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Volumn 23, Issue 8, 2012, Pages 1534-1547

Synthesis of a library of fucosylated glycoclusters and determination of their binding toward pseudomonas aeruginosa lectin B (PA-IIL) using a DNA-based carbohydrate microarray

Author keywords

[No Author keywords available]

Indexed keywords

ANTENNAS; BACTERIA; BINDING ENERGY; BIOFILMS; CARBOHYDRATES; DNA; SCAFFOLDS; SYNTHESIS (CHEMICAL);

EID: 84865150015     PISSN: 10431802     EISSN: 15204812     Source Type: Journal    
DOI: 10.1021/bc2006434     Document Type: Article
Times cited : (48)

References (49)
  • 1
    • 0035937499 scopus 로고    scopus 로고
    • Chemical glycobiology
    • DOI 10.1126/science.1059820
    • Bertozzi, C. R. and Kiessling, L. L. (2001) Chemical glycobiology Science 291, 2357-2364 (Pubitemid 32231790)
    • (2001) Science , vol.291 , Issue.5512 , pp. 2357-2364
    • Bertozzi, C.R.1    Kiessling, L.L.2
  • 2
    • 34247556420 scopus 로고    scopus 로고
    • Synthesis and medical applications of oligosaccharides
    • DOI 10.1038/nature05819, PII NATURE05819
    • Seeberger, P. H. and Werz, D. B. (2007) Synthesis and medical applications of oligosaccharides Nature 446, 1046-1051 (Pubitemid 46676067)
    • (2007) Nature , vol.446 , Issue.7139 , pp. 1046-1051
    • Seeberger, P.H.1    Werz, D.B.2
  • 3
    • 0027318961 scopus 로고
    • Biological roles of oligosaccharides: All of the theories are correct
    • Varki, A. (1993) Biological Roles of Oligosaccharides-All of the Theories Are Correct Glycobiology 3, 97-130 (Pubitemid 23132602)
    • (1993) Glycobiology , vol.3 , Issue.2 , pp. 97-130
    • Varki, A.1
  • 4
    • 0000358206 scopus 로고
    • Carbohydrate-Protein Interactions: Basis of Glycobiology
    • Lee, Y. C. and Lee, R. T. (1995) Carbohydrate-Protein Interactions: Basis of Glycobiology Acc. Chem. Res. 28, 321-327
    • (1995) Acc. Chem. Res. , vol.28 , pp. 321-327
    • Lee, Y.C.1    Lee, R.T.2
  • 5
    • 1442348321 scopus 로고    scopus 로고
    • Structures of the lectins from Pseudomonas aeruginosa: Insights into the molecular basis for host glycan recognition
    • DOI 10.1016/j.micinf.2003.10.016, PII S128645790300323X
    • Imberty, A., Wimmerova, M., Mitchell, E. P., and Gilboa-Garber, N. (2004) Structures of the lectins from Pseudomonas aeruginosa: insights into the molecular basis for host glycan recognition Microb. Infect. 6, 221-228 (Pubitemid 38293301)
    • (2004) Microbes and Infection , vol.6 , Issue.2 , pp. 221-228
    • Imberty, A.1    Wimmerova, M.2    Mitchell, E.P.3    Gilboa-Garber, N.4
  • 8
    • 0033844545 scopus 로고    scopus 로고
    • Identification and characterization of Pseudomonas aeruginosa PA-IIL lectin gene and protein compared to PA-IL
    • Gilboa-Garber, N., Katcoff, D. J., and Garber, N. C. (2000) Identification and characterization of Pseudomonas aeruginosa PA-IIL lectin gene and protein compared to PA-IL FEMS Immunol. Med. Microbiol. 29, 53-57
    • (2000) FEMS Immunol. Med. Microbiol. , vol.29 , pp. 53-57
    • Gilboa-Garber, N.1    Katcoff, D.J.2    Garber, N.C.3
  • 9
    • 34447122753 scopus 로고    scopus 로고
