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Volumn 8, Issue 8, 2013, Pages 1775-1784

Discovery of two classes of potent glycomimetic inhibitors of pseudomonas aeruginosa LecB with distinct binding modes

Author keywords

[No Author keywords available]

Indexed keywords

ANTIINFECTIVE AGENT; BACTERIAL PROTEIN; CARBOHYDRATE; GLYCOMIMETIC INHIBITOR; LECB PROTEIN; LECTIN; MANNOSE; METHYL MANNOSIDE; SULFONAMIDE; UNCLASSIFIED DRUG;

EID: 84882754814     PISSN: 15548929     EISSN: 15548937     Source Type: Journal    
DOI: 10.1021/cb400371r     Document Type: Article
Times cited : (77)

References (45)
  • 2
    • 77952298917 scopus 로고    scopus 로고
    • Hospital-acquired infections due to GRAM-negative bacteria
    • Peleg, A. Y. and Hooper, D. C. (2010) Hospital-acquired infections due to GRAM-negative bacteria New Engl. J. Med 362, 1804-1813
    • (2010) New Engl. J. Med , vol.362 , pp. 1804-1813
    • Peleg, A.Y.1    Hooper, D.C.2
  • 3
    • 0032839275 scopus 로고    scopus 로고
    • Cystic fibrosis: An inherited susceptibility to bacterial respiratory infections
    • Tümmler, B. and Kiewitz, C. (1999) Cystic fibrosis: an inherited susceptibility to bacterial respiratory infections Mol. Med. Today 5, 351-358
    • (1999) Mol. Med. Today , vol.5 , pp. 351-358
    • Tümmler, B.1    Kiewitz, C.2
  • 4
    • 84857660045 scopus 로고    scopus 로고
    • Pseudomonas aeruginosa: Resistance to the max
    • Poole, K. (2011) Pseudomonas aeruginosa: resistance to the max Front. Microbiol. 2, 65
    • (2011) Front. Microbiol. , vol.2 , pp. 65
    • Poole, K.1
  • 5
    • 0037313237 scopus 로고    scopus 로고
    • Understanding biofilm resistance to antibacterial agents
    • Davies, D. (2003) Understanding biofilm resistance to antibacterial agents Nat. Rev. Drug Discovery 2, 114-122
    • (2003) Nat. Rev. Drug Discovery , vol.2 , pp. 114-122
    • Davies, D.1
  • 7
    • 0020014208 scopus 로고
    • Pseudomonas aeruginosa lectins
    • Gilboa-Garber, N. (1982) Pseudomonas aeruginosa lectins Methods Enzymol. 83, 378-385
    • (1982) Methods Enzymol. , vol.83 , pp. 378-385
    • Gilboa-Garber, N.1
  • 8
    • 0033759695 scopus 로고    scopus 로고
    • The Pseudomonas aeruginosa lectins PA-IL and PA-IIL are controlled by quorum sensing and by RpoS
    • Winzer, K., Falconer, C., Garber, N. C., Diggle, S. P., Camara, M., and Williams, P. (2000) The Pseudomonas aeruginosa lectins PA-IL and PA-IIL are controlled by quorum sensing and by RpoS J. Bacteriol. 182, 6401-6411
    • (2000) J. Bacteriol. , vol.182 , pp. 6401-6411
    • Winzer, K.1    Falconer, C.2    Garber, N.C.3    Diggle, S.P.4    Camara, M.5    Williams, P.6
  • 9
    • 65449143628 scopus 로고    scopus 로고
    • Role of LecA and LecB lectins in Pseudomonas aeruginosa-induced lung injury and effect of carbohydrate ligands
    • Chemani, C., Imberty, A., de Bentzmann, S., Pierre, M., Wimmerová, M., Guery, B. P., and Faure, K. (2009) Role of LecA and LecB lectins in Pseudomonas aeruginosa-induced lung injury and effect of carbohydrate ligands Infect. Immun. 77, 2065-2075
