Modification of triclosan scaffold in search of improved inhibitors for enoyl-acyl carrier protein (ACP) Reductase in Toxoplasma gondii

ChemMedChem

Volumn 8, Issue 7, 2013, Pages 1138-1160

  Stec, Jozef ^a,h   Fomovska, Alina ^b,i   Afanador, Gustavo A ^c   Muench, Stephen P ^d   Zhou, Ying ^b   Lai, Bo Shiun ^b   El Bissati, Kamal ^b   Hickman, Mark R ^e   Lee, Patty J ^e   Leed, Susan E ^e   Auschwitz, Jennifer M ^e   Sommervile, Caroline ^f   Woods, Stuart ^f   Roberts, Craig W ^f   Rice, David ^g   Prigge, Sean T ^c   Mcleod, Rima ^b   Kozikowski, Alan P ^a  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

^b UNIVERSITY OF CHICAGO   (United States)

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

^d UNIVERSITY OF LEEDS   (United Kingdom)

^e WALTER REED ARMY INSTITUTE OF RESEARCH   (United States)

^f UNIVERSITY OF STRATHCLYDE   (United Kingdom)

^g UNIVERSITY OF SHEFFIELD   (United Kingdom)

^h CHICAGO STATE UNIVERSITY   (United States)

ⁱ MOUNT SINAI SCHOOL OF MEDICINE   (United States)

Author keywords

Enoyl reductase; Inhibitors; Medicinal chemistry; Toxoplasma gondii; Triclosan

Indexed keywords

1 [4 (2,4 DICHLOROPHENOXY) 3 HYDROXYPHENYL]PROPAN 1 ONE; 1 [4 (2,4 DICHLOROPHENOXY) 3 METHOXYBENZYL] 4 (TRIMETHYLSILYL) 1H 1,2,3 TRIAZOLE; 1 [4 (2,4 DICHLOROPHENOXY) 3 METHOXYBENZYL] 4 PHENYL 1H 1,2,3 TRIAZOLE; 2 (2,4 DICHLOROPHENOXY) 5 (1H 1,2,3 TRIAZOL 1 YL METHYL)PHENOL; 2 (2,4 DICHLOROPHENOXY) 5 (5 PHENYL 1,2 OXAZOL 3 YL)PHENOL; 2 (2,4 DICHLOROPHENOXY) 5 [(4 PHENYL 1H 1,2,3 TRIAZOL 1 YL)METHYL]PHENOL; 2 (2,4 DICHLOROPHENOXY) 5 [(HEXYLAMINO)METHYL]PHENOL; 2 (2,4 DICHLOROPHENOXY) 5 [(PHENYLAMINO)METHYL]PHENOL; 2 (2,4 DICHLOROPHENOXY) 5 [5 (TRIMETHYLSILYL) 1,2 OXAZOL 3 YL]PHENOL; 2 [1 [4 (2,4 DICHLOROPHENOXY) 3 METHOXYBENZYL] 1H 1,2,3 TRIAZOL 4 YL]ETHANOL; 2 [1 [4 (2,4 DICHLOROPHENOXY) 3 METHOXYBENZYL] 1H 1,2,3 TRIAZOLE 4 YL]ETHANOL; 2 [4 (5 BUTYL 1,2 OXAZOL 3 YL) 2 CHLOROPHENOXY] 5 CHLOROPHENOL; 2 [4 [(4 BUTYL 1H 1,2,3 TRIAZOL 1 YL)METHYL] 2 CHLOROPHENOXY] 5 CHLOROPHENOL; 4 (2,4 DICHLOROPHENOXY) 3 HYDROXY N PHENYLBENZAMIDE; 4 (2,4 DICHLOROPHENOXY) 3 HYDROXY N,N DIBUTYLBENZAMIDE; 4 (2,4 DICHLOROPHENOXY) 3 HYDROXYBENZONITRILE; 5 (5 BUTYL 1,2 OXAZOL 3 YL) 2 (2,4 DICHLOROPHENOXY)PHENOL; 5 CHLORO 2 [2 CHLORO 4 (5 PHENYL 1,2 OXAZOL 3 YL)PHENOXY]PHENOL; 5 CHLORO 2 [2 CHLORO 4 [(1H 1,2,3 TRIAZOL 1 YL)METHYL]PHENOXY]PHENOL; 5 CHLORO 2 [2 CHLORO 4 [(4 HENYL 1H 1,2,3 TRIAZOL 1 YL)METHYL]PHENOXY]PHENOL; 5 CHLORO 2 [2 CHLORO 4 [(HEXYLAMINO)METHYL]PHENOXY]PHENOL; 5 CHLORO 2 [2 CHLORO 4 [(PHENYLAMINO)METHYL]PHENOXY]PHENOL; 5 [(4 BUTYL 1H 1,2,3 TRIAZOL 1 YL)METHYL] 2 (2,4 DICHLOROPHENOXY)PHENOL; 5 [(CYCLOHEXYLAMINO)METHYL] 2 (2,4 DICHLOROPHENOXY)PHENOL; ENOYL ACYL CARRIER PROTEIN REDUCTASE (NADH); TRICLOSAN; UNCLASSIFIED DRUG; [4 (2,4 DICHLOROPHENOXY) 3 HYDROXYPHENYL](MORPHOLIN 4 YL)METHANONE; [4 (2,4 DICHLOROPHENOXY) 3 HYDROXYPHENYL](PHENYL)METHANONE;

