Inhibition studies of a β-carbonic anhydrase from Brucella suis with a series of water soluble glycosyl sulfanilamides

Bioorganic and Medicinal Chemistry Letters

Volumn 20, Issue 7, 2010, Pages 2178-2182

  Vullo, Daniela ^a   Nishimori, Isao ^b   Scozzafava, Andrea ^a   Köhler, Stephan ^c   Winum, Jean Yves ^d   Supuran, Claudiu T ^a  

^a UNIVERSITY OF FLORENCE   (Italy)

^b KOCHI MEDICAL SCHOOL   (Japan)

^c University of Montpellier I and II   (France)

^d UNIVERSITÉ DE MONTPELLIER   (France)

Author keywords

Brucella suis; Carbonic anhydrase; Enzyme inhibitor; Sugar sulfanilamide; Sulfonamide

Indexed keywords

ACETAZOLAMIDE; BETA CARBONIC ANHYDRASE; BICARBONATE; CARBON DIOXIDE; CARBONATE DEHYDRATASE; GALACTOSE; GLYCOSYL SULFANILAMIDE; RIBOSE; SULFANILAMIDE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BACTERIAL GROWTH; BRUCELLA SUIS; CATALYST; CELL CULTURE; CLONING; ENZYME INHIBITION; GROWTH INHIBITION; HYDRATION; INHIBITION KINETICS; KINETICS; NONHUMAN; NUCLEOTIDE SEQUENCE; PURIFICATION;

AMINO ACID SEQUENCE; BRUCELLA SUIS; CARBOHYDRATES; CARBONIC ANHYDRASE I; CARBONIC ANHYDRASE INHIBITORS; HUMANS; KINETICS; MOLECULAR SEQUENCE DATA; SEQUENCE ALIGNMENT; STRUCTURE-ACTIVITY RELATIONSHIP; SULFANILAMIDES; WATER;

BACTERIA (MICROORGANISMS); BRUCELLA MELITENSIS BIOVAR SUIS;

EID: 77949656028     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2010.02.042     Document Type: Article

References (60)

