Gold nanoparticles decorated with mannose-6-phosphate analogues.
Herein, the preparation of neoglycoconjugates bearing mannose-6-phosphate analogues is described by: (a) synthesis of a cyclic sulfate precursor to access the carbohydrate head-group by nucleophilic displacement with an appropriate nucleophile; (b) introduction of spacers on the mannose-6-phosphate analogues via Huisgen's cycloaddition, the Julia reaction, or the thiol-ene reaction under ultrasound activation. With the resulting compounds in hand, gold nanoparticles could be functionalized with various carbohydrate derivatives (glycoconjugates) and then tested for angiogenic activity. It was observed that the length and flexibility of the spacer separating the sugar analogue from the nanoparticle have little influence on the biological response. One particular nanoparticle system substantially inhibits blood vessel growth in contrast to activation by the corresponding monomeric glycoconjugate, thereby demonstrating the importance of multivalency in angiogenic activity.
Institut des Biomolécules Max Mousseron UMR 5247 UM2-UM1-CNRS-ENSCM 8 rue de l'Ecole Normale, Montpellier cedex 5 34296, France.
Stéphanie
S
Combemale
Institut des Biomolécules Max Mousseron UMR 5247 UM2-UM1-CNRS-ENSCM 8 rue de l'Ecole Normale, Montpellier cedex 5 34296, France.
Jean-Norbert
JN
Assam-Evoung
Institut des Biomolécules Max Mousseron UMR 5247 UM2-UM1-CNRS-ENSCM 8 rue de l'Ecole Normale, Montpellier cedex 5 34296, France.
Sabrina
S
Houaidji
Institut des Biomolécules Max Mousseron UMR 5247 UM2-UM1-CNRS-ENSCM 8 rue de l'Ecole Normale, Montpellier cedex 5 34296, France.
Rashda
R
Bibi
Institut des Biomolécules Max Mousseron UMR 5247 UM2-UM1-CNRS-ENSCM 8 rue de l'Ecole Normale, Montpellier cedex 5 34296, France. veronique.montero@univ-montp2.fr.
Véronique
V
Barragan-Montero
D043925:Angiogenesis Inducing Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D000818:Animals; D002642:Chick Embryo; D049033:Chorioallantoic Membrane / Q000098:blood supply; D057930:Click Chemistry; D061565:Cycloaddition Reaction; D006046:Gold / Q000737:chemistry*; D054879:Halogenation; D008360:Mannosephosphates / Q000737:chemistry*; D053768:Metal Nanoparticles / Q000737:chemistry*; D018919:Neovascularization, Physiologic / Q000187:drug effects; D010316:Particle Size
D043925:Angiogenesis Inducing Agents; D008360:Mannosephosphates; C027693:mannose-6-phosphate; D006046:Gold