Block Copolymer Nanoparticles of Ethylene Oxide and Isobutyl Cyanoacrylate

Choi, Young Kweon; Bae, You Han; Kim, Sung Wan

doi:10.1021/ma00128a062

Cited by 28 publications

(19 citation statements)

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“…17,18 As a result of their fast polymerization and excellent adhesive properties, alkyl cyanoacrylates are widely used for industrial and medical applications in super glues, sealants, and fuming systems. 16,19–21 Unfortunately, the limited number of initiator species available for cyanoacrylate polymerization limits the diversity of applications in which they are used. Furthermore, cyanoacrylates have biocompatibility concerns, because they can spontaneously degrade into formaldehyde and cyanoacetate compounds because of the existence of cyano groups in their chemical structures.…”

Section: Introductionmentioning

confidence: 99%

“…22 Therefore, alkyl cyanoacrylates are not widely integrated into medically relevant adhesive materials. 16,21,23–25 Thus, further efforts into improving the diversity of polymers that can undergo anionic polymerization, expanded options for initiator species, and milder polymerization conditions are needed to broaden the applicability of polymers synthesized using anionic polymerization.…”

Section: Introductionmentioning

confidence: 99%

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Anionic Polymerization of Methylene Malonate for High-Performance Coatings

Huang

Liu

Yang

et al. 2019

ACS Appl. Polym. Mater.

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Here, we demonstrate the anionic polymerization and the high reactivity of the novel monomer diethyl methylene malonate (DEMM). At room temperature and under atmospheric conditions, water and anionic functional groups (i.e., carboxyl, boronic, and phenol) quickly initiate DEMM. The polymerization of DEMM in water and the final molecular weight of the polymer were both demonstrated to be pH-dependent. Systematically, investigations were conducted to study the conversion rate of DEMM with various functional groups, and the polymerization was verified to occur with anionic groups using a carboxylate-initiated DEMM system. For coating applications, we also investigated a multifunctional derivative monomer called (DEMM)6 that is an oligomeric polyester of DEMM esterified with butanediol that contains on average six repeat units of reactive DEMM (commercially known as Forza B3000 XP). The incorporation of 15 wt % (DEMM)6 into latex containing methacrylate acid as a functional monomer yielded cross-linked coatings with a gel content of 76.25 wt % that had a 289% improvement in rub-resistance performance compared to controls (without (DEMM)6). This study provides a facile methodology to synthesize cross-linked latex coatings at room temperature.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Anionic Polymerization of Methylene Malonate for High-Performance Coatings

Huang

Liu

Yang

et al. 2019

ACS Appl. Polym. Mater.

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“…The PEGylation was achieved initiating the polymerization of the alkylcyanoacrylate monomers on the chain-end of PEG adapting the historical emulsion polymerization method [Lourenco et al, 1996, Perrachia et al, 1997. Other methods considered the synthesis of amphiphilic copolymers composed alkyl cyanoacrylate and PEG that were then converted into PEGcoated nanoparticles by nanoprecipitation [Choi et al, 1995, Peracchia et al, 1997. The method based on the synthesis of the poly(hexadecyl cyanoacrylate-co-methoxy PEG-hexadecyl cyanoacrylate [P[HDCA-co-MePEGCA) [Peracchia et al, 1997 was favored in many subsequent works [Stella et al, 2000, 2007, Nicolas et al, 2008, 2009, Le Droumadet et al, 2012.…”

Section: Designing Nanoparticles Controlling Their In Vivo Drug Delivmentioning

confidence: 99%

A journey through the emergence of nanomedicines with poly(alkylcyanoacrylate) based nanoparticles

Vauthier

2019

Journal of Drug Targeting

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Starting in the late 1970s, the pioneering work of Patrick Couvreur gave birth to the first biodegradable nanoparticles composed of a biodegradable synthetic polymer. These nanoparticles, made of poly(alkylcyanoacrylate) (PACA), were the first synthetic polymer based nanoparticulate drug carriers undergoing a phase III clinical trial so far. Analyzing the journey from the birth of PACA nanoparticles to their clinical evaluation, the paper highlights their remarkable adaptability to bypass various drug delivery challenges found on the way. At present, PACA nanoparticles includes a wide range of nanoparticles that can associate drugs of different chemical nature and be administered in vivo by different routes. The most recent technologies giving the nanoparticles customized functions could also be implemented on this family of nanoparticles. Through different examples, the paper discusses the seminal role of the PACA nanoparticles' family in the development of nanomedicines.

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“…Biodegradable PACA polymers were synthesized by emulsion polymerization that was initiated by the hydroxyl ions of water and elongation of the polymer chains occurs according to an anionic polymerization mechanism18, 38 [Figure 1 (a) and (b)]. To obtain ‘stealth’ nanoparticles, block PEG‐PACA copolymers (Figure 1 c) have been synthesized by initiating the polymerization of alkylcyanoacrylates either by monomethoxy (MeO)‐PEG‐triphenylphosphine or by triphenylphosphine‐PEG‐triphenylphosphine, leading to diblock MeO‐PEG‐PACA or triblock MeO‐PACA‐PEG‐PACA‐OMe linear copolymers, respectively 39. Branched PEG‐PACA copolymer is obtained by the Knoevenagel reaction of block copolymers, involving the condensation of a cyanoacetate derivative with formaldehyde.…”

Section: Pegylated Poly(alkylcyanoacrylates) Nanoparticlesmentioning

confidence: 99%

Polyalkylcyanoacrylate nanoparticles for delivery of drugs across the blood–brain barrier

Andrieux¹,

Couvreur²

2009

WIREs Nanomed Nanobiotechnol

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The major problem in drug delivery to the brain is the presence of the blood-brain barrier (BBB) which limits drug penetration even if in certain pathological situations the BBB is partly disrupted. Among noninvasive techniques to overcome this barrier, the use of nanoparticles has been proposed. This review focuses on poly(alkylcyanoacrylates) (PACA)-based nanoparticles which have been developed for brain targeting. Both types of 'stealth' PACA nanoparticles with modified surface, those coated with surfactant and those with chains of polyethylene glycol (PEG) linked to the hydrophobic core of PACA are presented. The synthesis of polymers, the preparation of nanoparticles with modified surface and their physicochemical characterization are described. The review of their in vivo results evidenced their ability to enter into the brain using healthy animals or models of central nervous system (CNS) diseases. The nature of the surface modification (surfactant nature, PEG linkage, drug loading interference) seems to have a great influence on the efficacy of brain targeting which can be related to the adsorption of some apolipoproteins (Apo E, B, A-I). The mechanism of their passage through the BBB has been studied by in vitro and in vivo experiments, which suggested the implication of receptor-mediated endocytosis processes. According to these data, some antibodies (OX26) and ligands (transferrin, Apo E/B/A-I) seem to be good candidates to be coupled with 'stealth' PACA nanoparticles in order to increase their passage through the BBB and to promote active targeting to the brain.

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Block Copolymer Nanoparticles of Ethylene Oxide and Isobutyl Cyanoacrylate

Cited by 28 publications

References 1 publication

Anionic Polymerization of Methylene Malonate for High-Performance Coatings

Anionic Polymerization of Methylene Malonate for High-Performance Coatings

A journey through the emergence of nanomedicines with poly(alkylcyanoacrylate) based nanoparticles

Polyalkylcyanoacrylate nanoparticles for delivery of drugs across the blood–brain barrier

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