Click-Chemistry Approach toward Antibacterial and Degradable Hybrid Hydrogels Based on Octa-Betaine Ester Polyhedral Oligomeric Silsesquioxane.

Abstract:

:An efficient process for the synthesis of degradable hydrogels containing octa-betaine ester polyhedral oligomeric silsesquioxane (POSS) through efficient thiol-ene and Menschutkin click reactions was developed. The hydrogels exhibited a yield strength of 0.36 MPa and a compressive modulus of 4.38 MPa and displayed excellent flexibility as well as torsion resistance. Antibacterial efficacy of hydrogels (and degradation products) was evaluated using Escherichia coli (Gram-negative) and Staphylococcus aureus (Gram-positive). Efficacy was found to increase with the concentration of cetyl chloroacetate (CCA) in the hydrogel network, reaching 93% and 99% for Escherichia coli and Staphylococcus aureus, respectively. Degradation of hydrogels was observed in weak alkali conditions (pH = 8) and at physiological conditions (pH = 7.4). The degradation time of the hydrogels could be finely tuned by variation of the CCA content in the hydrogel and environmental stimulus. The tunable degradation behavior under physiological conditions combined with high antibacterial efficacy could render the presented materials interesting for tissue engineering applications.

journal_name

Biomacromolecules

journal_title

Biomacromolecules

authors

Han J,Chen Q,Shen Y,Liu Z,Hao X,Zhong M,Zhao Z,Bockstaller MR

doi

10.1021/acs.biomac.0c00530

subject

Has Abstract

pub_date

2020-09-14 00:00:00

pages

3512-3522

issue

9

eissn

1525-7797

issn

1526-4602

journal_volume

21

pub_type

杂志文章
  • Identification of a marine benthic P(3HB)-degrading bacterium isolate and characterization of its P(3HB) depolymerase.

    abstract::A poly[(R)-3-hydroxybutyrate] (P(3HB))-degrading marine bacterium (strain NK-1, JCM10458) was isolated from the Pacific Ocean deep-sea floor (1165 m in depth) in Japan. The organism was a motile and Gram negative, aerobic, and rod-shaped bacterium, and its DNA had a guanine-plus-cytosine content of 57.7 mol%. On the b...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm9900186

    authors: Kasuya K,Mitomo H,Nakahara M,Akiba A,Kudo T,Doi Y

    更新日期:2000-07-01 00:00:00

  • Coating electrospun collagen and gelatin fibers with perlecan domain I for increased growth factor binding.

    abstract::Electrospun natural polymer membranes were fabricated from collagen or gelatin coated with a bioactive recombinant fragment of perlecan, a natural heparan sulfate proteoglycan. The electrospinning process allowed the facile processing of a three-dimensional, porous fibril (2-6 microm in diameter) matrix suitable for t...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm061003s

    authors: Casper CL,Yang W,Farach-Carson MC,Rabolt JF

    更新日期:2007-04-01 00:00:00

  • Single-walled carbon nanotube as a unique scaffold for the multivalent display of sugars.

    abstract::Single-walled carbon nanotube (SWNT) is a pseudo-one-dimensional nanostructure capable of carrying/displaying a large number of bioactive molecules and species in aqueous solution. In this work, a series of dendritic beta-D-galactopyranosides and alpha-D-mannopyranosides with a terminal amino group were synthesized an...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm800395e

    authors: Gu L,Luo PG,Wang H,Meziani MJ,Lin Y,Veca LM,Cao L,Lu F,Wang X,Quinn RA,Wang W,Zhang P,Lacher S,Sun YP

    更新日期:2008-09-01 00:00:00

  • Diffusion of 1-ethyl-3-methyl-imidazolium acetate in glucose, cellobiose, and cellulose solutions.

    abstract::Solutions of glucose, cellobiose and microcrystalline cellulose in the ionic liquid 1-ethyl-3-methyl-imidazolium ([C2mim][OAc]) have been examined using pulsed-field gradient (1)H NMR. Diffusion coefficients of the cation and anion across the temperature range 20-70 °C have been determined for a range of concentration...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm401652c

    authors: Ries ME,Radhi A,Keating AS,Parker O,Budtova T

    更新日期:2014-02-10 00:00:00

  • Pressure cell assisted solution characterization of polysaccharides. 2. Locust bean gum and tara gum.

    abstract::Following the work carried out on guar gum in our first paper of a series, the "pressure cell" solubilization method was applied to two other less highly substituted galactomannans: locust bean gum (LBG) and tara gum. True molecular solution of the polymers was achieved using appropriate temperature, time, and pressur...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm025517c

    authors: Picout DR,Ross-Murphy SB,Jumel K,Harding SE

    更新日期:2002-07-01 00:00:00

  • Environmentally Benign Nanoantibiotics with a Built-in Deactivation Switch Responsive to Natural Habitats.

