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Volumn 54, Issue 9, 2011, Pages 3348-3359

Immunosuppressive but non-LasR-inducing analogues of the pseudomonas aeruginosa quorum-sensing molecule N-(3-Oxododecanoyl)-l-homoserine Lactone

Author keywords

[No Author keywords available]

Indexed keywords

2 (1 NONYLHYDRAZINYL) N (2 OXOTETRAHYDROFURAN 3 YL)ACETAMIDE; 2 (N OCTYLSULFAMOYL) N (2 OXOTETRAHYDROFURAN 3 YL)ACETAMIDE; 2 [BENZYLOXY(NONYL)AMINO] N (2 OXOTETRAHYDROFURAN 3 YL)ACETAMIDE; 2 [HYDROXYL(NONYL)AMINO] N (2 OXOTETRAHYDROFURAN 3 YL)ACETAMIDE; 3 OXO N (THIAZOL 2 YL)DODECANAMIDE; IMMUNOSUPPRESSIVE AGENT; N (2 OXOTETRAHYDROFURAN 3 YL) 2 (UNDECYLSULFINYL)ACETAMIDE; N (2 OXOTETRAHYDROFURAN 3 YL) 2 (UNDECYLSULFONYL)ACETAMIDE; N (3 OXODODECANOYL)HOMOSERINE LACTONE; N OCTYL 2 [N (2 OXOTETRAHYDROFURAN 3 YL)SULFAMOYL]ACETAMIDE; N1 (2 CARBAMOYLPHENYL) N3 OCTYLMALONAMIDE; N1 (2 HYDROXYPHENYL) N3 OCTYLMALONAMIDE; N1 (3 CARBAMOYLPHENYL) N3 OCTYLMALONAMIDE; N1 (5 CHLORO 2 HYDROXYPHENYL) N3 OCTYLMALONAMIDE; N1 [2 (DIMETHYLCARBAMOYL)PHENYL] N3 OCTYLMALONAMIDE; N1 CYCLOHEPTYL N3 OCTYLMALONAMIDE; N1 OCTYL N3 (PYRIDIN 2 YL)MALONAMIDE; SULFONAMIDE; TRANSCRIPTION FACTOR; TRANSCRIPTION FACTOR LASR; UNCLASSIFIED DRUG;

EID: 79955851420     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm2001019     Document Type: Article
Times cited : (28)

References (42)
  • 1
    • 33644867594 scopus 로고    scopus 로고
    • Immune modulation by Pseudomonas aeruginosa quorum-sensing signal molecules
    • DOI 10.1016/j.ijmm.2006.01.037, PII S1438422106000385, Quorum Sensing in Human Pathogens
    • Pritchard, D. I. Immune modulation by Pseudomonas aeruginosa quorum-sensing signal molecules Int. J. Med. Microbiol. 2006, 296, 111-116 (Pubitemid 43375993)
    • (2006) International Journal of Medical Microbiology , vol.296 , Issue.2-3 , pp. 111-116
    • Pritchard, D.I.1
  • 4
    • 7044222233 scopus 로고    scopus 로고
    • Differential immune modulatory activity of Pseudomonas aeruginosa quorum-sensing signal molecules
    • DOI 10.1128/IAI.72.11.6463-6470.2004
    • Hooi, D. S.; Bycroft, B. W.; Chhabra, S. R.; Williams, P.; Pritchard, D. I. Differential immune modulatory activity of Pseudomonas aeruginosa quorum-sensing signal molecules Infect. Immun. 2004, 72, 6463-6470 (Pubitemid 39425427)
    • (2004) Infection and Immunity , vol.72 , Issue.11 , pp. 6463-6470
    • Hooi, D.S.W.1    Bycroft, B.W.2    Chhabra, S.R.3    Williams, P.4    Pritchard, D.I.5
  • 5
    • 4344618967 scopus 로고    scopus 로고
    • Lipopolysaccharides of Bacteroides fragilis, Chlamydia trachomatis and Pseudomonas aeruginosa signal via Toll-like receptor 2
    • DOI 10.1099/jmm.0.45598-0
    • Erridge, C.; Pridmore, A.; Eley, A.; Stewart, J.; Poxton, I. R. Lipopolysaccharides of Bacteroides fragilis, Chlamydia trachomati s and Pseudomonas aeruginosa signal via toll-like receptor 2 J. Med. Microbiol. 2004, 53, 735-740 (Pubitemid 39430358)
    • (2004) Journal of Medical Microbiology , vol.53 , Issue.8 , pp. 735-740
    • Erridge, C.1    Pridmore, A.2    Eley, A.3    Stewart, J.4    Poxton, I.R.5
