Gold Nanoparticles Decorated with Mannose-6-phosphate Analogues

Molecules

Stéphanie Combemale¹  Jean-Norbert Assam-Evoung¹  Sabrina Houaidji¹  Rashda Bibi¹ 

[1] id="af1-molecules-19-01120">Institut des Biomolécules Max Mousseron UMR 5247 UM2-UM1-CNRS-ENSCM 8 rue de l’Ecole Normale, Montpellier cedex 5 34296, Fran

关键词: C-C coupling reaction;    click chemistry;    glycoconjugate;    mannose-6-phosphate;    glyconanoparticle;    angiogenesis;   

DOI  :  10.3390/molecules19011120

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
© 2014 by the authors; licensee MDPI, Basel, Switzerland.