Preparation of Well-Defined and Degradable Aldehyde-Functionalized Glycopolymeric Nanospheres

Xiao, Naiyu; Zhong, Le; Zhai, Wan-Jing; Bai, Weidong

doi:10.3724/sp.j.1105.2012.11362

Cited by 6 publications

(6 citation statements)

References 21 publications

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“…Amphiphilic glycopolymers that self-assembled into degradable biocompatible and aldehyde-functionalized polymeric nanospheres without any surfactant were also reported. 16 The authors also envisioned the use of such particles as drug-delivery carriers. Gonsalves and co-workers 258 synthesized P(CKA27-co-VPA) and P(CKA27-co-VPE) with VPA for vinylphosphonic acid and VPE for dimethyl vinylphosphonate by free-radical copolymerization with the aim to prepare organic polymer− inorganic hybrid materials.…”

Section: Miscellaneous Applicationsmentioning

confidence: 99%

Section: Applicationsmentioning

confidence: 99%

“…rROP was extensively studied in the 1980’s and 1990’s but has been recently rejuvenated by the possibility to copolymerize cyclic vinyl monomers with classical vinyl monomers, leading to cleavable functions into the copolymer backbone (Figure a). This led to a broad range of novel (bio)degradable materials suitable for a large scope of applications, particularly in the biomedical field − where degradability and/or bioresorption are often required. It has to be noted that all these recent studies used well-known cyclic monomers (e.g., CKA, sulfide cyclic methacrylate, etc.)…”

Section: Introductionmentioning

confidence: 99%

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Radical Ring-Opening Polymerization: Scope, Limitations, and Application to (Bio)Degradable Materials

et al. 2017

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Cyclic monomers bearing either vinyl or exomethylene groups have the ability to be polymerized through a radical pathway via a ring-opening mechanism (addition-fragmentation process), leading to the introduction of functionalities in the polymer backbone. Radical ring-opening polymerization (rROP) combines the advantages of both ring-opening polymerization and radical polymerization, that is the preparation of polymers bearing heteroatoms in the backbone but with the ease and robustness of a radical process. This current review presents a comprehensive description of rROP by detailing: (i) the various monomers that polymerize through rROP; (ii) the main parameters that govern the rROP mechanism; (iii) the copolymerization by conventional or controlled/living radical polymerization between rROP monomers and traditional vinyl monomers to obtain copolymers with advanced properties; (iv) the different applications (low shrinkage materials and preparation of (bio)degradable materials) of rROP monomer-containing materials, and (v) the main alternatives to rROP to induce degradability to materials obtained by a radical polymerization.

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Section: Miscellaneous Applicationsmentioning

confidence: 99%

Section: Applicationsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Radical Ring-Opening Polymerization: Scope, Limitations, and Application to (Bio)Degradable Materials

et al. 2017

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“…[31][32][33] While a wide range of vinyl monomers has been copolymerized with CKAs, only a very few studies have reported glycosylated CKA-based vinyl copolymers (Figure 1c). [34][35][36] For instance, Bai and co-workers copolymerized 1,2:3,4-di-O-isopropylidene-6-O-(2'-formyl-4'-vinylphenyl)-D-galactopyranose (IVDG) and 5,6-benzo-2-methylene-1,3-dioxepane (BMDO) by RAFT to produce P(IVDG-co-BMDO) copolymers that were self-assembled into glycosylated nanoparticles after deprotection of the hydroxyls groups of the sugar moieties. 34 Maynard and co-workers obtained trehalose-functionalized copolymers containing BMDO units via consecutive RAFT polymerization and thiol-ene post-functionalization to install trehalose moieties on the copolymer backbone.…”

Section: Introductionmentioning

confidence: 99%

“…[34][35][36] For instance, Bai and co-workers copolymerized 1,2:3,4-di-O-isopropylidene-6-O-(2'-formyl-4'-vinylphenyl)-D-galactopyranose (IVDG) and 5,6-benzo-2-methylene-1,3-dioxepane (BMDO) by RAFT to produce P(IVDG-co-BMDO) copolymers that were self-assembled into glycosylated nanoparticles after deprotection of the hydroxyls groups of the sugar moieties. 34 Maynard and co-workers obtained trehalose-functionalized copolymers containing BMDO units via consecutive RAFT polymerization and thiol-ene post-functionalization to install trehalose moieties on the copolymer backbone. 35 By a combination of ROP and rROP, Stenzel and co-workers chain-extended a polycaprolactone (PCL) macro RAFT agent with 1-O-acryloyl-β-Dfructopyranose and BMDO to yield diblock copolymer micelles with a PCL core and a fructosefunctionalized acrylic shell containing ester units.…”

Section: Introductionmentioning

confidence: 99%

Degradable Glycopolyester-like Nanoparticles by Radical Ring-Opening Polymerization

et al. 2022

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A small library of degradable polyester-like glycopolymers was successfully prepared by the combination of radical ring-opening copolymerization (rROP) of 2-methylene-1,3-dioxepane (MDO) with vinyl ether (VE) derivatives, and a Pd-catalyzed thioglycoconjugation. The resulting thioglycopolymers were formulated into self-stabilized thioglyconanoparticles which were stable up to 4 months and were enzymatically degraded. Nanoparticles and their degradation products exhibited a good cytocompatibility on two healthy cell lines. Interactions between thioglyconanoparticles and lectins were investigated and highlighted the presence of both specific carbohydrate/lectin interactions and nonspecific hydrophobic interactions. Fluorescent thioglyconanoparticles were also prepared either by encapsulation of Nile Red, or by the functionalization of the polymer backbone with Rhodamine B. Such nanoparticles were used to prove the cell internalization of the thioglyconanoparticles by lung adenocarcinoma (A549) cells which underlined the great potential of P(CKA-co-VE) copolymers for biomedical applications

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New Aldehyde‐Functional Methacrylic Water‐Soluble Polymers

et al. 2021

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Aldehyde groups enable facile conjugation to proteins, enzymes, oligonucleotides or fluorescent dyes, yet there are no literature examples of water‐soluble aldehyde‐functional vinyl monomers. We report the synthesis of a new hydrophilic cis‐diol‐based methacrylic monomer (GEO5MA) by transesterification of isopropylideneglycerol penta(ethylene glycol) using methyl methacrylate followed by acetone deprotection via acid hydrolysis. The corresponding water‐soluble aldehyde monomer, AGEO5MA, is prepared by aqueous periodate oxidation of GEO5MA at 22 °C. RAFT polymerization of GEO5MA yields the water‐soluble homopolymer, PGEO5MA. Aqueous periodate oxidation of the terminal cis‐diol units on PGEO5MA at 22 °C affords a water‐soluble aldehyde‐functional homopolymer (PAGEO5MA). Moreover, a library of hydrophilic statistical copolymers bearing cis‐diol and aldehyde groups was prepared using sub‐stoichiometric periodate/cis‐diol molar ratios. The aldehyde groups on PAGEO5MA homopolymer were reacted in turn with three amino acids to demonstrate synthetic utility.

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Preparation of Well-Defined and Degradable Aldehyde-Functionalized Glycopolymeric Nanospheres

Cited by 6 publications

References 21 publications

Radical Ring-Opening Polymerization: Scope, Limitations, and Application to (Bio)Degradable Materials

Radical Ring-Opening Polymerization: Scope, Limitations, and Application to (Bio)Degradable Materials

Degradable Glycopolyester-like Nanoparticles by Radical Ring-Opening Polymerization

New Aldehyde‐Functional Methacrylic Water‐Soluble Polymers

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