    • (2009) Infect. Immun. , vol.77 , pp. 2065-2075
    • Chemani, C.1    Imberty, A.2    De Bentzmann, S.3    Pierre, M.4    Wimmerová, M.5    Guery, B.P.6    Faure, K.7
  • 10
    • 34347396244 scopus 로고    scopus 로고
    • Engineering of PA-IIL lectin from Pseudomonas aeruginosa - Unravelling the role of the specificity loop for sugar preference
    • Adam, J., Pokorná, M., Sabin, C., Mitchell, E. P., Imberty, A., and Wimmerová, M. (2007) Engineering of PA-IIL lectin from Pseudomonas aeruginosa-Unravelling the role of the specificity loop for sugar preference BMC Struct. Biol. 7, 36
    • (2007) BMC Struct. Biol. , vol.7 , pp. 36
    • Adam, J.1    Pokorná, M.2    Sabin, C.3    Mitchell, E.P.4    Imberty, A.5    Wimmerová, M.6
  • 13
    • 33745171425 scopus 로고    scopus 로고
    • The galactophilic lectin, LecA, contributes to biofilm development in Pseudomonas aeruginosa
    • Diggle, S. P., Stacey, R. E., Dodd, C., Cámara, M., Williams, P., and Winzer, K. (2006) The galactophilic lectin, LecA, contributes to biofilm development in Pseudomonas aeruginosa Environ. Microbiol. 8, 1095-1104
    • (2006) Environ. Microbiol. , vol.8 , pp. 1095-1104
    • Diggle, S.P.1    Stacey, R.E.2    Dodd, C.3    Cámara, M.4    Williams, P.5    Winzer, K.6
  • 14
    • 68249116079 scopus 로고    scopus 로고
    • From carbohydrate leads to glycomimetic drugs
    • Ernst, B. and Magnani, J. L. (2009) From carbohydrate leads to glycomimetic drugs Nat. Rev. Drug Discovery 8, 661-677
    • (2009) Nat. Rev. Drug Discovery , vol.8 , pp. 661-677
    • Ernst, B.1    Magnani, J.L.2
  • 15
    • 53849107196 scopus 로고    scopus 로고
    • Glycomimetics and glycodendrimers as high affinity microbial anti-adhesins
    • Imberty, A., Chabre, Y. M., and Roy, R. (2008) Glycomimetics and glycodendrimers as high affinity microbial anti-adhesins Chem.-Eur. J. 14, 7490-7499
    • (2008) Chem. - Eur. J. , vol.14 , pp. 7490-7499
    • Imberty, A.1    Chabre, Y.M.2    Roy, R.3
  • 16
    • 33646103431 scopus 로고    scopus 로고
    • Carbohydrates as future anti-adhesion drugs for infectious diseases
    • Sharon, N. (2006) Carbohydrates as future anti-adhesion drugs for infectious diseases Biochim. Biophys. Acta 1760, 527-537
    • (2006) Biochim. Biophys. Acta , vol.1760 , pp. 527-537
    • Sharon, N.1
  • 20
    • 0034837890 scopus 로고    scopus 로고
    • Successful treatment of Pseudomonas aeruginosa respiratory tract infection with a sugar solution - A case report on a lectin based therapeutic principle
    • von Bismarck, P., Schneppenheim, R., and Schumacher, U. (2001) Successful treatment of Pseudomonas aeruginosa respiratory tract infection with a sugar solution - a case report on a lectin based therapeutic principle Klin. Padiatr. 213, 285-287
    • (2001) Klin. Padiatr. , vol.213 , pp. 285-287
    • Von Bismarck, P.1    Schneppenheim, R.2    Schumacher, U.3
  • 21
    • 56749185534 scopus 로고    scopus 로고
    • Inhalation with fucose and galactose for treatment of Pseudomonas aeruginosa in cystic fibrosis patients
