3 Peptide Deformylase Inhibitors

Progress in Medicinal Chemistry

Volumn 44, Issue , 2006, Pages 109-143

  Aubart, Kelly ^a   Zalacain, Magdalena ^a  

^a GLAXOSMITHKLINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDASE; ANTIINFECTIVE AGENT; ENZYME INHIBITOR; PEPTIDE DEFORMYLASE;

ANIMAL; CHEMISTRY; DRUG ANTAGONISM; DRUG DESIGN; HUMAN; METABOLISM; REVIEW; STRUCTURE ACTIVITY RELATION;

AMIDOHYDROLASES; ANIMALS; ANTI-BACTERIAL AGENTS; DRUG DESIGN; ENZYME INHIBITORS; HUMANS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 33646498732     PISSN: 00796468     EISSN: None     Source Type: Book Series    
DOI: 10.1016/S0079-6468(05)44403-3     Document Type: Review

References (130)

1. Wenzel R.P. N. Engl. J. Med. 351 (2004) 523-526
2. World Health Organization (WHO) (2004) Annex Table 2: Deaths by cause, sex and mortality stratum in WHO regions, estimates for 2002. Geneva
3. Spellberg M., Powers J.H., Brass E.P., Miller L.G., and Edwards Jr. J.E. Clin. Infect. Dis. 38 (2004) 1279-1286
4. Lee C.S., Allwine D.A., Barbachyn M.R., Grega K.C., Dolak L.A., Ford C.W., Jensen R.M., Seest E.P., Hamel J.C., Schaadt R.D., Stapert D., Yagi B.H., Zurenko G.E., and Genin M.J. Bioorg. Med. Chem. 9 (2001) 3243-3253
5. Singh U., Raju B., Lam S., Zhou J., Gadwood R.C., Ford C.W., Zurenko G.E., Schaadt R.D., Morin S.E., Adams W.J., Friis J.M., Courtney M., Palandra J., Hackbarth C.J., Lopez S., Wu C., Mortell K.H., Trias J., Yuan Z., Patel D.V., and Gordeev M.F. Bioorg. Med. Chem. 13 (2003) 4209-4212
6. Reck F., Zhou F., Girardot M., Kern G., Eyermann C.J., Hales N.J., Ramsay R.R., and Gravestock M.B. J. Med. Chem. 48 (2005) 499-506
7. Meinnel T., Mechulam Y., and Blanquet S. Biochimie 75 (1993) 1061-1075
8. Adams J.M. J. Mol. Biol. 33 (1968) 571-589
9. Livingston D.M., and Leder P. Biochemistry 8 (1969) 435-443
10. Ball L.A., and Kaesberg P. J. Mol. Biol. 79 (1973) 531-537
11. Solbiati J., Chapman-Smith A., Miller J.L., Miller C.G., and Cronan Jr. J.E. J. Mol. Biol. 290 (1999) 607-614
12. Ye R.D., and Boulay F. Adv. Pharmacol. 39 (1997) 221-289
13. Panaro M.A., and Mitolo V. Immunopharmacol. Immunotoxicol. 21 (1999) 397-419
14. Fu H., Dahlgren C., and Bylund J. Antimicrob. Agents Chemother. 47 (2003) 2545-2550
15. Mazel D., Pochet S., and Marliere P. EMBO J. 13 (1994) 914-923
16. Meinnel T., and Blanquet S. J. Bacteriol. 176 (1994) 7387-7390
17. Margolis P.S., Hackbarth C.J., Young D.C., Wang W., Chen D., Yuan Z., White R., and Trias J. Antimicrob. Agents Chemother. 44 (2000) 1825-1831
18. Margolis P., Hackbarth C., Lopez S., Maniar M., Wang W., Yuan Z., White R., and Trias J. Antimicrob. Agents Chemother. 45 (2001) 2432-2435
19. Zhang L., Fan F., Palmer L.M., Lonetto M.A., Petit C., Voelker L.L., St. John A., Bankosky B., Rosenberg M., and McDevitt D. Gene 255 (2000) 297-305
20. Apfel C.M., Locher H., Evers S., Takács B., Hubschwerlen C., Pirson W., Page M.G.P., and Keck W. Antimicrob. Agents Chemother. 45 (2001) 1058-1064
