Synthesis, biological evaluation, and modeling studies of inhibitors aimed at the malarial proteases plasmepsins I and II

Bioorganic and Medicinal Chemistry

Volumn 13, Issue 18, 2005, Pages 5371-5390

  Muthas, Daniel ^a   Nöteberg, Daniel ^a   Sabnis, Yogesh A ^a   Hamelink, Elizabeth ^b   Vrang, Lotta ^b   Samuelsson, Bertil ^b   Karlén, Anders ^a   Hallberg, Anders ^a  

^a UPPSALA UNIVERSITY   (Sweden)

^b MEDIVIR AB   (Sweden)

Author keywords

Hydroxyethylamine; Malaria; Molecular modeling; Plasmepsin

Indexed keywords

1 (BENZYLAMINO) 3 [(TERT BUTYLOXYCARBONYL)AMINO] 4 PHENYLBUTAN 2 OL; 1 [(3 BROMOBENZYL)AMINO] 3 [(TERT BUTYLOXYCARBONYL)AMINO] 4 PHENYLBUTAN 2 OL; 1 [(4 BROMOBENZYL)AMINO] 3 [(TERT BUTYLOXYCARBONYL)AMINO] 4 PHENYLBUTAN 2 OL; 3 [(TERT BUTYLOXYCARBONYL)AMINO] 1 (ISOBUTYLAMINO) 4 PHENYLBUTAN 2 OL; 3 [(TERT BUTYLOXYCARBONYL)AMINO] 4 PHENYL 1 [(2 PHENYLETHYL)AMINO]BUTAN 2 OL; 3 [(TERT BUTYLOXYCARBONYL)AMINO] 4 PHENYL 1 [(3 PHENYLPROPYL)AMINO]BUTAN 2 OL; 3 AZA 3 (3 BROMOBENZYL) 5 HYDROXY 7 PHENYL 6 [(PICOLYLVALINYL)AMINO] HEPTANOYLAMIDE; 3 AZA 3 (3 BROMOBENZYL) 6 [(TERT BUTYLCARBONYL)AMINO] 5 HYDROXY 7 PHENYLHEPTANOYLAMIDE; 3 AZA 3 (3 BROMOBENZYL) 6 [[(TERT BUTYLCARBONYL)VALINYL]AMINO] 5 HYDROXY 7 PHENYLHEPTANOYLAMIDE; 3 AZA 3 (4 BROMOBENZYL) 5 HYDROXY 7 PHENYL 6 [(PICOLYLVALINYL)AMINO] HEPTANOYLAMIDE; 3 AZA 3 (4 BROMOBENZYL) 6 [(TERT BUTYLOXYCARBONYL)AMINO] 5 HYDROXY 7 PHENYLHEPTANOYLAMIDE; 3 AZA 3 (4 BROMOBENZYL) 6 [[(TERT BUTYLOXYCARBONYL)VALINYL]AMINO] 5 HYDROXY 7 PHENYLHEPTANOYLAMIDE; 3 AZA 3 BENZYL 5 HYDROXY 7 PHENYL 6 [(PICOLYLVALINYL)AMINO]HEPTANOYLAMIDE; 3 AZA 3 BENZYL 6 [(TERT BUTYLOXYCARBONYL)AMINO] 5 HYDROXY 7 PHENYLHEPTANOYLAMIDE; 3 AZA 3 BENZYL 6 [[(TERT BUTYLOXYCARBONYL)VALINYL]AMINO] 5 HYDROXY 7 PHENYLHEPTANOYLAMIDE; 3 AZA 3 ISOBUTYL 5 HYDROXY 7 PHENYL 6 [(PICOLYLVALINYL)AMINO] HEPTANOYLAMIDE; 3 AZA 5 HYDROXY 6 [(PICOLYLVALINYL)AMINO] 7 PHENYL 3 (3 PHENYLPROPYL)HEPTANOYLAMIDE; 3 AZA 5 HYDROXY 7 PHENYL 3 (2 PHENYLETHYL) 6 [(PICOLYLVALINYL)AMINO] HEPTANOYLAMIDE; 3 AZA 5 HYDROXY 7 PHENYL 3 (4 PHENYLBENZYL) 6 [(PICOLYLVALINYL)AMINO] HEPTANOYLAMIDE; 3 AZA 6 [(TERT BUTYLOXYCARBONYL)AMINO] 3 ISOBUTYL 5 HYDROXY 7 PHENYLHEPTANOYLAMIDE; 3 AZA 6 [(TERT BUTYLOXYCARBONYL)AMINO] 5 HYDROXY 7 PHENYL 3 (2 PHENYLETHYL)HEPTANOYLAMIDE; 3 AZA 6 [(TERT BUTYLOXYCARBONYL)AMINO] 5 HYDROXY 7 PHENYL 3 (3 PHENYLPROPYL)HEPTANOYLAMIDE; 3 AZA 6 [[(TERT BUTYLOXYCARBONYL)VALINYL]AMINO] 5 HYDROXY 7 PHENYL 3 (2 PHENYLETHYL)HEPTANOYLAMIDE; 3 AZA 6 [[(TERT BUTYLOXYCARBONYL)VALINYL]AMINO] 5 HYDROXY 7 PHENYL 3 (3 PHENYLPROPYL)HEPTANOYLAMIDE; 3 AZA 6 [[(TERT BUTYLOXYCARBONYL)VALINYL]AMINO] 5 HYDROXY 7 PHENYLHEPTANOYLAMIDE; PLASMEPSIN I; PLASMEPSIN II; PROTEINASE; PROTEINASE INHIBITOR; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ARTICLE; BIOLOGICAL ACTIVITY; BIOLOGICAL MODEL; CONTROLLED STUDY; DRUG SYNTHESIS; DRUG TARGETING; MALARIA; NONHUMAN; PLASMODIUM FALCIPARUM; QUANTITATIVE STRUCTURE ACTIVITY RELATION;

