Abstract:
:A new, convenient pathway is developed to synthesize highly hydrolytically labile poly(ortho ester amide) (POEA) copolymers that overcomes some of the major weaknesses of the traditional methods of synthesizing poly(ortho esters) and their derivatives. A diamine monomer containing a built-in, stabilized ortho ester group was synthesized and was used for polycondensation with diacid esters, giving rise to a series of POEA copolymers with unique stimuli-responsive properties. The POEA undergoes temperature-responsive, reversible sol-gel phase transition in water. Phase diagrams of the POEA/H(2)O mixture reveal the concentration-dependent existence of different phases, including hydrogel and opaque or clear solution. Such behavior may be attributed to the temperature-dependent hydrogen-bonding involving the amide groups in the POEA backbone and hydrophobic interactions between POEA chains, and it is tunable by selecting diacid monomers with different chemical structures. The kinetics of POEA mass loss in physiological aqueous buffers and release of a model macromolecular drug, fluorescently labeled dextran, are nearly zero-order, suggesting predominantly surface-restricted polymer erosion. The rates of polymer erosion and drug release are much faster at pH 5.0 than pH 7.4. No cytotoxicity was found for the polymer extracts and the polymer degradation products at concentrations as high as 1 mg/mL. The normal morphology of fibroblasts cultured directly in contact with POEA films was not altered. These novel acid-labile temperature-responsive POEA copolymers may be potentially useful for a wide range of biomedical applications such as minimal invasive delivery of controlled-release drug formulations that respond to biological temperature and acidic-pH environments in cells and tissues.
journal_name
Biomacromoleculesjournal_title
Biomacromoleculesauthors
Tang R,Palumbo RN,Ji W,Wang Cdoi
10.1021/bm9000475subject
Has Abstractpub_date
2009-04-13 00:00:00pages
722-7issue
4eissn
1525-7797issn
1526-4602journal_volume
10pub_type
杂志文章abstract::Disulfide bonds stabilize the tertiary- and quaternary structure of proteins. In addition, they can be used to engineer redox-sensitive (bio)materials and drug-delivery systems. Many of these applications require control of the stability of the disulfide bond. It has recently been shown that the charged microenvironme...
journal_title:Biomacromolecules
pub_type: 杂志文章
doi:10.1021/bm400501c
更新日期:2013-07-08 00:00:00
abstract::Several alternatives to the conventional alginate beads formulation were studied for encapsulation of invertase. Pectin was added to the alginate/enzyme solution while trehalose and β-cyclodextrin were added to the calcium gelation media. The effect of composition changes, freezing, drying methods (freeze, vacuum, or ...
journal_title:Biomacromolecules
pub_type: 杂志文章
doi:10.1021/bm2009075
更新日期:2011-09-12 00:00:00
abstract::A multiple targeted drug carrying bilayer membrane for preventing an abdominal adhesion is prepared by electrospinning. Two bioactive drugs were successfully incorporated into this bilayer membrane and can be independently released from nanofibrous scaffolds without losing structural integrity and functionality of the...
journal_title:Biomacromolecules
pub_type: 杂志文章
doi:10.1021/bm301997e
更新日期:2013-04-08 00:00:00
abstract::Cancer immunotherapy can be augmented with toll-like receptor agonist (TLRa) adjuvants, which interact with immune cells to elicit potent immune activation. Despite their potential, use of many TLRa compounds has been limited clinically due to their extreme potency and lack of pharmacokinetic control, causing systemic...
journal_title:Biomacromolecules
pub_type: 杂志文章
doi:10.1021/acs.biomac.0c00812
更新日期:2020-09-14 00:00:00
abstract::This work reports on the effect of CO2 at subcritical conditions and the gaseous state on the telechelic poly(epsilon-caprolactone) polymers. The tested polymers are semi-crystalline in nature and thus the effect of functional groups and their overall contribution to foaming and formation of microstructures with open-...
journal_title:Biomacromolecules
pub_type: 杂志文章
doi:10.1021/bm050223n
更新日期:2005-09-01 00:00:00
abstract::A new family of cationic dendron-bearing lipids (CDLs) with poly(amidoamine) dendrons of first to third generation (named as A1, A2, and A3, respectively) was synthesized through a synthesis approach that permits facile variation of chemical structures. All CDLs could effectively bind small interfering RNA (siRNA) to ...