    • Synthesis of glycodendrimers containing both fucoside and galactoside residues and their binding properties to Pa-IL and PA-IIL lectins from Pseudomonas aeruginosa
    • DOI 10.1039/b701237c
    • Deguise, I., Lagnoux, D., and Roy, R. (2007) Synthesis of glycodendrimers containing both fucoside and galactoside residues and their binding properties to PA-IL and PA-IIL lectins from Pseudomonas aeruginosa New J. Chem. 31, 1321-1331 (Pubitemid 47036640)
    • (2007) New Journal of Chemistry , vol.31 , Issue.7 , pp. 1321-1331
    • Deguise, I.1    Lagnoux, D.2    Roy, R.3
  • 10
    • 34447126555 scopus 로고    scopus 로고
    • Combinatorial variation of branching length and multivalency in a large (390 625 member) glycopeptide dendrimer library: Ligands for fucose-specific lectins
    • DOI 10.1039/b616051b
    • Johansson, E. M. V., Kolomiets, E., Rosenau, F., Jaeger, K. E., Darbre, T., and Reymond, J. L. (2007) Combinatorial variation of branching length and multivalency in a large (390 625 member) glycopeptide dendrimer library: ligands for fucose-specific lectins New J. Chem. 31, 1291-1299 (Pubitemid 47036624)
    • (2007) New Journal of Chemistry , vol.31 , Issue.7 , pp. 1291-1299
    • Johansson, E.M.V.1    Kolomiets, E.2    Rosenau, F.3    Jaeger, K.-E.4    Darbre, T.5    Reymond, J.-L.6
  • 11
    • 34548339632 scopus 로고    scopus 로고
    • Synthesis and binding properties of divalent and trivalent clusters of the Lewis a disaccharide moiety to Pseudomonas aeruginosa lectin PA-IIL
    • DOI 10.1039/b708227d
    • Marotte, K., Eville, C. P., Sabin, C., Pymbock, M. M., Imberty, A., and Roy, R. (2007) Synthesis and binding properties of divalent and trivalent clusters of the Lewis a disaccharide moiety to Pseudomonas aeruginosa lectin PA-IIL Org. Biomol. Chem. 5, 2953-2961 (Pubitemid 47340685)
    • (2007) Organic and Biomolecular Chemistry , vol.5 , Issue.18 , pp. 2953-2961
    • Marotte, K.1    Preville, C.2    Sabin, C.3    Moume-Pymbock, M.4    Imberty, A.5    Roy, R.6
  • 12
    • 34648813808 scopus 로고    scopus 로고
    • Fucosylated pentaerythrityl phosphodiester oligomers (PePOs): Automated synthesis of DNA-based glycoclusters and binding to Pseudomonas aeruginosa lectin (PA-IIL)
    • DOI 10.1021/bc070129z
    • Morvan, F., Meyer, A., Jochum, A., Sabin, C., Chevolot, Y., Imberty, A., Praly, J. P., Vasseur, J. J., Souteyrand, E., and Vidal, S. (2007) Fucosylated pentaerythrityl phosphodiester oligomers (PePOs): automated synthesis of DNA-based glycoclusters and binding to Pseudomonas aeruginosa lectin (PA-IIL) Bioconjugate Chem. 18, 1637-1643 (Pubitemid 47464074)
    • (2007) Bioconjugate Chemistry , vol.18 , Issue.5 , pp. 1637-1643
    • Morvan, F.1    Meyer, A.2    Jochum, A.3    Sabin, C.4    Chevolot, Y.5    Imberty, A.6    Praly, J.-P.7    Vasseur, J.-J.8    Souteyrand, E.9    Vidal, S.10
  • 14
    • 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
  • 16
    • 80054973442 scopus 로고    scopus 로고
    • Multivalent calixarene-based C-fucosyl derivative: A new Pseudomonas aeruginosa biofilm inhibitor
