Synthesis and biological evaluation of new 2-alkylaminoethyl-1,1- bisphosphonic acids against Trypanosoma cruzi and Toxoplasma gondii targeting farnesyl diphosphate synthase

Bioorganic and Medicinal Chemistry

Volumn 19, Issue 7, 2011, Pages 2211-2217

  Rosso, Valeria S ^a,b   Szajnman, Sergio H ^a   Malayil, Leena ^b   Galizzi, Melina ^b   Moreno, Silvia N J ^b   Docampo, Roberto ^b   Rodriguez, Juan B ^a  

^a UNIVERSIDAD DE BUENOS AIRES   (Argentina)

^b UNIVERSITY OF GEORGIA   (United States)

Author keywords

Chagas' disease; Farnesyl pyrophosphate synthase; Toxoplasma gondii; Toxoplasmosis; Trypanosoma cruzi

Indexed keywords

1 (2 ALKYLAMINOETHYL) 1,1 BISPHOSPHONIC ACID DERIVATIVE; 1 [(BENZYLAMINO)ETHYL] 1,1 BISPHOSPHONIC ACID; 1 [(N DEC 1 YLAMINO)ETHYL] 1,1 BISPHOSPHONIC ACID; 1 [(N DODEC 1 YLAMINO)ETHYL] 1,1 BISPHOSPHONIC ACID; 1 [(N HEXADEC 1 YLAMINO)ETHYL] 1,1 BISPHOSPHONIC ACID; 1 [(N NON 1 YLAMINO)ETHYL] 1,1 BISPHOSPHONIC ACID; 1 [(N OCTADEC 1 YLAMINO)ETHYL] 1,1 BISPHOSPHONIC ACID; 1 [(N TETRADEC 1 YLAMINO)ETHYL] 1,1 BISPHOSPHONIC ACID; 1 [(N UNDEC 1 YLAMINO)ETHYL] 1,1 BISPHOSPHONIC ACID; ANTIPROTOZOAL AGENT; BENZNIDAZOLE; GERANYLTRANSFERASE; MICROORGANISM PROTEIN; OCTAPRENYLTRANSFERASE; TETRAETHYL 1 [(BENZYLAMINO)ETHYL] 1,1 BISPHOSPHONATE; TETRAETHYL 1 [(N DEC 1 YLAMINO)ETHYL] 1,1 BISPHOSPHONATE; TETRAETHYL 1 [(N DODEC 1 YLAMINO)ETHYL] 1,1 BISPHOSPHONATE; TETRAETHYL 1 [(N HEXADEC 1 YLAMINO)ETHYL] 1,1 BISPHOSPHONATE; TETRAETHYL 1 [(N NON 1 YLAMINO)ETHYL] 1,1 BISPHOSPHONATE; TETRAETHYL 1 [(N OCTADEC 1 YLAMINO)ETHYL] 1,1 BISPHOSPHONATE; TETRAETHYL 1 [(N TETRADEC 1 YLAMINO)ETHYL] 1,1 BISPHOSPHONATE; TETRAETHYL 1 [(N UNDEC 1 YLAMINO)ETHYL] 1,1 BISPHOSPHONATE; UNCLASSIFIED DRUG;

AMASTIGOTE; ARTICLE; CHAGAS DISEASE; CONTROLLED STUDY; DRUG SCREENING; DRUG SYNTHESIS; DRUG TARGETING; ENZYME ACTIVITY; ENZYME INHIBITION; IC 50; NONHUMAN; TACHYZOITE; TOXOPLASMA GONDII; TRYPANOSOMA CRUZI;

ANIMALS; ANTIPROTOZOAL AGENTS; CERCOPITHECUS AETHIOPS; DIPHOSPHONATES; ENZYME INHIBITORS; GERANYLTRANSTRANSFERASE; MOLECULAR TARGETED THERAPY; STRUCTURE-ACTIVITY RELATIONSHIP; TOXOPLASMA; TRYPANOSOMA CRUZI; VERO CELLS;

TOXOPLASMA GONDII; TRYPANOSOMA CRUZI;

EID: 79953227657     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2011.02.037     Document Type: Article