21. Chan P.F., O'Dwyer K.M., Palmer L.M., Ambrad J.D., Ingraham K.A., So C., Lonetto M.A., Biswas S., Rosenberg M., Holmes D.J., and Zalacain M. J. Bacteriol. 185 (2003) 2051-2058
22. Guilloteau J.P., Mathieu M., Giglione C., Blanc V., Dupuy A., Chevrier M., Gil P., Famechon A., Meinnel T., and Mikol V. J. Mol. Biol. 320 (2002) 951-962
23. Giglione C., and Miennel T. Emerg. Ther. Targets 5 (2001) 41-57
24. Clements J.M., Beckett R.P., Brown A., Catlin Gr., Lobell M., Palan S., Thomas W., Whittaker M., Wood S., Salama S., Baker P.J., Rodgers H.F., Barynin V., Rice D.W., and Hunter M.G. Antimicrob. Agents Chemother. 45 (2001) 563-570
25. Bowker K.E., Noel A.R., and MacGowan A.P. Int. Antimicrob. Agents 22 (2003) 557-561
26. East S.P., Beckett R.P., Brookings D.C., Clements J.M., Doel S., Keavey K., Pain G., Smith H.K., Thomas W., Thompson A.J., Todd R.S., and Whittaker M. Bioorg. Med. Chem. Lett. 14 (2004) 59-62
27. Chen D., Hackbarth C., Ni Z.J., Wu C., Wang W., Jain R., He Y., Bracken K., Weidmann B., Patel D.V., Trias J., White R.J., and Yuan Z. Antimicrob. Agents Chemother. 48 (2004) 250-261
28. Fritsche T.R., Sader H.S., Cleeland R., and Jones R.N. Antimicrob. Agents Chemother. 49 (2005) 1468-1476
29. Edelstein P.H., Hu B., and Edelstein M.A.C. Antimicrob. Agents Chemother. 49 (2005) 2533-2535
30. Wise R., Andrews J.M., and Ashby J. Antimicrob. Agents Chemother. 46 (2002) 1117-1118
31. Roblin P.M., and Hammerschlag M.R. Antimicrob. Agents Chemother. 47 (2003) 1447-1448
32. Apfel C., Banner D.W., Bur D., Dietz M., Hirata T., Hubschwerlen C., Locher H., Page M.G.P., Pirson W., Rosse G., and Specklin J. J. Med. Chem. 43 (2000) 2324-2331
33. Waites K.B., Reddy N.B., Crabb D.M., and Duffy L.B. Antimicrob. Agents Chemother. 49 (2005) 2541-2542
34. Jones R.N., and Rhomberg P.R. J. Antimicrob. Chemother. 51 (2003) 157-161
35. Jones R.N., Fritsche T.R., and Sader H.S. Diagn. Microbiol. Infect. Dis. 49 (2004) 63-65
36. Cynamon M.H., Alvirez-Freites E., and Yeo A.E.T. J. Antimicrob. Chemother. 53 (2004) 403-405
37. Bracchi-Ricard V., Nguyen K., Zhou Y., Rajagopalan P.T.R., Chakrabarti D., and Pei D. Arch. Biochem. Biophys. 396 (2001) 162-170
38. Giglione C., Serero A., Pierre M., Boisson B., and Meinnel T. EMBO J. 19 (2000) 5916-5929
39. Dirk L.M., Williams M.A., and Houtz R.L. Plant Physiol. 127 (2001) 97-107
40. Serero A., Giglione C., and Meinnel T. J. Mol. Biol. 314 (2001) 695-708
41. Nguyen K.T., Hu X., Colton C., Chakrabarti R., Zhu M.X., and Pei D. Biochemistry 42 (2003) 9952-9958
42. Giglione C., Pierre M., and Miennel T. Mol. Microbiol. 36 (2000) 1197-1205
43. Serero A., Giglione C., Sardini A., Martinez-Sanz J., and Meinnel T. J. Biol. Chem. 278 (2003) 52953-52963
44. Chan, M.K., Gong, W., Rajagopalan, P.T.R., Hao, B., Tsai, C.M. and Pei, D. (1997) Biochemistry 36, 13904-13909. [Erratum published (1998) Biochemistry 37, 13042.]
