Novel TypeII Fatty Acid Biosynthesis (FAS II) Inhibitors as Multistage Antimalarial Agents

ChemMedChem

Volumn 8, Issue 3, 2013, Pages 442-461

  Schrader, Florian C ^a   Glinca, Serghei ^a   Sattler, Julia M ^b   Dahse, Hans Martin ^c   Afanador, Gustavo A ^d   Prigge, Sean T ^d   Lanzer, Michael ^b   Mueller, Ann Kristin ^b   Klebe, Gerhard ^a   Schlitzer, Martin ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

^b UNIVERSITY HOSPITAL HEIDELBERG   (Germany)

^c HANS KNÖLL INSTITUTE   (Germany)

^d JOHNS HOPKINS BLOOMBERG SCHOOL OF PUBLIC HEALTH   (United States)

Author keywords

Antimalarial agents; Fatty acid biosynthesis; Molecular modeling; Multistage inhibitors; Plasmodium falciparum; Virtual screening

Indexed keywords

2 (3 TOLYLAMINO)ACETOHYDRAZIDE; 2 (3 TOLYLOXY)ACETONITRILE; 2 (3 TOLYLSULFANYL)ACETONITRILE; 2 (4 ISOPROPYLPHENOXY)ACETONITRILE; 2 (5,6,7,8 TETRAHYDRONAPHTHALEN 2 YLOXY)ACETONITRILE; 2 (NAPHTHALEN 1 YLOXY)ACETONITRILE; 2 [(4 TOLYLAMINO)METHYL]ISOINDOLINE 1,3 DIONE; 2 HYDROXY N [2 (3 TOLYLOXY)ETHYL]BENZAMIDE; 3 [(3 TOLYLAMINO)METHYL]CHINOLIN 2 OL; 3 [(3 TOLYLIMINO)METHYL]QUINOLIN 2 OL; 4 (5 METHYLBENZ[D]OXAZOL 2 YL)BENZENE 1,3 DIOL; 4 [(2 HYDROXY 5 METHYLPHENYLIMINO)METHYL]BENZENE 1,3 DIOL; 4 CYCLOHEXYL 1 (4 HYDROXYBENZALDEHYDE)THIOSEMICARBAZONE; 4 CYCLOHEXYL 1 (4 HYDROXYBENZYL)THIOSEMICARBAZIDE; 5 (4 METHOXYBENZYLAMINO) 1H BENZ[D]IMIDAZOL 2 (3H) ONE; 5 (4 METHOXYBENZYLIDENEAMINO) 1H BENZ[D]IMIDAZOL 2 (3H) DIONE; AMIDE; ANTIMALARIAL AGENT; BENZOIC ACID DERIVATIVE; ENOYL ACYL CARRIER PROTEIN REDUCTASE INHIBITOR; FATTY ACID SYNTHASE INHIBITOR; METHYL 2 (3 TOLYLAMINO)ACETATE; N [(1H BENZO[D][1,2,3]TRIAZOL 1 YL)METHYL] 3 CHLOROANILINE; N' BENZYL 2 (3 TOLYLAMINO)ACETOHYDRAZIDE; N' BENZYLIDENE 2 (3 TOLYLAMINO)ACETOHYDRAZIDE; OXIDOREDUCTASE INHIBITOR; PRIMAQUINE; SALICYLIC ACID DERIVATIVE; TRICLOSAN DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG; ENOYL ACYL CARRIER PROTEIN REDUCTASE (NADH); ENZYME INHIBITOR; FATTY ACID;

ANTIMALARIAL ACTIVITY; ARTICLE; COMBINATORIAL LIBRARY; CONTROLLED STUDY; CRYSTAL STRUCTURE; CYTOTOXICITY; DRUG EFFICACY; DRUG SCREENING; HUMAN; HUMAN CELL; IC 50; MOLECULAR DOCKING; NONHUMAN; PLASMODIUM (LIFE CYCLE STAGE); PLASMODIUM BERGHEI; PLASMODIUM FALCIPARUM; PRIORITY JOURNAL; SPOROZOITE; STANDARD; STRUCTURE ACTIVITY RELATION; TOXOPLASMA GONDII; VIRTUAL REALITY; BINDING SITE; BIOSYNTHESIS; CELL SURVIVAL; CHEMISTRY; DRUG ANTAGONISM; DRUG EFFECT; ENZYMOLOGY; HELA CELL; METABOLISM; PROTEIN TERTIARY STRUCTURE; SYNTHESIS; TUMOR CELL LINE;

