Preparation of Amphiphilic Poly(ethylene glycol)- b-poly(γ-butyrolactone) Diblock Copolymer via Ring Opening Polymerization Catalyzed by a Cyclic Trimeric Phosphazene Base or Alkali Alkoxide.

Abstract:

:Biobased poly(γ-butyrolactone) (PγBL) as a fully biodegradable and bioabsorbable biomaterial has shown superior properties compared to those of other aliphatic polyesters. It is of great importance to prepare amphiphilic block copolymer containing PγBL block to make ordered nano-objects for biomedical applications such as drug delivery systems. However, such an amphiphilic copolymer containing PγBL segment was never successfully prepared mostly due to the synthetic challenges of ring-opening polymerization (ROP) of nonstrained γ-butyrolactone (γBL) monomer. Here, we reported the first preparation of amphiphilic poly(ethylene glycol)- b-poly(γ-butyrolactone) (PEG- b-PγBL) diblock copolymer by using PEG as a macroinitiator. We applied two types of bases to initiate the ROP of γBL. An organic cyclic trimeric phosphazene base (CTPB) was first applied to activate the terminal hydroxyl group of PEG as macroinitiator for ROP of γBL. On the other hand, sodium hydride was used to activate the hydroxyl group of PEG to form sodium alkoxide as an initiating system for ROP of γBL. Both catalytic/initiating system showed moderate control on ROP of γBL and successfully produced PEG- b-PγBL diblock copolymers with varied molecular weights and relatively narrow molecular weight distributions. The effects of catalytic systems, activation temperatures, and monomer concentrations on γBL conversion and molecular weight of PEG- b-PγBL were carefully explored. The thermal properties and phase behaviors of obtained PEG- b-PγBL were also investigated.

journal_name

Biomacromolecules

journal_title

Biomacromolecules

authors

Shen Y,Zhang J,Zhao Z,Zhao N,Liu F,Li Z

doi

10.1021/acs.biomac.8b01239

subject

Has Abstract

pub_date

2019-01-14 00:00:00

pages

141-148

issue

1

eissn

1525-7797

issn

1526-4602

journal_volume

20

pub_type

杂志文章
  • Fluorescence-tagged monolignols: synthesis, and application to studying in vitro lignification.

    abstract::Fluorescence-tagged coniferyl alcohols, coniferyl alcohol γ-coupled by ethylenediamine spacers to dimethylaminocoumarin or nitrobenzofuran fluorophores, were tested as photoprobes to study the oxidase-mediated polymerization of monolignols. The fluorescent coniferyl alcohol derivatives readily underwent peroxidase-cat...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm200136x

    authors: Tobimatsu Y,Davidson CL,Grabber JH,Ralph J

    更新日期:2011-05-09 00:00:00

  • Alterations in mucus barrier function and matrix structure induced by guluronate oligomers.

    abstract::The effect of guluronate oligomers on the barrier properties of mucous matrices was investigated in terms of the mobility of nanoparticles in mucous matrices by fluorescence recovery after photobleaching (FRAP), cellular uptake of nanoparticles in mucus secreting cells (HT29-MTX), and mucin matrix architecture by scan...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm500464b

    authors: Nordgård CT,Nonstad U,Olderøy MØ,Espevik T,Draget KI

    更新日期:2014-06-09 00:00:00

  • Analysis of adsorption function of polyhydroxybutyrate depolymerase from Alcaligenes faecalis T1 by using a quartz crystal microbalance.

    abstract::Enzymatic adsorption and degradation of three types of aliphatic polyester films and two types of polyolefin films by the extracellular PHB depolymerase from Alcaligenes faecalis T1 have been studied by using a quartz crystal microbalance (QCM) technique. Hydrolysis of poly[(R)-3-hydroxybutyrate] was quantitatively fo...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm0000844

    authors: Yamashita K,Aoyagi Y,Abe H,Doi Y

    更新日期:2001-04-01 00:00:00

  • Magnetic Fullerene-DNA/Hyaluronic Acid Nanovehicles with Magnetism/Reduction Dual-Responsive Triggered Release.