45. Groche D., Becker A., Schlichting I., Kabsch W., Schultz S., and Wagner A.F.V. Biochem. Biophys. Res. Commun. 246 (1998) 342-346
46. Smith K.J., Petit C.M., Aubart K., Smyth M., McManus E., Jones J., Fosberry A., Lewis C., Lonetto M., and Christensen S.B. Protein Sci. 12 (2003) 349-360
47. Kim H.W., Han B.W., Yoon H.J., Yang J.K., Lee B.I., Lee H.H., Ahn H.J., and Suh S.W. Acta Cryst. D58 (2002) 1874-1875
48. Kreusch A., Spraggon G., Lee C.C., Klock H., McMullan D., Ng K., Shin T., Vincent J., Warner I., Ericson C., and Lesley S.A. J. Mol. Biol. 330 (2003) 309-321
49. Kumar A., Nguyen K.T., Srivathsan S., Ornstein B., Turley S., Hirsh I., Pei D., and Hol W.G. Structure 10 (2002) 357-367
50. Park J.K., Moon J.H., Kim J.H., and Kim E.E.K. Acta Cryst. F61 (2005) 150-152
51. Meinnel T., Blanquet S., and Dardel F. J. Mol. Biol. 262 (1996) 375-386
52. Rajagopalan P.T.R., Yu X.C., and Pei D. J. Am. Chem. Soc. 119 (1997) 12418-12419
53. Rajagopalan P.T.R., and Pei D. J. Biol. Chem. 273 (1998) 22305-22310
54. Saxena R., and Chakraborti P.K. Biochem. Biophys. Res. Commun. 332 (2005) 418-425
55. Rajagopalan P.T.R., Grimme S., and Pei D. Biochemistry 39 (2000) 779-790
56. Becker A., Schlichting I., Kabsch W., Groche D., Schultz S., and Wagner A.F.V. Nature Struct. Biol. 5 (1998) 1053-1058
57. Lipscomb W.N., and Straeter N. Chem. Rev. 96 (1996) 2375-2433
58. Hao B., Gong W., Rajagopalan P.T.R., Zhou Y., Pei D., and Chan M.K. Biochemistry 38 (1999) 4712-4719
59. Matthews B.W. Acc. Chem. Res. 21 (1988) 333-340
60. Meinnel T., Lazennec C., and Blanquet S. J. Mol. Biol. 254 (1995) 175-183
61. Meinnel T., Blanquet S., and Dardel F. J. Mol. Biol. 262 (1996) 375-386
62. Meinnel T., and Blanquet S. J. Bacteriol. 177 (1995) 1883-1887
63. Hu Y., Wei Y., Zhou Y., Rajagopalan P.T.R., and Pei D. Biochemistry 38 (1999) 643-650
64. Meinnel T., Patiny L., Ragusa S., and Blanquet S. Biochemistry 38 (1999) 4287-4295
65. Huntington K.M., Yi T., Wei Y., and Pei D. Biochemistry 39 (2000) 4543-4551
66. Hu Y., Rajagopalan P.T.R., and Pei D. Bioorg. Med. Chem. Lett. 8 (1998) 2479-2482
67. Jain R., Hao B., Liu R., and Chan M.K. J. Am. Chem. Soc. 127 (2005) 4558-4559
68. Durand D.J., Green B.G., O'Connell J.F., and Grant S.K. Arch. Biochem. Biophys. 367 (1999) 297-302
69. Gordon J.J., Kelly B.K., and Miller G.A. Nature (London) 195 (1962) 701-702
70. Chen D.Z., Patel D.V., Hackbarth C.J., Wang W., Dreyer G., Young D.C., Margolis P.S., Wu C., Ni Z., Trias J., White R.J., and Yuan Z. Biochemistry 39 (2000) 1256-1262
71. Yoon H.J., Kim H.L., Lee S.K., Kim H.W., Kim H.W., Lee J.Y., Mikami B., and Suh S.W. Proteins 57 (2004) 639-642
72. Van Aller G.S., Nandigama R., Petit C.M., DeWolf Jr. W.E., Quinn C.J., Aubart K.M., Zalacain M., Christensen S.B., Copeland R.A., and Lai Z. Biochemistry 44 (2005) 253-260
73. Gordon, J.J., Devlin, J.P., East, A.J., Ollis, W.D., Sutherland, I.O., Wright, D.E. and Ninet, L. (1975) J. Chem. Soc., Perkin Trans. I, 819-825.
