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The multivalent presentation of partly optimized candidates on various dendritic scaffolds through Cu<jats:sup>I<\/jats:sup>\u2010catalyzed azide\u2013alkyne cycloaddition (CuAAc) has also been achieved. Biophysical investigations based on isothermal titration calorimetry (ITC) have indicated a dissociation constant in the low micromolar range for the best optimized monovalent conjugate (<jats:italic>K<\/jats:italic><jats:sub>d<\/jats:sub>=37\u2005\u03bc<jats:sc>M<\/jats:sc>). The results thus confirmed that stable <jats:italic>C<\/jats:italic>\u2010galactosides could represent efficient synthetic glycomimetics of natural \u03b1\u2010linked oligosaccharidic inhibitors of PA\u2010IL lectin (Lec\u2005A) from the pathogenic <jats:italic>Pseudomonas aeruginosa<\/jats:italic>. Striking enhancements in the avidity of the glycoconjugates were also observed for tri\u2010, hexa\u2010, and nonavalent derivatives, among which the most potent exhibited dissociation constants below 500\u2005n<jats:sc>M<\/jats:sc>, corresponding to a 400\u2010fold increase in affinity compared with the \u03b2\u2010<jats:sc>D<\/jats:sc>\u2010Gal\u2010<jats:italic>O<\/jats:italic>\u2010Me used as reference. To deepen our understanding of the binding mode of the best glycomimetics involved in the recognition process, molecular modeling studies, docking calculations, and NMR diffusion measurements have been performed. Although favorable complementary interactions induced by the addition of the hydrophobic aglycon might explain the affinity enhancement, experimental determination of the size and the topology of the multivalent conjugates further supported the formation of aggregative complexes as a major multivalent binding mode. This work represents a systematic and comprehensive study towards a thorough understanding of the protein\u2013carbohydrate interactions involved in <jats:italic>Pseudomonas aeruginosa<\/jats:italic> infection, and as such should prove useful for the development of stable and optimized anti\u2010adhesive agents.<\/jats:p>","DOI":"10.1002\/chem.201003402","type":"journal-article","created":{"date-parts":[[2011,4,26]],"date-time":"2011-04-26T08:45:13Z","timestamp":1303807513000},"page":"6545-6562","source":"Crossref","is-referenced-by-count":104,"title":["Combining Glycomimetic and Multivalent Strategies toward Designing Potent Bacterial Lectin Inhibitors"],"prefix":"10.1002","volume":"17","author":[{"given":"Yoann M.","family":"Chabre","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Denis","family":"Gigu\u00e8re","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Bertrand","family":"Blanchard","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jacques","family":"Rodrigue","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sylvain","family":"Rocheleau","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mathieu","family":"Neault","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Subhash","family":"Rauthu","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Alex","family":"Papadopoulos","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Alexandre A.","family":"Arnold","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Anne","family":"Imberty","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ren\u00e9","family":"Roy","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2011,4,26]]},"reference":[{"key":"e_1_2_6_1_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr940283b"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.1059820"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1093\/glycob\/3.2.97"},{"key":"e_1_2_6_4_2","first-page":"43","volume":"96","author":"Dwek R. 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