ARTICLE; CHEMICAL MODIFICATION; CONTROLLED STUDY; DRUG DESIGN; DRUG POTENCY; DRUG STRUCTURE; ENZYME ASSAY; HOST CELL; HUMAN; HUMAN CELL; IC 50; NONHUMAN; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; TACHYZOITE; TOXICITY; TOXOPLASMA GONDII; TOXOPLASMOSIS;

ANIMALS; ANTIPROTOZOAL AGENTS; CACO-2 CELLS; DISEASE MODELS, ANIMAL; DOSE-RESPONSE RELATIONSHIP, DRUG; ENOYL-(ACYL-CARRIER-PROTEIN) REDUCTASE (NADH); ENZYME INHIBITORS; HUMANS; MICE; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PARASITIC SENSITIVITY TESTS; PERMEABILITY; PLASMODIUM FALCIPARUM; STRUCTURE-ACTIVITY RELATIONSHIP; TOXOPLASMA; TOXOPLASMOSIS; TRICLOSAN;

EID: 84879779979     PISSN: 18607179     EISSN: 18607187     Source Type: Journal    
DOI: 10.1002/cmdc.201300050     Document Type: Article

References (77)

1. A. M. Tenter, A. R. Heckeroth, L. M. Weiss, Int. J. Parasitol. 2000, 30, 1217-1258.
2. C. G. Lüder, W. Bohne, D. Soldati, Trends Parasitol. 2001, 17, 460-463.
3. B. J. Luft, J. S. Remington, Clin. Infect. Dis. 1992, 15, 211-222.
4. M. Hayde, A. Pollak in Congenital Toxoplasmosis: Scientific Background, Clinical Management and Control (Eds.: P. Ambroise-Thomas, E. Petersen), Springer, Amsterdam, 2000; pp.153-164.
5. F. Roberts, M. B. Mets, D. J. Ferguson, R. O'Grady, C. O'Grady, P. Thulliez, A. P. Brézin, R. McLeod, Arch. Ophthalmol. 2001, 119, 51-58.
6. J. P. Dubey, D. S. Lindsay, C. A. Speer, Clin. Microbiol. Rev. 1998, 11, 267-299.
7. J. P. Dubey, J. Eukaryotic Microbiol. 2008, 55, 467-475.
8. J. G. Montoya, O. Liesenfeld, Lancet 2004, 363, 1965-1976.
9. G. I. McFadden, M. E. Reith, J. Munholland, N. Lang-Unnasch, Nature 1996, 381, 482.
10. S. Köhler, C. F. Delwiche, P. W. Denny, L. G. Tilney, P. Webster, R. J. Wilson, J. D. Palmer, D. S. Roos, Science 1997, 275, 1485-1489.
11. C. D. Goodman, G. I. McFadden, Curr. Drug Targets 2007, 8, 15-30.
12. J. Wiesner, A. Reichenberg, S. Heinrich, M. Schlitzer, H. Jomaa, Curr. Pharm. Des. 2008, 14, 855-871.
13. S. W. White, J. Zheng, Y. M. Zhang, C. O. Rock, Annu. Rev. Biochem. 2005, 74, 791-831.
14. C. O. Rock, S. Jackowski, Biochem. Biophys. Res. Commun. 2002, 292, 1155-1166.
15. S. Smith, FASEB J. 1994, 8, 1248-1259.
16. R. J. Heath, C. O. Rock, J. Biol. Chem. 1995, 270, 26538-26542.
17. R. J. Heath, N. Su, C. K. Murphy, C. O. Rock, J. Biol. Chem. 2000, 275, 40128-40133.
18. R. P. Massengo-Tiasse, J. E. Cronan, J. Biol. Chem. 2008, 283, 1308-1316.
19. H. Marrakchi, W. E. DeWolf, Jr., C. Quinn, J. West, B. J. Polizzi, C. Y. So, D. J. Holmes, S. L. Reed, R. J. Heath, D. J. Payne, C. O. Rock, N. G. Wallis, Biochem. J. 2003, 370, 1055-1062.
20. K. Ryall, J. T. Harper, P. J. Keeling, Gene 2003, 313, 139-148.
