In vitro and in vivo antimalarial activity of peptidomimetic protein farnesyltransferase inhibitors with improved membrane permeability

Bioorganic and Medicinal Chemistry

Volumn 12, Issue 24, 2004, Pages 6517-6526

  Carrico, Dora ^a   Ohkanda, Junko ^a   Kendrick, Howard ^b   Yokoyama, Kohei ^c   Blaskovich, Michelle A ^d   Bucher, Cynthia J ^d   Buckner, Frederick S ^c   Van Voorhis, Wesley C ^c   Chakrabarti, Debopam ^e   Croft, Simon L ^b   Gelb, Michael H ^c   Sebti, Saïd M ^d   Hamilton, Andrew D ^a  

^a YALE UNIVERSITY   (United States)

^b LONDON SCHOOL OF HYGIENE AND TROPICAL MEDICINE   (United Kingdom)

^c UNIVERSITY OF WASHINGTON   (United States)

^d H LEE MOFFITT CANCER CENTER AND RESEARCH INSTITUTE   (United States)

^e UNIVERSITY OF CENTRAL FLORIDA   (United States)

Author keywords

Ester prodrug; Peptidomimetic; Plasmodium falciparum; Protein farnesyltransferase

Indexed keywords

2 [[5 [[(1H IMIDAZOL 4 YLMETHYL)AMINO]METHYL] 2' METHYLBIPHENYL 2 CARBONYL]AMINO] 4 METHYLSULFANYL BUTYRIC ACID; 2 [[5 [[(1H IMIDAZOL 4 YLMETHYL)AMINO]METHYL] 2' METHYLBIPHENYL 2 CARBONYL]AMINO] 4 METHYLSULFANYL BUTYRIC ACID 2 ETHYLHEXYL ESTER; 2 [[5 [[(1H IMIDAZOL 4 YLMETHYL)AMINO]METHYL] 2' METHYLBIPHENYL 2 CARBONYL]AMINO] 4 METHYLSULFANYL BUTYRIC ACID ALLYL ESTER; 2 [[5 [[(1H IMIDAZOL 4 YLMETHYL)AMINO]METHYL] 2' METHYLBIPHENYL 2 CARBONYL]AMINO] 4 METHYLSULFANYL BUTYRIC ACID BENZYL ESTER; 2 [[5 [[(1H IMIDAZOL 4 YLMETHYL)AMINO]METHYL] 2' METHYLBIPHENYL 2 CARBONYL]AMINO] 4 METHYLSULFANYL BUTYRIC ACID CYCLOHEXYL ESTER; 2 [[5 [[(1H IMIDAZOL 4 YLMETHYL)AMINO]METHYL] 2' METHYLBIPHENYL 2 CARBONYL]AMINO] 4 METHYLSULFANYL BUTYRIC ACID ETHYL ESTER; 2 [[5 [[(1H IMIDAZOL 4 YLMETHYL)AMINO]METHYL] 2' METHYLBIPHENYL 2 CARBONYL]AMINO] 4 METHYLSULFANYL BUTYRIC ACID ISOPROPYL ESTER; 2 [[5 [[(1H IMIDAZOL 4 YLMETHYL)AMINO]METHYL] 2' METHYLBIPHENYL 2 CARBONYL]AMINO] 4 METHYLSULFANYL BUTYRIC ACID METHYL ESTER; ANTIMALARIAL AGENT; FTI 2148.2TFA; FTI 2153; FTI 2390; FTI 2391; FTI 2392; FTI 2393; FTI 2394; FTI 2628; PROTEIN FARNESYLTRANSFERASE; PROTEIN FARNESYLTRANSFERASE INHIBITOR; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIMALARIAL ACTIVITY; ARTICLE; CELL MEMBRANE PERMEABILITY; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG CONFORMATION; DRUG EFFICACY; DRUG POTENCY; DRUG SYNTHESIS; DRUG TARGETING; HYDROPHOBICITY; INHIBITION KINETICS; MALARIA; MOUSE; NONHUMAN; PARASITEMIA; PLASMODIUM FALCIPARUM;

ALKYL AND ARYL TRANSFERASES; ANIMALS; ANTIMALARIALS; CELL MEMBRANE PERMEABILITY; ERYTHROCYTES; ESTERS; FARNESYLTRANSTRANSFERASE; HYDROPHOBICITY; MALARIA; MICE; MOLECULAR MIMICRY; NIH 3T3 CELLS; PEPTIDES; PLASMODIUM BERGHEI; PLASMODIUM FALCIPARUM; STRUCTURE-ACTIVITY RELATIONSHIP;

MURINAE; PLASMODIUM BERGHEI; PLASMODIUM FALCIPARUM;