References (48)

1. J.A. Urbina, and R. Docampo Trends Parasitol. 19 2003 495
2. J.A. Urbina Acta Trop. 115 2010 55
3. J.A. Urbina Drugs Future 35 2010 409
4. G. García Liñares, E.L. Ravaschino, and J.B. Rodriguez Curr. Med. Chem. 13 2006 335
5. Z. Brener Annu. Rev. Microbiol. 27 1973 347
6. L.V. Kirchhoff N. Eng. J. Med. 329 1993 639
7. S.A. Galel, and L.V. Kirchhoff Transfusion 36 1996 227
8. V. Nussenzweig, R. Sonntag, A. Biancalana, J.L. Pedreira de Fleitas, V. Amato Neto, and J. Kloetzel Hospital (Rio de Janeiro) 44 1953 731
9. R. Docampo, and S.N.J. Moreno Rev. Biochem. Toxicol. 7 1985 159
10. J.A. Urbina Mem. Inst. Oswaldo Cruz 94 1999 349
11. R. Docampo, and S.N. Moreno Curr. Drug Targets: Infect. Disord. 1 2001 51
12. R. Docampo, and S.N.J. Moreno Curr. Pharm. Des. 14 2008 882
13. M.H. Gelb, W.C. Van Voorhis, F.S. Buckner, K. Yokoyama, R. Eastman, E.P. Carpenter, C. Panethymitaki, K.A. Brown, and D.F. Smith Mol. Biochem. Parasitol. 726 2003 155
14. A. Montalvetti, B.N. Bailey, M.B. Martin, G.W. Severin, E. Oldfield, and R. Docampo J. Biol. Chem. 276 2001 33930
15. A. Montalvetti, A. Fernandez, J.M. Sanders, S. Ghosh, E. Van Brussel, E. Oldfield, and R. Docampo J. Biol. Chem. 278 2003 17075
16. S.B. Gabelli, J.S. McLellan, A. Montalvetti, E. Oldfield, R. Docampo, and L.M. Amzel Proteins 62 2006 80
17. M. Ferella, A. Montalvetti, P. Rohloff, K. Miranda, J. Fang, S. Reina, M. Kawamukai, J. Búa, D. Nilsson, C. Pravia, A. Katzin, M.B. Cassera, L. Aslund, B. Andersson, R. Docampo, and E.J. Bontempi J. Biol. Chem. 281 2006 39339
18. A.A. Reszka, and G.A. Rodan Mini-Rev. Med. Chem. 4 2004 711
19. A.A. Reszka, and G.A. Rodan Curr. Osteoporos. Rep. 1 2003 45
20. M.B. Martin, J.S. Grimley, J.C. Lewis, H.T. Heath III, B.N. Bailey, H. Kendrick, V. Yardley, A. Caldera, R. Lira, J.A. Urbina, S.N.J. Moreno, R. Docampo, S.L. Croft, and E. Oldfield J. Med. Chem. 44 2001 909
21. D.E. Hughes, K.R. Wright, H.L. Uy, A. Sasaki, T. Yoneda, G.D. Roodman, G.R. Mundy, and B.F. Boyce J. Bone Miner. Res. 10 1995 1478
22. M.J. Rogers, J.C. Frith, S.P. Luckman, F.P. Coxon, H.L. Benford, J. Monkkonen, S. Auriola, K.M. Chilton, and R.G. Russell Bone 24 1999 73S
23. J.A. Urbina, B. Moreno, S. Vierkotter, E. Oldfield, G. Payares, C. Sanoja, B.N. Bailey, W. Yan, D.A. Scott, S.N.J. Moreno, and R. Docampo J. Biol. Chem. 274 1999 33609
24. M.B. Martin, J.M. Sanders, H. Kendrick, K. De Luca-Fradley, J.C. Lewis, J.S. Grimley, E.M. Van Brussel, J.R. Olsen, G.A. Meints, A. Burzynska, P. Kafarski, S.L. Croft, and E. Oldfield J. Med. Chem. 45 2002 2904
