Easy and effective method to produce functionalized particles for cellular uptake

被引：16

作者：

Collette, Floraine ^{[1
]}

Delatouche, Regis ^{[2
]}

Blanquart, Christophe ^{[3
]}

Gueugnon, Fabien ^{[3
]}

Gregoire, Marc ^{[3
]}

Bertrand, Philippe ^{[2
]}

Heroguez, Valerie ^{[1
]}

机构：

[1] Univ Bordeaux 1, Lab Chim Polymeres Organ, ENSCBP, IPB,CNRS,UMR 5629, F-33607 Pessac, France

[2] CNRS, UMR 6514, Lab Synth & React Subst Nat, F-86022 Poitiers, France

[3] Ctr Rech Cancerol Nantes Angers 8 Quai Moncousu, Inst Rech Therapeut, INSERM, U892, F-44007 Nantes 1, France

来源：

JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY | 2013年 / 51卷 / 01期

关键词：

biocompatibility; click chemistry; core-shell particles; poly(ethylene oxide); polynorbornene; ROMP; OPENING METATHESIS POLYMERIZATION; DRUG-DELIVERY; CLICK CHEMISTRY; 1,3-DIPOLAR CYCLOADDITION; OXIDE) MACROMONOMERS; BLOCK-COPOLYMERS; NANOPARTICLES; NORBORNENE; ROMP; NANOMATERIALS;

D O I：

10.1002/pola.26357

中图分类号：

O63 [高分子化学（高聚物）];

学科分类号：

070305 ; 080501 ; 081704 ;

摘要：

In this contribution, a versatile approach for the synthesis of functionalized particles for drug delivery is presented, using two nonaggressive standardized procedures. The first procedure considered is the functionalization of an azido-terminated a-norbornenyl poly(ethylene oxide) (PEO) macromonomer with an alkyne-containing active molecule via the copper catalyzed azide alkyne cycloaddition, click type reaction. The functionalized macromonomer is then polymerized by Ring-Opening Metathesis Polymerization (ROMP) in dispersion to form functionalized particles. The second procedure consists in synthesizing particles by ROMP in dispersed media of norbornene with azido-terminated a-norbornenyl PEO macromonomer. The ROMP was initiated by the first generation Grubbs catalyst. Such functionalized core-shell particles have stealthy properties due to their PEO shell and can be viewed as universal nanocarriers on which any alkyne-modified active molecule can be grafted by click chemistry. (C) 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2013

引用

页码：176 / 189

页数：14

共 52 条

[1]

ABUCHOWSKI A, 1977, J BIOL CHEM, V252, P3578

[2] Multifunctional polymeric nanoparticles from diverse bioactive agents [J].

Bertin, PA ;

Gibbs, JM ;

Shen, CKF ;

Thaxton, CS ;

Russin, WA ;

Mirkin, CA ;

Nguyen, ST .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (13) :4168-4169

[3] Combining ring-opening metathesis polymerization (ROMP) with sharpless-type "click" reactions: An easy method for the preparation of side chain functionalized poly(oxynorbornenes) [J].

Binder, WH ;

Kluger, C .

MACROMOLECULES, 2004, 37 (25) :9321-9330

[4] Organic azides:: An exploding diversity of a unique class of compounds [J].

Bräse, S ;

Gil, C ;

Knepper, K ;

Zimmermann, V .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (33) :5188-5240

[5] Nanomaterials and nanoparticles: Sources and toxicity [J].

Buzea, Cristina ;

Pacheco, Ivan I. ;

Robbie, Kevin .

BIOINTERPHASES, 2007, 2 (04) :MR17-MR71

[6]

Chapyshev S., 1997, CHEM HETEROCYCL COMP, V33, P1315

[7] Dispersion ring-opening metathesis polymerization of norbornene using PEO-based stabilizers [J].

Chemtob, A ;

Héroguez, V ;

Gnanou, Y .

MACROMOLECULES, 2002, 35 (25) :9262-9269

[8] Synthesis of a Molecular Charm Bracelet via Click Cyclization and Olefin Metathesis Clipping [J].

Clark, Paul G. ;

Guidry, Erin N. ;

Chan, Wing Yan ;

Steinmetz, Wayne E. ;

Grubbs, Robert H. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (10) :3405-3412

[9] Novel ruthenium-based catalyst systems for the ring-opening metathesis polymerization of low-strain cyclic olefins [J].

Demonceau, A ;

Stumpf, AW ;

Saive, E ;

Noels, AF .

MACROMOLECULES, 1997, 30 (11) :3127-3136

[10] Darkfield-Confocal Microscopy detection of nanoscale particle internalization by human lung cells [J].

Gibbs-Flournoy, Eugene A. ;

Bromberg, Philip A. ;

Hofer, Thomas P. J. ;

Samet, James M. ;

Zucker, Robert M. .

PARTICLE AND FIBRE TOXICOLOGY, 2011, 8

← 1 2 3 4 5 6 →