Exploring the chemical space of ureidothiophene-2-carboxylic acids as inhibitors of the quorum sensing enzyme PqsD from Pseudomonas aeruginosa

European Journal of Medicinal Chemistry

Volumn 96, Issue , 2015, Pages 14-21

  Sahner, J Henning ^a   Empting, Martin ^a   Kamal, Ahmed ^a   Weidel, Elisabeth ^a   Groh, Matthias ^a   Börger, Carsten ^b   Hartmann, Rolf W ^a  

^a SAARLAND UNIVERSITY   (Germany)

^b PharmBioTec GmbH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACID; ENZYME; ENZYME INHIBITOR; FUNCTIONAL GROUP; PQSD ENZYME; UNCLASSIFIED DRUG; UREIDOTHIOPHENE 2 CARBOXYLIC ACID; BACTERIAL PROTEIN; THIOPHENE DERIVATIVE; UREA;

ARTICLE; BIOSYNTHESIS; DRUG ACTIVITY; DRUG STRUCTURE; ENZYME INHIBITION; NONHUMAN; PSEUDOMONAS AERUGINOSA; QUORUM SENSING; STRUCTURE ACTIVITY RELATION; ANALOGS AND DERIVATIVES; ANTAGONISTS AND INHIBITORS; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; DRUG EFFECTS; ENZYMOLOGY; GENETICS; METABOLISM; SYNTHESIS;

BACTERIAL PROTEINS; DOSE-RESPONSE RELATIONSHIP, DRUG; ENZYME INHIBITORS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PSEUDOMONAS AERUGINOSA; QUORUM SENSING; STRUCTURE-ACTIVITY RELATIONSHIP; THIOPHENES; UREA;

EID: 84927145444     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2015.04.007     Document Type: Article

References (38)

