CECIONI, Samy, Jean-Pierre PRALY, Susan E MATTHEWS, Michaela WIMMEROVÁ, Anne IMBERTY a Sebastien VIDAL. Rational Design and Synthesis of Optimized Glycoclusters for Multivalent Lectin-Carbohydrate Interactions: Influence of the Linker Arm. Chemistry - A European Journal. WEINHEIM: WILEY-VCH, 2012, roč. 18, č. 20, s. 6250-6263. ISSN 0947-6539. Dostupné z: https://dx.doi.org/10.1002/chem.201200010. |
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@article{1073530, author = {Cecioni, Samy and Praly, JeanandPierre and Matthews, Susan E and Wimmerová, Michaela and Imberty, Anne and Vidal, Sebastien}, article_location = {WEINHEIM}, article_number = {20}, doi = {http://dx.doi.org/10.1002/chem.201200010}, keywords = {carbohydrates; click chemistry; glycoclusters; lectin; multivalency}, language = {eng}, issn = {0947-6539}, journal = {Chemistry - A European Journal}, title = {Rational Design and Synthesis of Optimized Glycoclusters for Multivalent Lectin-Carbohydrate Interactions: Influence of the Linker Arm}, url = {http://onlinelibrary.wiley.com/doi/10.1002/chem.201200010/suppinfo}, volume = {18}, year = {2012} }
TY - JOUR ID - 1073530 AU - Cecioni, Samy - Praly, Jean-Pierre - Matthews, Susan E - Wimmerová, Michaela - Imberty, Anne - Vidal, Sebastien PY - 2012 TI - Rational Design and Synthesis of Optimized Glycoclusters for Multivalent Lectin-Carbohydrate Interactions: Influence of the Linker Arm JF - Chemistry - A European Journal VL - 18 IS - 20 SP - 6250-6263 EP - 6250-6263 PB - WILEY-VCH SN - 09476539 KW - carbohydrates KW - click chemistry KW - glycoclusters KW - lectin KW - multivalency UR - http://onlinelibrary.wiley.com/doi/10.1002/chem.201200010/suppinfo L2 - http://onlinelibrary.wiley.com/doi/10.1002/chem.201200010/suppinfo N2 - The design of multivalent glycoclusters requires the conjugation of biologically relevant carbohydrate epitopes functionalized with linker arms to multivalent core scaffolds. The multigram-scale syntheses of three structurally modified triethyleneglycol analogues that incorporate amide moiety(ies) and/or a phenyl ring offer convenient access to a series of carbohydrate probes with different water solubilities and rigidities. Evaluation of flexibility and determination of preferred conformations were performed by conformational analysis. Conjugation of the azido-functionalized carbohydrates with tetra-propargylated core scaffolds afforded a library of 18 tetravalent glycoclusters, in high yields, by CuI-catalyzed azidealkyne cycloaddition (CuAAC). The compounds were evaluated for their ability to bind to PA-IL (the LecA lectin from the opportunistic pathogen Pseudomonas aeruginosa). Biochemical evaluation through inhibition of hemagglutination assays (HIA), enzyme-linked lectin assays (ELLA), surface plasmon resonance (SPR), and isothermal titration microcalorimetry (ITC) revealed improved and unprecedented affinities for one of the monovalent probes (K-d=5.8 mu M) and also for a number of the tetravalent compounds that provide several new nanomolar ligands for this tetrameric lectin. ER -
CECIONI, Samy, Jean-Pierre PRALY, Susan E MATTHEWS, Michaela WIMMEROVÁ, Anne IMBERTY a Sebastien VIDAL. Rational Design and Synthesis of Optimized Glycoclusters for Multivalent Lectin-Carbohydrate Interactions: Influence of the Linker Arm. \textit{Chemistry - A European Journal}. WEINHEIM: WILEY-VCH, 2012, roč.~18, č.~20, s.~6250-6263. ISSN~0947-6539. Dostupné z: https://dx.doi.org/10.1002/chem.201200010.
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