    abstract::The massive use of antibiotics in healthcare and agriculture has led to their artificial accumulation in natural habitats, which risks the structure and function of the microbial communities in ecosystems, threatens food and water security, and accelerates the development of resistome. Ideally, antibiotics should rema...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/acs.biomac.0c00163

    authors: Zheng W,Anzaldua M,Arora A,Jiang Y,McIntyre K,Doerfert M,Winter T,Mishra A,Ma H,Liang H

    更新日期:2020-06-08 00:00:00

  • Biodistribution of Filamentous Plant Virus Nanoparticles: Pepino Mosaic Virus versus Potato Virus X.

    abstract::Nanoparticles with high aspect ratios have favorable attributes for drug delivery and bioimaging applications based on their enhanced tissue penetration and tumor homing properties. Here, we investigated a novel filamentous viral nanoparticle (VNP) based on the Pepino mosaic virus (PepMV), a relative of the establishe...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/acs.biomac.8b01365

    authors: Le DHT,Méndez-López E,Wang C,Commandeur U,Aranda MA,Steinmetz NF

    更新日期:2019-01-14 00:00:00

  • De novo designed protein transduction domain mimics from simple synthetic polymers.

    abstract::Protein transduction domains (PTDs) that readily transverse cellular membranes are of great interest and are attractive tools for the intracellular delivery of bioactive molecules. Learning to program synthetic polymers and oligomers with the appropriate chemical information to capture adequately the biological activi...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm200694u

    authors: Tezgel AÖ,Telfer JC,Tew GN

    更新日期:2011-08-08 00:00:00

  • Kinetic Pathway of 3-Helix Micelle Formation.

    abstract::A subtle but highly pertinent factor in the self-assembly of hierarchical nanostructures is the kinetic landscape. Self-assembly of a hierarchical multicomponent system requires the intricate balance of noncovalent interactions on a similar energy scale that can result in several self-assembly processes occurring at d...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/acs.biomac.6b01831

    authors: Ang J,Jung BT,Dong H,Xu T

    更新日期:2017-03-13 00:00:00

  • Macromolecule-induced assembly of coiled-coils in alternating multiblock polymers.

    abstract::The bioconjugation of proteins and peptides with synthetic polymers is a promising method for tailoring the chemical, biological, and physical properties of both the polymeric and protein-based components. Here, we describe macromolecular assemblies of polyethylene glycol-coiled-coil alternating multiblock polymers gu...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm900474k

    authors: Sahin E,Kiick KL

    更新日期:2009-10-12 00:00:00

  • Supramolecular GAG-like Self-Assembled Glycopeptide Nanofibers Induce Chondrogenesis and Cartilage Regeneration.

    abstract::Glycosaminoglycans (GAGs) and glycoproteins are vital components of the extracellular matrix, directing cell proliferation, differentiation, and migration and tissue homeostasis. Here, we demonstrate supramolecular GAG-like glycopeptide nanofibers mimicking bioactive functions of natural hyaluronic acid molecules. Sel...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/acs.biomac.5b01669

    authors: Ustun Yaylaci S,Sardan Ekiz M,Arslan E,Can N,Kilic E,Ozkan H,Orujalipoor I,Ide S,Tekinay AB,Guler MO

    更新日期:2016-02-08 00:00:00

  • Size- and coating-dependent uptake of polymer-coated gold nanoparticles in primary human dermal microvascular endothelial cells.

    abstract::A library-orientated approach is used to gain understanding of the interactions of well-defined nanoparticles with primary human endothelial cells, which are a key component of the vasculature. Fifteen sequentially modified gold nanoparticles (AuNPs) based on three different core sizes (18, 35, 65 nm) and five polymer...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm300248u

    authors: Freese C,Gibson MI,Klok HA,Unger RE,Kirkpatrick CJ

    更新日期:2012-05-14 00:00:00

  • Measurement of the molecular weight distribution of debranched starch.

    abstract::Combining molecular weight distribution (MWD) data for linear chains of debranched starch from capillary electrophoresis and from size exclusion chromatography (SEC) with detection by differential refractive index and by multi-angle laser light scattering has enabled Mark-Houwink parameters to be determined for linear...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm050041t

    authors: Castro JV,Ward RM,Gilbert RG,Fitzgerald MA

    更新日期:2005-07-01 00:00:00

  • Solubility of Softwood Hemicelluloses.

    abstract::It is demonstrated that the molecular solubility of softwood hemicelluloses is significantly influenced by pretreatment of the fibers, extraction, and downstream processing. To quantify these effects, four hemicellulose samples were extracted from different thermomechanical pulps of Norway spruce. The molecular solubi...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/acs.biomac.8b00088

    authors: Kishani S,Vilaplana F,Xu W,Xu C,Wågberg L

    更新日期:2018-04-09 00:00:00

  • Encapsulation of Doxorubicin in Furcellaran/Chitosan Nanocapsules by Layer-by-Layer Technique for Selectively Controlled Drug Delivery.