EID: 20844437245     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2004.09.020     Document Type: Article

References (26)

1. J. Sachs, and P. Malaney Nature 415 2002 680 685
2. P. Wilairatana, S. Krudsood, S. Treeprasertsuk, K. Chalermrut, and S. Looareesuwan Arch. Med. Res. 33 2002 416 421
3. J. Wiesner, R. Ortmann, H. Jomaa, and M. Schlitzer Angew. Chem., Int. Ed. 42 2003 5274 5293
4. K. Yokoyama, P. Trobridge, F.S. Buckner, W.C. Van Voorhis, K.D. Stuart, and M.H. Gelb J. Biol. Chem. 273 1998 26497 26505
5. F.S. Buckner, K. Yokoyama, L. Nguyen, A. Grewal, H. Erdjument-Bromage, P. Tempst, C.L. Strickland, L. Xiao, W.C. Van Voorhis, and M.H. Gelb J. Biol. Chem. 275 2000 21870 21876
6. D. Chakrabarti, T. Azam, C. DelVecchio, L. Qiu, Y. Park, and C.M. Allen Mol. Biochem. Parasitol. 94 1998 175 184
7. J. Wiesner, K. Kettler, J. Sakowski, R. Ortmann, A.M. Katzin, E.A. Kimura, K. Silber, G. Klebe, H. Jomaa, and M. Schlitzer Angew. Chem., Int. Ed. 43 2004 251 254
8. P.J. Casey, and M.C. Seabra J. Biol. Chem. 271 1996 5289 5292
9. K. Yokoyama, P. Trobridge, F.S. Buckner, J. Sholten, K.D. Stuart, W.C. Van Voorhis, and M.H. Gelb Mol. Biochem. Parasitol. 94 1998 87 97
10. A.S. Couto, E.A. Kimura, V.J. Peres, M.L. Uhrig, and A.M. Katzin Biochem. J. 341 1999 629 637
11. J.L. Nepomuceno-Silva, K. Yokoyama, L.D.B. de Mello, S.M. Mendonca, J.C. Paixao, R. Baron, J.C. Faye, F.S. Buckner, W.C. Van Voorhis, M.H. Gelb, and U.G. Lopes J. Biol. Chem. 276 2001 29711 29718
12. J. Ohkanda, J.W. Lockman, K. Yokoyama, M.H. Gelb, S.L. Croft, H. Kendrick, M.I. Harrell, J.E. Feagin, M.A. Blaskovich, S.M. Sebti, and A.D. Hamilton Bioorg. Med. Chem. Lett. 11 2001 761 764
13. For examples see: M.E. Taub, B.D. Larsen, B. Steffansen, and S. Frokjaer Int. J. Pharm. 146 1997 205 212
14. R.B. Greenwald, A. Pendri, C.D. Conover, C. Lee, Y.H. Choe, C. Gilbert, A. Martinez, J. Xia, D. Wu, and M. Hsue Bioorg. Med. Chem. 6 1998 551 562
15. M.P. Hay, W.R. Wilson, and W.A. Denny Tetrahedron 56 2000 645 657
16. M.J. Kavarana, E.G. Kovaleva, D.J. Creighton, M.B. Wollman, and J.L. Eiseman J. Med. Chem. 42 1999 221 228
17. R.B. Greenwald, C.D. Conover, and Y.H. Choe Crit. Rev. Ther. Drug 17 2000 101 161
18. QikProp, Version 1.6, Schrodinger, New York, 2001
19. W. Peters, J.H. Portus, and B.L. Robinson Ann. Trop. Med. Parasitol. 69 1975 155 171
20. W.L. Jorgensen, and E.M. Duffy Adv. Drug Delivery Rev. 54 2002 355 366
21. W.L. Jorgensen, and E.M. Duffy Bioorg. Med. Chem. Lett. 10 2000 1155 1158
22. E.M. Duffy, and W.L. Jorgensen J. Am. Chem. Soc. 122 2000 2878 2888
23. R.E. Desjardins, C.J. Canfield, J.D. Haynes, and J.D. Chulay Antimicrob. Agents Chemother. 16 1979 710 718
24. A. Vogt, Y. Qian, T.F. McGuire, A.D. Hamilton, and S.M. Sebti Oncogene 13 1996 1991 1999
25. D.L. Pompliano, E. Rands, M.D. Schaber, S.D. Mosser, N.J. Anthony, and J.B. Gibbs Biochemistry 31 1992 3800 3807
26. D. Chakrabarti, T. Da Silva, J. Barger, S. Paquette, H. Patel, S. Patterson, and C.M. Allen J. Biol. Chem. 277 2002 42066 42073