Thermoresponsive Self-Immolative Polyglyoxylamides.

Abstract:

:Thermoresponsive polymers with lower critical solution temperatures (LCSTs) are of significant interest for a wide range of applications from sensors to drug delivery vehicles. However, the most widely investigated LCST polymers have nondegradable backbones, limiting their applications in vivo or in the environment. Described here are thermoresponsive polymers based on a self-immolative polyglyoxylamide (PGAM) backbone. Poly(ethyl glyoxylate) was amidated with six different alkoxyalkyl amines to afford the corresponding PGAMs, and their cloud point temperatures (Tcps) were studied in water and buffer. Selected examples with promising thermoresponsive behavior were also studied in cell culture media, and their aggregation behavior was investigated using dynamic light scattering (DLS). The Tcps were effectively tuned by varying the pendent functional groups. These polymers depolymerized end-to-end following the cleavage of end-caps from their termini. The structures and aggregation behavior of the polymers influenced their rates of depolymerization, and, in turn, the depolymerization influenced their Tcp. Cell culture experiments indicated that the polymers exhibited low toxicity to C2C12 mouse myoblast cells. This interplay between LCST and depolymerization behavior, combined with low toxicity, makes this new class of polymers of particular interest for biomedical applications.

journal_name

Biomacromolecules

journal_title

Biomacromolecules

authors

Rabiee Kenaree A,Sirianni QEA,Classen K,Gillies ER

doi

10.1021/acs.biomac.0c00899

subject

Has Abstract

pub_date

2020-09-14 00:00:00

pages

3817-3825

issue

9

eissn

1525-7797

issn

1526-4602

journal_volume

21

pub_type

杂志文章
  • 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

  • Enhanced antitumor activity of the photosensitizer meso-Tetra(N-methyl-4-pyridyl) porphine tetra tosylate through encapsulation in antibody-targeted chitosan/alginate nanoparticles.

    abstract::meso-Tetra(N-methyl-4-pyridyl) porphine tetra tosylate (TMP) is a photosensitizer that can be used in photodynamic therapy (PDT) to induce cell death through generation of reactive oxygen species in targeted tumor cells. However, TMP is highly hydrophilic, and therefore, its ability to accumulate intracellularly is li...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm301858a

    authors: Abdelghany SM,Schmid D,Deacon J,Jaworski J,Fay F,McLaughlin KM,Gormley JA,Burrows JF,Longley DB,Donnelly RF,Scott CJ

    更新日期:2013-02-11 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

  • Electric field induced assembly of vimentin microscaffolds around metallic electrodes.

    abstract::The self-assembly properties of fibrous proteins such as collagen are frequently used to form three-dimensional scaffolds. In this study we investigated the effect of nonuniform alternating and static electric-fields on the self-assembly properties of a dilute solution of vimentin. In the presence of both types of fie...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm900398n

    authors: Colbourne TR,Hill IG,Kreplak L

    更新日期:2009-07-13 00:00:00

  • Poly(ethylene glycol)-poly(ester-carbonate) block copolymers carrying PEG-peptidyl-doxorubicin pendant side chains: synthesis and evaluation as anticancer conjugates.

    abstract::Water soluble polymer anticancer conjugates can improve the pharmacokinetics of covalently bound drugs by limiting cellular uptake to the endocytic route, thus prolonging plasma circulation time and consequently facilitating tumor targeting by the enhanced permeability and retention (EPR) effect. Many of the first gen...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm049381p

    authors: Andersson L,Davies J,Duncan R,Ferruti P,Ford J,Kneller S,Mendichi R,Pasut G,Schiavon O,Summerford C,Tirk A,Veronese FM,Vincenzi V,Wu G

    更新日期:2005-03-01 00:00:00

  • Structure and Biocompatibility of Bioabsorbable Nanocomposites of Aliphatic-Aromatic Copolyester and Cellulose Nanocrystals.

    abstract::Poly(butylene adipate-co-terephthalate) (PBAT) was first chemically modified via free radical grafting with maleic anhydride (MA) and the MA-g-PBAT graft copolymer was then used as a matrix material to obtain cellulose nanocrystal (CNC)-reinforced MA-g-PBAT bionanocomposites via reactive extrusion process to accelerat...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/acs.biomac.7b00578

    authors: Kashani Rahimi S,Aeinehvand R,Kim K,Otaigbe JU

    更新日期:2017-07-10 00:00:00

  • Engineered Polymeric Micelles for Combinational Oxidation Anticancer Therapy through Concurrent HO-1 Inhibition and ROS Generation.