    abstract::Minimization of drug side effects is a hallmark of advanced targeted therapy. Herein we describe the synthesis of polysaccharide-based nanocapsules prepared from furcellaran and chitosan via layer-by-layer deposition using electrostatic interaction. Using doxorubicin as a model drug, prepared nanocapsules showed excel...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/acs.biomac.9b01175

    authors: Milosavljevic V,Jamroz E,Gagic M,Haddad Y,Michalkova H,Balkova R,Tesarova B,Moulick A,Heger Z,Richtera L,Kopel P,Adam V

    更新日期:2020-02-10 00:00:00

  • Novel injectable pH and temperature sensitive block copolymer hydrogel.

    abstract::A novel pH and temperature sensitive block copolymer was prepared by adding pH sensitive moiety to temperature sensitive block copolymer. This block copolymer solution showed a reversible sol-gel transition by a small pH change in the range of pH 7.4-8.0 and also by the temperature change in the region of body tempera...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm050521k

    authors: Shim WS,Yoo JS,Bae YH,Lee DS

    更新日期:2005-11-01 00:00:00

  • Altering peptide fibrillization by polymer conjugation.

    abstract::A strategy is presented that exploits the ability of synthetic polymers of different nature to disturb the strong self-assembly capabilities of amyloid based β-sheet forming peptides. Following a convergent approach, the peptides of interest were synthesized via solid-phase peptide synthesis (SPPS) and the polymers vi...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm3007117

    authors: Dehn S,Castelletto V,Hamley IW,Perrier S

    更新日期:2012-09-10 00:00:00

  • Endothelial Cell Migration on Poly(ε-caprolactone) Nanofibers Coated with a Nanohybrid Shish-Kebab Structure Mimicking Collagen Fibrils.

    abstract::Regulating cell migration dynamics is of significance in tissue engineering and regenerative medicine. A 3D scaffold was created to provide various topographies based on a poly(ε-caprolactone) (PCL) self-induced nanohybrid shish-kebab structure, which consisted of aligned PCL nanofibers and spaced PCL crystal lamellae...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/acs.biomac.9b01638

    authors: Guo X,Wang X,Li X,Jiang YC,Han S,Ma L,Guo H,Wang Z,Li Q

    更新日期:2020-03-09 00:00:00

  • Biocompatible micro-gel particles from cross-linked casein micelles.

    abstract::The stability of internally cross-linked casein micelles against disruption by urea (which disrupts hydrogen bonds and hydrophobic interactions) and trisodium citrate (which sequesters micellar calcium phosphate) was investigated. Addition of urea (0-6 mol L-1) and/or citrate (0-50 mmol L-1) progressively reduced the ...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm061070m

    authors: Huppertz T,Smiddy MA,de Kruif CG

    更新日期:2007-04-01 00:00:00

  • Synthesis and biological evaluation of a polysialic acid-based hydrogel as enzymatically degradable scaffold material for tissue engineering.

    abstract::Restorative medicine has a constant need for improved scaffold materials. Degradable biopolymers often suffer from uncontrolled chemical or enzymatic hydrolysis by the host. The need for a second surgery on the other hand is a major drawback for nondegradable scaffold materials. In this paper we report the design and ...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm800327s

    authors: Berski S,van Bergeijk J,Schwarzer D,Stark Y,Kasper C,Scheper T,Grothe C,Gerardy-Schahn R,Kirschning A,Dräger G

    更新日期:2008-09-01 00:00:00

  • An approach to modulate degradation and mesenchymal stem cell behavior in poly(ethylene glycol) networks.

    abstract::A simple, sequential approach for creation of hydrolytically degradable poly(ethylene glycol) (PEG) hydrogels has been developed and characterized. The chemistry involves an initial step growth polymerization reaction between PEG-diacrylate and dithiothreitol (DTT) to form acrylate-terminated (-PEG-DTT-)n PEG chains, ...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm701179s

    authors: Hudalla GA,Eng TS,Murphy WL

    更新日期:2008-03-01 00:00:00

  • Biodegradable and pH-sensitive hydrogels for cell encapsulation and controlled drug release.

    abstract::Hydrogels with pH-sensitive poly(acrylic acid) (PAAc) chains and biodegradable acryloyl-poly(-caprolactone)-2-hydroxylethyl methacrylate (AC-PCL-HEMA) chains were designed and synthesized. The morphology of hydrogel was observed by scanning electron microscopy. The degradation of the hydrogel in the presence of Pseudo...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm7010328

    authors: Wu DQ,Sun YX,Xu XD,Cheng SX,Zhang XZ,Zhuo RX

    更新日期:2008-04-01 00:00:00

  • Enhanced bioactivity of internally functionalized cationic dendrimers with PEG cores.