    • Hauber, H.-P., Schulz, M., Pforte, A., Mack, D., Zabel, P., and Schumacher, U. (2008) Inhalation with fucose and galactose for treatment of Pseudomonas aeruginosa in cystic fibrosis patients Int. J. Med. Sci. 5, 371-376
    • (2008) Int. J. Med. Sci. , vol.5 , pp. 371-376
    • Hauber, H.-P.1    Schulz, M.2    Pforte, A.3    Mack, D.4    Zabel, P.5    Schumacher, U.6
  • 22
    • 0042667040 scopus 로고    scopus 로고
    • Structural basis of carbohydrate recognition by the lectin LecB from Pseudomonas aeruginosa
    • Loris, R., Tielker, D., Jaeger, K.-E., and Wyns, L. (2003) Structural basis of carbohydrate recognition by the lectin LecB from Pseudomonas aeruginosa J. Mol. Biol. 331, 861-870
    • (2003) J. Mol. Biol. , vol.331 , pp. 861-870
    • Loris, R.1    Tielker, D.2    Jaeger, K.-E.3    Wyns, L.4
  • 25
    • 43949136485 scopus 로고    scopus 로고
    • X-ray structures and thermodynamics of the interaction of PA-IIL from Pseudomonas aeruginosa with disaccharide derivatives
    • Marotte, K., Sabin, C., Préville, C., Moumé-Pymbock, M., Wimmerová, M., Mitchell, E. P., Imberty, A., and Roy, R. (2007) X-ray structures and thermodynamics of the interaction of PA-IIL from Pseudomonas aeruginosa with disaccharide derivatives ChemMedChem 2, 1328-1338
    • (2007) ChemMedChem , vol.2 , pp. 1328-1338
    • Marotte, K.1    Sabin, C.2    Préville, C.3    Moumé-Pymbock, M.4    Wimmerová, M.5    Mitchell, E.P.6    Imberty, A.7    Roy, R.8
  • 26
    • 77955768892 scopus 로고    scopus 로고
    • Monovalent and bivalent N-fucosyl amides as high affinity ligands for Pseudomonas aeruginosa PA-IIL lectin
    • Andreini, M., Anderluh, M., Audfray, A., Bernardi, A., and Imberty, A. (2010) Monovalent and bivalent N-fucosyl amides as high affinity ligands for Pseudomonas aeruginosa PA-IIL lectin Carbohydr. Res. 345, 1400-1407
    • (2010) Carbohydr. Res. , vol.345 , pp. 1400-1407
    • Andreini, M.1    Anderluh, M.2    Audfray, A.3    Bernardi, A.4    Imberty, A.5
  • 27
    • 31444445581 scopus 로고    scopus 로고
    • Binding of different monosaccharides by lectin PA-IIL from Pseudomonas aeruginosa: Thermodynamics data correlated with X-ray structures
    • Sabin, C., Mitchell, E. P., Pokorná, M., Gautier, C., Utille, J.-P., Wimmerová, M., and Imberty, A. (2006) Binding of different monosaccharides by lectin PA-IIL from Pseudomonas aeruginosa: thermodynamics data correlated with X-ray structures FEBS Lett. 580, 982-987
    • (2006) FEBS Lett. , vol.580 , pp. 982-987
    • Sabin, C.1    Mitchell, E.P.2    Pokorná, M.3    Gautier, C.4    Utille, J.-P.5    Wimmerová, M.6    Imberty, A.7
  • 28
    • 0037442109 scopus 로고    scopus 로고
    • Cutting edge: Carbohydrate profiling identifies new pathogens that interact with dendritic cell-specific ICAM-3-grabbing nonintegrin on dendritic cells
    • Appelmelk, B. J., van Die, I., van Vliet, S. J., Vandenbroucke-Grauls, C. M. J. E., Geijtenbeek, T. B. H., and van Kooyk, Y. (2003) Cutting edge: carbohydrate profiling identifies new pathogens that interact with dendritic cell-specific ICAM-3-grabbing nonintegrin on dendritic cells J. Immunol. 170, 1635-1639