    abstract::Cancer cells have a large amount of ROS (reactive oxygen species) because of disturbed ROS homeostasis. Cancer cells therefore undertake redox adaptation to drive proliferation in tumor environments and even survive during anticancer treatment by upregulating endogenous antioxidants. As one of antioxidant defense syst...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/acs.biomac.8b01802

    authors: Noh J,Jung E,Lee J,Hyun H,Hong S,Lee D

    更新日期:2019-02-11 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

  • Amino acid grafted chitosan for high performance gene delivery: comparison of amino acid hydrophobicity on vector and polyplex characteristics.

    abstract::To develop a safe, effective, and biocompatible gene delivery vector, a series of hydrophobic amino acid grafted chitosan (AGC) derivatives were synthesized by carbodiimide mediated coupling reaction. Chemical characterization of AGC polymers was performed by NMR and elemental analysis. AGC polymers demonstrated excel...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm301720g

    authors: Layek B,Singh J

    更新日期:2013-02-11 00:00:00

  • X-ray structure of mercerized cellulose II at 1 a resolution.

    abstract::A revised crystal structure for mercerized cellulose based on high-resolution synchrotron X-ray data collected from ramie fibers is reported (space group P2(1), a = 8.10(3) A, b = 9.03(3) A, c = 10.31(5) A, gamma = 117.10(5) degrees; 751 reflections in 304 composite spots; theta < 21.11 degrees; lambda = 0.7208 A; LAL...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm005612q

    authors: Langan P,Nishiyama Y,Chanzy H

    更新日期:2001-07-01 00:00:00

  • Complexation models of N-(2-carboxyethyl)chitosans with copper(II) ions.

    abstract::The copper(II) complex formation equilibria of N-(2-carboxyethyl)chitosans with three different degrees of substitution (DS = 0.42, 0.92, and 1.61) were studied in aqueous solution by pH-potentiometric and UV-spectrophotometric techniques. It was demonstrated that the complexation model of CE-chitosans depends on DS: ...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm049597r

    authors: Skorik YA,Gomes CA,Podberezskaya NV,Romanenko GV,Pinto LF,Yatluk YG

    更新日期:2005-01-01 00:00:00

  • Enhancing biocompatibility of D-oligopeptide hydrogels by negative charges.

    abstract::Oligopeptide hydrogels are emerging as useful matrices for cell culture with commercial products on the market, but L-oligopeptides are labile to proteases. An obvious solution is to create D-oligopeptide hydrogels, which lack enzymatic recognition. However, D-oligopeptide matrices do not support cell growth as well a...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm301598g

    authors: Hyland LL,Twomey JD,Vogel S,Hsieh AH,Yu YB

    更新日期:2013-02-11 00:00:00

  • Design of renewable hydrogel release systems from fiberboard mill wastewater.

    abstract::A new route for the design of renewable hydrogels is presented. The soluble waste from masonite production was isolated, fractionized, and upgraded. The resulting hemicellulose rich fraction was alkenyl-functionalized and used in the preparation of covalently cross-linked hydrogels capable of sustained release of inco...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm100253e

    authors: Albertsson AC,Voepel J,Edlund U,Dahlman O,Söderqvist-Lindblad M

    更新日期:2010-05-10 00:00:00

  • Fully convergent solid phase synthesis of antifreeze glycoprotein analogues.

    abstract::The convergent solid phase synthesis of C-linked analogues of antifreeze glycoprotein (AFGP) has been achieved. In this approach, three to six carbohydrate residues are simultaneously coupled to a resin-bound polypeptide. Glycopeptides ranging from 1.6 to 3.0 kDa are easily prepared in 26-44% yield demonstrating the u...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm0155120

    authors: Eniade A,Ben RN

    更新日期:2001-07-01 00:00:00

  • Material properties and cytocompatibility of injectable MMP degradable poly(lactide ethylene oxide fumarate) hydrogel as a carrier for marrow stromal cells.

    abstract::Injectable in situ crosslinkable biomaterials seeded with multipotent progenitor cells and coupled with minimally invasive arthroscopic techniques are an attractive alternative for treating irregularly shaped osteochondral defects. An in situ crosslinkable poly(lactide-co-ethylene oxide-co-fumarate) (PLEOF) macromer h...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm060671a

    authors: He X,Jabbari E

    更新日期:2007-03-01 00:00:00

  • Synthesis and self-assembly of RGD-functionalized PEO-PB amphiphiles.

