Structural basis for selective inhibition of purine nucleoside phosphorylase from Schistosoma mansoni: Kinetic and structural studies

Bioorganic and Medicinal Chemistry

Volumn 18, Issue 4, 2010, Pages 1421-1427

  Castilho, Marcelo S ^a   Postigo, Matheus P ^b   Pereira, Humberto M ^b   Oliva, Glaucius ^b   Andricopulo, Adriano D ^b  

^a FEDERAL UNIVERSITY OF BAHIA   (Brazil)

^b UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

Enzyme inhibition; Neglected tropical diseases; Schistosomiasis; Selectivity

Indexed keywords

ANTISCHISTOSOMAL AGENT; PURINE NUCLEOSIDE PHOSPHORYLASE;

ARTICLE; BINDING AFFINITY; BINDING SITE; CRYSTALLOGRAPHY; DRUG POTENCY; ENZYME ACTIVE SITE; ENZYME ACTIVITY; ENZYME INHIBITION; ENZYME KINETICS; ENZYME STRUCTURE; FLUORESCENCE; IC 50; NONHUMAN; SCHISTOSOMA MANSONI; STRUCTURE ACTIVITY RELATION; X RAY DIFFRACTION;

AMINO ACID SEQUENCE; ANIMALS; CRYSTALLOGRAPHY, X-RAY; ENZYME INHIBITORS; HUMANS; KINETICS; MOLECULAR SEQUENCE DATA; PURINE-NUCLEOSIDE PHOSPHORYLASE; SCHISTOSOMA MANSONI; SEQUENCE HOMOLOGY, AMINO ACID;

SCHISTOSOMA MANSONI;

EID: 75849116605     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2010.01.022     Document Type: Article

References (45)