    • (2003) J. Immunol. , vol.170 , pp. 1635-1639
    • Appelmelk, B.J.1    Van Die, I.2    Van Vliet, S.J.3    Vandenbroucke-Grauls, C.M.J.E.4    Geijtenbeek, T.B.H.5    Van Kooyk, Y.6
  • 30
    • 4644260095 scopus 로고    scopus 로고
    • Fluorescence polarization as an analytical tool to evaluate galectin-ligand interactions
    • Sörme, P., Kahl-Knutsson, B., Huflejt, M., Nilsson, U. J., and Leffler, H. (2004) Fluorescence polarization as an analytical tool to evaluate galectin-ligand interactions Anal. Biochem. 334, 36-47
    • (2004) Anal. Biochem. , vol.334 , pp. 36-47
    • Sörme, P.1    Kahl-Knutsson, B.2    Huflejt, M.3    Nilsson, U.J.4    Leffler, H.5
  • 32
    • 34248575675 scopus 로고    scopus 로고
    • Lanthanum trifluoromethanesulfonate-catalyzed facile synthesis of per-O-acetylated sugars and their one-pot conversion to S-aryl and O-alkyl/aryl glycosides
    • Dasgupta, S., Rajput, V. K., Roy, B., and Mukhopadhyay, B. (2007) Lanthanum trifluoromethanesulfonate-catalyzed facile synthesis of per-O-acetylated sugars and their one-pot conversion to S-aryl and O-alkyl/aryl glycosides J. Carbohydr. Chem. 26, 91-106
    • (2007) J. Carbohydr. Chem. , vol.26 , pp. 91-106
    • Dasgupta, S.1    Rajput, V.K.2    Roy, B.3    Mukhopadhyay, B.4
  • 33
    • 0027906299 scopus 로고
    • An imino-linked carba-disaccharide alpha-D-mannosidase inhibitor
    • Cottaz, S., Brimacombe, J. S., and Ferguson, M. A. (1993) An imino-linked carba-disaccharide alpha-D-mannosidase inhibitor Carbohydr. Res. 247, 341-345
    • (1993) Carbohydr. Res. , vol.247 , pp. 341-345
    • Cottaz, S.1    Brimacombe, J.S.2    Ferguson, M.A.3
  • 34
    • 0037099395 scopus 로고    scopus 로고
    • A stepwise huisgen cycloaddition process: Copper(I)-catalyzed regioselective ″ligation″ of azides and terminal alkynes
    • Rostovtsev, V. V., Green, L. G., Fokin, V. V., and Sharpless, K. B. (2002) A stepwise huisgen cycloaddition process: copper(I)-catalyzed regioselective ″ligation″ of azides and terminal alkynes Angew. Chem., Int. Ed. 41, 2596-2599
    • (2002) Angew. Chem., Int. Ed. , vol.41 , pp. 2596-2599
    • Rostovtsev, V.V.1    Green, L.G.2    Fokin, V.V.3    Sharpless, K.B.4
  • 35
    • 0037012920 scopus 로고    scopus 로고
    • Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides
    • Tornøe, C. W., Christensen, C., and Meldal, M. (2002) Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides J. Org. Chem. 67, 3057-3064
    • (2002) J. Org. Chem. , vol.67 , pp. 3057-3064
    • Tornøe, C.W.1    Christensen, C.2    Meldal, M.3
  • 36
    • 0000096835 scopus 로고    scopus 로고
    • Click Chemistry: Diverse chemical function from a few good reactions
    • Kolb, H. C., Finn, M. G., and Sharpless, K. B. (2001) Click Chemistry: Diverse chemical function from a few good reactions Angew. Chem., Int. Ed. 40, 2004-2021
    • (2001) Angew. Chem., Int. Ed. , vol.40 , pp. 2004-2021
    • Kolb, H.C.1    Finn, M.G.2    Sharpless, K.B.3
  • 37
    • 0020014209 scopus 로고
    • Escherichia coli surface lectins