25. S. Ghosh, J.M. Chan, C.R. Lea, G.A. Meints, J.C. Lewis, Z.S. Tovian, R.M. Flessner, T.C. Loftus, I. Bruchhaus, H. Kendrick, S.L. Croft, R.G. Kemp, S. Kobayashi, T. Nozaki, and E. Oldfield J. Med. Chem. 47 2004 175
26. S.H. Szajnman, G.E. García Liñares, Z.-H. Li, M. Galizzi, C. Jiang, E. Bontempi, M. Ferella, S.N.J. Moreno, R. Docampo, and J.B. Rodriguez Bioorg. Med. Chem. 16 2008 3283
27. S.H. Szajnman, B.N. Bailey, R. Docampo, and J.B. Rodriguez Bioorg. Med. Chem. Lett. 11 2001 789
28. S.H. Szajnman, A. Montalvetti, Y. Wang, R. Docampo, and J.B. Rodriguez Bioorg. Med. Chem. Lett. 13 2003 3231
29. S.H. Szajnman, E.L. Ravaschino, R. Docampo, and J.B. Rodriguez Bioorg. Med. Chem. Lett. 15 2005 4685
30. Y. Ling, G. Sahota, S. Odeh, J.M.W. Chan, F.G. Araujo, S.N.J. Moreno, and E. Oldfield J. Med. Chem. 48 2005 3130
31. B. Bouzahzah, L.A. Jelicks, S.A. Morris, L.M. Weiss, and H.B. Tanowitz Parasitol. Res. 96 2005 184
32. Amzel, L. M. Personal communication.
33. D.J. Hosfield, Y. Zhang, D.R. Dougan, A. Broun, L.W. Tari, R.V. Swanson, and J. Finn J. Biol. Chem. 278 2003 18401
34. L.C. Tarshis, P.J. Proteau, B.A. Kellogg, J.C. Sacchettini, and C.D. Poulter Proc. Natl. Acad. Sci. U.S.A. 93 1996 15018
35. C.-H. Huang, S.B. Gabelli, E. Oldfield, and L.M. Amzel Proteins 78 2010 888
36. R. Cao, C.K.-M. Chen, R.-T. Guo, A.H.-J. Wang, and E. Oldfield Proteins 73 2008 431
37. S.H. Szajnman, G.E. García Liñares, P. Moro, and J.B. Rodríguez Eur. J. Org. Chem. 2005 3687
38. C.R. Degenhardt, and D.C. Burdsall J. Org. Chem. 51 1986 3488
39. P.C. Bulman Page, P.G. Jonathan, J.P.G. Moore, I. Mansfield, M.J. McKenzie, W.B. Bowler, and J.A. Gallagher Tetrahedron 57 2001 1837
40. L. Lazzarato, B. Rolando, M.L. Lolli, G.C. Tron, R. Fruttero, A. Gasco, G. Deleide, and H.L. Guenther J. Med. Chem. 48 2005 1322
41. J.A. Urbina, J.L. Concepcion, A. Montalvetti, J.B. Rodriguez, and R. Docampo Antimicrob. Agents Chemother. 47 2003 2047
42. C.O. Rodrigues, D.A. Scott, B. Bailey, W. de Souza, M. Benchimol, B. Moreno, J.A. Urbina, E. Oldfield, and S.N.J. Moreno Biochem. J. 349 2000 737
43. A.M. Canavaci, J.M. Bustamante, A.M. Padilla, C.M. Pereza Brandan, L.J. Simpson, D. Xu, C.L. Boehlke, and R.L. Tarleton PLOS Negl. Trop. Dis. 4 2010 e740
44. M.J. Gubbels, C. Li, and B. Striepen Antimicrob. Agents Chemother. 43 2003 309
45. S. Agrawal, G.G. van Dooren, W.L. Beatty, and B. Striepen J. Biol. Chem. 284 2009 33683
46. E.L. Ravaschino, R. Docampo, and J.B. Rodriguez J. Med. Chem. 49 2006 426
47. K. Ogura, T. Nishino, T. Shinka, and S. Seto Methods Enzymol. 110 1985 167
48. H.C. Rilling Methods Enzymol. 110 1985 145