  • 7
    • 0141780934 scopus 로고    scopus 로고
    • The Pseudomonas aeruginosa autoinducer N-3-oxododecanoyl homoserine lactone accelerates apoptosis in macrophages and neutrophils
    • DOI 10.1128/IAI.71.10.5785-5793.2003
    • Tateda, K.; Ishii, Y.; Horikawa, M.; Matsumoto, T.; Miyairi, S.; Pechere, J. C.; Standiford, T. J.; Ishiguro, M.; Yamaguchi, K. The Pseudomonas aeruginosa autoinducer N -3-oxododecanoyl homoserine lactone accelerates apoptosis in macrophages and neutrophils Infect. Immun. 2003, 71, 5785-5793 (Pubitemid 37205632)
    • (2003) Infection and Immunity , vol.71 , Issue.10 , pp. 5785-5793
    • Tateda, K.1    Ishii, Y.2    Horikawa, M.3    Matsumoto, T.4    Miyairi, S.5    Pechere, J.C.6    Standiford, T.J.7    Ishiguro, M.8    Yamaguchi, K.9
  • 8
    • 67349208014 scopus 로고    scopus 로고
    • Influence of Pseudomonas aeruginosa quorum sensing signal molecule N -(3-oxododecanoyl) homoserine lactone on mast cells
    • Li, H.; Wang, L.; Ye, L.; Mao, Y.; Xie, X.; Xia, C.; Chen, J.; Lu, Z.; Song, J. Influence of Pseudomonas aeruginosa quorum sensing signal molecule N -(3-oxododecanoyl) homoserine lactone on mast cells Med. Microbiol. Immunol. 2009, 198, 113-121
    • (2009) Med. Microbiol. Immunol. , vol.198 , pp. 113-121
    • Li, H.1    Wang, L.2    Ye, L.3    Mao, Y.4    Xie, X.5    Xia, C.6    Chen, J.7    Lu, Z.8    Song, J.9
  • 9
    • 0032720626 scopus 로고    scopus 로고
    • The Pseudomonas aeruginosa quorum-sensing signal molecule, N-(3-oxododecanoyl)-L-homoserine lactone, inhibits porcine arterial smooth muscle contraction
    • DOI 10.1038/sj.bjp.0702870
    • Lawrence, R. N.; Dunn, W. R.; Bycroft, B.; Camara, M.; Chhabra, S. R.; Williams, P.; Wilson, V. G. The Pseudomonas aeruginos a quorum-sensing signal molecule, N -(3-oxododecanoyl)- l -homoserine lactone, inhibits porcine arterial smooth muscle contraction Br. J. Pharmacol. 1999, 128, 845-848 (Pubitemid 29494699)
    • (1999) British Journal of Pharmacology , vol.128 , Issue.4 , pp. 845-848
    • Lawrence, R.N.1    Dunn, W.R.2    Bycroft, B.3    Camara, M.4    Chhabra, S.R.5    Williams, P.6    Wilson, V.G.7
  • 11
    • 0035399999 scopus 로고    scopus 로고
    • 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
    • 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-kappa B and activator protein-2 J. Immunol. 2001, 167, 366-374 (Pubitemid 32567801)
    • (2001) Journal of Immunology , vol.167 , Issue.1 , pp. 366-374
    • Smith, R.S.1    Fedyk, E.R.2    Springer, T.A.3    Mukaida, N.4    Iglewski, B.H.5    Phipps, R.P.6
  • 13
    • 46049108150 scopus 로고    scopus 로고
    • Peroxisome proliferator-activated receptors mediate host cell proinflammatory responses to Pseudomonas aeruginosa autoinducer
    • DOI 10.1128/JB.01444-07
    • Jahoor, A.; Patel, R.; Bryan, A.; Do, C.; Krier, J.; Watters, C.; Wahli, W.; Li, G.; Williams, S. C.; Rumbaugh, K. P. Peroxisome proliferator-activated receptors mediate host cell proinflammatory responses to Pseudomonas aeruginosa autoinducer J. Bacteriol. 2008, 190, 4408-4415 (Pubitemid 351898956)