    • Consoli, G. M. L., Granata, G., Cafiso, V., Stefani, S., and Geraci, C. (2011) Multivalent calixarene-based C-fucosyl derivative: a new Pseudomonas aeruginosa biofilm inhibitor Tetrahedron Lett. 52, 5831-5834
    • (2011) Tetrahedron Lett. , vol.52 , pp. 5831-5834
    • Consoli, G.M.L.1    Granata, G.2    Cafiso, V.3    Stefani, S.4    Geraci, C.5
  • 17
    • 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
  • 18
    • 35649003866 scopus 로고    scopus 로고
    • Intervention with bacterial adhesion by multivalent carbohydrates
    • DOI 10.1002/med.20089
    • Pieters, R. J. (2007) Intervention with bacterial adhesion by multivalent carbohydrates Med. Res. Rev. 27, 796-816 (Pubitemid 350035120)
    • (2007) Medicinal Research Reviews , vol.27 , Issue.6 , pp. 796-816
    • Pieters, R.J.1
  • 19
    • 0002773690 scopus 로고
    • Neoglycoconjugates: Preparation and Applications
    • In (Lee, R. T. and Lee, Y. C. Eds.) pp, Academic Press, San Diego
    • Lee, R., T. and Lee, Y., C. (1994) Neoglycoconjugates: Preparation and Applications. In Enhanced Biochemical Affinities of Multivalent Neoglycoconjugates (Lee, R., T. and Lee, Y., C., Eds.) pp 23-50, Academic Press, San Diego.
    • (1994) Enhanced Biochemical Affinities of Multivalent Neoglycoconjugates , pp. 23-50
    • Lee . R, T.1    Lee . Y, C.2
  • 20
    • 11544358874 scopus 로고    scopus 로고
    • Lectins: Carbohydrate-specific proteins that mediate cellular recognition
    • Lis, H. and Sharon, N. (1998) Lectins: Carbohydrate-Specific Proteins That Mediate Cellular Recognition Chem. Rev. 98, 637-674 (Pubitemid 128631438)
    • (1998) Chemical Reviews , vol.98 , Issue.2 , pp. 637-674
    • Lis, H.1    Sharon, N.2
  • 21
    • 0036462602 scopus 로고    scopus 로고
    • The cluster glycoside effect
    • DOI 10.1021/cr000418f
    • Lundquist, J. J. and Toone, E. J. (2002) The cluster glycoside effect Chem. Rev. 102, 555-578 (Pubitemid 35377623)
    • (2002) Chemical Reviews , vol.102 , Issue.2 , pp. 555-578
    • Lundquist, J.J.1    Toone, E.J.2
  • 22
    • 77954914845 scopus 로고    scopus 로고
    • Design and Creativity in Synthesis of Multivalent Neoglycoconjugates
    • Chabre, Y. M. and Roy, R. (2010) Design and Creativity in Synthesis of Multivalent Neoglycoconjugates Adv. Carbohydr. Chem. Biochem. 63, 165-393
    • (2010) Adv. Carbohydr. Chem. Biochem. , vol.63 , pp. 165-393
    • Chabre, Y.M.1    Roy, R.2
  • 25
    • 0033105089 scopus 로고    scopus 로고
    • DNA-directed immobilization: Efficient, reversible, and site-selective surface binding of proteins by means of covalent DNA-streptavidin conjugates
    • DOI 10.1006/abio.1998.3017
    • Niemeyer, C. M., Boldt, L., Ceyhan, B., and Blohm, D. (1999) DNA-directed immobilization: efficient, reversible, and site-selective surface binding of proteins by means of covalent DNA-streptavidin conjugates Anal. Biochem. 268, 54-63 (Pubitemid 29115510)
    • (1999) Analytical Biochemistry , vol.268 , Issue.1 , pp. 54-63
    • Niemeyer, C.M.1    Boldt, L.2    Ceyhan, B.3    Blohm, D.4
  • 26
    • 2942605493 scopus 로고    scopus 로고
    • DDI-μFIA - A readily configurable microarray-fluorescence immunoassay based on DNA-directed immobilization of proteins
