메뉴 건너뛰기




Volumn 13, Issue 2, 2012, Pages 1284-1299

Imidazolines as Non-classical bioisosteres of N-Acyl homoserine lactones and quorum sensing inhibitors

Author keywords

AHL bioisosteres; Chromobacterium violaceum; Imidazoline synthesis; Quorum sensing

Indexed keywords

2 IMIDAZOLINE DERIVATIVE; 7 HEXYLOXYPHENYL 2 IMIDAZOLINE; 7 NONYLOXYPHENYL 2 IMIDAZOLINE; 8 HEXYLOXYPHENYL 2 IMIDAZOLINE; 8 NONYLOXYPHENYL 2 IMIDAZOLINE; ANTIINFECTIVE AGENT; N [4 PHENYL(IMIDAZO 2 YL)]HEXYLAMIDE; N [4 PHENYL(IMIDAZO 2 YL)]NONAMIDE; N ACYLHOMOSERINE LACTONE; PIGMENT; PRODIGIOSIN; UNCLASSIFIED DRUG; VIOLACEIN; GAMMA BUTYROLACTONE DERIVATIVE; INDOLE DERIVATIVE;

EID: 84857670062     PISSN: None     EISSN: 14220067     Source Type: Journal    
DOI: 10.3390/ijms13021284     Document Type: Article
Times cited : (10)