    abstract::We created the dual-responsive nanovehicle that can effectively combine and abundantly utilize magnetic and glutathione (GSH)-reductive triggers to control the drug delivery and achieve more intelligent and powerful targeting. In the nanovehicles, paramagnetic fullerene (C60@CTAF) was prepared via one-step modificatio...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/acs.biomac.6b01939

    authors: Wang L,Wang Y,Hao J,Dong S

    更新日期:2017-03-13 00:00:00

  • Synthetic 3D PEG-Anisogel Tailored with Fibronectin Fragments Induce Aligned Nerve Extension.

    abstract::An enzymatically cross-linked polyethylene glycol (PEG)-based hydrogel was engineered to promote and align nerve cells in a three-dimensional manner. To render the injectable, otherwise bioinert, PEG-based material supportive for cell growth, its mechanical and biochemical properties were optimized. A recombinant fibr...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/acs.biomac.9b00891

    authors: Licht C,Rose JC,Anarkoli AO,Blondel D,Roccio M,Haraszti T,Gehlen DB,Hubbell JA,Lutolf MP,De Laporte L

    更新日期:2019-11-11 00:00:00

  • Complex coacervation-controlled release from monoolein cubic phase containing silk fibroin and alginate.

    abstract::pH-dependent release from monoolein (MO) cubic phase was obtained by taking advantage of complex coacervation between hydrophobically modified alginate (HmAL) and hydrophobically modified silk fibroin (HmSF) in the water channels. The degree of coacervation was investigated at pH 3.0 by a light scattering method and t...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm101249e

    authors: Kwon TK,Kim JC

    更新日期:2011-02-14 00:00:00

  • Electrically conductive bacterial cellulose by incorporation of carbon nanotubes.

    abstract::Electrically conducting polymeric membranes were prepared by incorporating multiwalled carbon nanotubes (MWCNTs) into bacterial cellulose pellicles produced by Gluconacetobacter xylinum. The MWCNTs were dispersed in a surfactant (cationic cetyl trimethylammonium bromide) solution, and cellulose pellicles were dipped i...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm050597g

    authors: Yoon SH,Jin HJ,Kook MC,Pyun YR

    更新日期:2006-04-01 00:00:00

  • Nanometer to millimeter scale peptide-porphyrin materials.

    abstract::AQ-Pal14 is a 30-residue polypeptide that was designed to form an α-helical coiled coil that contains a metal-binding 4-pyridylalanine residue on its solvent-exposed surface. However, characterization of this peptide shows that it exists as a three-stranded coiled coil, not a two-stranded one as predicted from its des...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm100540t

    authors: Zaytsev DV,Xie F,Mukherjee M,Bludin A,Demeler B,Breece RM,Tierney DL,Ogawa MY

    更新日期:2010-10-11 00:00:00

  • Kinetic chain lengths in highly cross-linked networks formed by the photoinitiated polymerization of divinyl monomers: a gel permeation chromatography investigation.

    abstract::Highly cross-linked networks formed by the photoinitiated polymerization of multifunctional monomers are finding application in the field of biomaterials because of their chemical versatility, reaction control, and ability to polymerize under physiological conditions. Typically, degradation is introduced into these ne...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm025677o

    authors: Burdick JA,Lovestead TM,Anseth KS

    更新日期:2003-01-01 00:00:00

  • Polymeric Materials for Eye Surface and Intraocular Applications.

    abstract::Ocular applications of polymeric materials have been widely investigated for medical diagnostics, treatment, and vision improvement. The human eye is a vital organ that connects us to the outside world so when the eye is injured, infected, or impaired, it needs immediate medical treatment to maintain clear vision and ...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/acs.biomac.0c01525

    authors: Karayilan M,Clamen L,Becker ML

    更新日期:2021-01-06 00:00:00

  • α-Synuclein Penetrates Mucin Hydrogels Despite Its Mucoadhesive Properties.