74. Broughton, B.J., Chaplen, P., Freeman, W.A., Warren, P.J., Wooldridge, K.R.H. and Wright, D.E. (1975) J. Chem. Soc., Perkin Trans. I, 857-860.
75. Lelievre Y., Bouboutou R., Boiziau J., and Cartwright T. Pathol. Biol. 37 (1989) 43-46
76. Xu Y., Lai L.T., Gabrilove J.L., and Scheinberg D.A. Clin. Cancer Res. 4 (1998) 171-176
77. Hachisu M., Hiranuma T., Murata S., Aoyagi T., and Umezawa H. Life Sci. 41 (1987) 235-240
78. Umezawa H., Aoyagi T., Tanaka T., Suda H., Okuyama A., Naganawa H., Hamada M., and Takeuchi T. J. Antibiot. 38 (1985) 1629-1630
79. Tieku S., and Hooper N.M. Biochem. Pharmacol. 44 (1992) 1725-1730
80. Smith H.K., Beckett R.P., Clements J.M., Doel S., East S.P., Launchbury S.B., Pratt L.M., Spavold Z.M., Thomas W., Todd R.S., and Whittaker M. Bioorg. Med. Chem. Lett. 12 (2002) 3595-3599
81. Davies S.J., Ayscough A.P., Beckett R.P., Bragg R.A., Clements J.M., Doel S., Grew C., Launchbury S.B., Perkins G.M., Pratt L.M., Smith H.K., Spavold Z.M., Thomas S.W., Todd R.S., and Whittaker M. Bioorg. Med. Chem. Lett. 13 (2003) 2709-2713
82. Davies S.J., Ayscough A.P., Beckett R.P., Clements J.M., Doel S., Pratt L.M., Spavold Z.M., Thomas S.W., and Whittaker M. Bioorg. Med. Chem. Lett. 13 (2003) 2715-2718
83. Lofland D., Difuntorum S., Waller A., Clements J.M., Weaver M.K., Karlowsky J.A., and Johnson K. J. Antimicrob. Chemother. 53 (2004) 664-668
84. Ramanathan-Girish S., McColm J., Clements J.M., Taupin P., Barrowcliffe S., Hevizi J., Safrin S., Moore C., Patou G., Moser H., Gadd A., Hoch U., Jiang V., Lofland D., and Johnson K.W. Antimicrob. Agents Chemother. 48 (2004) 4835-4842
85. Hackbarth C.J., Chen D.Z., Lewis J.G., Clark K., Mangold J.B., Cramer J.A., Margolis P.S., Wang W., Koehn J., Wu C., Lopez S., Withers G., Gu H., Dunn E., Kulathila R., Pan S., Porter W.L., Jacobs J., Trias J., Patel D.V., Weidmann B., White R.J., and Yuan Z. Antimicrob. Agents Chemother. 46 (2002) 2752-2764
86. Jain, R., Sundram, A., Lopez, S., Neckermann, G., Wu, C., Hackbarth, C., Chen, D., Wang, W., Ryder, N.S., Weidmann, B., Patel, D., Trias, J., White, R. and Yuan, Z. (2003) Bioorg. Med. Chem. Lett. 13, 4223-4228. [Erratum published (2004) Bioorg. Med. Chem. Lett. 14, 2373-2374.]
87. Fritsche, T.R., Rhomberg, P.R. and Jones, R.N. (2004) 44th Interscience Conference on Antimicrobial Agents and Chemotherapy, Washington, DC, USA, Poster D-1919.
88. Jones, R.N., Fritsche, T.R. and Sadar, H.S. (2004) 14th European Congress of Clinical Microbiology and Infectious Diseases, Prague, Czech Republic, Poster P914.
89. Ryder, N.S., Dzink-Fox, J., Kubik, B., Mlineritsch, W., Alvaraz, S., Bracken, K., Dean, K., Jain, R., Sundaram, A., Weidmann, B. and Yuan, Z. (2004) 44th Interscience Conference on Antimicrobial Agents and Chemotherapy, Washington, DC, USA, Poster F-1959.
