| 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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