    abstract::Recent research indicates that the progression of Parkinson's disease can start from neurons of the enteric nervous system, which are in close contact with the gastrointestinal epithelium: α-synuclein molecules can be transferred from these epithelial cells in a prion-like fashion to enteric neurons. Thin mucus layers...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/acs.biomac.9b00905

    authors: Marczynski M,Rickert CA,Semerdzhiev SA,van Dijk WR,Segers-Nolten IMJ,Claessens MMAE,Lieleg O

    更新日期:2019-12-09 00:00:00

  • Filamentous condensation of DNA induced by pegylated poly-L-lysine and transfection efficiency.

    abstract::In this paper we propose a detailed analysis of structural and morphological properties of two poly-L-lysine (PLL)-based transfection formulations, PLL/DNA and pegylated PLL (PLL-g-PEG)/DNA, by means of atomic force microscopy (AFM) and transmission electron microscopy (TEM). Comparing PLL-g-PEG/DNA with PLL/DNA polyp...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm800287z

    authors: Stanić V,Arntz Y,Richard D,Affolter C,Nguyen I,Crucifix C,Schultz P,Baehr C,Frisch B,Ogier J

    更新日期:2008-07-01 00:00:00

  • Cell membrane as a model for the design of ion-active nanostructured supramolecular systems.

    abstract::The synthesis and polymerization of six AB(3) tapered self-assembling methacrylate monomers (5a, 5b, 5c,5d, 17a, and 17b) based on first generation alkyl substituted benzyl ether monodendrons (i.e., minidendrons) containing oligooxyethylene units at their focal point and the polymerizable group on their periphery are ...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm010138p

    authors: Percec V,Bera TK

    更新日期:2002-01-01 00:00:00

  • Giant bent-core mesogens in the thread forming process of marine mussels.

    abstract::In marine mussels (Mytilus), byssal threads are made in minutes from prefabricated smectic polymer liquid crystals by a process resembling reaction injection molding. The mesogens in these arrays are known to be natural block copolymers with rodlike collagen cores. Using atomic force microscopy, it was shown that thes...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm049899t

    authors: Hassenkam T,Gutsmann T,Hansma P,Sagert J,Waite JH

    更新日期:2004-07-01 00:00:00

  • Cofibrillization of Pathogenic and Functional Amyloid Proteins with Gold Nanoparticles against Amyloidogenesis.

    abstract::Biomimetic nanocomposites and scaffolds hold the key to a wide range of biomedical applications. Here we show, for the first time, a facile scheme of cofibrillizing pathogenic and functional amyloid fibrils via gold nanoparticles (AuNPs) and their applications against amyloidogenesis. This scheme was realized by β-she...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/acs.biomac.7b01359

    authors: Javed I,Sun Y,Adamcik J,Wang B,Kakinen A,Pilkington EH,Ding F,Mezzenga R,Davis TP,Ke PC

    更新日期:2017-12-11 00:00:00

  • Culture of Tumorigenic Cells on Protein Fibers Reveals Metastatic Cell Behaviors.

    abstract::Tumorigenic cell behaviors can be suppressed or enhanced by their physicochemical environment. As a first step toward developing materials that allow tumorigenic behaviors to be observed and manipulated, we cultured related MCF10 breast cell lines on fibers composed of the Drosophila protein Ultrabithorax (Ubx). These...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/acs.biomac.6b01311

    authors: Hsiao HC,Santos A,Howell DW,Patterson JL,Fuchs-Young RS,Bondos SE

    更新日期:2016-11-14 00:00:00

  • Noninvasive in vivo monitoring of the biofate of 195 kDa poly(vinyl alcohol) by multispectral fluorescence imaging.