References (36)
  • 1
    • 84857665441 scopus 로고
    • Presented At Nobel Lecture 1945, Sweden, 11 December
    • Fleming, A. Penicillin. Presented at Nobel Lecture 1945, Sweden, 11 December 1945.
    • (1945)
    • Fleming, A.P.1
  • 2
    • 13244269901 scopus 로고    scopus 로고
    • Bacterial communication ("Quorum Sensing") via ligands and receptors: A novel pharmacologic target for the design of antibiotic drugs
    • and references therein
    • Raffa, R.B.; Iannuzzo, J.R.; Levine, D.R.; Saeid, K.K.; Schwartz, R.C.; Sucic, N.T.; Terleckyj, O.D.; Young, J.M. Bacterial communication ("Quorum Sensing") via ligands and receptors: A novel pharmacologic target for the design of antibiotic drugs. J. Pharmacol. Exp. Ther. 2005, 312, 417-423 and references therein.
    • (2005) J. Pharmacol. Exp. Ther , vol.312 , pp. 417-423
    • Raffa, R.B.1    Iannuzzo, J.R.2    Levine, D.R.3    Saeid, K.K.4    Schwartz, R.C.5    Sucic, N.T.6    Terleckyj, O.D.7    Young, J.M.8
  • 3
    • 0036174583 scopus 로고    scopus 로고
    • Effects of quorum-sensing deficiency on Pseudomonas aeruginosa biofilm formation and antibiotic resistance
    • Shih, P.-Ch.; Wang, Ch.-T. Effects of quorum-sensing deficiency on Pseudomonas aeruginosa biofilm formation and antibiotic resistance. J. Antimicrob. Chemother. 2002, 49, 309-314.
    • (2002) J. Antimicrob. Chemother , vol.49 , pp. 309-314
    • Shih, P.-C.H.1    Wang, C.H.-T.2
  • 5
    • 78651408197 scopus 로고    scopus 로고
    • Quorum Sensing in gram-negative bacteria: Small-molecule modulation of AHL and AI-2 Quorum Sensing pathways
    • Galloway, W.R.; Hodgkinson, J.T.; Bowden, S.D.; Welch, M.; Spring, D.R. Quorum Sensing in gram-negative bacteria: Small-molecule modulation of AHL and AI-2 Quorum Sensing pathways. Chem. Rev. 2011, 111, 28-67.
    • (2011) Chem. Rev , vol.111 , pp. 28-67
    • Galloway, W.R.1    Hodgkinson, J.T.2    Bowden, S.D.3    Welch, M.4    Spring, D.R.5
  • 6
    • 78651410943 scopus 로고    scopus 로고
    • Introduction to bacterial signals and chemical communication
    • Blackwell, H.E.; Fuqua, C. Introduction to bacterial signals and chemical communication. Chem. Rev. 2011, 111, 1-3.
    • (2011) Chem. Rev , vol.111 , pp. 1-3
    • Blackwell, H.E.1    Fuqua, C.2
  • 7
    • 84857674653 scopus 로고    scopus 로고
    • Note
    • Quorum sensing is a word which consists of a Latin word "quorum" and a English word "sensing" but his origin is Latin; in consequence we consider all the term must be written in italics.
  • 8
    • 11844255399 scopus 로고    scopus 로고
    • Bioisosterism: A useful strategy for molecular modification and drug design
    • Moreira, L.L.; Barreiro, E.J. Bioisosterism: A useful strategy for molecular modification and drug design. Curr. Med. Chem. 2005, 12, 23-49.
    • (2005) Curr. Med. Chem , vol.12 , pp. 23-49
    • Moreira, L.L.1    Barreiro, E.J.2
  • 9
    • 7744243992 scopus 로고    scopus 로고
    • Bioisosterism. A rational approach in drug design
    • Patani, A.G.; LaVoie, J.E. Bioisosterism. A rational approach in drug design. Chem. Rev. 1996, 96, 3147-3176.
    • (1996) Chem. Rev , vol.96 , pp. 3147-3176
    • Patani, A.G.1    Lavoie, J.E.2
  • 10
    • 12844275341 scopus 로고    scopus 로고
    • Rational design and synthesis of new Quorum-sensing inhibitors derived from acylated homoserine lactones and natural products from garlic
    • Persson, T.; Hansen, T.H.; Rasmussen, T.B.; Skindersø, M.E.; Givskov, M.; Nielsen, J. Rational design and synthesis of new Quorum-sensing inhibitors derived from acylated homoserine lactones and natural products from garlic. Org. Biomol. Chem. 2005, 3, 253-262.
    • (2005) Org. Biomol. Chem , vol.3 , pp. 253-262
    • Persson, T.1    Hansen, T.H.2    Rasmussen, T.B.3    Skindersø, M.E.4    Givskov, M.5    Nielsen, J.6
  • 12
    • 25144448174 scopus 로고    scopus 로고
    • Small molecule inhibitors of bacterial Quorum Sensing and biofilm formation
    • Geske, G.D.; Wezeman, R.J.; Siegel, A.P.; Blackwell, H.E. Small molecule inhibitors of bacterial Quorum Sensing and biofilm formation. J. Am. Chem. Soc. 2005, 127, 12762-12763.
    • (2005) J. Am. Chem. Soc , vol.127 , pp. 12762-12763
    • Geske, G.D.1    Wezeman, R.J.2    Siegel, A.P.3    Blackwell, H.E.4
  • 13
    • 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
    • Geske, G.D.; O'Neill, 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.
    • (2007) J. Am. Chem. Soc , vol.129 , pp. 13613-13625
    • Geske, G.D.1    O'Neill, J.C.2    Miller, D.M.3    Mattmann, M.E.4    Blackwell, H.E.5
  • 16
    • 0037256665 scopus 로고    scopus 로고
    • Induction and inhibition of Pseudomonas aeruginosa Quorum Sensing by synthetic autoinducer analogs
    • Smith, K.M.; Yigong, B.; Suga, H. Induction and inhibition of Pseudomonas aeruginosa Quorum Sensing by synthetic autoinducer analogs. Chem. Biol. 2003, 10, 81-89.
    • (2003) Chem. Biol , vol.10 , pp. 81-89