1. J. Davies, Bacteria on the rampage, Nature 383 (1996) 219-220.
2. C. Walsh, Molecular mechanisms that confer antibacterial drug resistance, Nature 406 (2000) 775-781.
3. J.-F. Dubern, S.P. Diggle, Quorum sensing by 2-alkyl-4-quinolones in Pseudomonas aeruginosa and other bacterial species, Mol. Biosyst. 4 (2008) 882-888.
4. N. Bagge, O. Ciofu, L.T. Skovgaard, N. Høiby, Rapid development in vitro and in vivo of resistance to ceftazidime in biofilm-growing Pseudomonas aeruginosa due to chromosomal b-lactamase, APMIS 108 (2000) 589-600.
5. A.R.M. Coates, G. Halls, Y. Hu, Novel classes of antibiotics or more of the same? Brit. J. Pharmcol. 163 (2011) 184-194.
6. F. von Nussbaum, M. Brands, B. Hinzen, S. Weigand, D. Haebich, Antibacterial natural products in medicinal chemistry-exodus of revival? Angew. Chem. Int. Ed. 45 (2006) 5072-5129.
7. S. Scutera, M. Zucca, D. Savoia, Novel approaches for the design and discovery of quorum-sensing inhibitors Expert Opin. Drug. Discov. 9 (2014) 353-366.
8. S. Swift, J.A. Downie, N.A. Whitehead, A.M. Barnard, G.P. Salmond, P. Williams, Quorum sensing as a population-density-dependent determinant of bacterial physiology, Org. Biomol. Chem. 12 (2001) 6094-6104.
9. S. Diggle, P. Lumjiaktase, F. Dipilato, K. Winzer, M. Kunakorn, D.A. Barrett, S.R. Chhabra, M. C-amara, P. Williams, Functional genetic analysis reveals a 2-alkyl-4-quinolone signaling system in the human pathogen Burkholderia pseudomallei and related bacteria, Chem. Biol. 13 (2006) 701-710.
10. A.K. Bera, V. Atanasova, H. Robinson, E. Eisenstein, J.P. Coleman, E.C. Pesci, J.F. Parsons, Structure of PqsD, a Pseudomonas quinolone signal biosynthetic enzyme, in complex with anthranilate, Biochemistry 48 (2009) 8644-8655.
11. L. Yang, M. Nilsson, M. Gjermansen, M. Givskov, T. Toker-Nielsen, Pyoverdine and PQS mediated subpopulation interactions involved in Pseudomonas aeruginosa biofilm formation, Mol. Microbiol. 74 (2009) 1380-1392.
12. L. Gallagher, S.L. McKnight, M.S. Kuznetsova, E.C. Pesci, C. Manoil, Functions required for extracellular quinolone signaling by Pseudomonas aeruginosa, J. Bacteriol. 184 (2002) 6472-6480.
13. D.S. Wade, M. Worth Calfee, E.R. Rocha, E.A. Ling, E. Engstrom, J.P. Coleman, E.C. Pesci, Regulation of Pseudomonas quinolone signal synthesis in Pseudomonas aeruginosa, J. Bacteriol. 187 (2005) 4372-4380.
14. G. Xiao, E. D-eziel, J. He, F. L-epine, B. Lesic, M.-H. Castonguay, S. Milot, A.P. Tampakaki, S.E. Stachel, L.G. Rahme, MvfR, a key Pseudomonas aeruginosa pathogenicity LTTR-class regulatory protein, has dual ligands, Mol. Microbiol. 62 (2006) 1689-1699.
15. A. Bandyopadhaya, M. Kesarwani, Y.-A. Que, J. He, K. Padfield, R. Tompkins, L.G. Rahme, The quorum sensing volatile molecule 2-amino acetophenon modulates host immune response in a manner that promotes life with unwanted guests, PLoS Pathog. 8 (2012) e1003024.
16. K. Kim, Y.U. Kim, B.H. Koh, S.S. Hwang, S.-H. Kim, F. L-epine, Y.-H. Cho, G.R. Lee, HHQ and PQS, two Pseudomonas aeruginosa quorum-sensing molecules, down regulate the innate immune responses through the nuclear factor-kB pathway, Immunology 129 (2010) 578-588.
17. C.E. Dulcey, V. Dekimpe, D.-A. Fauvelle, S. Milot, M.-C. Groleau, N. Doucet, L.G. Rahme, F. L-epine, E. D-eziel, The end of an old hypothesis: the Pseudomonas signaling molecules 4-hydroxy-2-alkylquinolines derive from fatty acids, not 3-ketofatty acids, Chem. Biol. 20 (2013) 1481-1491.
18. C. Lu, C.K. Maurer, B. Kirsch, A. Steinbach, R.W. Hartmann, Overcoming unexpected functional inversion of a PqsR antagonist in Pseudomonas aeruginosa: an in vivo potent antivirulence agent targeting pqs quorum sensing, Angew. Chem. Int. Ed. 53 (2014) 1109-1112.
19. M.P. Storz, C.K. Maurer, C. Zimmer, N. Wagner, C. Brengel, J.C. de Jong, S. Lucas, M. Müsken, S. Haussler, A. Steinbach, R.W. Hartmann, Validation of PqsD as an anti-biofilm target in Pseudomonas aeruginosa by development of smallmolecule inhibitors, J. Am. Chem. Soc. 134 (2012) 16143-16146.
