An inhibitor-like binding mode of a carbonic anhydrase activator within the active site of isoform II

Bioorganic and Medicinal Chemistry Letters

Volumn 21, Issue 9, 2011, Pages 2764-2768

  Dave, Khyati ^a,b   Ilies, Marc A ^a,b   Scozzafava, Andrea ^c   Temperini, Claudia ^c   Vullo, Daniela ^c   Supuran, Claudiu T ^c  

^a TEMPLE UNIVERSITY SCHOOL OF PHARMACY   (United States)

^b TEMPLE UNIVERSITY   (United States)

^c UNIVERSITY OF FLORENCE   (Italy)

Author keywords

Carbonic anhydrase; Enzyme activator; Enzyme inhibitor; Histamine; Pyridinium salt; X ray crystallography

Indexed keywords

1 [2 (1H IMIDAZOL 4 YL)ETHYL] 2,4,6 TRIMETHYLPYRIDINIUM; 2,4,6 TRIMETHYLPYRIDINIUM HISTAMINE DERIVATIVE; CARBONIC ANHYDRASE ACTIVATOR; ENZYME ACTIVATOR; HISTAMINE; HISTAMINE DERIVATIVE; ISOENZYME; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

BINDING KINETICS; CHEMICAL INTERACTION; COMPLEX FORMATION; CONFERENCE PAPER; CRYSTAL STRUCTURE; DRUG POTENCY; DRUG PROTEIN BINDING; ENZYME ACTIVE SITE; ENZYME INHIBITION; HYDROPHOBICITY; X RAY CRYSTALLOGRAPHY;

EID: 79953171497     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2010.10.045     Document Type: Conference Paper

References (49)

