Catechol-rhodanine derivatives: Specific and promiscuous inhibitors of Escherichia coli deoxyxylulose phosphate reductoisomerase (DXR)

Bioorganic and Medicinal Chemistry

Volumn 22, Issue 14, 2014, Pages 3713-3719

  Zinglé, Catherine ^a   Tritsch, Denis ^a   Grosdemange Billiard, Catherine ^a   Rohmer, Michel ^a  

^a UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

Catechol rhodanines; DXR; False positives; Isoprenoid; Promiscuous inhibitors

Indexed keywords

2 (5 BENZYLIDENE 4 OXO 2 THIOXOTHIAZOLIDIN 3 YL)ACETIC ACID; 2 [5 (2,3 DIHYDROXYBENZYLIDENE) 4 OXO 2 THIOXOTHIAZOLIDIN 3 YL] N [4 (4 TOLYLOXY)PHENYL]ACETAMIDE; 2 [5 (3,4 DIHYDROXYBENZYLIDENE) 4 OXO 2 THIOXOTHIAZOLIDIN 3 YL] N ACETIC ACID; 2 [5 (3,4 DIHYDROXYBENZYLIDENE) 4 OXO 2 THIOXOTHIAZOLIDIN 3 YL] N HYDROXYACETAMIDE; 2 [5 (3,4 DIHYDROXYBENZYLIDENE) 4 OXO 2 THIOXOTHIAZOLIDIN 3 YL] N [4 (4 TOLYLOXY)PHENYL]ACETAMIDE; ANTIINFECTIVE AGENT; BACTERIAL ENZYME; DEOXYXYLULOSE PHOSPHATE REDUCTOISOMERASE; FOSMIDOMYCIN; HISTIDINE; N [4 (4 CHLOROPHENOXY)PHENYL] 2 [5 (2,3 DIHYDROXYBENZYLIDENE) 4 OXO 2 THIOXOTHIAZOLIDIN 3 YL]ACETAMIDE; N [4 (4 CHLOROPHENOXY)PHENYL] 2 [5 (2,4 DIHYDROXYBENZYLIDENE) 4 OXO 2 THIOXOTHIAZOLIDIN 3 YL]ACETAMIDE; N [4 (4 CHLOROPHENOXY)PHENYL] 2 [5 (3,4 DIHYDROXYBENZYLIDENE) 4 OXO 2 THIOXOTHIAZOLIDIN 3 YL]ACETAMIDE; TRITON X 100; UNCLASSIFIED DRUG; 1-DEOXY-D-XYLULOSE 5-PHOSPHATE REDUCTOISOMERASE; CATECHOL; CATECHOL DERIVATIVE; ENZYME INHIBITOR; ISOMERASE; RHODANINE;

ANTIBACTERIAL ACTIVITY; ARTICLE; BINDING SITE; CONTROLLED STUDY; DRUG DESIGN; DRUG DETERMINATION; DRUG SCREENING; DRUG STRUCTURE; ENZYME ASSAY; ENZYME INHIBITION; ESCHERICHIA COLI; FALSE POSITIVE RESULT; IC 50; NONHUMAN; ANTAGONISTS AND INHIBITORS; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; DRUG EFFECTS; ENZYMOLOGY; GROWTH, DEVELOPMENT AND AGING; METABOLISM; MICROBIAL SENSITIVITY TEST; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ESCHERICHIA COLI;

ALDOSE-KETOSE ISOMERASES; ANTI-BACTERIAL AGENTS; CATECHOLS; DOSE-RESPONSE RELATIONSHIP, DRUG; ENZYME INHIBITORS; ESCHERICHIA COLI; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; RHODANINE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84902549867     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2014.05.004     Document Type: Article

References (56)