    abstract::Amphiphilic block copolymer self-assembly provides a versatile means to prepare nanoscale micelles in solution. The utilization of these structures as targeted drug delivery vehicles has motivated efforts to prepare bioactive ligand-functionalized polymer micelles. The impact of ligand conjugation on micelle morpholog...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm900149b

    authors: Zupancich JA,Bates FS,Hillmyer MA

    更新日期:2009-06-08 00:00:00

  • Polymersomes from dual responsive block copolymers: drug encapsulation by heating and acid-triggered release.

    abstract::A series of well-defined thermoresponsive diblock copolymers (PEO45-b-PtNEAn, n=22, 44, 63, 91, 172) were prepared by the atom transfer radical polymerization of trans-N-(2-ethoxy-1,3-dioxan-5-yl) acrylamide (tNEA) using a poly(ethylene oxide) (PEO45) macroinitiator. All copolymers are water-soluble at low temperature...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm400180n

    authors: Qiao ZY,Ji R,Huang XN,Du FS,Zhang R,Liang DH,Li ZC

    更新日期:2013-05-13 00:00:00

  • Modular Polymer Antigens To Optimize Immunity.

    abstract::Subunit vaccines can have excellent safety profiles, but their ability to give rise to robust immune responses is often compromised. For glycan-based vaccines, insufficient understanding of B and T cell epitope combinations that yield optimal immune activation hinders optimization. To determine which antigen features ...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/acs.biomac.9b01049

    authors: Bennett NR,Jarvis CM,Alam MM,Zwick DB,Olson JM,Nguyen HV,Johnson JA,Cook ME,Kiessling LL

    更新日期:2019-12-09 00:00:00

  • Dual Thermosensitive Hydrogels Assembled from the Conserved C-Terminal Domain of Spider Dragline Silk.

    abstract::Stimuli-responsive hydrogels have great potentials in biomedical and biotechnological applications. Due to the advantages of precise control over molecular weight and being biodegradable, protein-based hydrogels and their applications have been extensively studied. However, protein hydrogels with dual thermosensitive ...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/acs.biomac.5b01231

    authors: Qian ZG,Zhou ML,Song WW,Xia XX

    更新日期:2015-11-09 00:00:00

  • PEG-modified carbon nanotubes in biomedicine: current status and challenges ahead.

    abstract::Since their discovery at the end of the previous millennium, carbon nanotubes (CNTs) have been the object of thousands of papers describing their applications in fields ranging from physics to electronics, photonics, chemistry, biology, and medicine. The development of chemical approaches to modify their graphitic sid...

    journal_title:Biomacromolecules

    pub_type: 杂志文章,评审

    doi:10.1021/bm201020h

    authors: Bottini M,Rosato N,Bottini N

    更新日期:2011-10-10 00:00:00

  • Synthesis, characterization, and in vitro degradation of a biodegradable photo-cross-linked film from liquid poly(epsilon-caprolactone-co-lactide-co-glycolide) diacrylate.

    abstract::There has been little study on the effect of composition or molecular weight on the biodegradation rate of photo-cross-linked biodegradable aliphatic polyesters though such information is important for tissue engineering scaffolds. We have synthesized a new series of photopolymerizable linear poly(epsilon-caprolactone...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm060766c

    authors: Shen JY,Pan XY,Lim CH,Chan-Park MB,Zhu X,Beuerman RW

    更新日期:2007-02-01 00:00:00

  • Langmuir and Langmuir-Blodgett films of organophosphorus acid anhydrolase.

    abstract::In this paper, we describe the preparation and characterization of Langmuir and Langmuir-Blodgett (LB) monolayers of the enzyme organophosphorus acid anhydrolase (OPAA). Langmuir films of OPAA were characterized on different subphases, such as phosphate, ammonium carbonate, and bis-tris-propane buffers. Monolayers at ...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm025775+

    authors: Mello SV,Mabrouki M,Cao X,Leblanc RM,Cheng TC,DeFrank JJ

    更新日期:2003-07-01 00:00:00

  • Facile synthetic procedure for omega, primary amine functionalization directly in water for subsequent fluorescent labeling and potential bioconjugation of RAFT-synthesized (co)polymers.

