Chem. 19 (2004) 199
4. Supuran C.T. Curr. Pharm. Des. 14 (2008) 641
5. Hilvo M., Supuran C.T., and Parkkila S. Curr. Top. Med. Chem. 7 (2007) 893
6. Zimmerman S.A., Ferry J.G., and Supuran C.T. Curr. Top. Med. Chem. 7 (2007) 901
7. Krungkrai J., Krungkrai S.R., and Supuran C.T. Curr. Top. Med. Chem. 7 (2007) 909
8. Thiry A., Dogné J.-M., Masereel B., and Supuran C.T. Trends Pharmacol. Sci. 27 (2006) 566
9. Supuran C.T. Curr. Top. Med. Chem. 7 (2007) 825
10. Scozzafava A., Mastrolorenzo A., and Supuran C.T. Expert Opin. Ther. Pat. 16 (2006) 1627
11. Supuran C.T., and Scozzafava A.. Bioorg. Med. Chem. 15 (2007) 4336
12. Supuran C.T., Scozzafava A., and Casini A. Med. Res. Rev. 23 (2003) 146
13. Engberg P., Millqvist E., Pohl G., and Lindskog S. Arch. Biochem. Biophys. 241 (1985) 628
14. Rowlett R.S., Gargiulo III N.J., Santoli F.A., Jackson J.M., and Corbett A.H. J. Biol. Chem. 266 (1991) 933
15. Eriksson A.E., and Liljas A. Proteins 16 (1993) 29
16. Wistrand P.J. Ups. J. Med. Sci. 107 (2002) 77
17. Duda D.M., Tu C., Fisher S.Z., An H., Yoshioka C., Govindasamy L., Laipis P.J., Agbandje-McKenna M., Silverman D.N., and McKenna R. Biochemistry 44 (2005) 10046
18. De Simone G., Di Fiore A., and Supuran C.T. Curr. Pharm. Des. 14 (2008) 655
19. Supuran C.T. Expert Opin. Ther. Pat. 13 (2003) 1545
20. Supuran C.T., Di Fiore A., and De Simone G. Expert Opin. Emerg. Drugs 13 (2008) 383
21. Liu M., Walter G.A., Pathare N.C., Forster R.E., and Vandenborne K. Proc. Natl. Acad. Sci. U.S.A. 104 (2007) 371
22. Li L., and Falany C.N.. J. Cyst. Fibros. 6 (2007) 23
23. Yamamoto T., Kikkawa R., Yamada H., and Horii I. J. Toxicol. Sci. 31 (2006) 49
24. Zimmerman U.J., Wang P., Zhang X., Bogdanovich S., and Forster R. IUBMB Life 56 (2004) 343
25. Räisänen S.R., Lehenkari P., Tasanen M., Rahkila P., Härkönen P.L., and Väänänen H.K. FASEB J. 13 (1999) 513
26. Gill G.A., Johnston N., Buda A., Pignatelli M., Pearson J., Dettmar P.W., and Koufman J. Ann. Otol. Rhinol. Laryngol. 114 (2005) 913
27. Kim G., and Levine R.L. Antioxid. Redox. Signal. 7 (2005) 849
28. Mallis R.J., Hamann M.J., Zhao W., Zhang T., Hendrich S., and Thomas J.A. Biol. Chem. 383 (2002) 649
29. Dai, H. Y.; Hong, C. C.; Liang, S. C.; Yan, M. D.; Lai, G. M.; Cheng, A. L.; Chuang, S. E. Mol. Carcinog. 2008, (in press).