ANTIMALARIALS; BINDING SITES; CELL LINE, TUMOR; CELL SURVIVAL; ENOYL-(ACYL-CARRIER-PROTEIN) REDUCTASE (NADH); ENZYME INHIBITORS; FATTY ACIDS; HELA CELLS; HUMANS; MOLECULAR DOCKING SIMULATION; PLASMODIUM BERGHEI; PROTEIN STRUCTURE, TERTIARY; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84874315157     PISSN: 18607179     EISSN: 18607187     Source Type: Journal    
DOI: 10.1002/cmdc.201200407     Document Type: Article

References (48)

1. C. J. L. Murray, L. C. Rosenfeld, S. S. Lim, K. G. Andrews, K. J. Foreman, D. Haring, N. Fullman, M. Naghavi, R. Lozano, A. D. Lopez, Lancet 2012, 379, 413-431.
2. A. Sturm, Science 2006, 313, 1287-1290.
3. World Malaria Report 2010, World Health Organization (WHO) Global Malaria Programme, 2010; available here: http://www.who.int/malaria/world_malaria_report_2010/worldmalariareport2010.pdf (Last accessed: December 8, 2012) .
4. M. Yu, T. R. S. Kumar, L. J. Nkrumah, A. Coppi, S. Retzlaff, C. D. Li, B. J. Kelly, P. A. Moura, V. Lakshmanan, J. S. Freundlich, J.-C. Valderramos, C. Vilcheze, M. Siedner, J. H.-C. Tsai, B. Falkard, A. birSinghSidhu, L. A. Purcell, P. Gratraud, L. Kremer, A. P. Waters, G. Schiehser, etal., Cell Host Microbe 2008, 4, 567-578.
5. A. S. Tarun, A. M. Vaughan, S. H. I. Kappe, Trends Parasitol. 2009, 25, 545-550.
6. H. J. Vial, M. J. Thuet, J. R. Philippot, J. Protozool. 1982, 29, 258-263.
7. L. M. McMurry, M. Oethinger, S. B. Levy, Nature 1998, 394, 531-532.
8. G. I. McFadden, M. E. Reith, J. Munholland, N. Lang-Unnasch, Nature 1996, 381, 482;
9. S. Kohler, Science 1997, 275, 1485-1489.
10. M. Kapoor, M. J. Dar, A. Surolia, N. Surolia, Biochem. Biophys. Res. Commun. 2001, 289, 832-837.
11. N. Surolia, A. Surolia, Nat. Med. 2001, 7, 167-173.
12. R. McLeod, S. P. Muench, J. B. Rafferty, D. E. Kyle, E. J. Mui, M. J. Kirisits, D. G. Mack, C. W. Roberts, B. U. Samuel, R. E. Lyons, M. Dorris, W. K Milhous, D. W. Rice, Int. J. Parasitol. 2001, 31, 109-113.
13. A. M. Vaughan, M. T. O'Neill, A. S. Tarun, N. Camargo, T. M. Phuong, A. S. I. Aly, A. F. Cowman, S. H. I. Kappe, Cell. Microbiol. 2009, 11, 506-520.
14. M. D. Spalding, S. T. Prigge, Cell Host Microbe 2008, 4, 509-511.
15. S. D. Kohlwein, S. Eder, C.-S. Oh, C. E. Martin, K. Gable, D. Bacikova, T. Dunn, Mol. Cell. Biol. 2001, 21, 109-125.
16. S. H. Lee, J. L. Stephens, K. S. Paul, P. T. Englund, Cell 2006, 126, 691-699.
17. S. P. Muench, S. T. Prigge, R. McLeod, J. B. Rafferty, M. J. Kirisits, C. W. Roberts, E. J. Mui, D. W. Rice, Acta Crystallogr. Sect. D 2007, 63, 328-338.
18. D. Tasdemir, G. Lack, R. Brun, P. Rüedi, L. Scapozza, R. Perozzo, J. Med. Chem. 2006, 49, 3345-3353.
19. D. Tasdemir, B. Topaloglu, R. Perozzo, R. Brun, R. O'Neill, N. M. Carballeira, X. Zhang, P. J. Tonge, A. Linden, P. Rüedi, Bioorg. Med. Chem. 2007, 15, 6834-6845.
20. J. S. Freundlich, F. Wang, H.-C. Tsai, M. Kuo, H.-M. Shieh, J. W. Anderson, L. J. Nkrumah, J.-C. Valderramos, M. Yu, T. R. S. Kumar, J. Biol. Chem. 2007, 282, 25436-25444.