1. M. Rohmer Nat. Prod. Rep. 16 1999 565
2. H. Jomaa, J. Wiesner, S. Sanderbrand, B. Altincicek, C. Weidemeyer, M. Hintz, I. Türbachova, M. Eberl, J. Zeidler, H.K. Lichtenthaler, D. Soldati, and E. Beck Science 285 1999 1573
3. M. Rohmer, C. Grosdemange-Billiard, M. Seemann, and D. Tritsch Curr. Opin. Invest. Drugs 5 2004 154
4. M. Okuhara, Y. Kuroda, T. Goto, M. Okamoto, H. Terano, M. Kohsaka, H. Aoki, and H. Imanaka J. Antibiot. 33 1980 24
5. T. Kuzuyama, T. Shimizu, S. Takahashi, and H. Seto Tetrahedron Lett. 39 1998 7913
6. E.R. Jackson, and C.C. Dowd Curr. Top. Med. Chem. 12 2012 706
7. A.S. Messiaen, T. Verbrugghen, C. Declerck, R. Ortmann, M. Schlitzer, H. Nelis, S. Van Calenbergh, and T. Coenye Int. J. Antimicrob. Agents 38 2011 261
8. R.S. Mackie, E.S. McKenney, and M.L. van Hoek Front. Microbiol. 3 2012 226
9. S. Steinbacher, J. Kaiser, W. Eisenreich, R. Huber, A. Bacher, and F. Rohdich J. Biol. Chem. 278 2003 18401
10. L.M. Henriksson, T. Unge, J. Carlsson, J. Aqvist, S.L. Mowbray, and T.A. Jones J. Biol. Chem. 282 2007 19905
11. M. Takenoya, A. Ohtaki, K. Noguchi, K. Endo, Y. Sasaki, K. Ohsawa, S. Yashima, and M. Yohda J. Struct. Biol. 170 2010 532
12. S. Yajima, K. Hara, D. Iino, Y. Sasaki, T. Kuzuyama, K. Ohsawa, and H. Seto Acta Crystallogr., F 63 2007 466
13. M. Andaloussi, L.M. Henriksson, A. Wieckowska, M. Lindh, C. Björkelid, A.M. Larsson, S. Suresh, H. Iyer, B.R. Srinivasa, T. Bergfors, T. Unge, S.L. Mowbray, M. Larhed, T.A. Jones, and A. Karlén J. Med. Chem. 54 2011 4964
14. C.T. Behrendt, A. Kunfermann, V. Illarionova, A. Matheeussen, M.K. Pein, T. Gräwert, J. Kaiser, A. Bacher, W. Eisenreich, B. Illarionov, M. Fischer, L. Maes, M. Groll, and T. Kurz J. Med. Chem. 54 2011 6796
15. C. Zinglé, L. Kuntz, D. Tritsch, C. Grosdemange-Billiard, and M. Rohmer J. Org. Chem. 75 2010 3203
16. T. Kurz, D. Geffken, and C. Wackendorff Z. Naturforsch. 58b 2003 106
17. M. Courtois, Z. Mincheva, F. Andreu, M. Rideau, and M.C. Viaud-Massuard J. Enzyme Inhib. Med. Chem. 19 2004 559
18. C. ZingleÍ, L. Kuntz, D. Tritsch, C. Grosdemange-Billiard, and M. Rohmer Bioorg. Med. Chem. Lett. 22 2012 6563
19. E. Farkas, E.A. Enyedy, and H. Csóka J. Inorg. Chem. 79 2000 205
20. V.T. Athavale, L.H. Prabhu, and D.G. Vartak J. Inorg. Nucl. Chem. 28 1966 1237
21. L. Deng, S. Sundriyal, V. Rubio, Z. Shi, and Y. Song J. Med. Chem. 52 2009 6539
22. X. Ge, B. Wakim, and D.S. Sem J. Med. Chem. 51 2008 4571
23. B.Y. Feng, and B.K. Shoichet Nat. Prot. 1 2006 550
24. J. Seidler, S.L. McGovern, T.N. Doman, and B.K. Shoichet J. Med. Chem. 46 2003 4477
25. A.T. Koppisch, D.T. Fox, B.S. Blagg, and C.D. Poulter Biochemistry 41 2002 236
26. S.L. McGovern, E. Caselli, N. Grigorieff, and B.K. Shoichet J. Med. Chem. 45 2002 1712
27. S.L. McGovern, B.T. Helfand, B. Feng, and B.K. Shoichet J. Med. Chem. 46 2003 4265
28. S.L. McGovern, and B.K. Shoichet J. Med. Chem. 46 2003 1478
29. K.E.D. Coan, D.A. Maltby, A.L. Burlingame, and B.K. Shoichet J. Med. Chem. 52 2009 2067