    • (2008) Journal of Bacteriology , vol.190 , Issue.13 , pp. 4408-4415
    • Jahoor, A.1    Patel, R.2    Bryan, A.3    Do, C.4    Krier, J.5    Watters, C.6    Wahli, W.7    Li, G.8    Williams, S.C.9    Rumbaugh, K.P.10
  • 15
    • 76549126323 scopus 로고    scopus 로고
    • Pseudomonas signal molecule 3-oxo-C12-homoserine lactone interferes with binding of rosiglitazone to human PPARgamma
    • Cooley, M. A.; Whittall, C.; Rolph, M. S. Pseudomonas signal molecule 3-oxo-C12-homoserine lactone interferes with binding of rosiglitazone to human PPARgamma Microbes Infect. 2010, 12, 231-237
    • (2010) Microbes Infect. , vol.12 , pp. 231-237
    • Cooley, M.A.1    Whittall, C.2    Rolph, M.S.3
  • 16
    • 42449149418 scopus 로고    scopus 로고
    • A eukaryotic binding protein for the immune modulatory bacterial quorum sensing molecule N-(3-oxododecanoyl)-L-homoserine lactone
    • Seabra, R.; Brown, A.; Hooi, D.; Kerkhoff, C.; Chhabra, S. R.; Harty, C.; Williams, P.; Pritchard, D. I. A eukaryotic binding protein for the immune modulatory bacterial quorum sensing molecule N -(3-oxododecanoyl)- l -homoserine lactone Calcium Binding Proteins 2008, 3, 31-37 (Pubitemid 351567531)
    • (2008) Calcium Binding Proteins , vol.3 , Issue.1 , pp. 31-37
    • Seabra, R.1    Brown, A.2    Hooi, D.S.W.3    Kerkhoff, C.4    Chhabra, S.R.5    Harty, C.6    Williams, P.7    Pritchard, D.I.8
  • 17
    • 0037413582 scopus 로고    scopus 로고
    • Synthetic analogues of the bacterial signal (quorum sensing) molecule N-(3-oxododecanoyl)-L-homoserine lactone as immune modulators
    • DOI 10.1021/jm020909n
    • Chhabra, S. R.; Harty, C.; Hooi, D. S. W.; Daykin, M.; Williams, P.; Telford, G.; Pritchard, D. I.; Bycroft, B. W. Synthetic analogues of the bacterial signal (quorum sensing) molecule N -(3-oxododecanoyl)- l -homoserine lactone as immune modulators J. Med. Chem. 2003, 46, 97-104 (Pubitemid 36043789)
    • (2003) Journal of Medicinal Chemistry , vol.46 , Issue.1 , pp. 97-104
    • Chhabra, S.R.1    Harty, C.2    Hooi, D.S.W.3    Daykin, M.4    Williams, P.5    Telford, G.6    Pritchard, D.I.7    Bycroft, B.W.8
  • 18
    • 0029091957 scopus 로고
    • A convenient two-step procedure for the synthesis of substituted allylic amines from allylic alcohols
    • Sen, S. E.; Roach, S. L. A convenient two-step procedure for the synthesis of substituted allylic amines from allylic alcohols Synthesis 1995, 756-758
    • (1995) Synthesis , pp. 756-758
    • Sen, S.E.1    Roach, S.L.2
  • 19
    • 4043071644 scopus 로고
    • The cyanoborohydride anion as a selective reducing agent
    • Borch, R. F.; Bernstein, M. D.; Durst, H. D. The cyanoborohydride anion as a selective reducing agent J. Am. Chem. Soc. 1971, 93, 2897-2904
    • (1971) J. Am. Chem. Soc. , vol.93 , pp. 2897-2904
    • Borch, R.F.1    Bernstein, M.D.2    Durst, H.D.3
  • 20
    • 0000844109 scopus 로고    scopus 로고
    • Reductive amination of aldehydes and ketones with sodium triacetoxyborohydride. Studies on direct and indirect reductive amination procedures
