Rational design of the first difluorostatone-based PfSUB1 inhibitors

Bioorganic and Medicinal Chemistry Letters

Volumn 24, Issue 15, 2014, Pages 3582-3586

  Giovani, Simone ^a,b   Penzo, Maria ^c   Brogi, Simone ^a,b   Brindisi, Margherita ^a,b   Gemma, Sandra ^a,b   Novellino, Ettore ^a,d   Savini, Luisa ^a,b   Blackman, Michael J ^c   Campiani, Giuseppe ^a,b   Butini, Stefania ^a,b  

^a UNIVERSITY OF SIENA   (Italy)

^b UNIVERSITY OF PERUGIA   (Italy)

^c NATIONAL INSTITUTE FOR MEDICAL RESEARCH   (United Kingdom)

^d UNIVERSITY OF NAPLES FEDERICO II   (Italy)

Author keywords

Difluorostatone; Egress; Malaria; PfSUB1; Serine protease

Indexed keywords

ANTIMALARIAL AGENT; PLASMODIUM FALCIPARUM SUBTILISIN LIKE PROTEASE 1 INHIBITOR; SERINE PROTEINASE INHIBITOR; UNCLASSIFIED DRUG; ENZYME INHIBITOR; PLASMODIUM FALCIPARUM SERINE PROTEASE SUBTILISIN LIKE PROTEASE 1 INHIBITOR; OLIGOPEPTIDE; PROTEINASE INHIBITOR; PROTOZOAL PROTEIN; SUBTILISIN; SUBTILISIN-LIKE PROTEASE 1, PLASMODIUM FALCIPARUM;

ANTIMALARIAL ACTIVITY; ARTICLE; BIOINFORMATICS; DRUG DESIGN; DRUG IDENTIFICATION; DRUG POTENCY; DRUG SELECTIVITY; DRUG SYNTHESIS; EVALUATION STUDY; IC 50; BINDING AFFINITY; DRUG SCREENING; DRUG STRUCTURE; ANTAGONISTS AND INHIBITORS; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; DOSE RESPONSE; DRUG EFFECTS; ENZYMOLOGY; METABOLISM; PLASMODIUM FALCIPARUM; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

PLASMODIUM FALCIPARUM;

DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DESIGN; MODELS, MOLECULAR; MOLECULAR CONFORMATION; OLIGOPEPTIDES; PLASMODIUM FALCIPARUM; PROTEASE INHIBITORS; PROTOZOAN PROTEINS; STRUCTURE-ACTIVITY RELATIONSHIP; SUBTILISINS;

EID: 84903957340     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2014.05.044     Document Type: Article

References (30)