    • DOI 10.1002/cbic.200300788
    • Wacker, R. and Niemeyer, C. M. (2004) DDI-mu FIA-a readily configurable microarray-fluorescence immunoassay based on DNA-directed immobilization of proteins ChemBioChem 5, 453-459 (Pubitemid 39257101)
    • (2004) ChemBioChem , vol.5 , Issue.4 , pp. 453-459
    • Wacker, R.1    Niemeyer, C.M.2
  • 31
    • 0042062568 scopus 로고    scopus 로고
    • Surface hydroxylation and silane grafting on fumed and thermal silica
    • DOI 10.1016/S0021-9797(03)00552-6
    • Dugas, V. and Chevalier, Y. (2003) Surface hydroxylation and silane grafting on fumed and thermal silica J. Colloid Interface Sci. 264, 354-361 (Pubitemid 36959973)
    • (2003) Journal of Colloid and Interface Science , vol.264 , Issue.2 , pp. 354-361
    • Dugas, V.1    Chevalier, Y.2
  • 32
    • 2542475504 scopus 로고    scopus 로고
    • Immobilization of single-stranded DNA fragments to solid surfaces and their repeatable specific hybridization: Covalent binding or adsorption?
    • Dugas, V., Depret, G., Chevalier, B., Nesme, X., and Souteyrand, E. (2004) Immobilization of single-stranded DNA fragments to solid surfaces and their repeatable specific hybridization: covalent binding or adsorption? Sens. Actuators, B 101, 112-121
    • (2004) Sens. Actuators, B , vol.101 , pp. 112-121
    • Dugas, V.1    Depret, G.2    Chevalier, B.3    Nesme, X.4    Souteyrand, E.5
  • 33
    • 67651146599 scopus 로고    scopus 로고
    • Design of Triazole-Tethered Glycoclusters Exhibiting Three Different Spatial Arrangements and Comparative Study of their Affinities towards PA-IL and RCA 120 by Using a DNA-Based Glycoarray
    • Moni, L., Pourceau, G., Zhang, J., Meyer, A., Vidal, S., Souteyrand, E., Dondoni, A., Morvan, F., Chevolot, Y., Vasseur, J. J., and Marra, A. (2009) Design of Triazole-Tethered Glycoclusters Exhibiting Three Different Spatial Arrangements and Comparative Study of their Affinities towards PA-IL and RCA 120 by Using a DNA-Based Glycoarray ChemBioChem 10, 1369-1378
    • (2009) ChemBioChem , vol.10 , pp. 1369-1378
    • Moni, L.1    Pourceau, G.2    Zhang, J.3    Meyer, A.4    Vidal, S.5    Souteyrand, E.6    Dondoni, A.7    Morvan, F.8    Chevolot, Y.9    Vasseur, J.J.10    Marra, A.11
  • 35
    • 0037099395 scopus 로고    scopus 로고
    • A stepwise huisgen cycloaddition process: Copper(I)-catalyzed regioselective ligation of azides and terminal alkynes
    • DOI 10.1002/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO;2-4
    • 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 (Pubitemid 34803480)
    • (2002) Angewandte Chemie - International Edition , vol.41 , Issue.14 , pp. 2596-2599
    • Rostovtsev, V.V.1    Green, L.G.2    Fokin, V.V.3    Sharpless, K.B.4
  • 36
    • 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
    • DOI 10.1021/jo011148j
    • Tornoe, 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 (Pubitemid 34457265)
    • (2002) Journal of Organic Chemistry , vol.67 , Issue.9 , pp. 3057-3064
    • Tornoe, C.W.1    Christensen, C.2    Meldal, M.3
  • 37
    • 37549013666 scopus 로고    scopus 로고