    • Abdel-Magid, A. F.; Carson, K. G.; Harris, B. D.; Maryanoff, C. A.; Shah, R. D. Reductive amination of aldehydes and ketones with sodium triacetoxyborohydride. Studies on direct and indirect reductive amination procedures J. Org. Chem. 1996, 61, 3849-3862 (Pubitemid 126532674)
    • (1996) Journal of Organic Chemistry , vol.61 , Issue.11 , pp. 3849-3862
    • Abdel-Magid, A.F.1    Carson, K.G.2    Harris, B.D.3    Maryanoff, C.A.4    Shah, R.D.5
  • 21
    • 0001686474 scopus 로고
    • Conformational perturbations induced by N-amination and N-hydroxylation of peptides
    • Dupont, V.; Lecoq, A.; Mangeot, J. P.; Aubry, A.; Boussard, G.; Marraud, M. Conformational perturbations induced by N-amination and N-hydroxylation of peptides J. Am. Chem. Soc. 1993, 115, 8898-8906
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 8898-8906
    • Dupont, V.1    Lecoq, A.2    Mangeot, J.P.3    Aubry, A.4    Boussard, G.5    Marraud, M.6
  • 22
    • 0342325522 scopus 로고
    • Addition of thioglycolic acid to a-alkenes
    • Smith, B.; Hernestam, S. Addition of thioglycolic acid to a-alkenes Acta Chem. Scand. 1954, 8, 1111-1119
    • (1954) Acta Chem. Scand. , vol.8 , pp. 1111-1119
    • Smith, B.1    Hernestam, S.2
  • 23
    • 0037010793 scopus 로고    scopus 로고
    • Lewis acid assisted permanganate oxidations
    • DOI 10.1016/S0040-4020(02)01227-9, PII S0040402002012279
    • Lai, S.; Lee, D. G. Lewis acid assisted permanganate oxidations Tetrahedron 2002, 58, 9879-9887 (Pubitemid 35351439)
    • (2002) Tetrahedron , vol.58 , Issue.49 , pp. 9879-9887
    • Lai, S.1    Lee, D.G.2
  • 24
    • 0032477856 scopus 로고    scopus 로고
    • Inhibitors of acyl-CoA:cholesterol O-acyltransferase (ACAT) as hypocholesterolemic agents: Synthesis and structure-activity relationships of novel series of sulfonamides, acylphosphonamides and acylphosphoramidates
    • DOI 10.1016/S0960-894X(98)00011-0, PII S0960894X98000110
    • Lee, H. T.; Roark, W. H.; Picard, J. A.; Sliskovic, D. R.; Roth, B. D.; Stanfield, R. L.; Hamelehle, K. L.; Bousley, R. F.; Krause, B. R. Inhibitors of acyl-CoA:cholesterol O -acyltransferase (ACAT) as hypocholesterolemic agents: synthesis and structure-activity relationships of novel series of sulfonamides, acylphosphonamides and acylphosphoramidates Bioorg. Med. Chem. Lett. 1998, 8, 289-294 (Pubitemid 28066350)
    • (1998) Bioorganic and Medicinal Chemistry Letters , vol.8 , Issue.3 , pp. 289-294
    • Lee, H.T.1    Roark, W.H.2    Picard, J.A.3    Sliskovic, D.R.4    Roth, B.D.5    Stanfield, R.L.6    Hamelehle, K.L.7    Bousley, R.F.8    Krause, B.R.9
  • 26
    • 45749113796 scopus 로고    scopus 로고
    • Expanding dialogues: From natural autoinducers to non-natural analogues that modulate quorum sensing in Gram-negative bacteria
    • Geske, G. D.; ONeill, J. C.; Blackwell, H. E. Expanding dialogues: from natural autoinducers to non-natural analogues that modulate quorum sensing in Gram-negative bacteria Chem. Soc. Rev. 2008, 37, 1432-1447
    • (2008) Chem. Soc. Rev. , vol.37 , pp. 1432-1447
    • Geske, G.D.1    Oneill, J.C.2    Blackwell, H.E.3
  • 27
