ORBi: Nicolas Julien - Synthesis of highly functionalized poly(alkyl cyanoacrylate) nanoparticles by means of click chemistry

Reference : Synthesis of highly functionalized poly(alkyl cyanoacrylate) nanoparticles by means of c...


	Document type :	Scientific journals : Article
	Discipline(s) :	Physical, chemical, mathematical & earth Sciences : Chemistry Engineering, computing & technology : Materials science & engineering
	To cite this reference:	http://hdl.handle.net/2268/14232

Title :	Synthesis of highly functionalized poly(alkyl cyanoacrylate) nanoparticles by means of click chemistry
Language :	English
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 [University of Liège (ULg) > Department of Chemistry > Center for Education and Research on Macromolecules (CERM) > >]
	Detrembleur, Christophe [University of Liège (ULg) > 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 > >]
Publication date :	25-Nov-2008
Journal title :	Macromolecules
Publisher :	American Chemical Society
Volume :	41
Issue/season :	22
Pages :	8418-8428
Audience :	International
ISSN :	0024-9297
City :	Washington
Country :	DC
Keywords :	[en] 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 units :	Center for Education and Research on Macromolecules (CERM)
Funders :	The french Ministry of Research ; The "CNRS"
Target :	Researchers
Permalink :	http://hdl.handle.net/2268/14232
DOI :	10.1021/ma8013349
Other URL :	http://pubs.acs.org/doi/pdf/10.1021/ma8013349

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