30. Whitney P.L., and Briggle T.V. J. Biol. Chem. 257 (1982) 12056
31. Sly W.S., and Hu P.Y. Annu. Rev. Biochem. 64 (1995) 375
32. Zhu X.L., and Sly W.S. J. Biol. Chem. 265 (1990) 8795
33. Baird Jr. T.T., Waheed A., Okuyama T., Sly W.S., and Fierke C.A. Biochemistry 36 (1997) 2669
34. Temperini C., Scozzafava A., and Supuran C.T. Curr. Pharm. Des. 14 (2008) 708
35. Briganti F., Mangani S., Orioli P., Scozzafava A., Vernaglione G., and Supuran C.T. Biochemistry 36 (1997) 10384
36. Ilies M., Scozzafava A., and Supuran C.T. Carbonic anhydrase activators. In: Supuran C.T., Scozzafava A., and Conway J. (Eds). Carbonic Anhydrase-Its Inhibitors and Activators (2004), CRC Press, Boca Raton (FL), USA 317-352
37. Supuran C.T., and Scozzafava A. Activation of carbonic anhydrase isozymes. In: Chegwidden W.R., Carter N., and Edwards Y. (Eds). The Carbonic Anhydrases-New Horizons (2000), Birkhauser Verlag, Basel, Switzerland 197-219
38. Supuran C.T. Therapy 4 (2007) 355
39. Scozzafava A., and Supuran C.T. J. Med. Chem. 45 (2002) 284
40. Scozzafava A., and Supuran C.T. Bioorg. Med. Chem. Lett. 12 (2002) 1177
41. Ilies M., Banciu M.D., Ilies M.A., Scozzafava A., Caproiu M.T., and Supuran C.T. J. Med. Chem. 45 (2002) 504
42. Scozzafava A., Iorga B., and Supuran C.T. J. Enz. Inhib. 15 (2000) 139
43. Temperini C., Scozzafava A., Vullo D., and Supuran C.T. J. Med. Chem. 49 (2006) 3019
44. Innocenti A., Firnges M.A., Antel J., Wurl M., Scozzafava A., and Supuran C.T. Bioorg. Med. Chem. Lett. 15 (2005) 1149
45. Shelton J.B., and Chegwidden W.R. Biochem. Soc. Trans. 16 (1988) 853
46. Shelton J.B., and Chegwidden W.R. Comp. Biochem. Physiol. 114A (1996) 283
47. Parkkila S., Vullo D., Puccetti L., Parkkila A.K., Scozzafava A., and Supuran C.T. Bioorg. Med. Chem Lett. 16 (2006) 3955
48. Vullo D., Nishimori I., Innocenti A., Scozzafava A., and Supuran C.T. Bioorg. Med. Chem. Lett. 17 (2007) 1336
49. Vullo D., Innocenti A., Nishimori I., Scozzafava A., Kaila K., and Supuran C.T. Bioorg. Med. Chem Lett. 17 (2007) 4107
50. Nishimori I., Onishi S., Vullo D., Innocenti A., Scozzafava A., and Supuran C.T. Bioorg. Med. Chem. 15 (2007) 5351
51. Temperini C., Scozzafava A., Vullo D., and Supuran C.T. Chemistry 12 (2006) 7057
52. Temperini C., Innocenti A., Scozzafava A., Mastrolorenzo A., and Supuran C.T. Bioorg. Med. Chem. Lett. 17 (2007) 628
53. Vullo D., Nishimori I., Innocenti A., Scozzafava A., and Supuran C.T. Bioorg. Med. Chem. Lett. 17 (2007) 1336
54. Vullo D., Innocenti A., Nishimori I., Scozzafava A., Kaila K., and Supuran C.T. Bioorg. Med. Chem. Lett. 17 (2007) 4107
55. Pastorekova S., Vullo D., Nishimori I., Scozzafava A., Pastorek J., and Supuran C.T. Bioorg. Med. Chem. 16 (2008) 3530
56. 18,19
57. Stams T., Nair S.K., Okuyama T., Waheed A., Sly W.S., and Christianson D.W. Proc. Natl. Acad. Sci. U.S.A. 93 (1996) 13589
58. Tashian R.E., Venta P.J., Nicewander P.H., and Hewett-Emmett D. Progr. Clin. Biol. Res. 344 (1990) 159
59. Nair S.K., and Christianson D.W. J. Am. Chem. Soc. 113 (1991) 9455
60. Christianson D.W., and Fierke C.A. Acc. Chem. Res. 29 (1996) 331
61. Whittington D.A., Grubb J.H., Waheed A., Shah G.N., Sly W.S., and Christianson D.W. J. Biol. Chem. 279 (2004) 7223