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

Gold Nanoparticles Decorated with Mannose-6-phosphate Analogues

, , ,  and *
Received: 25 November 2013; in revised form: 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)
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Abstract: 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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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.


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