    abstract::We describe a facile method to amine functionalize and subsequently fluorescently label polymethacrylamides synthesized via reversible addition-fragmentation chain transfer (RAFT) polymerization. RAFT-generated poly(N-(2-hydroxypropyl) methacrylamide-b-N-[3-(dimethylamino)propyl] methacrylamide) (poly(HPMA-b-DMAPMA)),...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm700514q

    authors: York AW,Scales CW,Huang F,McCormick CL

    更新日期:2007-08-01 00:00:00

  • Photoluminescence Control of Cellulose via Surface Functionalization Using Oxidative Polymerization.

    abstract::Control of the photoluminescence properties of cellulose is conducted by introduction of conducting polymers including fluorene (F) and 3-hexylthiophene (3HT) on cellulose surface through FeCl3 oxidative polymerization. The UV-vis absorption peak of cellulose grafted with the 3-hexylthiophene and fluorene copolymer wa...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/acs.biomac.7b01067

    authors: Phung Hai TA,Sugimoto R

    更新日期:2017-12-11 00:00:00

  • Hemopressin forms self-assembled fibrillar nanostructures under physiologically relevant conditions.

    abstract::The nonapeptide hemopressin, which is derived from the α chain of hemoglobin, has been reported to exhibit inverse agonist activity against the CB1 receptor. Administration of this peptide in animal models led to decreased food intake and elicited hypotensive and antinociceptive effects. On the basis of hemopressin's ...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm201836f

    authors: Bomar MG,Samuelsson SJ,Kibler P,Kodukula K,Galande AK

    更新日期:2012-03-12 00:00:00

  • In Situ Synthesis of Magnetic Field-Responsive Hemicellulose Hydrogels for Drug Delivery.

    abstract::A one-pot synthetic methodology for fabricating stimuli-responsive hemicellulose-based hydrogels was developed that consists of the in situ formation of magnetic iron oxide (Fe3O4) nanoparticles during the covalent cross-linking of O-acetyl-galactoglucomannan (AcGGM). The Fe3O4 nanoparticle content controlled the ther...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/acs.biomac.5b00801

    authors: Zhao W,Odelius K,Edlund U,Zhao C,Albertsson AC

    更新日期:2015-08-10 00:00:00

  • Differentiation of osteoblasts on pectin-coated titanium.

    abstract::The gold standard for implant metals is titanium, and coatings such as collagen-I, RGD-peptide, chondroitin sulfate, and calcium phosphate have been used to modify its biocompatibility. We investigated how titanium coated with pectins, adaptable bioactive plant polysaccharides with anti-inflammatory effects, supports ...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm800356b

    authors: Kokkonen H,Cassinelli C,Verhoef R,Morra M,Schols HA,Tuukkanen J

    更新日期:2008-09-01 00:00:00

  • Transiently Responsive Block Copolymer Micelles Based on N-(2-Hydroxypropyl)methacrylamide Engineered with Hydrolyzable Ethylcarbonate Side Chains.

    abstract::The lack of selectivity and low solubility of many chemotherapeutics impels the development of different biocompatible nanosized drug carriers. Amphiphilic block copolymers, composed of a hydrophilic and hydrophobic domain, show great potential because of their small size, large solubilizing power and loading capacity...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/acs.biomac.5b01252

    authors: Kasmi S,Louage B,Nuhn L,Van Driessche A,Van Deun J,Karalic I,Risseeuw M,Van Calenbergh S,Hoogenboom R,De Rycke R,De Wever O,Hennink WE,De Geest BG

    更新日期:2016-01-11 00:00:00

  • Polyelectrolyte complexes stabilize and controllably release vascular endothelial growth factor.

    abstract::Angiogenesis has long been a desired therapeutic approach to improve clinical outcomes of conditions typified by ischemia. Vascular endothelial growth factor (VEGF) has demonstrated the ability to generate new blood vessels in vivo, but trials using intravenous delivery have not yet produced clinical success. Localize...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm061211k

    authors: Huang M,Vitharana SN,Peek LJ,Coop T,Berkland C

    更新日期:2007-05-01 00:00:00

  • Poly(Ethylene Glycol) Interacts with Hyaluronan in Aqueous Media.

    abstract::We report here the first evidence for the interaction of poly(ethylene glycol) (PEG) with hyaluronan (HA) in aqueous solutions. PEG-HA complexes (Kapp = 45,000 ± 8000 M-1) contained about 3.3 ± 0.1 of ethylene glycol units per disaccharide of HA. The carboxyl of the D-glucuronic acid and the amide of the N-acetyl-D-gl...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/acs.biomac.0c01504

    authors: Le-Deygen IM,Musatova OE,Orlov VN,Melik-Nubarov NS,Grozdova ID

    更新日期:2020-12-16 00:00:00