30. L. Deng, K. Endo, M. Kato, G. Cheng, S. Yajima, and Y. Song ACS Med. Chem. Lett. 2 2011 165
31. I.H. Segel Enzyme Kinetics: Behavior and Analysis of Rapid Equilibrium and Steady-State Enzyme Systems 1975 Wiley-Interscience NewYork 161 226
32. C.A. Free, E. Majchrowicz, and S.M. Hess Biochem. Pharmacol. 20 1971 1421
33. H. Terashima, K. Hama, R. Yamamoto, M. Tsuboshima, R. Kikkawa, I. Hatanaka, and Y. Shigeta J. Pharmacol. Exp. Ther. 229 1984 226
34. Y. Ohishi, T. Mukai, M. Nagahara, M. Yajima, N. Kajikawa, K. Miyahara, and T. Takano Chem. Pharm. Bull. 38 1990 1911
35. K. Kato, K. Nakayama, M. Mizota, I. Miwa, and J. Okuda Chem. Pharm. Bull. 39 1991 1540
36. G. Bruno, L. Costantino, C. Curinga, R. Maccari, F. Monforte, F. Nicolò, R. Ottanà, and M.G. Vigorita Bioorg. Med. Chem. 10 2002 1077
37. N. Potier, P. Barth, D. Tritsch, J.-F. Biellmann, and A. Van Dorsselaer Eur. J. Biochem. 243 1997 274
38. N.S. Cutshall, C. O'Day, and M. Prezhdo Bioorg. Med. Chem. Lett. 15 2005 3374
39. C.A. Whitesitt, R.L. Simon, J.K. Reel, S.K. Sigmund, M.L. Phillips, J.K. Shadle, L.J. Heinz, G.A. Koppel, D.C. Hunden, S.L. Lifer, D. Berry, J. Ray, S.P. Little, X. Liu, W.S. Marshall, and J.A. Panetta Bioorg. Med. Chem. Lett. 6 1996 2157
40. G. Kumar, P. Parasuraman, S.K. Sharma, T. Banerjee, K. Karmodiya, N. Surolia, and A. Surolia J. Med. Chem. 50 2007 2665
41. G. Kumar, T. Banerjee, N. Kapoor, N. Surolia, and A. Surolia IUBMB Life 62 2010 204
42. M.W. Irvine, G.L. Patrick, J. Kewney, S.F. Hastings, and S.J. MacKenzie Bioorg. Med. Chem. Lett. 18 2008 2032
43. M. Soltero-Higgin, E.E. Carlson, J.H. Philips, and L.L. Kiessling J. Am. Chem. Soc. 126 2004 10532
44. M.M. Sim, S.B. Ng, A.D. Buss, S.C. Crasta, K.L. Goh, and S.K. Lee Bioorg. Med. Chem. Lett. 12 2002 697
45. T. Tomašić, N. Zidar, A. Kovač, S. Turk, M. Simčič, D. Blanot, M. Müller-Premru, M. Filipič, S.G. Grdadolnik, A. Zega, M. Anderluh, S. Gobec, D. Kikelj, and L.P. Mašič ChemMedChem 5 2010 286
46. T. Tomašić, and L.P. Mašič Curr. Med. Chem. 16 2009 1596
47. M.A. Ramirez, and N.L. Borja Pharmacotherapy 28 2008 646
48. J.B. Baell, and G.A. Holloway J. Med. Chem. 53 2010 2719
49. T. Mendgen, C. Steuer, and C.D. Klein J. Med. Chem. 55 2012 743
50. O. Meyer, J.-F. Hoeffler, C. Grosdemange-Billiard, and M. Rohmer Tetrahedron 60 2004 12153
51. L. Kuntz, D. Tritsch, C. Grosdemange-Billiard, A. Hemmerlin, A. Willem, T.J. Bach, and M. Rohmer Biochem. J. 386 2005 127
52. D.S. Sem, B. Bertolaet, B. Baker, E. Chang, A.D. Costache, S. Coutts, Q. Dong, M. Hansen, V. Hong, X. Huang, R.M. Jack, R. Kho, H. Lang, C.-T. Ma, D. Meininger, M. Pellecchia, F. Pierre, H. Villar, and L. Yu Chem. Biol. 11 2004 185
53. X. Ge, and D.S. Sem Anal. Biochem. 370 2007 171
54. M.M. Bradford Anal. Biochem. 72 1976 248
55. M. Nishiyama, N. Matsubara, K. Yamamoto, S. Iijima, T. Uozumi, and T. Beppu J. Biol. Chem. 261 1986 14178
56. T. Tomita, S. Fushinobu, T. Kuzuyama, and M. Nishiyama Biochem. Biophys. Res. Commun. 347 2006 502