21. B. U. Samuel, B. Hearn, D. Mack, P. Wender, J. Rothbard, M. J. Kirisits, E. Mui, S. Wernimont, C. W. Roberts, S. P. Muench, D. W. Rice, S. T. Prigge, A. B. Law, R. McLeod, Proc. Natl. Acad. Sci. USA 2003, 100, 14281-14286.
22. D. J. Ferguson, F. L. Henriquez, M. J. Kirisits, S. P. Muench, S. T. Prigge, D. W. Rice, C. W. Roberts, R. L. McLeod, Eukaryotic Cell 2005, 4, 814-826.
23. 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.
24. N. Surolia, A. Surolia, Nat. Med. 2001, 7, 167-173.
25. E. S. Martins-Duarte, S. M. Jones, I. H. Gilbert, G. C. Atella, W. deSouza, R. C. Vommaro, Parasitol. Int. 2009, 58, 411-415.
26. J. Z. Lu, S. P. Muench, M. Allary, S. Campbell, C. W. Roberts, E. Mui, R. L. McLeod, D. W. Rice, S. T. Prigge, Parasitology 2007, 134, 1949-1962.
27. L. M. McMurry, M. Oethinger, S. B. Levy, Nature 1998, 394, 531-532.
28. R. J. Heath, Y. T. Yu, M. A. Shapiro, E. Olson, C. O. Rock, J. Biol. Chem. 1998, 273, 30316-30320.
29. W. H. Ward, G. A. Holdgate, S. Rowsell, E. G. McLean, R. A. Pauptit, E. Clayton, W. W. Nichols, J. G. Colls, C. A. Minshull, D. A. Jude, A. Mistry, D. Timms, R. Camble, N. J. Hales, C. J. Britton, I. Taylor, Biochemistry 1999, 38, 12514-12525.
30. M. Kapoor, C. C. Reddy, M. V. Krishnasastry, N. Surolia, A. Surolia, Biochem. J. 2004, 381, 719-724.
31. R. Perozzo, M. Kuo, A. S. Sidhu, J. T. Valiyaveettil, R. Bittman, W. R. J. Jacobs, D. A. Fidock, J. C. Sacchettini, J. Biol. Chem. 2002, 277, 13106-13114.
32. S. Sivaraman, T. J. Sullivan, F. Johnson, P. Novichenok, G. Cui, C. Simmerling, P. J. Tonge, J. Med. Chem. 2004, 47, 509-518.
33. J. S. Freundlich, J. W. Anderson, D. Sarantakis, H. M. Shieh, M. Yu, J. C. Valderramos, E. Lucumi, M. Kuo, W. R. J. Jacobs, D. A. Fidock, G. A. Schiehser, D. P. Jacobus, J. C. Sacchettini, Bioorg. Med. Chem. Lett. 2005, 15, 5247-5252.
34. M. Chhibber, G. Kumar, P. Parasuraman, T. N. Ramya, N. Surolia, A. Surolia, Bioorg. Med. Chem. 2006, 14, 8086-8098.
35. S. K. Tipparaju, D. C. Mulhearn, G. M. Klein, Y. Chen, S. Tapadar, M. H. Bishop, S. Yang, J. Chen, M. Ghassemi, B. D. Santarsiero, J. L. Cook, M. Johlfs, A. D. Mesecar, M. E. Johnson, A. P. Kozikowski, ChemMedChem 2008, 3, 1250-1268.
36. J. S. Freundlich, F. Wang, C. Vilchèze, G. Gulten, R. Langley, G. A. Schiehser, D. P. Jacobus, W. R. J. Jacobs, J. C. Sacchettini, ChemMedChem 2009, 4, 241-248.
37. 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.
38. A. A. Divo, T. G. Geary, J. B. Jensen, Antimicrob. Agents Chemother. 1985, 27, 21-27.
39. B. Wang, Y. Gua, G. Songa, T. Yang, L. Yang, J. Suob, J. Mol. Catal. A 2005, 233, 121-126.
40. T. Goebel, N. Gauvry, P. Ducray (Novartis), WO2005/058802 A1, 2005.
41. R. Sterzycki, Synthesis 1979, 724-725.
42. Z. Lu, C. Hu, J. Guo, J. Li, Y. Cui, Y. Jia, Org. Lett. 2010, 12, 480-483.