90. Credito K., Lin G., Ednie L.M., and Appelbaum P.C. Antimicrob. Agents Chemother. 48 (2004) 4033-4036
91. Credito, K.L., Lin, G., Jacobs, M.R. and Appelbaum, P.C. (2004) 14th European Congress of Clinical Microbiology and Infectious Diseases, Prague, Czech Republic, Poster P919.
92. Ednie L.M., Pankuch G., and Appelbaum P.C. Antimicrob. Agents Chemother. 48 (2004) 4027-4032
93. Pankuch, G.A., Jacobs, M.R. and Appelbaum, P.C. (2004) 14th European Congress of Clinical Microbiology and Infectious Diseases, Prague, Czech Republic, Poster P920.
94. Chen, D., Tembe, V., Cramer, J., Ramos, L., Press, B., Withers, G., Jain, R., Sundaram, A., Alvaraz, S., Bracken, K., Dean, K., Weidmann, B., Patel, D., White, R. and Yuan, Z. (2004) 44th Interscience Conference on Antimicrobial Agents and Chemotherapy, Washington, DC, USA, Poster F-1965.
95. Fujita, M., Sakamoto, M., Horiuchi, N., Yamamoto, T., Tomita, K., Mizuno, K., Niga, T., Ito, H. and Kashimoto, S. (2004) PCT Int. Appl. WO 04 018453; (2004) Chem. Abstr. 140, 236096.
96. Chong, L., Frechette, R., Scott, C., Tester, R., Smith, W., Chiba, K., Sakamoto, M. and Gluchowski, C. (2002) PCT Int. Appl. WO 02 028829; (2002) Chem. Abstr. 136, 310184.
97. Takayama, W., Shirasaki, M. and Inoue, A. (2004) Jpn. Kokai Tokkyo Koho JP 04 143053; (2004) Chem. Abstr. 140, 391128.
98. Gane, P., Porter, B., Willems, H., Beckett, R.P. and Keavey, K. (2003) PCT Int. Appl. WO 03 048115; (2003) Chem. Abstr. 139, 36350.
99. Jayasekera M.M.K., Kendall A., Shammas R., Dermyer M., Tomala M., Shapiro M.A., and Holler T.P. Arch. Biochem. Biophys. 381 (2000) 313-316
100. Bhat, A., Christensen, S.B., Frazee, J.S., Head, M.S., Leber, J.D. and Li, M. (2002) PCT Int. Appl. WO 02 081426; (2002) Chem. Abstr. 137, 310696.
101. Bhat, A., Christensen, S.B., Frazee, J.S., Head, M.S., Leber, J.D. and Li, M. (2003) PCT Int. Appl. WO 03 002522; (2003) Chem. Abstr. 138, 89584.
102. Green B.G., Toney J.H., Kozarich J.W., and Grant S.K. Arch. Biochem. Biophys. 375 (2000) 355-358
103. Aubart, K.M., Christensen, S.B. and Briand, J. (2001) PCT Int. Appl. WO 01 085160; (2001) Chem. Abstr. 135, 352763.
104. Christensen, S.B., Cummings, M.D. and Karpinski, J.M. (2002) PCT Int. Appl. WO 02 098901; (2002) Chem. Abstr. 138, 11391.
105. Karpinski, J.M., Christensen, S.B., Aubart, K.M., Van Aller, G.S., DeMarsh, P.L., Lewandowski, T.F., Rittenhouse, S., Kulkarni, S.G., McIntyre, T.A., Woods, L.C., Lonetto, M.A., Pearson, S.C., Smith, K.J., Bhat, A., Cummings, M. and Saylers, K. (2005) 229th ACS National Meeting, San Diego, CA, USA, Abstracts of Papers.