    • New strategies for cyclization and bicyclization of oligonucleotides by click chemistry assisted by microwaves
    • Lietard, J., Meyer, A., Vasseur, J. J., and Morvan, F. (2008) New strategies for cyclization and bicyclization of oligonucleotides by click chemistry assisted by microwaves J. Org. Chem. 73, 191-200
    • (2008) J. Org. Chem. , vol.73 , pp. 191-200
    • Lietard, J.1    Meyer, A.2    Vasseur, J.J.3    Morvan, F.4
  • 38
    • 77955795023 scopus 로고    scopus 로고
    • Oligonucleotide Carbohydrate-Centered Galactosyl Cluster Conjugates Synthesized by Click and Phosphoramidite Chemistries
    • Pourceau, G., Meyer, A., Chevolot, Y., Souteyrand, E., Vasseur, J. J., and Morvan, F. (2010) Oligonucleotide Carbohydrate-Centered Galactosyl Cluster Conjugates Synthesized by Click and Phosphoramidite Chemistries Bioconjugate Chem. 21, 1520-1529
    • (2010) Bioconjugate Chem. , vol.21 , pp. 1520-1529
    • Pourceau, G.1    Meyer, A.2    Chevolot, Y.3    Souteyrand, E.4    Vasseur, J.J.5    Morvan, F.6
  • 40
    • 69549092102 scopus 로고    scopus 로고
    • Azide Solid Support for 3′-Conjugation of Oligonucleotides and Their Circularization by Click Chemistry
    • Pourceau, G., Meyer, A., Vasseur, J. J., and Morvan, F. (2009) Azide Solid Support for 3′-Conjugation of Oligonucleotides and Their Circularization by Click Chemistry J. Org. Chem. 74, 6837-6842
    • (2009) J. Org. Chem. , vol.74 , pp. 6837-6842
    • Pourceau, G.1    Meyer, A.2    Vasseur, J.J.3    Morvan, F.4
  • 41
    • 34247620302 scopus 로고    scopus 로고
    • Sulfuric acid immobilized on silica: An excellent catalyst for Fischer type glycosylation
    • DOI 10.1016/j.tetlet.2007.03.165, PII S0040403907006429
    • Roy, B. and Mukhopadhyay, B. (2007) Sulfuric acid immobilized on silica: an excellent catalyst for Fischer type glycosylation Tetrahedron Lett. 48, 3783-3787 (Pubitemid 46671600)
    • (2007) Tetrahedron Letters , vol.48 , Issue.22 , pp. 3783-3787
    • Roy, B.1    Mukhopadhyay, B.2
  • 42
    • 37049153205 scopus 로고
    • Studies on Phosphorylation 0.2. The Reaction of Dialkyl Phosphites with Polyhalogen Compounds in Presence of Bases-A New Method for the Phosphorylation of Amines
    • Atherton, F. R., Openshaw, H. T., and Todd, A. R. (1945) Studies on Phosphorylation 0.2. The Reaction of Dialkyl Phosphites with Polyhalogen Compounds in Presence of Bases-A New Method for the Phosphorylation of Amines J. Chem. Soc. 660-663
    • (1945) J. Chem. Soc. , pp. 660-663
    • Atherton, F.R.1    Openshaw, H.T.2    Todd, A.R.3
  • 43
    • 0029992927 scopus 로고    scopus 로고
    • 2): Synthesis and thermal stability of duplexes with DNA and RNA targets
    • DOI 10.1093/nar/24.10.1841
    • Peyrottes, S., Vasseur, J. J., Imbach, J. L., and Rayner, B. (1996) Oligodeoxynucleoside Phosphoramidates (P-NH2)-Synthesis and Thermal Stability of Duplexes With DNAand RNA Targets Nucleic Acids Res. 24, 1841-1848 (Pubitemid 26160087)
    • (1996) Nucleic Acids Research , vol.24 , Issue.10 , pp. 1841-1848
    • Peyrottes, S.1    Vasseur, J.-J.2    Imbach, J.-L.3    Rayner, B.4
  • 44
    • 0032828316 scopus 로고    scopus 로고
