Amino end-functionalized poly(ethylene oxide)-block-poly(methylidene malonate 2.1.2) block copolymers: synthesis, characterization, and chemical modification for targeting purposes

Studer, Peggy; Larras, Virginie; Riess, Gérard

doi:10.1016/j.eurpolymj.2008.04.003

Cited by 14 publications

(10 citation statements)

References 32 publications

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“…The presence of functionalizable groups such as hydroxyl and carboxylate in polyesters can efficiently increase their hydrophilicity and degradability, plus modulate their mechanical, thermal, chemical, and biologic properties [8, 9, 11]. Furthermore, these functional groups provide access to versatile routes to conjugate a variety of bioactive molecules such as peptides [12], saccharides [13], and biotin [14]. This can lead to novel biomaterials with diverse bioactivities.…”

Section: Introductionmentioning

confidence: 99%

A functionalizable polyester with free hydroxyl groups and tunable physiochemical and biological properties

et al. 2010

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Polyesters with free functional groups allow facile modifications with biomolecules, which can lead to versatile biomaterials that afford controlled interactions with cells and tissues. Efficient synthesis of functionalizable polyesters is still a challenge that greatly limits the availability and widespread applications of biofunctionalized synthetic polymers. Here we report a simple route to prepare a functionalizable polyester, poly(sebacoyl diglyceride) (PSeD) bearing free hydroxyl groups. The key synthetic step is an epoxide ring-opening polymerization, instead of the traditional polycondensation, that produces poly(glycerol sebacate) (PGS) [1]. PSeD has a more defined structure with mostly linear backbone, more free hydroxyl groups, higher molecular weight, and lower polydispersity than PGS. Crosslinking PSeD with sebacic acid yields a polymer five times tougher and more elastic than cured PGS. PSeD exhibits good cytocompatibility in vitro. Furthermore, functionalization by glycine proceeds with high efficiency. This versatile synthetic platform can offer a large family of biodegradable, functionalized polymers with tunable physiochemical and biological properties useful for a wide range of biomedical applications.

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Section: Introductionmentioning

confidence: 99%

A functionalizable polyester with free hydroxyl groups and tunable physiochemical and biological properties

et al. 2010

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“…October 2013 | 80 | e50874 | Page 6 of 7 explosive, and toxic gas!). 22,23 MM prepared from this homemade PEG-NH 2 (B3) yielded improved results compared to the commercial MMs.…”

confidence: 97%

“…We first describe the synthesis and purification of PEG-MM B from 3 kDa O-(2-aminoethyl)polyethylene glycol (PEG-NH 2 ) and norbornene-Nhydroxysuccinimidyl (NHS) ester. The former compound can be purchased from Sigma Aldrich Inc., or prepared via anionic polymerization according to literature procedures 22,23 . The latter compound can be prepared in two steps according to a published procedure 21 .…”

Section: Protocolmentioning

confidence: 99%

Particles without a Box: Brush-first Synthesis of Photodegradable PEG Star Polymers under Ambient Conditions

Liu

Gao

Johnson

2013

JoVE

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Convenient methods for the rapid, parallel synthesis of diversely functionalized nanoparticles will enable discovery of novel formulations for drug delivery, biological imaging, and supported catalysis. In this report, we demonstrate parallel synthesis of brush-arm star polymer (BASP) nanoparticles by the "brush-first" method. In this method, a norbornene-terminated poly(ethylene glycol) (PEG) macromonomer (PEG-MM) is first polymerized via ring-opening metathesis polymerization (ROMP) to generate a living brush macroinitiator. Aliquots of this initiator stock solution are added to vials that contain varied amounts of a photodegradable bis-norbornene crosslinker. Exposure to crosslinker initiates a series of kinetically-controlled brush+brush and star+star coupling reactions that ultimately yields BASPs with cores comprised of the crosslinker and coronas comprised of PEG. The final BASP size depends on the amount of crosslinker added. We carry out the synthesis of three BASPs on the benchtop with no special precautions to remove air and moisture. The samples are characterized by gel permeation chromatography (GPC); results agreed closely with our previous report that utilized inert (glovebox) conditions. Key practical features, advantages, and potential disadvantages of the brush-first method are discussed.

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“…14 The acidand metal-catalyzed polycondensation of malonate derivatives bearing aliphatic residues 15 was also reported together with the sequential anionic polymerization of ethylene oxide and methylidene malonate to obtain poly(ethylene oxide)-blockpoly(methylidene malonate 2.1.2) block copolymers bearing a primary amino group at the PEO chain end. 16 The only work where the malonate unit was changed from a malonic acid or dialkyl ester to being part of the main chain, is the work of Doğan and Küsefoğlu, published in 2008, that reported the 1,4-diazabicyclo[2.2.2]octane-catalyzed synthesis of a biodegradable polymeric foam from epoxidized soybean oil and malonic acid. 17 There has been increased interest in elemental sustainability in recent years.…”

Section: Introductionmentioning

confidence: 99%

Enzyme-catalyzed synthesis of malonate polyesters and their use as metal chelating materials

et al. 2021

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Amino end-functionalized poly(ethylene oxide)-block-poly(methylidene malonate 2.1.2) block copolymers: synthesis, characterization, and chemical modification for targeting purposes

Cited by 14 publications

References 32 publications

A functionalizable polyester with free hydroxyl groups and tunable physiochemical and biological properties

A functionalizable polyester with free hydroxyl groups and tunable physiochemical and biological properties

Particles without a Box: Brush-first Synthesis of Photodegradable PEG Star Polymers under Ambient Conditions

Enzyme-catalyzed synthesis of malonate polyesters and their use as metal chelating materials

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