    • 34250357654 scopus 로고    scopus 로고
    • Molecular insights into quorum sensing in the human pathogen Pseudomonas aeruginosa from the structure of the virulence regulator LasR bound to its autoinducer
    • DOI 10.1074/jbc.M700556200
    • Bottomley, M. J.; Muraglia, E.; Bazzo, R.; Carfi, A. Molecular insights into quorum sensing in the human pathogen Pseudomonas aeruginosa from the structure of the virulence regulator LasR bound to its autoinducer J. Biol. Chem. 2007, 282, 13592-13600 (Pubitemid 47100513)
    • (2007) Journal of Biological Chemistry , vol.282 , Issue.18 , pp. 13592-13600
    • Bottomley, M.J.1    Muraglia, E.2    Bazzo, R.3    Carfi, A.4
  • 28
    • 27644507318 scopus 로고    scopus 로고
    • Alleviation of insulitis and moderation of diabetes in NOD mice following treatment with a synthetic Pseudomonas aeruginosa signal molecule, N-(3-oxododecanoyl)-L-homoserine lactone
    • DOI 10.1007/s00592-005-0190-2
    • Pritchard, D. I.; Todd, I.; Brown, A.; Bycroft, B. W.; Chhabra, S. R.; Williams, P.; Wood, P. Alleviation of insulitis and moderation of diabetes in NOD mice following treatment with a synthetic Pseudomonas aeruginos a signal molecule, N -(3-oxododecanoyl)- l -homoserine lactone Acta Diabetol. 2005, 42, 119-122 (Pubitemid 41551998)
    • (2005) Acta Diabetologica , vol.42 , Issue.3 , pp. 119-122
    • Pritchard, D.I.1    Todd, I.2    Brown, A.3    Bycroft, B.W.4    Chhabra, S.R.5    Williams, P.6    Wood, P.7
  • 29
    • 0019123552 scopus 로고
    • Biochemical and biological characterization of lymphocyte regulatory molecules. V. Identification of an interleukin 2-producing human leukemia T cell line
    • DOI 10.1084/jem.152.6.1709
    • Gillis, S.; Watson, J. Biochemical and biological characterization of lymphocyte regulatory molecules. V. Identification of an interleukin 2-producing human leukemia T cell line J. Exp. Med. 1980, 152, 1709-1719 (Pubitemid 11210348)
    • (1980) Journal of Experimental Medicine , vol.152 , Issue.6 , pp. 1709-1719
    • Gillis, S.1    Watson, J.2
  • 30
    • 0021245601 scopus 로고
    • The role of T3 surface molecules in the activation of human T cells: A two-stimulus requirement for IL 2 production reflects events occuring at a pre-translational level
    • Weiss, A.; Wiskocil, R. L.; Stobo, J. D. The role of T3 surface molecules in the activation of human T cells: a two-stimulus requirement for IL 2 production reflects events occurring at a pre-translational level J. Immunol. 1984, 133, 123-128 (Pubitemid 14076697)
    • (1984) Journal of Immunology , vol.133 , Issue.1 , pp. 123-128
    • Weiss, A.1    Wiskocil, R.L.2    Stobo, J.D.3
  • 35
    • 32844473495 scopus 로고    scopus 로고
    • Stereoisomers of P. aeruginosa autoinducer analog to probe the regulator binding site
    • DOI 10.1016/j.chembiol.2005.12.013, PII S1074552106000378
    • Jog, G. J.; Igarashi, J.; Suga, H. Stereoisomers of P. aeruginosa autoinducer analog to probe the regulator binding site Chem. Biol. 2006, 13, 123-128 (Pubitemid 43255584)
    • (2006) Chemistry and Biology , vol.13 , Issue.2 , pp. 123-128