    • The prooligonucleotide approach: Synthesis of mixed phosphodiester and SATE phosphotriester prooligonucleotides using H-phosphonate and phosphoramidite chemistries
    • Bologna, J. C., Morvan, F., and Imbach, J. L. (1999) The prooligonucleotide approach: synthesis of mixed phosphodiester and SATE phosphotriester prooligonucleotides using H-phosphonate and phosphoramidite chemistries Eur. J. Org. Chem. 2353-2358
    • (1999) Eur. J. Org. Chem. , pp. 2353-2358
    • Bologna, J.C.1    Morvan, F.2    Imbach, J.L.3
  • 45
    • 34547193249 scopus 로고    scopus 로고
    • Carbohydrate-appended curdlans as a new family of glycoclusters with binding properties both for a polynucleotide and lectins
    • DOI 10.1039/b703720a
    • Hasegawa, T., Numata, M., Okumura, S., Kimura, T., Sakurai, K., and Shinkai, S. (2007) Carbohydrate-appended curdlans as a new family of glycoclusters with binding properties both for a polynucleotide and lectins Org. Biomol. Chem. 5 (15) 2404-2412 (Pubitemid 47118874)
    • (2007) Organic and Biomolecular Chemistry , vol.5 , Issue.15 , pp. 2404-2412
    • Hasegawa, T.1    Numata, M.2    Okumura, S.3    Kimura, T.4    Sakurai, K.5    Shinkai, S.6
  • 46
    • 0032004118 scopus 로고    scopus 로고
    • A highly diastereoselective, practical synthesis of allyl, propargyl 2,3,4,6-tetra- O -acetyl-beta- d -gluco, beta- d -galactopyranosides and allyl, propargyl heptaacetyl-beta- d -lactosides
    • Mereyala, H. B. and Gurrala, S. R. (1998) A highly diastereoselective, practical synthesis of allyl, propargyl 2,3,4,6-tetra- O -acetyl-beta- d -gluco, beta- d -galactopyranosides and allyl, propargyl heptaacetyl-beta- d -lactosides Carbohydr. Res. 307, 351-354
    • (1998) Carbohydr. Res. , vol.307 , pp. 351-354
    • Mereyala, H.B.1    Gurrala, S.R.2
  • 47
    • 36049013740 scopus 로고    scopus 로고
    • An efficient reagent for 5′-azido oligonucleotide synthesis
    • DOI 10.1016/j.tetlet.2007.10.081, PII S0040403907020898
    • Lietard, J., Meyer, A., Vasseur, J. J., and Morvan, F. (2007) An efficient reagent for 5 ′-azido oligonucleotide synthesis Tetrahedron Lett. 48, 8795-8798 (Pubitemid 350088053)
    • (2007) Tetrahedron Letters , vol.48 , Issue.50 , pp. 8795-8798
    • Lietard, J.1    Meyer, A.2    Vasseur, J.-J.3    Morvan, F.4
  • 49
    • 62949190366 scopus 로고    scopus 로고
    • DNA-directed immobilisation of glycomimetics for glycoarrays application: Comparison with covalent immobilisation, and development of an on-chip IC50 measurement assay
    • Zhang, J., Pourceau, G., Meyer, A., Vidal, S., Praly, J.-P., Souteyrand, E., Vasseur, J.-J., Morvan, F., and Chevolot, Y. (2009) DNA-directed immobilisation of glycomimetics for glycoarrays application: comparison with covalent immobilisation, and development of an on-chip IC50 measurement assay Biosens. Bioelectron. 24, 2515-2521
    • (2009) Biosens. Bioelectron. , vol.24 , pp. 2515-2521
    • Zhang, J.1    Pourceau, G.2    Meyer, A.3    Vidal, S.4    Praly, J.-P.5    Souteyrand, E.6    Vasseur, J.-J.7    Morvan, F.8    Chevolot, Y.9


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