Next Article in Journal
A Greener, Efficient Approach to Michael Addition of Barbituric Acid to Nitroalkene in Aqueous Diethylamine Medium
Next Article in Special Issue
Synthesis of a 2ꞌꞌ-Deoxy-β-GalCer
Previous Article in Journal
Invasive Fungal Infections in the ICU: How to Approach, How to Treat
Previous Article in Special Issue
Stimulation of Natural Killer T Cells by Glycolipids
Open AccessArticle

Gold Nanoparticles Decorated with Mannose-6-phosphate Analogues

Institut des Biomolécules Max Mousseron UMR 5247 UM2-UM1-CNRS-ENSCM 8 rue de l'Ecole Normale, Montpellier cedex 5 34296, France
Author to whom correspondence should be addressed.
Molecules 2014, 19(1), 1120-1149;
Received: 25 November 2013 / Revised: 7 January 2014 / Accepted: 10 January 2014 / Published: 17 January 2014
(This article belongs to the Special Issue Synthesis, Structure, Analysis and Properties of Glycolipids)
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. View Full-Text
Keywords: C-C coupling reaction; click chemistry; glycoconjugate; mannose-6-phosphate; glyconanoparticle; angiogenesis C-C coupling reaction; click chemistry; glycoconjugate; mannose-6-phosphate; glyconanoparticle; angiogenesis
Show Figures

Graphical abstract

MDPI and ACS Style

Combemale, S.; Assam-Evoung, J.-N.; Houaidji, S.; Bibi, R.; Barragan-Montero, V. Gold Nanoparticles Decorated with Mannose-6-phosphate Analogues. Molecules 2014, 19, 1120-1149.

AMA Style

Combemale S, Assam-Evoung J-N, Houaidji S, Bibi R, Barragan-Montero V. Gold Nanoparticles Decorated with Mannose-6-phosphate Analogues. Molecules. 2014; 19(1):1120-1149.

Chicago/Turabian Style

Combemale, Stéphanie; Assam-Evoung, Jean-Norbert; Houaidji, Sabrina; Bibi, Rashda; Barragan-Montero, Véronique. 2014. "Gold Nanoparticles Decorated with Mannose-6-phosphate Analogues" Molecules 19, no. 1: 1120-1149.

Find Other Styles

Article Access Map by Country/Region

Only visits after 24 November 2015 are recorded.
Search more from Scilit
Back to TopTop