    • Jog, G.J.1    Igarashi, J.2    Suga, H.3
  • 36
    • 35948991561 scopus 로고    scopus 로고
    • Modulation of bacterial quorum sensing with synthetic ligands: Systematic evaluation of N-acylated homoserine lactones in multiple species and new insights into their mechanisms of action
    • DOI 10.1021/ja074135h
    • Geske, G. D.; ONeill, J. C.; Miller, D. M.; Mattmann, M. E.; Blackwell, H. E. Modulation of bacterial quorum sensing with synthetic ligands: systematic evaluation of N-acylated homoserine lactones in multiple species and new insights into their mechanisms of action J. Am. Chem. Soc. 2007, 129, 13613-13625 (Pubitemid 350071790)
    • (2007) Journal of the American Chemical Society , vol.129 , Issue.44 , pp. 13613-13625
    • Geske, G.D.1    O'Neill, J.C.2    Miller, D.M.3    Mattmann, M.E.4    Blackwell, H.E.5
  • 38
    • 19444363444 scopus 로고    scopus 로고
    • Sourcing a chemical succession for cyclosporin from parasites and human pathogens
    • DOI 10.1016/S1359-6446(05)03395-7, PII S1359644605033957
    • Pritchard, D. I. Sourcing a chemical succession for cyclosporin from parasites and human pathogens Drug Discovery Today 2005, 10, 688-691 (Pubitemid 40724550)
    • (2005) Drug Discovery Today , vol.10 , Issue.10 , pp. 688-691
    • Pritchard, D.I.1
  • 39
    • 0002714675 scopus 로고
    • Rapid chromatographic technique for preparative separations with moderate resolution
    • Still, W. C.; Kahn, M.; Mitra, A. Rapid chromatographic technique for preparative separations with moderate resolution J. Org. Chem. 1978, 43, 2923-2925
    • (1978) J. Org. Chem. , vol.43 , pp. 2923-2925
    • Still, W.C.1    Kahn, M.2    Mitra, A.3
  • 40
    • 79955839627 scopus 로고
    • Esters of sulfoacetic acid. I. Sulfochlorinated carboxylic esters and their derivatives
    • Vieillefosse, R. Esters of sulfoacetic acid. I. Sulfochlorinated carboxylic esters and their derivatives Bull. Soc. Chim. Fr. 1947, 351-356
    • (1947) Bull. Soc. Chim. Fr. , pp. 351-356
    • Vieillefosse, R.1
  • 41
    • 0033729216 scopus 로고    scopus 로고
    • Integration-proficient Pseudomonas aeruginosa vectors for isolation of single-copy chromosomal lacZ and lux gene fusions
    • Becher, A.; Schweizer, H. P. Integration-proficient Pseudomonas aeruginosa vectors for isolation of single-copy chromosomal lacZ and lux gene fusions BioTechniques 2000, 29 (948-950) 952
    • (2000) BioTechniques , vol.29 , Issue.948-950 , pp. 952
    • Becher, A.1    Schweizer, H.P.2
  • 42
    • 0036282814 scopus 로고    scopus 로고
    • Quorum sensing is not required for twitching motility in Pseudomonas aeruginosa
    • DOI 10.1128/JB.184.13.3598-3604.2002
    • Beatson, S. A.; Whitchurch, C. B.; Semmler, A. B.; Mattick, J. S. Quorum sensing is not required for twitching motility in Pseudomonas aeruginosa J. Bacteriol. 2002, 184, 3598-3604 (Pubitemid 34625668)
    • (2002) Journal of Bacteriology , vol.184 , Issue.13 , pp. 3598-3604
    • Beatson, S.A.1    Whitchurch, C.B.2    Semmler, A.B.T.3    Mattick, J.S.4


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