1. C.T. Supuran Nat. Rev. Drug Disc. 7 2008 168
2. C.T. Supuran Carbonic Anhydrases as Drug Targets: General Presentation C.T. Supuran, J.-Y. Winum, Drug Design of Zinc-Enzyme Inhibitors: Functional, Structural, and Disease Applications 2009 Wiley Hoboken 13 38
3. V.M. Krishnamurthy , G.K. Kaufman , A.R. Urbach , I. Gitlin , K.L. Gudiksen , D.B. Weibel , and G.M. Whitesides Chem. Rev. 108 2008 946
4. V. Alterio , A. Di Fiore , K. D'Ambrosio , C.T. Supuran , and G. De Simone X-Ray crystallography of CA inhibitors and its importance in drug design C.T. Supuran, J.Y. Winum, Drug Design of Zinc-Enzyme Inhibitors: Functional Structural and Disease Applications 2009 Wiley Hoboken 73 138
5. C.T. Supuran Carbonic anhydrases: Catalytic inhibition mechanisms distribution and physiological roles C.T. Supuran, A. Scozzafava, J. Conway, Carbonic Anhydrase: Its Inhibitors and Activators 2004 CRC Press Boca Raton 1 23
6. D.W. Christianson , and C.A. Fierke Acc. Chem. Res. 29 1996 331
7. I. Elder , C. Tu , L.J. Ming , R. McKenna , and D.N. Silverman Arch. Biochem. Biophys. 437 2005 106
8. S.K. Nair , and D.W. Christianson J. Am. Chem. Soc. 113 1991 9455
9. D.N. Silverman , and R. McKenna Acc. Chem. Res. 40 2007 669
10. D. Duda , C. Tu , M. Qian , P. Laipis , M. Agbandje-McKenna , D.N. Silverman , and R. McKenna Biochemistry 40 2001 1741
11. C.T. Supuran Bioorg. Med. Chem. Lett. 20 2010 3467
12. J.-Y. Winum , J.-L. Montero , A. Scozzafava , and C.T. Supuran Zinc Binding Functions in the Design of Carbonic Anhydrase Inhibitors C.T. Supuran, J.-Y. Winum, Drug Design of Zinc-Enzyme Inhibitors: Functional, Structural, and Disease Applications 2009 Wiley Hoboken 39 72
13. C.T. Supuran , A. Casini , and A. Scozzafava Development of sulfonamide carbonic anhydrase inhibitors C.T. Supuran, A. Scozzafava, J. Conway, Carbonic Anhydrase: Its Inhibitors and Activators 2004 CRC Press Boca Raton 67 147
14. C.T. Supuran , A. Scozzafava , and A. Casini Med. Res. Rev. 23 2003 146
15. M. Ilies , A. Scozzafava , and C.T. Supuran Carbonic anhydrase activators C.T. Supuran, A. Scozzafava, J. Conway, Carbonic Anhydrase: Its inhibitors and activators 2004 CRC Press Boca Raton 317 352
16. C. Temperini , A. Scozzafava , and C.T. Supuran Drug Design Studies of Carbonic Anhydrase Activators C.T. Supuran, J.Y. Winum, Drug Design of Zinc-Enzyme Inhibitors: Functional, Structural, and Disease Applications 2009 Wiley Hoboken 473 486
17. M. Leiner , and G. Leiner Naturwissenschaften 29 1941 195
18. D.N. Silverman , C. Tu , and G.C. Wynns J. Biol. Chem. 253 1978 2563
19. D.N. Silverman , L. Backman , and C. Tu J. Biol. Chem. 254 1979 2588
20. J.L. Parkes , and P.S. Coleman Arch. Biochem. Biophys. 275 1989 459
21. C. Temperini , A. Scozzafava , and C.T. Supuran Curr. Pharm. Des. 14 2008 708
22. C.T. Supuran , and A. Scozzafava Activation of carbonic anhydrase isozymes W.R. Chegwidden, N. Carter, Y. Edwards, The Carbonic Anhydrases - New Horizons 2000 Birkhauser Basel, Switzerland 197 219
23. C.T. Supuran , M. Barboiu , C. Luca , E. Pop , M.E. Brewster , and A. Dinculescu Eur. J. Med. Chem. 31 1996 597
24. M.A. Ilies , M.D. Banciu , M. Ilies , F. Chiraleu , F. Briganti , A. Scozzafava , and C.T. Supuran Eur. J. Med. Chem. 32 1997 911
25. M. Ilies , M.D. Banciu , M.A. Ilies , A. Scozzafava , M.T. Caproiu , and C.T. Supuran J. Med. Chem. 45 2002 504
26. F. Briganti , S. Mangani , P. Orioli , A. Scozzafava , G. Vernaglione , and C.T. Supuran Biochemistry 36 1997 10384
27. C. Temperini , A. Scozzafava , L. Puccetti , and C.T. Supuran Bioorg. Med. Chem. Lett. 15 2005 5136
28. C. Temperini , A. Scozzafava , and C.T. Supuran Bioorg. Med. Chem. Lett. 16 2006 5152
29. C. Temperini , A. Scozzafava , D. Vullo , and C.T. Supuran Chem. Eur. J. 12 2006 7057
30. C. Temperini , D. Vullo , A. Scozzafava , and C.T. Supuran J. Med. Chem. 49 2006 3019
31. C. Temperini , A. Innocenti , A. Scozzafava , and C.T. Supuran Bioorg. Med. Chem. 16 2008 8373
32. C.T. Supuran , and A. Scozzafava Bioorg. Med. Chem. 7 1999 2915
33. F. Briganti , A. Scozzafava , and C.T. Supuran Bioorg. Med. Chem. Lett. 9 1999 2043
34. C.T. Supuran , and A. Scozzafava J. Enzyme Inhib. 15 2000 471
35. C.T. Supuran , and B.W. Clare Eur. J. Med. Chem. 30 1995 687
36. C.T. Supuran , A. Scozzafava , M.A. Ilies , B. Iorga , T. Cristea , F. Chiraleu , and M.D. Banciu Eur. J. Med. Chem. 33 1998 577
37. C.T. Supuran , A. Scozzafava , M.A. Ilies , and F. Briganti J. Enzyme Inhib. 15 2000 381
38. A. Scozzafava , F. Briganti , M.A. Ilies , and C.T. Supuran J. Med. Chem. 43 2000 292
39. V. Menchise , G. De Simone , V. Alterio , A. Di Fiore , C. Pedone , A. Scozzafava , and C.T. Supuran J. Med. Chem. 48 2005 5721
40. T.S. Balaban , and A.T. Balaban Pyrylium Salts Science of Synthesis. Houben-Weyl Methods of Molecular Transformations Vol. 14 2003 Georg Thieme Stuttgart 11 200
41. + PF 6 - : C, 46.28/46.60; H; 5.70/5.48; N, 10.79/11.05. The perchlorate of 8 has been reported earlier by: Dinculescu, A.; Balaban, A.T. Rrev. Roum. Chim. 1980, 25, 1505. The compound has been synthesized and characterized but not assayed for its CA activating action. It has been discussed in: Balaban, A.T.; Dinculescu, A.; Dorofeenko, G.N.; Fischer, G.W.; Koblik, A.V.; Mezheritskii V.V.; Schroth, W. Pyrylium Salts. Syntheses, Reactions and Physical Properties. In Advances in Heterocyclic Chemistry; Katritzky, A. R., Ed.; Academic Press: New York, 1982; Vol. 2, p. 298.
42. 31-33
43. D. Vullo , A. Innocenti , I. Nishimori , A. Scozzafava , K. Kaila , and C.T. Supuran Bioorg. Med. Chem. Lett. 17 2007 4107
44. M.-R. Abdo , D. Vullo , M.-C. Saada , J.-L. Montero , A. Scozzafava , J.-Y. Winum , and C.T. Supuran Bioorg. Med. Chem. Lett. 19 2009 2440
45. 37 Coordinates and structure factors have been deposited in the Protein Data Bank as entry 3HFP .
46. Oxford Diffraction. CrysAlis RED. 2006, Version 1.171.32.2. Oxford Diffraction Ltd.
47. T.A. Jones , J.Y. Zhou , S.W. Cowan , and M.s. Kjeldoard Acta Crystallogr. A47 1991 110
48. A.T. Brünger , P.D. Adams , G.M. Clore , W.L. De Lano , P. Gros , R.W. Grosse-Kunstleve , J.S. Jiang , J. Kuszewski , M. Nilges , N.S. Pannu , R.J. Read , L.M. Rice , T. Simonson , and G.L. Warren Acta Crystallogr., Sect. D 54 1998 905
49. R.A. Laskowski , M.W. MacArthur , D.S. Moss , J.M. Thornton , and J.M. Thornton J. Appl. Crystallogr. 26 1993 283