    abstract::Hybrid dendritic-linear block copolymers based on a 4-arm poly(ethylene glycol) (PEG) core were synthesized using an accelerated AB2/CD2 dendritic growth approach through orthogonal amine/epoxy and thiol-yne chemistries. The biological activity of these 4-arm and the corresponding 2-arm hybrid dendrimers revealed an e...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm301384y

    authors: Albertazzi L,Mickler FM,Pavan GM,Salomone F,Bardi G,Panniello M,Amir E,Kang T,Killops KL,Bräuchle C,Amir RJ,Hawker CJ

    更新日期:2012-12-10 00:00:00

  • PM-IRRAS investigation of the interaction of serum albumin and fibrinogen with a biomedical-grade stainless steel 316LVM surface.

    abstract::Polarization modulation infrared reflection absorption spectroscopy (PM-IRRAS) was applied to investigate the interaction of bovine serum albumin (BSA) and fibrinogen with a biomedical-grade 316LVM stainless steel surface, in terms of the adsorption thermodynamics and adsorption-induced secondary structure changes of ...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm070289d

    authors: Desroches MJ,Chaudhary N,Omanovic S

    更新日期:2007-09-01 00:00:00

  • Alpha-D-glucan-based dendritic nanoparticles prepared by in vitro enzymatic chain extension of glycogen.

    abstract::The recombinant amylosucrase from Neisseria polysaccharea was used to glucosylate glycogen particles in vitro in the presence of sucrose as the glucosyl donor. The morphology and structure of the resulting insoluble products were shown to strongly depend on the initial sucrose/glycogen weight ratio. For the lower rati...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm050988v

    authors: Putaux JL,Potocki-Véronèse G,Remaud-Simeon M,Buleon A

    更新日期:2006-06-01 00:00:00

  • Polarity and motility of large polymer-actin complexes.

    abstract::The polarity of polymer-actin complexes obtained by mixing F-actin with synthetic polymers carrying positive charges such as poly(L-lysine), x,y-ionene bromide polymers, and poly(N-[3-(dimethylamino)propyl]acrylamide) (PDMAPAA-Q) have been investigated. Actin complexes formed with poly(L-lysine) and PDMAPAA-Q, which c...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm0494038

    authors: Kakugo A,Shikinaka K,Takekawa N,Sugimoto S,Osada Y,Gong JP

    更新日期:2005-03-01 00:00:00

  • Wet-spinning of regenerated silk fiber from aqueous silk fibroin solution: discussion of spinning parameters.

    abstract::Regenerated silk fibroin (RSF) fibers were obtained by extruding a concentrated aqueous silk fibroin solution into an ammonium sulfate coagulation bath. A custom-made simplified industrial-type wet-spinning device with continuous mechanical postdraw was used. The effect of dope concentration, coagulation bath, extrusi...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm900840h

    authors: Yan J,Zhou G,Knight DP,Shao Z,Chen X

    更新日期:2010-01-11 00:00:00

  • Structure-activity relationships of antibacterial and biocompatible copolymers.

    abstract::The development of polymers that are both bactericidal and biocompatible would have many applications and are currently of research interest. Following the development of strongly bactericidal copolymers of 4-vinylpyridine and poly(ethylene glycol) methyl ether methacrylate, biocompatibility assays have been completed...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm1000839

    authors: Stratton TR,Howarter JA,Allison BC,Applegate BM,Youngblood JP

    更新日期:2010-05-10 00:00:00

  • Biodegradable polymers from renewable sources: rheological characterization of hemicellulose-based hydrogels.

    abstract::Hemicellulose-based hydrogels were prepared by radical polymerization of 2-hydroxyethyl methacrylate or poly(ethylene glycol) dimethacrylate with oligomeric hydrosoluble hemicellulose modified with well-defined amounts of methacrylic functions. The polymerization reaction was carried out in water at 40 degrees C using...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm049515z

    authors: Söderqvist Lindblad M,Albertsson AC,Ranucci E,Laus M,Giani E

    更新日期:2005-03-01 00:00:00

  • Emulsifying properties of biodegradable polylactide-grafted dextran copolymers.

    abstract::Amphiphilic glycopolymers, polylactide-grafted dextran copolymers (Dex-g-PLA), were synthesized with a well-controlled architecture obtained through a three-step procedure: partial silylation of the dextran hydroxyl groups, ring-opening polymerization of D,L-lactide initiated from remaining hydroxyl groups, silylether...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm701101n

    authors: Raynaud J,Choquenet B,Marie E,Dellacherie E,Nouvel C,Six JL,Durand A

    更新日期:2008-03-01 00:00:00