43. T. W. Baughman, J. C. Sworen, K. B. Wagener, Tetrahedron 2004, 60, 10943-10948.
44. F. Shi, J. P. Waldo, Y. Chen, R. C. Larock, Org. Lett. 2008, 10, 2409-2412.
45. F. Himo, T. Lovell, R. Hilgraf, V. V. Rostovtsev, L. Noodleman, K. B. Sharpless, V. V. Fokin, J. Am. Chem. Soc. 2005, 127, 210-216.
46. B. N. Naidu, J. Banville, F. Beaulieu, T. P. Connolly, M. R. Krystal, J. D. Matiskella, C. Ouellet, S. Plamondon, R. Remillard, M. E. Sorenson, Y. Ueda, M. A. Walker (Bristol-Myers Squibb), WO2007/064316 A1, 2007.
47. P. R. Brooks, M. C. Wirtz, M. G. Vetelino, D. M. Rescek, G. F. Woodworth, B. P. Morgan, J. W. Coe, J. Org. Chem. 1999, 64, 9719-9721.
48. Y. Xia, K. Cao, Y. Zhou, M. R. Alley, F. Rock, M. Mohan, M. Meewan, S. J. Baker, S. Lux, C. Z. Ding, G. Jia, M. Kully, J. J. Plattner, Bioorg. Med. Chem. Lett. 2011, 21, 2533-2536.
49. G. Charalambidis, K. Ladomenou, B. Boitrel, A. G. Coutsolelos, Eur. J. Org. Chem. 2009, 1263-1268.
50. S. Wittich, H. Scherf, C. Xie, G. Brosch, P. Loidl, C. Gerhäuser, M. Jung, J. Med. Chem. 2002, 45, 3296-3309.
51. C. W. Liskey, X. Liao, J. F. Hartwig, J. Am. Chem. Soc. 2010, 132, 11389-11391.
52. V. Ehmke, C. Heindl, M. Rottmann, C. Freymond, W. B. Schweizer, R. Brun, A. Stich, T. Schirmeister, F. Diederich, ChemMedChem 2011, 6, 273-278.
53. J. C. Barrow, K. E. Rittle, T. S. Reger, Z. Q. Yang, P. Bondiskey, G. B. McGaughey, M. G. Bock, G. D. Hartman, C. Tang, J. Ballard, Y. Kuo, T. Prueksaritanont, C. E. Nuss, S. M. Doran, S. V. Fox, S. L. Garson, R. L. Kraus, Y. Li, M. J. Marino, V. K. Graufelds, V. N. Uebele, J. J. Renger, ACS Med. Chem. Lett. 2010, 1, 75-79.
54. 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.
55. E. M. L. Cohen, K. S. Machado, M. Cohen, O. N. deSouza, BMC Genomics 2011, 12, S7.
56. M. J. Soltis, H. J. Yeh, K. A. Cole, N. Whittaker, R. P. Wersto, E. C. Kohn, Drug Metab. Dispos. 1996, 24, 799-806.
57. 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.
58. J. H. Zhang, T. D. Chung, K. R. Oldenburg, J. Biomol. Screening 1999, 4, 67-73.
59. E. J. Mui, D. Jacobus, W. K. Milhous, G. Schiehser, H. Hsu, C. W. Roberts, M. J. Kirisits, R. McLeod, Antimicrob. Agents Chemother. 2005, 49, 3463-3467.
60. D. G. Mack, R. McLeod, Antimicrob. Agents Chemother. 1984, 26, 26-30.
61. R. McLeod, D. Mack, R. Foss, K. Boyer, S. Withers, S. Levin, J. Hubbell, Antimicrob. Agents Chemother. 1992, 36, 1040-1048.
62. E. Holfels, J. McAuley, D. Mack, W. K. Milhous, R. McLeod, Antimicrob. Agents Chemother. 1994, 38, 1392-1396.
63. F. Roberts, C. W. Roberts, J. J. Johnson, D. E. Kyle, T. Krell, J. R. Coggins, G. H. Coombs, W. K. Milhous, S. Tzipori, D. J. Ferguson, D. Chakrabarti, R. McLeod, Nature 1998, 393, 801-805.