    • Smith, K.M.1    Yigong, B.2    Suga, H.3
  • 18
    • 0038167466 scopus 로고    scopus 로고
    • Library screening for synthetic agonists and antagonists of a Pseudomonas aeruginosa autoinducer
    • Smith, K.M.; Bu, Y.; Suga, H. Library screening for synthetic agonists and antagonists of a Pseudomonas aeruginosa autoinducer. Chem. Biol. 2003, 10, 563-571.
    • (2003) Chem. Biol , vol.10 , pp. 563-571
    • Smith, K.M.1    Bu, Y.2    Suga, H.3
  • 20
    • 33750582503 scopus 로고    scopus 로고
    • Novel Pseudomonas aeruginosa Quorum-sensing inhibitors identified in an ultra-high-throughput screen
    • Müh, U.; Schuster, M.; Heim, R.; Singh, A.; Olson, E.R.; Greenberg, P.E. Novel Pseudomonas aeruginosa Quorum-sensing inhibitors identified in an ultra-high-throughput screen. Antimicrob. Agents Chemother. 2006, 50, 3674-3679.
    • (2006) Antimicrob. Agents Chemother , vol.50 , pp. 3674-3679
    • Müh, U.1    Schuster, M.2    Heim, R.3    Singh, A.4    Olson, E.R.5    Greenberg, P.E.6
  • 21
    • 53849119474 scopus 로고    scopus 로고
    • Inhibition of bacterial quorum sensing regulated behaviors by Tremella fuciformis extract
    • Zhu, H.; Sun, S.J. Inhibition of bacterial quorum sensing regulated behaviors by Tremella fuciformis extract. Curr. Microbiol. 2008, 57, 418-422.
    • (2008) Curr. Microbiol , vol.57 , pp. 418-422
    • Zhu, H.1    Sun, S.J.2
  • 24
    • 37349025483 scopus 로고    scopus 로고
    • N-Acylhomoserine lactone regulates violacein production in Chromobacterium violaceum type strain ATCC 12472
    • Tomohiro, M.; Masashi, K.; Katsumasa, F.; Norihiro, K.; Tsukasa, I. N-Acylhomoserine lactone regulates violacein production in Chromobacterium violaceum type strain ATCC 12472. FEMS Microbiol. Lett. 2008, 279, 124-130.
    • (2008) FEMS Microbiol. Lett , vol.279 , pp. 124-130
    • Tomohiro, M.1    Masashi, K.2    Katsumasa, F.3    Norihiro, K.4    Tsukasa, I.5
  • 27
    • 77049143790 scopus 로고
    • Derivatives of n-Hexyl phenyl ether as antituberculous compounds
    • Partridge, M.W.; Turner, H.A. Derivatives of n-Hexyl phenyl ether as antituberculous compounds. J. Pharm. Pharmacol. 1953, 5, 111-116.
    • (1953) J. Pharm. Pharmacol , vol.5 , pp. 111-116
    • Partridge, M.W.1    Turner, H.A.2
  • 28
    • 0017874339 scopus 로고
    • 2-(Alkoxyaryl)-2-imidazoline monoamine oxidase inhibitors with antidepressant activity
    • Harfenist, M.; Soroko, F.E.; McKenzie, G.M. 2-(Alkoxyaryl)-2-imidazoline monoamine oxidase inhibitors with antidepressant activity. J. Med. Chem. 1978, 21, 405-409.
    • (1978) J. Med. Chem , vol.21 , pp. 405-409
    • Harfenist, M.1    Soroko, F.E.2    McKenzie, G.M.3
  • 29
    • 33845344358 scopus 로고    scopus 로고
    • One-pot synthesis of imidazolines from aldehydes: Detailed study about solvents and substrates
    • Fujioka, H.; Murai, K.; Kubo, O.; Ohbay, Y.; Kita, Y. One-pot synthesis of imidazolines from aldehydes: Detailed study about solvents and substrates. Tetrahedron 2007, 63, 638-643.
    • (2007) Tetrahedron , vol.63 , pp. 638-643
    • Fujioka, H.1    Murai, K.2    Kubo, O.3    Ohbay, Y.4    Kita, Y.5
  • 32
    • 73949099410 scopus 로고    scopus 로고
    • Synthesis, characterization and mesomorphic properties of unsymmetrical N-(O-hydroxybenzylidene)-N-(4-n-alkoxybenzylidene) azines and their copper(II) complexes
    • Sing, B.; Pandey, A. Synthesis, characterization and mesomorphic properties of unsymmetrical N-(O-hydroxybenzylidene)-N-(4-n-alkoxybenzylidene) azines and their copper(II) complexes. Mol. Cryst. Liq. Cryst. 2010, 37, 57-67.
    • (2010) Mol. Cryst. Liq. Cryst , vol.37 , pp. 57-67
    • Sing, B.1    Pandey, A.2
  • 33
    • 4844221703 scopus 로고    scopus 로고
    • Effects of natural and chemically synthesized furanones on Quorum Sensing in Chromobacterium violaceum
    • Martinelli, D.; Grossmann, G.; Séquin, U.; Brandl, H.; Bachofen, R. Effects of natural and chemically synthesized furanones on Quorum Sensing in Chromobacterium violaceum. BMC Microbiol. 2004, 4, 25.
    • (2004) BMC Microbiol , vol.4 , pp. 25
    • Martinelli, D.1    Grossmann, G.2    Séquin, U.3    Brandl, H.4    Bachofen, R.5
  • 34
    • 0031467411 scopus 로고    scopus 로고
    • Quorum Sensing and Chromobacterium violaceum: Exploitation of violacein production and inhibition for the detection of N-acyl homoserine lactones
    • McClean, K.H.; Winson, M.K.; Fish, L.; Taylor, A.; Chhabra, S.R.; Camara, M.; Daykin, M.; Lamb, J.H.; Swift, S.; Bycroft, B.W.; et al. Quorum Sensing and Chromobacterium violaceum: Exploitation of violacein production and inhibition for the detection of N-acyl homoserine lactones. Microbiology 1997, 143, 3703-3711.
    • (1997) Microbiology , vol.143 , pp. 3703-3711
    • McClean, K.H.1    Winson, M.K.2    Fish, L.3    Taylor, A.4    Chhabra, S.R.5    Camara, M.6    Daykin, M.7    Lamb, J.H.8    Swift, S.9    Bycroft, B.W.10


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.