Synthesis of highly functionalized poly(alkyl cyanoacrylate) nanoparticles by means of click chemistry

Nicolas, Julien; Bensaid, Fehti; Desmaële, Didier; Grogna, Mathurin; Detrembleur, Christophe; Andrieux, Karine; Couvreur, Patrick

doi:10.1021/ma8013349

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Article (Scientific journals)

Synthesis of highly functionalized poly(alkyl cyanoacrylate) nanoparticles by means of click chemistry

Nicolas, Julien; Bensaid, Fehti; Desmaële, Didier et al.

2008 • In Macromolecules, 41 (22), p. 8418-8428

Peer Reviewed verified by ORBi

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https://hdl.handle.net/2268/14232

DOI
10.1021/ma8013349

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Keywords :

organic nanoparticle; click chemistry; copper-mediated Huisgen's cycloaddition

Abstract :

[en] A general methodology was proposed to prepare highly functionalized poly(alkyl cyanoacrylate) nanoparticles by means of Huisgen 1,3-dipolar cyclo-addition, the so-called click chemistry. To achieve this goal, different protocols were investigated to obtain azidopoly(ethylene glycol) cyanoacetate of variable molar mass, followed by a Knoevenagel condensation−Michael addition reaction with hexadecyl cyanoacetate to produce a poly[(hexadecyl cyanoacrylate)-co-azidopoly(ethylene glycol) cyanoacrylate] (P(HDCA-co-N3PEGCA)) copolymer, displaying azide functionalities at the extremity of the PEG chains. As a proof of concept, model alkynes were quantitatively coupled either to the P(HDCA-co-N3PEGCA) copolymers in homogeneous medium followed by self-assembly in aqueous solution or directly at the surface of the preformed P(HDCA-co-N3PEGCA) nanoparticles in aqueous dispersed medium, both yielding highly functionalized nanoparticles. This versatile approach, using alkyl cyanoacrylate derivatives, opened the door to ligand-functionalized and biodegradable nanoparticles with “stealth” properties for biomedical applications.

Research center :

Center for Education and Research on Macromolecules (CERM)

Disciplines :

Materials science & engineering
Chemistry

Author, co-author :

Nicolas, Julien; Université de Paris-Sud, France > Laboratoire de Physico-Chimie, Pharmacotechnie et Biopharmacie

Bensaid, Fehti; Université de Paris-Sud, France > Laboratoire de Physico-Chimie, Pharmacotechnie et Biopharmacie

Desmaële, Didier; Université de Paris-Sud, France > Laboratoire Biocis

Grogna, Mathurin ; Université de Liège - ULiège > Department of Chemistry > Center for Education and Research on Macromolecules (CERM)

Detrembleur, Christophe ; Université de Liège - ULiège > Department of Chemistry > Center for Education and Research on Macromolecules (CERM)

Andrieux, Karine; Université de Paris-Sud, France > Laboratoire de Physico-Chimie, Pharmacotechnie et Biopharmacie

Couvreur, Patrick; Université de Paris-Sud, France > Laboratoire de Physico-Chimie, Pharmacotechnie et Biopharmacie

Language :

English

Title :

Synthesis of highly functionalized poly(alkyl cyanoacrylate) nanoparticles by means of click chemistry

Publication date :

25 November 2008

Journal title :

Macromolecules

ISSN :

0024-9297

eISSN :

1520-5835

Publisher :

American Chemical Society, Washington, United States - District of Columbia

Volume :

Issue :

Pages :

8418-8428

Peer reviewed :

Peer Reviewed verified by ORBi

Additional URL :

http://pubs.acs.org/doi/pdf/10.1021/ma8013349

Funders :

The french Ministry of Research
CNRS - Centre National de la Recherche Scientifique [FR]

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since 10 June 2009

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