1. Bzowska A., Kulikowska E., and Shugar D. Pharmacol. Ther. 88 (2000) 349
2. Kelley J.L., McLean E.W., Crouch R.C., Averett D.R., and Tuttle J.V. J. Med. Chem. 38 (1995) 1005
3. Montgomery J.A. Med. Chem. Rev. 13 (1993) 209
4. Pereira H.M., Cleasby A., Pena S.D., Franco G.R., and Garratt R.C. Acta Crystallogr., Sect. D 59 (2003) 1096
5. Kicska G.A., Tyler P.C., Evans G.B., Furneaux R.H., Schramm V.L., and Kim K. J. Mol. Biol. 277 (2002) 3226
6. Pereira H.D., Franco G.R., Cleasby A., and Garratt R.C. J. Mol. Biol. 353 (2005) 584
7. Shi W., Ting L.M., Kicska G.A., Lewandowicz A., Tyler P.C., Evans G.B., Furneaux R.H., Kim K., Almo S.C., and Schramm V.L. J. Biol. Chem. 279 (2004) 18103
8. http://www.who.int/mediacentre/factsheets/fs115/en/. Accessed in June 2009.
9. Sabra A.N., and Botros S.S. J. Parasitol. 94 (2008) 537
10. Andricopulo A.D., and Montanari C.A. Mini-Rev. Med. Chem. 5 (2005) 585
11. Guido R.V.C., Oliva G., and Andricopulo A.D. Curr. Med. Chem. 15 (2008) 37
12. Andricopulo A.D., Willain A., Correa R., Correa A.R.S., Nunes R.J., Yunes R.A., and Cechinel V. Pharmazie 53 (1998) 493
13. Andricopulo A.D., Akoachere M.B., Krogh R., Nickel C., McLeish M.J., Kenyon G.L., Arscott L.D., Williams C.H., Davioud-Charvet E., and Becker K. Bioorg. Med. Chem. Lett. 16 (2006) 2283
14. Senft A.W., and Crabtree G.W. Biochem. Pharmacol. 26 (1977) 1847
15. Pereira H.D., Berdini V., Cleasby A., and Garratt R.C. FEBS Lett. 581 (2007) 5082
16. Elliott A.J., Morris P.E., Petty S.L., and Williams C.H. J. Org. Chem. 62 (1997) 8071
17. Elliott, A. J.; Walsh, D. A.; Morris, P. E. US Pat. Appl. Publ., 2,004,254,181, 2004.
18. Secrist, J. A.; Montgomery, J. A.; Ealick, S. E.; Erion, M. D.; Guida, W. C. US Pat 4,985,433, 1991.
19. Pathak V.P. Org. Process Res. Dev. 4 (2000) 129
20. Montgomery J.A., Niwas S., Rose J.D., Secrist J.A., Babu Y.S., Bugg C.E., Erion M.D., Guida W.C., and Ealick S.E. J. Med. Chem. 36 (1993) 55
21. Acton E.M., Ryan K.J., Henry D.W., and Goodman L.J. Chem. Soc., D: Chem. Commun. 16 (1971) 986
22. Farutin V., Masterson L., Andricopulo A.D., Cheng J., Riley B., Hakimi R., Frazer J.W., and Cordes E.H. J. Med. Chem. 42 (1999) 2422
23. Andricopulo A.D., and Yunes R.A. Chem. Pharm. Bull. 49 (2001) 10
24. Kim B.K., Cha S., and Parks Jr. R.E. J. Biol. Chem. 243 (1968) 1771
25. Leslie A.G.W. Acta Crystallogr., Sect. D 55 (1999) 1696
26. The CCP4 suite: programs for protein crystallography. Acta Crystallogr., Sect. D 1994, 50, 760.
27. Vagin A., and Teplyakov A. Acta Crystallogr. 56 (2000) 1622
28. Murshudov G.N., Vagin A., and Dodson E.J. Acta Crystallogr. 53 (1997) 240
29. Emsley P., and Cowtan K. Acta Crystallogr., Sect. D 60 (2004) 2126
30. Larson E.T., Deng W., Krumm B.E., Napuli A., Mueller N., Van Voorhis W.C., Buckner F.S., Fan E., Lauricella A., DeTitta G., Luft J., Zucker F., Hol1 W.G.J., Verlinde C.L.M.J., and Merritt E.A. J. Mol. Biol. 381 (2008) 975
31. Andricopulo A.D., Salum L.B., and Abraham D.J. Curr. Top. Med. Chem. 9 (2009) 771
32. Castilho M.S., Postigo M.P., Paula C.B.V., Montanari C.A., Oliva G., and Andricopulo A.D. Bioorg. Med. Chem. 14 (2006) 516
33. Erion M.D., Niwas S., Rose J.D., Ananthan S., Allen M., Secrist J.A., Babu Y.S., Bugg C.E., Guida W.C., Ealick S.E., and Montgomery J.A. J. Med. Chem. 36 (1993) 3771
34. Merino P., Tejero T., and Delso I. Curr. Med. Chem. 15 (2008) 954
35. Clinch K., Evans G.B., Fröhlich R.F., Furneaux R.H., Kelly P.M., Legentil L., Murkin A.S., Li L., Schramm V.L., Tyler P.C., and Woolhouse A.D. J. Med. Chem. 52 (2009) 1126
36. Kamath V.P., Xue J., Juarez-Brambila J.J., Morris C.B., Ganorkar R., and Morris Jr. P.E. Bioorg. Med. Chem Lett. 19 (2009) 2624
37. Kamath V.P., Xue J., and Juarez-Brambila J.J. Bioorg. Med. Chem Lett. 19 (2009) 2627
38. Secrist J.A., Niwas S., Rose J.D., Babu Y.S., Bugg C.E., Erion M.D., Guida W.C., Ealick S.E., and Montgomery J.A. J. Med. Chem. 36 (1993) 1847
39. Woo P.W., Kostlan C.R., Sircar J.C., Dong M.K., and Gilbertsen R.B. J. Med. Chem. 35 (1992) 1451
40. Ladame S., Castilho M.S., Silva C.H.T.P., Denier C., Hannaert V., Perie J., Oliva G., and Willson M. Eur. J. Biochem. 270 (2003) 4574
41. Guido R.V.C., Oliva G., Montanari C.A., and Andricopulo A.D. J. Chem. Inf. Model. 48 (2008) 918
42. Honorio K.M., Garratt R.C., Polikarpov I., and Andricopulo A.D. J. Mol. Graphics Modell. 25 (2007) 921
43. Salum L.B., Polikarpov I., and Andricopulo A.D. J. Chem. Inf. Model. 48 (2008) 2243
44. Leeson P.D., and Springthorpe B. Nat. Rev. Drug Disc. 6 (2007) 881
45. Copeland R.A. Evaluation of Enzyme inhibitors in Drug Discovery: A Guide for Medicinal Chemists and Pharmacologists Vol. 48 (2005), Wiley-Interscience, New Jersey