21. G. Jones, P. Willett, R. C. Glen, J. Mol. Biol. 1995, 245, 43-53.
22. G. Neudert, G. Klebe, J. Chem. Inf. Model. 2011, 51, 2731-2745.
23. R. Perozzo, M. Kuo, A. b. S. Sidhu, J. T. Valiyaveettil, R. Bittman, W. R. Jacobs, D. A. Fidock, J. C. Sacchettini, J. Biol. Chem. 2002, 277, 13106-13114.
24. M. R. Hollingdale, P. Leland, A. L. Schwartz, Am. J. Trop. Med. Hyg. 1983, 32, 682-684.
25. M. Tsuji, D. Mattei, R. S. Nussenzweig, D. Eichinger, F. Zavala, Parasitol. Res. 1994, 80, 16-21.
26. C. Pinzon-Ortiz, J. Friedman, J. Esko, P. Sinnis, J. Biol. Chem. 2001, 276, 26784-26791.
27. S. Choi, B. Sainz Jr., P. Corcoran, S. Uprichard, H. Jeong, Xenobiotica 2009, 39, 205-217.
28. J. L. Vennerstrom, E. O. Nuzum, R. E. Miller, A. Dorn, L. Gerena, P. A. Dande, W. Y. Ellis, R. G. Ridley, W. K. Milhous, Antimicrob. Agents Chemother. 1999, 43, 598-602.
29. T. Qidwai, F. Khan, Chem. Biol. Drug Des. 2012, 80, 155-172.
30. A. R. Katritzky, S. Rachwal, J. Wu, Can. J. Chem. 1990, 68, 446-455.
31. M. B. Winstead, H. W. Heine, J. Am. Chem. Soc. 1955, 77, 1913-1914.
32. M. C. Cruz, F. Jiménez, F. Delgado, J. Tamariz, Synlett 2006, 749-755.
33. G. C. Finger, D. R. Dickerson, L. D. Starr, D. E. Orlopp, J. Med. Chem. 1965, 8, 405-407.
34. P. Jütten, W. Schumann, A. Härtl, H.-M. Dahse, U. Gräfe, J. Med. Chem. 2007, 50, 3661-3666.
35. P. E. Morris Jr., A. J. Elliott, S. P. Walton, C. H. Williams, J. A. Montgomery, Nucleosides Nucleotides Nucleic Acids 2000, 19, 379-404.
36. H. Köster, T. Craan, S. Brass, C. Herhaus, M. Zentgraf, L. Neumann, A. Heine, G. Klebe, J. Med. Chem. 2011, 54, 7784-7796.
37. Molecular Operating Environment (MOE), version2010.10, Chemical Computing Group Inc. (Montreal, Canada), 2010.
38. W. T. M. Mooij, M. L. Verdonk, Proteins 2005, 61, 272-287.
39. The PyMOL Molecular Graphics System, version1.2r2, Schrödinger, LLC; http://www.pymol.org/.
40. J. J. Irwin, B. K. Shoichet, J. Chem. Inf. Model. 2005, 45, 177-182.
41. G. Neudert, G. Klebe, Bioinformatics 2011, 27, 1021-1022.
42. BioSolveIT, BioSolveIT GmbH (Sankt Augustin, Germany); http://www.biosolveit.de/.
43. W. Trager, J. B. Jensen, J. Parasitol. 2005, 91, 484-486.
44. C. Lambros, J. P. Vanderberg, J. Parasitol. 1979, 65, 418-420.
45. R. E. Desjardins, C. J. Canfield, J. D. Haynes, J. D. Chulay, Antimicrob. Agents Chemother. 1979, 16, 710-718;
46. M. Smilkstein, N. Sriwilaijaroen, J. X. Kelly, P. Wilairat, M. Riscoe, Antimicrob. Agents Chemother. 2004, 48, 1803-1806.
47. S. P. Muench, S. T. Prigge, L. Zhu, M. J. Kirisits, C. W. Roberts, S. Wernimont, R. McLeod, D. W. Rice, Acta Crystallogr. Sect. F 2006, 62, 604-606.
48. S. K. Tipparaju, S. P. Muench, E. J. Mui, S. N. Ruzheinikov, J. Z. Lu, S. L. Hutson, M. J. Kirisits, S. T. Prigge, C. W. Roberts, F. L. Henriquez, A. P. Kozikowski, D. W. Rice, R. L. McLeod, J. Med. Chem. 2010, 53, 6287-6300.