1. DelVecchio V.G., Kapatral V., Redkar R.J., Patra G., Mujer C., Los T., Ivanova N., Anderson I., Bhattacharyya A., Lykidis A., Reznik G., Jablonski L., Larsen N., D'Souza M., Bernal A., Mazur M., Goltsman E., Selkov E., Elzer P.H., Hagius S., O'Callaghan D., Letesson J.J., Haselkorn R., Kyrpides N., and Overbeek R. Proc. Natl. Acad. Sci. U.S.A. 99 (2002) 443
2. Paulsen I.T., Seshadri R., Nelson K.E., Eisen J.A., Heidelberg J.F., Read T.D., Dodson R.J., Umayam L., Brinkac L.M., Beanan M.J., Daugherty S.C., Deboy R.T., Durkin A.S., Kolonay J.F., Madupu R., Nelson W.C., Ayodeji B., Kraul M., Shetty J., Malek J., Van Aken S.E., Riedmuller S., Tettelin H., Gill S.R., White O., Salzberg S.L., Hoover D.L., Lindler L.E., Halling S.M., Boyle S.M., and Fraser C.M. Proc. Natl. Acad. Sci. U.S.A. 99 (2002) 13148
3. Halling S.M., Peterson-Burch B.D., Bricker B.J., Zuerner R.L., Qing Z., Li L.L., Kapur V., Alt D.P., and Olsen S.C. J. Bacteriol. 187 (2005) 2715
4. Köhler S., Foulongne V., Ouahrani-Bettache S., Bourg G., Teyssier J., Ramuz M., and Liautard J.P. Proc. Natl. Acad. Sci. U.S.A. 99 (2002) 15711
5. Gorvel J.P. Microbes Infect. 10 (2008) 1010
6. Lopes-Goni I., and Moriyon I. Brucella: Molecular and Cellular Biology (2004), Horizon Bioscience
7. Whatmore A.M. Infect. Genet. Evol. 9 (2009) 1168
8. Guerra H. Crit. Rev. Microbiol. 33 (2007) 325
9. Godfroid J., Cloeckaert A., Liautard J.-P., Köhler S., Fretin D., Walravens K., Garin-Bastuji B., and Letesson J.-J. Vet. Res. 36 (2005) 313
10. Pappas G., Papadimitriou P., Akritidis N., Christou L., and Tsianos E.V. Lancet Infect. Dis. 6 (2006) 91
11. Franco M.P., Mulder M., Gilman R.H., and Smits H.L. Lancet Infect. Dis. 7 (2007) 775
12. Pappas G., Panagopoulou P., Christou L., and Akritidis N. Cell. Mol. Life Sci. 63 (2006) 2229
13. Baykam N., Esener H., Ergonul O., Eren S., Celikbas A.K., and Dokuzoguz B. Int. J. Antimicrob. Agents 23 (2004) 405
14. Sungur G.K., Hazirolan D., Gurbuz Y., Unlu N., Duran S., and Duman S. Can. J. Ophthalmol. 44 (2009) 598
15. Ravanel N., Gestin B., and Maurin M. Int. J. Antimicrob. Agents 34 (2009) 76
16. Nickerson C.A., and Schurr M.J. Molecular Paradigms of Infectious Disease: A Bacterial Perspective (2006), Springer Verlag 1-617
17. Payne D.J., Gwynn M.N., Holmes D.J., and Pompliano D.L. Nat. Rev. Drug Disc. 6 (2007) 29
18. Tsolis R.M., Young G.M., Solnick J.V., and Bäumler A.J. Nat. Rev. Microbiol. 6 (2008) 883
19. Dye C. Nat. Rev. Microbiol. 7 (2009) 81
20. Ginsberg A.M. Semin. Respir. Crit. Care Med. 29 (2008) 552
21. Showalter H.D., and Denny W.A. Tuberculosis (Edinb) 88 (2008) S3
22. Boigegrain R.-A., Liautard J.P., and Köhler S. Antimicrob. Agents Chemother. 49 (2005) 3922
23. Liautard J.P., Jubier-Maurin V., Boigegrain R.A., and Köhler S. Trends Microbiol. 14 (2006) 109
24. Joseph P., Turtaut F., Köhler S., and Winum J.-Y. Inhibitors of Histidinol Dehydrogenases as Antibacterial Agents. In: Supuran C.T., and Winum J.Y. (Eds). Drug Design of Zinc-Enzyme Inhibitors: Functional, Structural, and Disease Applications (2009), Wiley, Hoboken 937-950
25. Winum J.-Y., Köhler S., Scozzafava A., Montero J.-L., and Supuran C.T. Anti-Infect. Agents Med. Chem. 7 (2008) 169
26. Joseph P., Abdo M.-R., Boigegrain R.-A., Montero J.-L., Winum J.-Y., and Köhler S. Antimicrob. Agents Chemother. 51 (2007) 3752
27. Supuran C.T. Nat. Rev. Drug Disc. 7 (2008) 168
28. Krungkrai J., Krungkrai S.R., and Supuran C.T. Bioorg. Med. Chem. Lett. 18 (2008) 5466
29. Krungkrai J., and Supuran C.T. Curr. Pharm. Des. 14 (2008) 631