106. Apfel C., Banner D.W., Bur D., Dietz M., Hubschwerlen C., Locher H., Marlin F., Masciadri R., Pirson W., and Stalder H. J. Med. Chem. 44 (2001) 1847-1852
107. Takayama W., Shirasaki Y., Sakai Y., Nakajima E., Fujita S., Sakamoto-Mizutani K., and Inoue J. Bioorg. Med. Chem. Lett. 13 (2003) 3273-3276
108. Molteni V., He X., Nabakka J., Yang K., Kreusch A., Gordon P., Bursulaya B., Warner I., Shin T., Biorac T., Ryder N.S., Goldberg R., Doughty J., and He Y. Bioorg. Med. Chem. Lett. 14 (2004) 1477-1481
109. Cali P., Naerum L., Mukhija S., and Hjelmencrantz A. Bioorg. Med. Chem. Lett. 14 (2004) 5997-6000
110. Hu X., Nguyen K.T., Verlinde C.L.M.J., Hol W.G.J., and Pei D. J. Med. Chem. 46 (2003) 3771-3774
111. Hu X., Nguyen K.T., Jiang V.C., Lofland D., Moser H.E., and Pei D. J. Med. Chem. 47 (2004) 4941-4949
112. Pei, D. (2005) US Pat. Appl. Publ. US 05 026821; (2005) Chem. Abstr. 142, 198353.
113. Nguyen K.T., Hu X., and Pei D. Bioorg. Chem. 32 (2004) 178-191
114. Capet, M., Genevois-Borella, A., Martin, J.P., Mikol, V., Carrez, C. and Wentzler, S. (2001) PCT Int. Appl. WO 01 040198; (2001) Chem. Abstr. 135, 33496.
115. Aubart, K.M., Benowitz, A.B., Christensen, S.B., Lee, J. and Silva, D.J. (2005) PCT Int. Appl. WO 05 017124; (2005) Chem. Abstr. 142, 235497.
116. Chu M., Mierzwa R., He L., Xu L., Gentile F., Terracciano J., Patel M., Miesel L., Bohanon S., Kravec C., Cramer C., Fischman T.O., Hruza A., Ramanathan L., Shipkova P., and Chan T.M. Tet. Lett. 42 (2001) 3549-3551
117. Coats R.A., Lee S., Davis K.A., Patel K.M., Rhoads E.K., and Howard M.H. J. Org. Chem. 69 (2004) 1734-1737
118. Aubart, K.M., Benowitz, A.B., Christensen, S.B., IV, Karpinski, J.M., Lee, J. and Silva, D.J. (2003) PCT Int. Appl. WO 03 101442; (2003) Chem. Abstr. 140, 41828.
119. Patel, D.V., Yuan, Z., Jain, R.K., Lewis, J.G. and Jacobs, J. (2002) PCT Int. Appl. WO 02 102791; (2002) Chem. Abstr. 138, 55864.
120. Beckett, P.R., Launchbury, S., Pain, G. and Pratt, L.M. (2002) PCT Int. Appl. WO 02 041886; (2002) Chem. Abstr. 136, 401760.
121. Karpinski, J.M., Aubart, K.M. and Christensen, S.B., IV. (2003) PCT Int. Appl. WO 03 104209; (2003) Chem. Abstr. 140, 42176.
122. Aubart, K.M., Bhat, A., Christensen, S.B., IV, Leber, J.D. and Liao, X. (2003) PCT Int. Appl. WO 03 077913; (2003) Chem. Abstr. 139, 255322.
123. Aubart, K.M., Xiang, J., Christensen, S.B., IV, Liao, X. and Cummings, M.D. (2002) PCT Int. Appl. WO 02 070540; (2002) Chem. Abstr. 137, 226582.
124. Wei Y., and Pei D. Bioorg. Med. Chem. Lett. 10 (2000) 1073-1076
125. Sergeeva, M.V. and Doppalapudi, V.R. (2002) PCT Int. Appl. WO 02 089739; (2002) Chem. Abstr. 137, 358150.
126. Sergeeva, M.V. and Doppalapudi, V.R. (2003) PCT Int. Appl. WO 03 088913; (2003) Chem. Abstr. 139, 354460.
127. Azoulay-Dupuis E., Mohler J., and Bedos J.P. Antimicrob. Agents Chemother. 48 (2004) 80-85
128. Craig, W.A. and Andes, D.R. (2004) 14th European Congress of Clinical Microbiology and Infectious Diseases, Prague, Czech Republic, Poster P922.
129. Jain R., Chen D., White R.J., Patel D.V., and Yuan Z. Curr. Med. Chem. 12 (2005) 1607-1621
130. Bush K., Macielag M., and Weidner-Wells M. Curr. Opin. Microbiol. 7 (2004) 466-476