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
Article Menu

Export Article

Open AccessArticle
Molecules 2014, 19(1), 1120-1149; doi:10.3390/molecules19011120

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.
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)
View Full-Text   |   Download PDF [715 KB, uploaded 18 June 2014]   |  


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.
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

This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

Scifeed alert for new publications

Never miss any articles matching your research from any publisher
  • Get alerts for new papers matching your research
  • Find out the new papers from selected authors
  • Updated daily for 49'000+ journals and 6000+ publishers
  • Define your Scifeed now

SciFeed Share & Cite This Article

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.

Show more citation formats Show less citations formats

Related Articles

Article Metrics

Article Access Statistics



[Return to top]

Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top