30. Nishimori I., Minakuchi T., Morimoto K., Sano S., Onishi S., Takeuchi H., Vullo D., Scozzafava A., and Supuran C.T. J. Med. Chem. 49 (2006) 2117
31. Nishimori I., Onishi S., Takeuchi H., and Supuran C.T. Curr. Pharm. Des. 14 (2008) 622
32. Nishimori I., Minakuchi T., Kohsaki T., Onishi S., Takeuchi H., Vullo D., Scozzafava A., and Supuran C.T. Bioorg. Med. Chem. Lett. 17 (2007) 3585
33. Innocenti A., Mühlschlegel F.A., Hall R.A., Steegborn C., Scozzafava A., and Supuran C.T. Bioorg. Med. Chem. Lett. 18 (2008) 5066
34. Schlicker C., Hall R.A., Vullo D., Middelhaufe S., Gertz M., Supuran C.T., Mühlschlegel F.A., and Steegborn C. J. Mol. Biol. 385 (2009) 1207
35. Innocenti A., Hall R.A., Schlicker C., Mühlschlegel F.A., and Supuran C.T. Bioorg. Med. Chem. 17 (2009) 2654
36. Isik S., Kockar F., Aydin M., Arslan O., Ozensoy Guler O., Innocenti A., Scozzafava A., and Supuran C.T. Bioorg. Med. Chem. 17 (2009) 1158
37. Minakuchi T., Nishimori I., Vullo D., Scozzafava A., and Supuran C.T. J. Med. Chem. 52 (2009) 2226
38. Nishimori I., Minakuchi T., Vullo D., Scozzafava A., Innocenti A., and Supuran C.T. J. Med. Chem. 52 (2009) 3116
39. Güzel O., Maresca A., Scozzafava A., Salman A., Balaban A.T., and Supuran C.T. J. Med. Chem. 52 (2009) 4063
40. Carta F., Maresca A., Suarez Covarrubias A., Mowbray S.L., Jones T.A., and Supuran C.T. Bioorg. Med. Chem. Lett. 19 (2009) 6649
41. Cronk J.D., Rowlett R.S., Zhang K.Y., Tu C., Endrizzi J.A., Lee J., Gareiss P.C., and Preiss J.R. Biochemistry 45 (2006) 4351
42. Cronk J.D., Endrizzi J.A., Cronk M.R., O'Neill J W., and Zhang K.Y. Protein Sci. 10 (2001) 911
43. Smith K.S., Jakubzick C., Whittam T.S., and Ferry J.G. Proc. Natl. Acad. Sci. U.S.A. 96 (1999) 15184
44. Rowlett, R.S. Biochim. Biophys. Acta 2010, in press.
45. 15 and represent the mean from at least three different determinations.
46. Suarez Covarrubias A., Larsson A.M., Hogbom M., Lindberg J., Bergfors T., Bjorkelid C., Mowbray S.L., Unge T., and Jones T.A. J. Biol. Chem. 280 (2005) 18782
47. Suarez Covarrubias A., Bergfors T., Jones T.A., and Hogbom M. J. Biol. Chem. 281 (2006) 4993
48. 6 tag has been removed in a small sample of the protein by treatment with enterokinase (Sigma-Aldrich). However the catalytic activity and acetazolamide inhibition of the His-tagged and untagged enzymes were identical (data not shown), so that the data of Tables 1 and 2 refer to the enzyme with the (6x)His-tag.
49. Supuran C.T., Scozzafava A., and Casini A. Med. Res. Rev. 23 (2003) 146
50. Supuran C.T. Expert Opin. Ther. Patents 13 (2003) 1545
51. Supuran C.T., Di Fiore A., and De Simone G. Expert Opin. Emerg. Drugs 13 (2008) 383
52. De Simone G., Di Fiore A., and Supuran C.T. Curr. Pharm. Des. 14 (2008) 655
53. Thiry A., Dogné J.M., Masereel B., and Supuran C.T. Trends Pharmacol. Sci. 27 (2006) 566
54. Stiti M., Cecchi A., Rami M., Abdaoui M., Barragan-Montero V., Scozzafava A., Guari Y., Winum J.Y., and Supuran C.T. J. Am. Chem. Soc. 130 (2008) 16130
55. Maresca A., Temperini C., Pochet L., Masereel B., Scozzafava A., and Supuran C.T. J. Med. Chem. 53 (2010) 335
56. Winum J.-Y., Casini A., Mincione F., Starnotti M., Montero J.-L., Scozzafava A., and Supuran C.T. Bioorg. Med. Chem. Lett. 14 (2004) 225
57. Dozot M., Boigegrain R.A., Delrue R.M., Hallez R., Ouahrani-Bettache S., Danese I., Letesson J.J., De Bolle X., and Köhler S. Cell. Microbiol. 8 (2006) 1791
58. Hazen S.A., Waheed A., Sly W.S., Lanoue K.F., and Lynch C.J. FASEB J. 10 (1996) 481
59. Chegwidden W.R., and Spencer I.M. Comp. Biochem. Physiol. B 115 (1996) 247
60. Aguilera J., Petit T., Winde J.H., and Pronk J.T. FEMS Yeast Res. 5 (2005) 579