20. D. Pistorius, A. Ullrich, S. Lucas, R.W. Hartmann, U. Kazmaier, R. Müller, Biosynthesis of 2-alkyl-4(1H)-quinolones in Pseudomonas aeruginosa: potential for therapeutic interference with pathogenicity, ChemBioChem 12 (2011) 850-853.
21. J.H. Sahner, C. Brengel, M.P. Storz, M. Groh, A. Plaza, R. Müller, R.W. Hartmann, Combining in silico and biophysical methods for the development of Pseudomonas aeruginosa quorum sensing inhibitors: an alternative approach for structure-based drug design, J. Med. Chem. 56 (2013) 8656-8664.
22. E. Weidel, J.C. de Jong, C. Brengel, M.P. Storz, A. Braunshausen, M. Negri, A. Plaza, A. Steinbach, R. Müller, R.W. Hartmann, Structure optimization of 2-Benzamidobenzoic acids as PqsD inhibitors for Pseudomonas aeruginosa infections and elucidation of binding mode by SPR, STD NMR, and molecular docking, J. Med. Chem. 56 (2013) 6146-6155.
23. M. Storz, G. Allegretta, B. Kirsch, M. Empting, R.W. Hartmann, From in vitro to in cellulo: structure-activity relationship of (2-nitrophenyl)methanol derivatives as inhibitors of PqsD in Pseudomonas aeruginosa, Org. Biomol. Chem. 12 (2014) 6094-6104.
24. M. Storz, C. Brengel, E. Weidel, M. Hoffmann, K. Hollemeyer, A. Steinbach, R. Müller, M. Empting, R.W. Hartmann, Biochemical and biophysical analysis of chiral PqsD inhibitor revealing tight-binding behavior and enantiomers with contrary thermodynamic signatures, ACS Chem. Biol. 8 (2013) 2794-2801.
25. S. Hinsberger, Johannes C. de Jong, M. Groh, J. Haupenthal, R.W. Hartmann, Benzamidobenzoic acids as potent PqsD inhibitors for the treatment of Pseudomonas aeruginosa infections, Eur. J. Med. Chem. 76 (2014) 343-351.
26. F.A. Cotton, V.W. Day, E.E. Hazen Jr., S. Larsen, S.T.K. Wong, Structure of bis(methylguanidinium) monohydrogen orthophosphate. A model for the arginine-phosphate interactions at the active site of staphylococcal nuclease and other phosphohydrolytic enzymes, J. Am. Chem. Soc. 96 (1974) 4471-4478.
27. A.S. Woods, S. Ferr-e, Amazing stability of the arginine-phosphate electrostatic interaction, J. Proteome Res. 4 (2005) 1397-1402.
28. H. Nikaido, E.Y. Rosenberg, J. Foulds, Porin channels in Escherichia coli: studies with b-lactams in intact cells, J. Bacteriol. 153 (1983) 232-240.
29. F. Yoshimura, H. Nikaido, Diffusion of b-lactam antibiotics through the porin channels of Escherichia coli K-12, Antimicrob. Agents Chemother. 27 (1985) 84-92.
30. A. Kirschning, F. Taft, T. Knobloch, Total synthesis approaches to natural product derivatives based on the combination of chemical synthesis and metabolic engineering, Org. Biomol. Chem. 5 (2007) 3245-3259.
31. H. Hartmann, J. Liebscher, A simple method for the synthesis of 5-aryl-3-amino-2-alkoxycarbonylthiophenes, Synthesis (1984) 275-276.
32. F. Fabis, S. Jolivet-Fouchet, M. Robba, H. Landelle, S. Rault, Thiaisatoic anhydrides: efficient synthesis under microwave heating conditions and study of their reactivity, Tetrahedron 54 (1998) 10789-10800.
33. L. Foulon, E. Braud, F. Fabis, J.C. Lancelot, S. Rault, Synthesis and combinatorial approach of the reactivity of 6-and 7-arylthieno [3, 2-d] [1, 3] oxazine-2, 4-diones, Tetrahedron 59 (2003) 10051-10057.
34. F.X. Le Foulon, E. Braud, F. Fabis, J.C. Lancelot, S. Rault, Solution-phase parallel synthesis of a 1140-member ureidothiophene carboxylic acid library, J. Comb. Chem. 7 (2005) 253-257.
35. N. Miyaura, K. Yamada, A. Suzuki, A new stereospecific cross-coupling by palladium-catalyzed reaction of 1-alkenylboranes with 1-alkenyl or 1-alkynyl halides, Tetrahedron Lett. 20 (1979) 3437-3440.
36. F. L-epine, S. Milot, E. D-eziel, J. He, L.G. Rahme, Electrospray/mass spectrometric identification and analysis of 4-hydroxy-2-alkylquinolines (HAQs) produced by Pseudomonas aeruginosa, J. Am. Soc. Mass. Spectrom. 15 (2004) 862-869.
37. C. Henn, S. Boettcher, A. Steinbach, R.W. Hartmann, Catalytic enzyme activity on a biosensor chip: combination of surface plasmon resonance and mass spectrometry, Anal. Biochem. 428 (2012) 28-30.
38. O. Trott, A.J. Olson, AutoDock Vina: improving the speed and accuracy pf docking with a new scoring function, efficient optimization, and multithreading, J. Comput. Chem. 31 (2009) 455-461