journal_title:Biomacromolecules
pub_type: 杂志文章
doi:10.1021/bm4011563
更新日期:2013-12-09 00:00:00
abstract::Recombinant Escherichia coli strains harboring a plasmid containing a novel artificial polyhydroxyalkanoate (PHA) operon consisting of the Aeromonas PHA biosynthesis related genes and Ralstonia eutropha reductase gene were developed for the production of poly(3-hydroxybutyrate-co-hydroxyhexanoate) [P(3HB-co-3HHx)] fro...
journal_title:Biomacromolecules
pub_type: 杂志文章
doi:10.1021/bm000105u
更新日期:2001-04-01 00:00:00
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
更新日期:2002-07-01 00:00:00
abstract::As an aim toward developing biologically mimetic and functional nanofiber-based tissue engineering scaffolds, we demonstrated the encapsulation of a model protein, fluorescein isothiocyanate-conjugated bovine serum albumin (fitcBSA), along with a water-soluble polymer, poly(ethylene glycol) (PEG), within the biodegrad...
journal_title:Biomacromolecules
pub_type: 杂志文章
doi:10.1021/bm050743i
更新日期:2006-04-01 00:00:00
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
更新日期:2019-01-14 00:00:00
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
更新日期:2017-07-10 00:00:00
abstract::Coiled coils are a common structural motif in many natural proteins that can also be utilized in the design and preparation of drug delivery systems for the noncovalent connection of two macromolecules. In this work, two different pairs of peptides forming coiled coil hetero-oligomers were designed, synthesized, and c...
journal_title:Biomacromolecules
pub_type: 杂志文章
doi:10.1021/bm500436p
更新日期:2014-07-14 00:00:00
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
更新日期:2019-12-09 00:00:00
abstract::Light-harvesting antenna core (LH1-RC) complexes isolated from Rhodoseudomonas palustris were self-assembled on a gold electrode modified with self-assembled monolayers (SAMs) of the alkanethiols NH2(CH2)nSH, n = 2, 6, 8, 11; HOOC(CH2)7SH; and CH3(CH2)7SH, respectively. Adsorption of the LH1-RC complexes on the SAMs d...
journal_title:Biomacromolecules
pub_type: 杂志文章
doi:10.1021/bm070352z
更新日期:2007-08-01 00:00:00
abstract::This paper describes the synthesis and cytotoxicity of poly(anhydride esters) that are composed of several salicylate derivatives, including halogenated salicylates, aminosalicylates, salicylsalicylic acid, and thiolsalicylic acid. The incorporation of these nonsteroidal antiinflammatory drugs (NSAIDs) into a biodegra...
journal_title:Biomacromolecules
pub_type: 杂志文章
doi:10.1021/bm049544+
更新日期:2005-01-01 00:00:00
abstract::Candida antarctica Lipase B (CALB) was covalently immobilized onto epoxy-activated macroporous poly(methyl methacrylate) Amberzyme beads (235 microm particle size, 220 A pore size) and nanoparticles (nanoPSG, diameter 68 nm) with a poly(glycidyl methacrylate) outer region. Amberzyme beads allowed CALB loading up to 0....
journal_title:Biomacromolecules
pub_type: 杂志文章
doi:10.1021/bm700949x
更新日期:2008-02-01 00:00:00
abstract::PLGA nanoparticles are among the most studied polymer nanoformulations for several drugs against different kinds of malignant diseases, thanks to their in vivo stability and tumor localization exploiting the well-documented "enhanced permeation and retention" (EPR) effect. In this paper, we have developed uniform curc...
journal_title:Biomacromolecules
pub_type: 杂志文章
doi:10.1021/bm3017324
更新日期:2013-03-11 00:00:00
abstract::A well-defined N-(2-hydroxypropyl)methacrylamide-s-N-(3-aminopropyl)methacrylamide (HPMA-s-APMA) copolymer, synthesized via reversible addition-fragmentation chain transfer (RAFT) polymerization, was utilized for the rational design of multiconjugates containing both a gene therapeutic, small interfering RNA (siRNA), ...
journal_title:Biomacromolecules
pub_type: 杂志文章
doi:10.1021/bm901249n
更新日期:2010-02-08 00:00:00
abstract::Spider dragline silk with its superlative tensile properties provides an ideal system to study the relationship between morphology and mechanical properties of a structural protein. Accordingly, we synthesized two hybrid multiblock copolymers by condensing poly(alanine) [(Ala)(5)] blocks of the structural proteins (sp...
