Synthetic analogues of the bacterial signal (quorum sensing) molecule N-(3-oxododecanoyl)-L-homoserine lactone as immune modulators

Journal of Medicinal Chemistry

Volumn 46, Issue 1, 2003, Pages 97-104

  Chhabra, Siri Ram ^a   Harty, Chris ^a   Hooi, Doreen S W ^a   Daykin, Mavis ^a   Williams, Paul ^a   Telford, Gary ^a   Pritchard, David I ^a   Bycroft, Barrie W ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

IMMUNOMODULATING AGENT; LACTONE; LIPOPOLYSACCHARIDE; N (3 OXODODECANOYL)HOMOSERINE LACTONE; TUMOR NECROSIS FACTOR ALPHA; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; AUTOIMMUNE DISEASE; CELL ASSAY; CELL PROLIFERATION; CONTROLLED STUDY; CYTOKINE RELEASE; DRUG POTENCY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IC 50; IMMUNOMODULATION; INSULIN DEPENDENT DIABETES MELLITUS; LEUKOCYTE; MONONUCLEAR CELL; NONHUMAN; PSEUDOMONAS AERUGINOSA; PSORIASIS; RHEUMATOID ARTHRITIS; STRUCTURE ACTIVITY RELATION;

ADJUVANTS, IMMUNOLOGIC; ANIMALS; CELL DIVISION; HOMOSERINE; HUMANS; LACTONES; LEUKOCYTES, MONONUCLEAR; LIPOPOLYSACCHARIDES; MICE; MICE, INBRED BALB C; NEUTROPHIL ACTIVATION; PSEUDOMONAS AERUGINOSA; SPLEEN; STRUCTURE-ACTIVITY RELATIONSHIP; TUMOR NECROSIS FACTOR-ALPHA;

EID: 0037413582     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm020909n     Document Type: Article

References (20)

1. Jacobson, D. L.; Gange, S. J.; Rose, N. R.; Graham, N. M. H. Epidemiology and estimated population burden of selected autoimmune diseases in the United States. Clin. Immun. Immunopathol. 1997, 84, 223-243.
2. Allison, A. C. Immunosuppressive drugs: The first fifty years and a glance forward. Immunopharmacology 2000, 47, 63-83.
3. Telford, G.; Wheeler, D.; Williams, P.; Tomkins, P. T.; Appleby, P.; Sewell, H.; Stewart, G. S. A. B.; Bycroft, B. W.; Pritchard, D. I. The Pseudomonas aeruginosa quorum-sensing signal molecule N-(3-oxododecanoyl)-L-homoserine lactone has immunomodulatory activity. Infect. Immun. 1998, 66, 36-42.
4. In the Experimental Section, systematic nomenclature is employed for the N-acylhomoserine lactones (AHLs). In the text, shorthand notations, now generally found in the biology literature, are used.
5. Lawrence, R. N.; Dunn, W. R.; Bycroft, B. W.; Camara, M.; Chhabra, S. R.; Williams, P.; Wilson, V. G. The Pseudomonas aeruginosa quorum-sensing signal molecule, N-(3-oxododecanoyl)L-homoserine lactone, inhibits porcine arterial smooth muscle contraction. Br. J. Pharmacol. 1999, 128, 845-848.
6. Smith, R. S.; Harris, S. G.; Phipps, R.; Iglewski, B. The Pseudomonas aeruginosa quorum-sensing molecule N-(3-oxododecanoyl)homoserine lactone contributes to virulence and induces inflammation in vivo. J. Bacteriol. 2002, 184, 1132-1139.
7. Smith, R. S.; Fedyk, E. R.; Springer, T. A.; Mukaida, N.; Iglewski, B. H.; Phipps, R. P. IL-8 Production in human lung fibroblasts and epithelial cells activated by the Pseudomonas autoinducer N-3-oxododecanoyl homoserine lactone is transcriptionally regulated by NF-κB and activator protein-2. J. Immunol. 2001, 167, 366-374.
8. Bainton, N. J.; Bycroft, B. W.; Chhabra, S. R.; Stead, P.; Gledhill, L.; Hill, P. J.; Rees, C. E. D.; Winson, M. K.; Salmond, G. P. C.; Stewart, G. S. A. B.; Williams, P. A general role for the autoinducer in bacterial cell signalling: Control of antibiotic biosynthesis in Erwinia. Gene 1992, 116, 87-91.
9. Bainton, N. J.; Stead, P.; Chhabra, S. R.; Bycroft, B. W.; Salmond, G. P. C.; Stewart, G. S. A. B.; Williams, P. N-(3-oxododecanoyl)-L-homoserine lactone regulates carbapenem antibiotic production in Erwinia carotovora. Biochem. J. 1992, 288, 997-1004.
10. Chhabra, S. R.; Stead, P.; Bainton, N. J.; Salmond, G. P. C.; Stewart, G. S. A. B.; Williams, P.; Bycroft, B. W. Autoregulation of carbapenem biosynthesis in Erwinia carotovora by analogues ofN-(3-oxododecanoyl)-L-homoserine lactone. J. Antibiot. 1993, 46, 441-454.
11. Camara, M.; Daykin, M.; Chhabra, S. R. Detection, purification and synthesis of N-acylhomoserine lactone quorum sensing signal molecules. Methods Microbiol. 1998, 27, 319-330.
12. Eberhard, A.; Widrig, C. A.; McBath, P.; Schineller, B. Analogues of the autoinducer of bioluminescence in Vibrio fischeri. Arch. Microbiol. 1986, 146, 35-40.
13. Dekhane, M.; Douglas, K. T.; Gilbert, P. A. A novel convenient route to the naturally occurring 3-oxoacyl-L-homoserine lactones and related bacterial autoinducers. Tetrahedron Lett. 1996, 37, 1883-1884.
14. Zhu, J.; Beaber, J. W.; More, M. I.; Fuqua, C.; Eberhard, A.; Winans, S. C. Analogues of the autoinducer 3-oxooctanoyl-homoserine lactone strongly inhibit activity of the TraR protein. J. Bacteriol. 1998, 180, 5398-5405.
15. Zhang, L.; Murphy, P. J.; Kerr, A.; Tate, M. E. Agrobacterium conjugation and gene regulation by N-Acyl-L-homoserine lactones. Nature 1993, 362, 446-448.
16. Maibaum, J.; Rich, D. H. Synthesis of the novel π-(benzyloxymethyl)-protected histidine analogue of statine. Inhibition of penicillopepsin by pepstatin-derived peptides containing different statin side-chain derivatives. J. Med. Chem. 1989, 32, 1571-1576.
17. Weber, H.; Khorana, H. G. Polynucleotides. CIV. Total synthesis of the structural gene for an alanine transfer ribonucleic acid from yeast. Chemical synthesis of an icosadeoxynucleotide corresponding to the nucleotide sequence 21 to 40. J. Mol. Biol. 1972, 72, 219-249.
18. Zhdanov, R. I.; Zhenodarova, S. M. Chemical methods of oligonucleotide synthesis. Synthesis 1975, 222-245.
19. Bowers, A.; Halsall, T. G.; Jones, E. R. H.; Lemin, A. J. The chemistry of triterpines and related compounds. Part XVIII. Elucidation of the structure of polyporenic acid C. J. Chem. Soc. 1953, 2548-2560.
20. Fretz, H.; Albers, M. W.; Galat, A.; Standaert, R. F.; Lane, W. S.; Burakoff, S. J.; Bierer, B. E.; Schreiber, S. L. Rapamycin and FK506 binding proteins (immunophilins). J. Am. Chem. Soc. 1991, 113, 1409-1411.