    abstract::A comprehensive knowledge of the in vivo fate of polymers is essential for their potential application in humans. In this study, the body distribution, accumulation, and elimination processes of intraperitoneally (ip) administered poly(vinyl alcohol) (PVA) in mice were investigated in detail. Two derivatives of PVA (1...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm200899h

    authors: Schädlich A,Naolou T,Amado E,Schöps R,Kressler J,Mäder K

    更新日期:2011-10-10 00:00:00

  • Interplay between covalent and physical interactions within environment sensitive hydrogels.

    abstract::A systematic study is carried out to understand how physical and covalent crosslinks affect the mechanical properties of an eight-arm poly(ethyleneglycol)-based hydrogel. Heparin and heparin-binding peptide are used as a physical crosslinker, and an enzymatically cleavable peptide with a cysteine on each end serves as...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm801270k

    authors: Jeong KJ,Panitch A

    更新日期:2009-05-11 00:00:00

  • Fiber Alignment and Liquid Crystal Orientation of Cellulose Nanocrystals in the Electrospun Nanofibrous Mats.

    abstract::Sulfate cellulose nanocrystal (CNC) dispersions always present specific self-assembled cholesteric mesophases which is easily affected by the inherent properties of particle size, surface charge, and repulsion or affinity interaction, and external field force generated from ionic potential of added electrolytes, magne...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/acs.biomac.7b00927

    authors: Song W,Liu D,Prempeh N,Song R

    更新日期:2017-10-09 00:00:00

  • The Influence of Biomaterials on Cytokine Production in 3D Cultures.

    abstract::As a result of improved relevance to in vivo physiology, in vitro studies are increasingly performed in diverse, three-dimensional (3D) biomaterials. However, material-cell type pairing effects on cytokine availability remain unclear. We cultured five cell types in agarose, alginate, collagen, Matrigel, or RGD-functio...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/acs.biomac.6b01469

    authors: Regier MC,Montanez-Sauri SI,Schwartz MP,Murphy WL,Beebe DJ,Sung KE

    更新日期:2017-03-13 00:00:00

  • Sequential Thiol-Ene and Tetrazine Click Reactions for the Polymerization and Functionalization of Hydrogel Microparticles.

    abstract::Click chemistry is a versatile tool for the synthesis and functionalization of polymeric biomaterials. Here, we describe a versatile new strategy for producing bioactive, protein-functionalized poly(ethylene glycol) (PEG) hydrogel microparticles that is based on sequential thiol-ene and tetrazine click reactions. Brie...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/acs.biomac.6b00990

    authors: Jivan F,Yegappan R,Pearce H,Carrow JK,McShane M,Gaharwar AK,Alge DL

    更新日期:2016-11-14 00:00:00

  • Triblock Copolymer Nanovesicles for pH-Responsive Targeted Delivery and Controlled Release of siRNA to Cancer Cells.

    abstract::New pH-responsive polymersomes for active anticancer oligonucleotide delivery were prepared from triblock copolymers. The delivery systems were formed by two terminal hydrophilic blocks, PEG and polyglycerolmethacrylate (poly-GMA), and a central weakly basic block, polyimidazole-hexyl methacrylate (poly-ImHeMA), which...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/acs.biomac.5b00286

    authors: Gallon E,Matini T,Sasso L,Mantovani G,Armiñan de Benito A,Sanchis J,Caliceti P,Alexander C,Vicent MJ,Salmaso S

    更新日期:2015-07-13 00:00:00

  • Effects of polymer structure on the inhibition of cholera toxin by linear polypeptide-based glycopolymers.

    abstract::A variety of important biological events are mediated by the multivalent interaction between relevant oligosaccharides and multiple saccharide receptors on lectins, toxins, and cell surfaces; a variety of glycopolymeric materials have therefore been investigated in studies aimed at manipulating these events. The synth...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm050672n

    authors: Polizzotti BD,Kiick KL

    更新日期:2006-02-01 00:00:00

  • Sequential Self-Assembly Using Tannic Acid and Phenylboronic Acid-Modified Copolymers for Potential Protein Delivery.