ANIMALS; ANTIMALARIALS; ASPARTIC ENDOPEPTIDASES; COMPUTER SIMULATION; MODELS, BIOLOGICAL; MODELS, MOLECULAR; PLASMODIUM FALCIPARUM; PROTEASE INHIBITORS; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP;

PLASMODIUM FALCIPARUM;

EID: 23644450055     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2005.06.048     Document Type: Article

References (40)

1. J.G. Breman Am. J. Trop. Med. Hyg. 64 2001 1 11
2. P.J. Guerin, P. Olliaro, F. Nosten, P. Druilhe, R. Laxminarayan, F. Binka, L. Kilama Wen, N. Ford, and J. White Nicholas Lancet Infect. Dis. 2 2002 564 573
3. M.J. Gardner, N. Hall, E. Fung, O. White, M. Berriman, R.W. Hyman, J.M. Carlton, A. Pain, K.E. Nelson, S. Bowman, I.T. Paulsen, K. James, J.A. Eisen, K. Rutherford, S.L. Salzberg, A. Craig, S. Kyes, M.-S. Chan, V. Nene, S.J. Shallom, B. Suh, J. Peterson, S. Angiuoli, M. Pertea, J. Allen, J. Selengut, D. Haft, M.W. Mather, A.B. Vaidya, D.M.A. Martin, A.H. Fairlamb, M.J. Fraunholz, D.S. Roos, S.A. Ralph, G.I. McFadden, L.M. Cummings, G.M. Subramanian, C. Mungall, J.C. Venter, D.J. Carucci, S.L. Hoffman, C. Newbold, R.W. Davis, C.M. Fraser, and B. Barrell Nature 419 2002 498 511
4. S.E. Francis, D.J. Sullivan Jr., and D.E. Goldberg Annu. Rev. Microbiol. 51 1997 97 123
5. P.J. Rosenthal, J.H. McKerrow, M. Aikawa, H. Nagasawa, and J.H. Leech J. Clin. Invest. 82 1988 1560 1566
6. P.J. Rosenthal, and S.R. Meshnick Mol. Biochem. Parasitol. 83 1996 131 139
7. K.K. Eggleson, K.L. Duffin, and D.E. Goldberg J. Biol. Chem. 274 1999 32411 32417
8. D.M. Wyatt, and C. Berry FEBS Lett. 513 2002 159 162
9. R. Banerjee, J. Liu, W. Beatty, L. Pelosof, M. Klemba, and E. Goldberg Daniel Proc. Natl. Acad. Sci. U.S.A. 99 2002 990 995
10. J. Liu, I.Y. Gluzman, M.E. Drew, and D.E. Goldberg J. Biol. Chem. 280 2005 1432 1437
11. S.E. Francis, I.Y. Gluzman, A. Oksman, A. Knickerbocker, R. Mueller, M.L. Bryant, D.R. Sherman, D.G. Russell, and D.E. Goldberg EMBO J. 13 1994 306 317
12. J.B. Dame, G.R. Reddy, C.A. Yowell, B.M. Dunn, J. Kay, and C. Berry Mol. Biochem. Parasitol. 64 1994 177 190
13. A.M. Silva, A.Y. Lee, J.W. Erickson, and D.E. Goldberg Adv. Exp. Med. Biol. 436 1998 363 373
14. A.M. Silva, A.Y. Lee, S.V. Gulnik, P. Majer, J. Collins, T.N. Bhat, P.J. Collins, R.E. Cachau, K.E. Luker, I.Y. Gluzman, S.E. Francis, A. Oksman, D.E. Goldberg, and J.W. Erickson Proc. Natl. Acad. Sci. U.S.A. 93 1996 10034 10039
15. T.S. Haque, A.G. Skillman, C.E. Lee, H. Habashita, I.Y. Gluzman, T.J.A. Ewing, D.E. Goldberg, I.D. Kuntz, and J.A. Ellman J. Med. Chem. 42 1999 1428 1440
16. M. Foley, and L. Tilley Int. J. Parasitol. 27 1997 231 240