    • Eshdat, Y. and Sharon, N. (1982) Escherichia coli surface lectins Methods. Enzymol. 83, 386-391
    • (1982) Methods. Enzymol. , vol.83 , pp. 386-391
    • Eshdat, Y.1    Sharon, N.2
  • 38
    • 7744243992 scopus 로고    scopus 로고
    • Bioisosterism: A rational approach in drug design
    • Patani, G. A. and LaVoie, E. J. (1996) Bioisosterism: A rational approach in drug design Chem. Rev. 96, 3147-3176
    • (1996) Chem. Rev. , vol.96 , pp. 3147-3176
    • Patani, G.A.1    Lavoie, E.J.2
  • 39
    • 75649146955 scopus 로고    scopus 로고
    • A kit for the investigation of live Escherichia coli cell adhesion to glycosylated surfaces
    • Hartmann, M., Horst, A. K., Klemm, P., and Lindhorst, T. K. (2010) A kit for the investigation of live Escherichia coli cell adhesion to glycosylated surfaces Chem. Commun. (Camb) 46, 330-332
    • (2010) Chem. Commun. (Camb) , vol.46 , pp. 330-332
    • Hartmann, M.1    Horst, A.K.2    Klemm, P.3    Lindhorst, T.K.4
  • 41
    • 79955037995 scopus 로고    scopus 로고
    • Squaric acid monoamide mannosides as ligands for the bacterial lectin FimH: Covalent inhibition or not?
    • Grabosch, C., Hartmann, M., Schmidt-Lassen, J., and Lindhorst, T. K. (2011) Squaric acid monoamide mannosides as ligands for the bacterial lectin FimH: covalent inhibition or not? ChemBioChem 12, 1066-1074
    • (2011) ChemBioChem , vol.12 , pp. 1066-1074
    • Grabosch, C.1    Hartmann, M.2    Schmidt-Lassen, J.3    Lindhorst, T.K.4
  • 42
    • 0026718835 scopus 로고
    • On the specificity of the D-galactose-binding lectin (PA-I) of Pseudomonas aeruginosa and its strong binding to hydrophobic derivatives of D-galactose and thiogalactose
    • Garber, N., Guempel, U., Belz, A., Gilboa-Garber, N., and Doyle, R. J. (1992) On the specificity of the D-galactose-binding lectin (PA-I) of Pseudomonas aeruginosa and its strong binding to hydrophobic derivatives of D-galactose and thiogalactose Biochim. Biophys. Acta 1116, 331-333
    • (1992) Biochim. Biophys. Acta , vol.1116 , pp. 331-333
    • Garber, N.1    Guempel, U.2    Belz, A.3    Gilboa-Garber, N.4    Doyle, R.J.5
  • 44
    • 35348855865 scopus 로고    scopus 로고
    • Probing multivalent carbohydrate-lectin interactions by an enzyme-linked lectin assay employing covalently immobilized carbohydrates
    • Maierhofer, C., Rohmer, K., and Wittmann, V. (2007) Probing multivalent carbohydrate-lectin interactions by an enzyme-linked lectin assay employing covalently immobilized carbohydrates Bioorg. Med. Chem. 15, 7661-7676
    • (2007) Bioorg. Med. Chem. , vol.15 , pp. 7661-7676
    • Maierhofer, C.1    Rohmer, K.2    Wittmann, V.3
  • 45
    • 34548108138 scopus 로고    scopus 로고
    • Targeting virulence: A new paradigm for antimicrobial therapy
    • Clatworthy, A. E., Pierson, E., and Hung, D. T. (2007) Targeting virulence: a new paradigm for antimicrobial therapy Nat. Chem. Biol. 3, 541-548
    • (2007) Nat. Chem. Biol. , vol.3 , pp. 541-548
    • Clatworthy, A.E.1    Pierson, E.2    Hung, D.T.3


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