Adhesion Inhibition of F1C-Fimbriated Escherichia coli and Pseudomonas aeruginosa PAK and PAO by Multivalent Carbohydrate Ligands

ChemBioChem

Volumn 4, Issue 12, 2003, Pages 1317-1325

  Autar, Reshma ^a   Khan, A Salam ^b   Schad, Matthias ^b   Hacker, Jörg ^b   Liskamp, Rob M J ^a   Pieters, Roland J ^a  

^a UTRECHT UNIVERSITY   (Netherlands)

^b UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

Anti adhesion; Antibacterial; Carbohydrates; Dendrimers; Glycoconjugates

Indexed keywords

3,5' BIS(2 AMINOETHOXY)BENZOIC ACID; ADHESIN; ANTIADHESIN; CARBOHYDRATE DERIVATIVE; DISACCHARIDE; DIVALENT CATION; GALACTOSE; GLUCOSAMINE; LIGAND; N ACETYLGALACTOSAMINE; PROTEIN INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; BACTERIUM ADHERENCE; CARBOHYDRATE SYNTHESIS; CONJUGATION; DRUG POTENCY; ENZYME LINKED IMMUNOSORBENT ASSAY; ESCHERICHIA COLI; EVALUATION; FIMBRIA; IC 50; INHIBITION KINETICS; LIGAND BINDING; MULTIVALENCE; NONHUMAN; PATHOGENESIS; PRIORITY JOURNAL; PRODUCT RECOVERY; PSEUDOMONAS AERUGINOSA; SEQUENCE ANALYSIS; STATISTICAL SIGNIFICANCE; STRAIN DIFFERENCE; STRAIN IDENTIFICATION; VALENCE;

BACTERIAL ADHESION; CARBOHYDRATE CONFORMATION; CARBOHYDRATE SEQUENCE; CARBOHYDRATES; DISACCHARIDES; ESCHERICHIA COLI; FIMBRIAE, BACTERIAL; INHIBITORY CONCENTRATION 50; LIGANDS; MOLECULAR SEQUENCE DATA; PSEUDOMONAS AERUGINOSA;

BACTERIA (MICROORGANISMS); ESCHERICHIA COLI; PSEUDOMONAS; PSEUDOMONAS AERUGINOSA;

EID: 0346787607     PISSN: 14394227     EISSN: None     Source Type: Journal    
DOI: 10.1002/cbic.200300719     Document Type: Article

References (60)