journal_title:Biomacromolecules
pub_type: 杂志文章
doi:10.1021/bm060199t
更新日期:2006-08-01 00:00:00
abstract::Gelatin microspheres are well-known for their capacity to release growth factors in a controlled manner, but gelatin microspheres do not calcify in the absence of so-called bioactive substances that induce deposition of calcium phosphate (CaP) bone mineral. This study has investigated if CaP nanocrystals can be incorp...
journal_title:Biomacromolecules
pub_type: 杂志文章
doi:10.1021/bm1006344
更新日期:2010-10-11 00:00:00
abstract::Novel biodegradable materials with tunable hydrolytic degradation rate are prepared by grafting of phosphonoethylated polyglycidols with polyesters. First, the hydrolytically degradable polyester grafts are attached to polyglycidols partially grafted with phosphonoethylated diethyl esters through chemical-catalyzed gr...
journal_title:Biomacromolecules
pub_type: 杂志文章
doi:10.1021/bm401428b
更新日期:2013-11-11 00:00:00
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
更新日期:2019-02-11 00:00:00
abstract::Acrylic acid (AAc) has been utilized to introduce reactive carboxyl groups to a temperature-responsive polymer, poly(N-isopropylacrylamide) (PIPAAm). However, AAc introduction shifts the copolymer phase transition temperatures higher and dampens the steep homopolymer phase transition with increasing AAc content. We pr...
journal_title:Biomacromolecules
pub_type: 杂志文章
doi:10.1021/bm025692t
更新日期:2003-03-01 00:00:00
abstract::Over the past 10 years, polyglycerols and their structurally related analogs have received considerable attention in the biomedical field. Poly(glycidyl methacrylate) (PGMA) is a versatile polymer because its pendant epoxide groups can be opened with different functional groups to generate poly(glycerol methacrylate)s...
journal_title:Biomacromolecules
pub_type: 杂志文章
doi:10.1021/bm901241k
更新日期:2010-04-12 00:00:00
abstract::These studies illustrate synthetic paths to covalently attach T1 and Φ11 bacteriophages (phages) to inert polymeric surfaces while maintaining the bacteriophage's biological activities capable of killing deadly human pathogens. The first step involved the formation of acid (COOH) groups on polyethylene (PE) and polyte...
journal_title:Biomacromolecules
pub_type: 杂志文章
doi:10.1021/bm400290u
更新日期:2013-05-13 00:00:00
abstract::We show that functionalizing polymer-coated colloidal nanoplatelets with guanosine groups allows synergistic increase of mechanical properties in nacre-mimetic lamellar self-assemblies. Anionic montmorillonite (MTM) was first coated using cationic poly(diallyldimethylammonium chloride) (PDADMAC) to prepare core-shell ...
journal_title:Biomacromolecules
pub_type: 杂志文章
doi:10.1021/bm400056c
更新日期:2013-08-12 00:00:00
abstract::Chitin is a nitrogen-rich polysaccharide that is abundant in crustaceans, mollusks, insects, and fungi and is the second most abundant organic material found in nature next to cellulose. Chitosan, the N-deacetylated derivative of chitin, is environmentally friendly, nontoxic, biodegradable, and antibacterial. Fibrous ...
journal_title:Biomacromolecules
pub_type: 杂志文章
doi:10.1021/bm7006983
更新日期:2007-09-01 00:00:00
abstract::Lignin-carbohydrate complexes (LCCs) were prepared in quantitative yield from spruce wood and from the corresponding kraft and oxygen-delignified pulps and were separated into different fractions on the basis of their carbohydrate composition. To obtain an understanding of the differences in lignin structure and react...
journal_title:Biomacromolecules
pub_type: 杂志文章
doi:10.1021/bm058014q
更新日期:2005-11-01 00:00:00
abstract::This paper describes the synthesis and evaluation of a series of multifunctional poly-l-glutamic acid derivatives that can be used as vectors for gene delivery. They readily form polyelectrolyte complexes with DNA, resulting in a reduced surface charge and size of the DNA. The formation of a polymer-DNA complex and th...
journal_title:Biomacromolecules
pub_type: 杂志文章
doi:10.1021/bm034014j
更新日期:2003-09-01 00:00:00
abstract::Photoexcited TiO2 degrades biomolecules such as nucleic acids, cell membrane proteins, and enzymes. Stabilization of enzyme activity against the deactivation caused by the combination of TiO2-UV is essential if we are to develop novel hybrid materials exhibiting photocatalytic and biocatalytic activities useful for de...
journal_title:Biomacromolecules
pub_type: 杂志文章
doi:10.1021/bm049728o
更新日期:2004-09-01 00:00:00