17. J.G. Dann, D.K. Stammers, C.J. Harris, R.J. Arrowsmith, D.E. Davies, G.W. Hardy, and J.A. Morton Biochem. Biophys. Res. Commun. 134 1986 71 77
18. N.A. Roberts, J.A. Martin, D. Kinchington, A.V. Broadhurst, J.C. Craig, I.B. Duncan, S.A. Galpin, B.K. Handa, J. Kay, and A. Krohn Science 248 1990 358 361
19. J. Brånalt, I. Kvarnström, B. Classon, B. Samuelsson, U. Nillroth, U.H. Danielson, A. Karlén, and A. Hallberg Tetrahedron Lett. 38 1997 3483 3486
20. D. Nöteberg, E. Hamelink, J. Hultén, M. Wahlgren, L. Vrang, B. Samuelsson, and A. Hallberg J. Med. Chem. 46 2003 734 746
21. D. Nöteberg, W. Schaal, E. Hamelink, L. Vrang, and M. Larhed J. Comb. Chem. 5 2003 456 464
22. S. Romeo, and D.H. Rich Tetrahedron Lett. 35 1994 4939 4942
23. M. Alterman, H.O. Andersson, N. Garg, G. Ahlsen, S. Lövgren, B. Classon, U.H. Danielson, I. Kvarnström, L. Vrang, T. Unge, B. Samuelsson, and A. Hallberg J. Med. Chem. 42 1999 3835 3844
24. M. Larhed, G. Lindeberg, and A. Hallberg Tetrahedron Lett. 37 1996 8219 8222
25. P. Artursson, and J. Karlsson Biochem. Biophys. Res. Commun. 175 1991 880 885
26. C. McMartin, and R.S. Bohacek J. Comput.-Aided Mol. Des. 11 1997 333 344
27. O.A. Asojo, E. Afonina, S.V. Gulnik, B. Yu, J.W. Erickson, R. Randad, D. Medjahed, and A.M. Silva Acta Crystallogr., Sect. D D58 2002 2001 2008
28. O.A. Asojo, S.V. Gulnik, E. Afonina, B. Yu, J.A. Ellman, T.S. Haque, and A.M. Silva J. Mol. Biol. 327 2003 173 181
29. Lindberg, J.; Johansson, P.-O.; Rosenquist, Å.; Kvarnström, I.; Vrang, L.; Samuelsson, B.; Unge, T. PDB release on publication.
30. M. Clark, and R.D. Cramer III Quant. Struct.-Act. Relat. 12 1993 137 145
31. Copeland, R.A. (Ed.), Enzymes: A Practical Introduction to Structure, Mechanism, and Data Analysis, 1996, 300 pp.
32. Y. Cheng, and W.H. Prusoff Biochem. Pharmacol. 22 1973 3099 3108
33. Sybyl; 6.9 ed.; Tripos Inc.: St. Louis, Missouri.
34. R.D. Cramer III, D.E. Patterson, and J.D. Bunce J. Am. Chem. Soc. 110 1988 5959 5967
35. F. Mohamadi, N.G.J. Richards, W.C. Guida, R. Liskamp, M. Lipton, C. Caufield, G. Chang, T. Hendrickson, and W.C. Still J. Comput. Chem. 11 1990 440 467
36. H.M. Berman, J. Westbrook, Z. Feng, G. Gilliland, T.N. Bhat, H. Weissig, I.N. Shindyalov, and P.E. Bourne Nucleic Acids Res. 28 2000 235 242
37. D.Q. McDonald, and W.C. Still Tetrahedron Lett. 33 1992 7743 7746
38. I. Kolossvary, and W.C. Guida J. Comput. Chem. 20 1999 1671 1684
39. K. Ersmark, I. Feierberg, S. Bjelic, E. Hamelink, F. Hackett, M.J. Blackman, J. Hultén, B. Samuelsson, J. Åqvist, and A. Hallberg J. Med. Chem. 47 2004 110 122
40. S. Wold Quant. Struct.-Act. Relat. 10 1991 191 193