1. S. B. Levy, Sci. Am. March 1998, 32.
2. H. Breithaupt, Nat. Biotechnol. 1999, 17, 1165.
3. N. Sharon, FEBS Lett. 1987, 217, 145.
4. K.-A. Karlsson, Mol. Microbiol. 1998, 29, 1.
5. D. Zopf, S. Roth, Lancet 1996, 347, 1017.
6. I. Ofek, N. Sharon, Cell. Mol. Life Sci. 2002, 59, 1666.
7. R. T. Irvin, D. L. Bautista, Nat. Biotechnol. 1999, 17, 20.
8. T. Oelschlaeger, A. S. Khan, C. Meier, J. Hacker, Nova Acta Leopold. NF75 1997, 301, 195.
9. A. S. Khan, N. C. Johnston, H. Goldfine, D. M. Schifferli, Infect. Immun. 1996, 64, 3688.
10. K. F. Johnson, Glycoconjugate J. 1999, 16, 141.
11. a) M. Mammen, S.-K. Chio, G. M. Whitesides, Angew. Chem. 1998, 110, 2908; Angew. Chem. Int. Ed. 1998, 37, 2754;
12. a) M. Mammen, S.-K. Chio, G. M. Whitesides, Angew. Chem. 1998, 110, 2908; Angew. Chem. Int. Ed. 1998, 37, 2754;
13. b) L. L. Kiessling, L. E. Strong, J. E. Gestwicki, Annu. Rep. Med. Chem. 2000, 35, 321;
14. c) J. J. Lundquist, E. J. Toone, Chem. Rev. 2002, 102, 555;
15. d) T. K. Lindhorst, Top. Curr. Chem. 2002, 218, 201;
16. e) R. Roy, Curr. Opin. Struct. Biol. 1996, 6, 692;
17. f) R. T. Lee, Y. C. Lee, Glycoconjugate J. 2000, 17, 543;
18. g) W. B. Turnbull, J. F. Stoddart, Rev. Mol. Biotechnol. 2002, 90, 231;
19. h) M. J. Cloninger, Curr. Opin. Chem. Biol. 2002, 6, 742.
20. H. C. Hansen, S. Haataja, J. Finne, G. Magnusson, J. Am. Chem. Soc. 1997 119, 6974.
21. T. K. Lindhorst, C. Kieburg, U. Krallmann-Wenzel, Glycoconj. J. 1998, 15, 605.
22. a) T. K. Lindhorst, M. Dubber, U. Krallmann-Wenzel, S. Ehlers, Eur. J. Org. Chem. 2000, 2027;
23. b) T. K. Lindhorst, S. Kötter, U. Krallmann-Wenzel, S. Ehlers, J. Chem. Soc. Perkin Trans. 1 2001, 823.
24. N. Nagahori, R. T. Lee, S.-I. Nishimura, D. Pagé, R. Roy, Y. C. Lee, ChemBioChem 2002, 3, 836.
25. A. S. Khan, I. Mühldorfer, V. Demuth, U. Wallner, T. K. Korhonen, J. Hacker, Mol. Gen. Genet. 2000, 263, 96.
26. A. S. Khan, B. Kniep, T. A. Oelschlaeger, I. van Die, T. Korhonen, J. Hacker, Infect. Immun. 2000, 68, 3541.
27. A. S. Khan, J. Hacker, Adv. Exp. Med. Biol. 2000, 485, 213.
28. a) S. J. E. Mulders, A. J. Brouwer, R. M. J. Liskamp, Tetrahedron Lett. 1997, 38, 3085;
29. S. J. E. Mulders, A. J. Brouwer, P. G. J. van der Meer, R. M. J. Liskamp, Tetrahedron Lett. 1997, 38, 631;
30. A. J. Brouwer, S. J. E. Mulders, R. M. J. Liskamp, Eur. J. Org. Chem. 2001, 1903;
31. I. Vrasidas, PhD thesis, Utrecht University (The Netherlands), 2003.
32. a) I. Vrasidas, N. J. de Mol, R. M. J. Liskamp, R. J. Pieters, Eur. J. Org. Chem. 2001, 4685;
33. b) S. André, R. J. Pieters, I. Vrasidas, H. Kaltner, I. Kuwabara, F.-T. Liu, R. M. J. Liskamp, H.-J. Gabius, ChemBioChem 2001, 2, 822;
34. c) I. Vrasidas, S. André, P. Valentini, C. Böck, M. Lensch, H. Kaltner, R. M. J. Liskamp, H.-J. Gabius, R. J. Pieters, Org. Biomol. Chem. 2003, 1, 803.
35. H. C. Krivan, D. D. Roberts, V. Ginsburg, Proc. Natl. Acad. Sci. USA 1988, 85, 6157.
36. L. Imundo, J. Barasch, A. Prince, Q. Al-Awqati, Proc. Natl. Acad. Sci. USA 1995, 92, 3019.
37. H. B. Sheth, K. K. Lee, W. Y. Wong, G. Srivastava, O. Hindsgaul, R. S. Hodges, W. Paranchych, R.T. Irvin, Mol. Microbiol. 1994, 11, 715.
38. D. W. Keizer, C. M. Slupsky, M. Kalisiak, A. P. Campbell, M. P. Crump, P. A. Sastry, B. Hazes, R. T. Irvin, B. D. Sykes, J. Biol. Chem. 2001, 276, 24186.
39. B. Hazes, P. A. Sastry, K. Hayakawa, R. J. Read, R. T. Irvin, J. Mol. Biol. 2000, 299, 1005.
40. S. Sabesan, K. Bock, R. L. Lemieux, Can. J. Chem. 1984, 62, 1034.
41. H. Jiao, O. Hindsgaul, J. Carbohydr. Chem. 1999, 18, 499.
42. K. Jansson, S. Ahlfors, T. Frejd, J. Kihlberg, G. Magnusson, J. Org. Chem. 1988, 53, 5629.
43. A. K. Misra, N. Roy, J. Carbohydr. Chem. 1998, 17, 1047.
44. Use of a donor containing a phthaloyl protecting group led to a mixture of inseparable isomers.
45. a) Z. Zhang, I. R. Ollmann, X.-S. Ye, R. Wischnat, T. Baasov, C.-H. Wong, J. Am. Chem. Soc. 1999, 121, 734;
46. b) S. Bhattacharyya, B. G. Magnusson, U. Wellmar, U. J. Nilsson, J. Chem. Soc. Perkin Trans. 1 2001, 886.
47. K. Higashi, H. Susaki, Chem. Pharm. Bull. 1992, 40, 2019.
48. M. Nitz, D. R. Bundle, J. Org. Chem. 2000, 65, 3064.
49. G. H. Veeneman, S. H. van Leeuwen, J. H. van Boom, Tetrahedron Lett. 1990, 31, 1331.
50. K. Bock, I. Lundt, C. Pedersen, Tetrahedron Lett. 1973, 13, 1073.
51. K. Bock, C. Pedersen, J. Chem. Soc. Perkin Trans. 2 1974, 293.
52. W. Dullenkopf, J. C. Castro-Palomino, L. Manzoni, R. R. Schmidt, Carbohydr. Res. 1996, 296, 135.
53. B. Dean, H. Oguchi, S. Cai, E. Otsuji, K. Tashiro, S.-I. Hakomori, T. Toyokuni, Carbohydr. Res. 1993, 245, 175.
54. M. Wilstermann, L. O. Kononov, U. Nilsson, A. K. Ray, G. Magnusson, J. Am. Chem. Soc. 1995, 117, 4742.
55. F. Schweizer, H. Jiao, O. Hindsgaul, W. Y. Wong, R. T. Irvin, Can. J. Microbiol. 1998, 44, 307.
56. The adhesin of the F1C fimbriae has not yet been identified but none of the eight genes required for its biogenesis (see ref.[17]) has significant homology to the Pseudomonas adhesins.
57. F. Bäckhed, B. Alsén, N. Roche, J. Ångström, A. von Euler, M. E. Breimer, B. Westerlund-Wikström, S. Teneberg, A. Richter-Dahlfors, J. Biol. Chem. 2002, 277, 18198.
58. I. van Die, I. B. van Geffen, W. Hoekstra, H. Bergmans, Gene 1985, 34, 187.
59. C. Kiewitz, B. Tummler, J. Bacteriol. 2000, 182, 3125.
60. A. S. Khan, D. M. Schifferli, Infect. Immun. 1994, 62, 4233.