    abstract::Tannic acid (TA) can form stable complexes with proteins, attracting significant attention as protein delivery systems. However, its systemic application has been limited due to nonspecific interaction. Here, we report a simple technique to prepare systemically applicable protein delivery systems using sequential self...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/acs.biomac.0c00903

    authors: Honda Y,Nomoto T,Matsui M,Takemoto H,Kaihara Y,Miura Y,Nishiyama N

    更新日期:2020-09-14 00:00:00

  • Solid-solid interface adsorption of proteins and enzymes in nanophase-separated amphiphilic conetworks.

    abstract::Amphiphilic polymer conetworks (APCNs) are materials with a very large interface between their hydrophilic and hydrophobic phases due to their nanophase-separated morphologies. Proteins were found to enrich in APCNs by up to 2 orders of magnitude when incubated in aqueous protein solutions, raising the question of the...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm1015877

    authors: Dech S,Cramer T,Ladisch R,Bruns N,Tiller JC

    更新日期:2011-05-09 00:00:00

  • Polymersome nanoreactors for enzymatic ring-opening polymerization.

    abstract::Polystyrene-polyisocyanopeptide (PS-PIAT) polymersomes containing CALB in two different locations, one in the aqueous inner compartment and one in the bilayer, were investigated for enzymatic ring-opening polymerization of lactones in water. It is shown that the monomers 8-octanolactone and dodecalactone yield oligome...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm7005938

    authors: Nallani M,de Hoog HP,Cornelissen JJ,Palmans AR,van Hest JC,Nolte RJ

    更新日期:2007-12-01 00:00:00

  • Tunable Conformation-Dependent Engineered Protein·Gold Nanoparticle Nanocomposites.

    abstract::We demonstrate the fabrication of protein·gold nanoparticle (AuNP) nanocomposites in situ, leading to distinct assemblies dependent upon protein secondary structure. In the presence of pentameric coiled-coil proteins C and Q, which contain histidine tags and have helicities of 54 and 65%, respectively, templation of A...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/acs.biomac.5b00098

    authors: Hume J,Chen R,Jacquet R,Yang M,Montclare JK

    更新日期:2015-06-08 00:00:00

  • Curcumin encapsulation in submicrometer spray-dried chitosan/Tween 20 particles.

    abstract::Optimal curcumin delivery for medicinal applications requires a drug delivery system that both solubilizes curcumin and prevents degradation. To achieve this, curcumin has been encapsulated in submicrometer chitosan/Tween 20 particles via a benchtop spray-drying process. Spray-drying parameters have been optimized usi...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm300564v

    authors: O'Toole MG,Henderson RM,Soucy PA,Fasciotto BH,Hoblitzell PJ,Keynton RS,Ehringer WD,Gobin AS

    更新日期:2012-08-13 00:00:00

  • Synthesis and characterization of glycopolymer-polypeptide triblock copolymers.

    abstract::Glycopolymer-polypeptide triblock copolymers of the structure, poly(l-alanine)-b-poly(2-acryloyloxyethyl-lactoside)-b-poly(l-alanine) (AGA), have been synthesized by sequential atom transfer radical polymerization (ATRP) and ring-opening polymerization (ROP). Controlled free radical polymerization of 2-O-acryloyl-oxye...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm0343500

    authors: Dong CM,Sun XL,Faucher KM,Apkarian RP,Chaikof EL

    更新日期:2004-01-01 00:00:00

  • Temperature-induced conformational transition of a model elastin-like peptide GVG(VPGVG)(3) in water.

    abstract::The conformation of a single elastin-like peptide GVG(VPGVG)3 in liquid water is studied by computer simulations in the temperature interval between 280 and 440 K. Two main conformational states of the peptide can be distinguished: a rigid conformational state, dominating at low temperatures, and a flexible conformati...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm070233j

    authors: Krukau A,Brovchenko I,Geiger A

    更新日期:2007-07-01 00:00:00