64. R. Estes, N. Vogel, D. Mack, R. McLeod, Antimicrob. Agents Chemother. 1998, 42, 2036-2040.
65. E. Zuther, J. J. Johnson, R. Haselkorn, R. McLeod, P. Gornicki, Proc. Natl. Acad. Sci. USA 1999, 96, 13387-13392.
66. M. J. Kirisits, E. Mui, R. McLeod, Int. J. Parasitol. 2000, 30, 149-155.
67. C. W. Roberts, F. Roberts, F. L. Henriquez, D. Akiyoshi, B. U. Samuel, T. A. Richards, W. Milhous, D. Kyle, L. McIntosh, G. C. Hill, M. L. Chaudhuri, S. Tzipori, R. McLeod, Int. J. Parasitol. 2004, 34, 297-308.
68. E. J. Mui, G. A. Schiehser, W. K. Milhous, H. Hsu, C. W. Roberts, M. Kirisits, S. Muench, D. Rice, J. P. Dubey, J. W. Fowble, P. K. Rathod, S. F. Queener, S. R. Liu, D. P. Jacobus, R. McLeod, PLoS Neglected Trop. Dis. 2008, 2, e190.
69. A. Fomovska, Q. Q. Huang, K. ElBissati, E. J. Mui, W. H. Witola, G. Cheng, Y. Zhou, C. Sommerville, C. W. Roberts, S. Bettis, S. T. Prigge, G. A. Afanador, M. R. Hickman, P. J. Lee, S. E. Leed, J. M. Auschwitz, M. Pieroni, J. Stec, S. P. Muench, D. W. Rice, A. P. Kozikowski, R. McLeod, Antimicrob. Agents Chemother. 2012, 56, 2666-2682.
70. B.-S. Lai, W. Witola, K. ElBissati, E. Mui, A. Fomovska, R. McLeod, Proc. Natl. Acad. Sci. USA 2012, 109, 14182-14187.
71. A. Fomovska, R. D. Wood, E. Mui, J. P. Dubey, L. R. Ferriera, M. Hickman, P. J. Lee, S. E. Leed, J. M. Auschwitz, W. J. Welsh, C. Sommerville, S. Woods, C. W. Roberts, R. McLeod, J. Med. Chem. 2012, 55, 8375-8391.
72. J. D. Johnson, R. A. Dennull, L. Gerena, M. Lopez-Sanchez, N. E. Roncal, N. C. Waters, Antimicrob. Agents Chemother. 2007, 51, 1926-1933.
73. D. Plouffe, A. Brinker, C. H. McNamara, N. Kato, K. Kuhen, A. Nagle, F. Adrian, J. T. Matzen, P. Anderson, T. Nam, N. S. Gray, A. Chatterjee, J. Janes, S. F. Yan, R. Trager, J. S. Caldwell, P. G. Schultz, Y. Zhou, E. A. Winzeler, Proc. Natl. Acad. Sci. USA 2008, 105, 9059-9064.
74. M. Yu, T. R. 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. Tsai, B. Falkard, A. B. Sidhu, L. A. Purcell, P. Gratraud, L. Kremer, A. P. Waters, G. Schiehser, D. P. Jacobus, C. J. Janse, A. Ager, W. R. Jacobs, Jr., J. C. Sacchettini, V. Heussler, P. Sinnis, D. A. Fidock, Cell Host Microbe 2008, 4, 567-78.
75. A. M. Vaughan, M. T. O'Neill, A. S. Tarun, N. Camargo, T. M. Phuong, A. S. Aly, A. F. Cowman, S. H. Kappe, Cell. Microbiol. 2009, 11, 506-520.
76. G. Cheng, S. P. Muench, Y. Zhou, G. A. Afanador, E. J. Mui, A. Fomovska, B. S. Lai, S. T. Prigge, S. Woods, C. W. Roberts, M. R. Hickman, P. J. Lee, S. E. Leed, J. M. Auschwitz, D. W. Rice, R. McLeod, Bioorg. Med. Chem. Lett. 2013, 23, 2035-2043.
77. S. P. Muench, J. Stec, Y. Zhou, G. A. Afanador, M. J. McPhillie, M. R. Hickman, P. J. Lee, S. E. Leed, J. M. Auschwitz, S. T. Prigge, D. W. Rice, R. McLeod, Bioorg. Med. Chem. Lett. 2013, 23, 3551-3555.