1. D.L. Sonin, T. Wakatsuki, K.V. Routhu, L.M. Harmann, M. Petersen, J. Meyer, and J.L. Strande J. Cardiovasc. Pharmacol. Ther. 18 2013 460
2. S. Gemma, V. Travagli, L. Savini, E. Novellino, G. Campiani, and S. Butini Recent Pat. Antiinfect. Drug Discovery 5 2010 195
3. G. Edwards, and G.A. Biagini Br. J. Clin. Pharmacol. 61 2006 690
4. A.M. Dondorp, F. Nosten, P. Yi, D. Das, A.P. Phyo, J. Tarning, K.M. Lwin, F. Ariey, W. Hanpithakpong, S.J. Lee, P. Ringwald, K. Silamut, M. Imwong, K. Chotivanich, P. Lim, T. Herdman, S.S. An, S. Yeung, P. Singhasivanon, N.P. Day, N. Lindegardh, D. Socheat, N.J. White, and N. Engl J. Med. 361 2009 455
5. M. Enserink Science 328 2010 846
6. S.A. Mousa Methods Mol. Biol. 663 2010 157
7. D.L. Wyles J. Infect. Dis. 207 2013 S33
8. M.J. Blackman Cell. Microbiol. 10 2008 1925
9. K. Koussis, C. Withers-Martinez, S. Yeoh, M. Child, F. Hackett, E. Knuepfer, L. Juliano, U. Woehlbier, H. Bujard, and M.J. Blackman EMBO J. 28 2009 725
10. S. Yeoh, R.A. O'Donnell, K. Koussis, A.R. Dluzewski, K.H. Ansell, S.A. Osborne, F. Hackett, C. Withers-Martinez, G.H. Mitchell, L.H. Bannister, J.S. Bryans, C.A. Kettleborough, and M.J. Blackman Cell 131 2007 1072
11. C.R. Collins, F. Hackett, M. Strath, M. Penzo, C. Withers-Martinez, D.A. Baker, and M.J. Blackman PLoS Pathog. 9 2013 e1003344
12. S. Gemma, S. Giovani, M. Brindisi, P. Tripaldi, S. Brogi, L. Savini, I. Fiorini, E. Novellino, S. Butini, G. Campiani, M. Penzo, and M.J. Blackman Bioorg. Med. Chem. Lett. 22 2012 5317
13. C. Withers-Martinez, C. Suarez, S. Fulle, S. Kher, M. Penzo, J.P. Ebejer, K. Koussis, F. Hackett, A. Jirgensons, P. Finn, and M.J. Blackman Int. J. Parasitol. 42 2012 597
14. S. Arastu-Kapur, E.L. Ponder, U.P. Fonovic, S. Yeoh, F. Yuan, M. Fonovic, M. Grainger, C.I. Phillips, J.C. Powers, and M. Bogyo Nat. Chem. Biol. 4 2008 203
15. C. Withers-Martinez, M. Strath, F. Hackett, L.F. Haire, S.A. Howell, P.A. Walker, C. Evangelos, G.G. Dodson, and M.J. Blackman Nat. Commun. 2014 5 10.1038/ncomms4726
16. S. Fulle, C. Withers-Martinez, M.J. Blackman, G.M. Morris, and P.W. Finn J. Chem. Inf. Model. 53 2013 573
17. J.-A. Fehrentz, and B. Castro Synthesis 1983 1983 676
18. M.S. Wolfe, M. Citron, T.S. Diehl, W. Xia, I.O. Donkor, and D.J. Selkoe J. Med. Chem. 41 1998 6
19. C.L. Moore, D.D. Leatherwood, T.S. Diehl, D.J. Selkoe, and M.S. Wolfe J. Med. Chem. 43 2000 3434
20. A. Cappelli, M. Manini, S. Valenti, F. Castriconi, G. Giuliani, M. Anzini, S. Brogi, S. Butini, S. Gemma, G. Campiani, G. Giorgi, L. Mennuni, M. Lanza, A. Giordani, G. Caselli, O. Letari, and F. Makovec Eur. J. Med. Chem. 63 2013 85
21. S. Gemma, C. Camodeca, M. Brindisi, S. Brogi, G. Kukreja, S. Kunjir, E. Gabellieri, L. Lucantoni, A. Habluetzel, D. Taramelli, N. Basilico, R. Gualdani, F. Tadini-Buoninsegni, G. Bartolommei, M.R. Moncelli, R.E. Martin, R.L. Summers, S. Lamponi, L. Savini, I. Fiorini, M. Valoti, E. Novellino, G. Campiani, and S. Butini J. Med. Chem. 55 2012 10387
22. G. Jones, P. Willett, and R.C. Glen J. Mol. Biol. 245 1995 43
23. Prime, version 3.0, Schrödinger, LLC, New York, NY, 2011.
24. B. Imperiali, and R.H. Abeles Biochemistry 25 1986 3760
25. L.H. Takahashi, R. Radhakrishnan, R.E. Rosenfield, E.F. Meyer, and D.A. Trainor J. Am. Chem. Soc. 111 1989 3368
26. X. Ouyang, S. Zhou, C.T. Su, Z. Ge, R. Li, and C.K. Kwoh J. Comput. Chem. 34 2013 326
27. B.Y. Soh, H.O. Song, Y. Lee, J. Lee, K. Kaewintajuk, B. Lee, Y.Y. Choi, J.H. Cho, S. Choi, and H. Park Malar. J. 12 2013 47
28. A.K. Ghosh, G. Gong, V. Grum-Tokars, D.C. Mulhearn, S.C. Baker, M. Coughlin, B.S. Prabhakar, K. Sleeman, M.E. Johnson, and A.D. Mesecar Bioorg. Med. Chem. Lett. 18 2008 5684
29. Q. Wang, R.H. Mach, and D.E. Reichert J. Chem. Inf. Model. 49 2009 1963
30. J.D. Robertus, J. Kraut, R.A. Alden, and J.J. Birktoft Biochemistry 11 1972 4293