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PubMed1998

In vitro degradation study of polyester microspheres by a new HPLC method for monomer release determination.

Biodegradable polyesters have increasing importance as materials used for the preparation of microspheres. The knowledge of their degradation process is important to prepare microparticulate delivery systems with suitable drug release rates. In this work an in vitro degradation study of empty and drug loaded microspheres is described. Three different polyesters were used: two poly-d, l-lactides of different molecular weight and a poly-d, l-lactide-co-glycolide (50:50). Diazepam has been chosen as the model drug. Solvent evaporation and spray-drying were used as preparation methods. To study the polymer degradation process, a new HPLC method is proposed for the direct and (in the case of the copolymer) simultaneous determination of the monomer(s): lactic acid (LA) and glycolic acid (GA). SEM and particle size analysis highlight the different characteristics of the particles, depending on their preparation method: spray-dried spheres result to be always smaller with respect to particles obtained by solvent evaporation. The results obtained indicate in particular that: the preparation methods play an important role in determining the degradation behaviour of microspheres, as unloaded spray-dried particles are characterized by a higher monomer release rate with respect to microspheres obtained by solvent evaporation; PLGA spheres degrade faster than PDLLA microparticles, according to the higher hydrophilicity of the copolymer; the two monomers are released at a different rate in the case of PLGA (faster for GA, slower for LA); the presence of diazepam increases the polymer degradation rate, with respect to empty particles.

Biocompatible Materials↗
PubMed2003

In situ revascularization with silver-coated polyester grafts to treat aortic infection: early and midterm results.

PURPOSE: In this prospective study we analyzed the immediate and midterm outcome in patients with abdominal aorta infection (mycotic aneurysm, prosthetic graft infection) managed by excision of the aneurysm or the infected vascular prosthesis and in situ replacement with a silver-coated polyester prosthesis. METHODS: From January 2000 to December 2001, 27 consecutive patients (25 men, 2 women; mean age, 69 years) with an abdominal aortic infection were entered in the study at seven participating centers. Infection was managed with either total (n = 18) or partial (n = 6) excision of the infected aorta and in situ reconstruction with an InterGard Silver (IGS) collagen and silver acetate-coated polyester graft. Assessment of outcome was based on survival, limb salvage, persistent or recurrent infection, and prosthetic graft patency. RESULTS: Twenty-four patients had prosthetic graft infections, graft-duodenal fistula in 12 and graft-colonic fistula in 1; and the remaining 3 patients had primary aortic infections. Most organisms cultured were of low virulence. The IGS prosthesis was placed emergently in 11 patients (41%). Mean follow-up was 16.5 months (range, 3-30 months). Perioperative mortality was 15%; all four patients who died had a prosthetic graft infection. Actuarial survival at 24 months was 85%. No major amputations were noted in this series. Recurrent infection developed in only one patient (3.7%). Postoperative antibiotic therapy did not exceed 3 months, except in one patient. No incidence of prosthetic graft thrombosis was noted during follow-up. CONCLUSION: Preliminary results in this small series demonstrate favorable outcome with IGS grafts used to treat infection in abdominal aortic grafts and aneurysms caused by organisms with low virulence. Larger series and longer follow-up will be required to compare the role of IGS grafts with other treatment options in infected fields.

Adult↗
PubMed2002

Biologic fixation of polyester- versus polyurethane-covered stents in a porcine model.

PURPOSE: Migration of endoprostheses remains a concern in endovascular aneurysm treatment. Biologic fixation is supposed to enhance anchorage, but the diseased atherosclerotic aorta in humans has demonstrated a limited capacity to incorporate an endoprosthesis by cellular proliferation. The biologic response of two different types of endoprostheses was evaluated in the porcine aorta. MATERIALS AND METHODS: Two types of endoprostheses--four polyurethane-covered (PUC) stents with a macroporous polyurethane covering and four polyester-covered (PEC) stents with a woven polyester covering--were implanted in eight infrarenal porcine aortas for 6 weeks. Electron microscopy and qualitative and quantitative microscopy were performed on serial cross sections. RESULTS: The PUC stents demonstrated an increase in diameter (from 8 mm +/- 1 to 10 mm +/- 1, 12.5%; P = .009), whereas the PEC stents persisted in their original dimensions (8 mm +/- 1, 0%). PUC and PEC stents were covered by continuous thrombus-free neointima (269 microm +/- 51 vs 575 microm +/- 113, respectively; P < .01). The PUC stents demonstrated firm attachment to the aorta as a consequence of a granulation tissue with ingrowth into the pores of the polyurethane covering. The PEC stents remained in loose contact with the aorta in the absence of tissue ingrowth. CONCLUSIONS: Enhanced biologic fixation was achieved by extensive granulation tissue invading the pores of PUC endoprostheses. This finding can modify the design of future devices.

Animals↗
PubMed2003

Mechanisms of rupture of knitted polyester vascular prostheses: an in vitro analysis of virgin prostheses.

OBJECTIVES: Previous explant retrieval studies have shown ruptures occurring on the remeshing line and the guide line of two types of warp-knitted grafts. The aim of our study was to characterize the mechanisms these ruptures. MATERIALS AND METHODS: We performed an in vitro study of the mechanical and chemical characteristics of virgin prostheses. We studied 2 virgin polyester warp-knitted grafts models: the Cooley Double Velour and the Microvel Double Velour constructed by Meadox (USA), using the following techniques: characterization and de-knitting of the textile structure, circumferential tensile strength, filament dynamometry, critical dissolution time of the filaments and scanning electron microscopy. RESULTS: Both prostheses were constructed in the same way but the texturized yarns of the Cooley graft included twice as many filaments (54) than the Microvel (27). There was more adsorbed tension in the Cooley structure than in the Microvel. The circumferential tensile strength test demonstrated that the Cooley graft always ruptured on the remeshing line and the Microvel graft always ruptured at the interface between the remeshing line and the standard line. Filament dynamometry demonstrated a heterogeneous behavior of the filaments inside the yarns, mainly at the remeshing line of the Cooley graft (27.1 cN/tex +/- 11.5% versus 26.1 cN/tex +/- 2.2% for the guide line and 28 cN/tex +/- 6.7% for the standard knit). Critical dissolution time of the filaments was significantly lower for the Microvel grafts (2.5 sec versus 17.2 sec for the Cooley). CONCLUSIONS: Rupture of knitted polyester prostheses are probably an underestimated phenomenon. They may occur at specific areas of the graft. Further studies are required to determine whether all grafts of this type are at risk.

Blood Vessel Prosthesis↗
PubMed1997

Evaluation of genotoxic potential of styrene in furniture workers using unsaturated polyester resins.

Styrene is a widely used chemical, mostly in making synthetic rubber, resins, polyesters, plastics and insulators. Increasing attention has been focused on this compound since experiments using cytogenetic end-points have implicated styrene as a potential carcinogen and mutagen. In order to perform biological monitoring of genotoxic exposure to styrene monomer, we evaluated the urinary thioether (UT) excretion, and sister chromatid exchanges (SCEs) and micronuclei (MN) in peripheral lymphocytes from 53 furniture workers employed in small workplaces where polyester resin lamination processings were done and from 41 matched control subjects. The mean air concentration of styrene in the breathing zone of workers was 30.3 ppm. As a metabolic marker for styrene exposure, mandelic acid + phenylglyoxylic acid was measured in the urine and the mean value was 207 mg/g creatinine. The mean +/- SD value of UT excretions of workers was 4.43 +/- 3.42 mmol SH-/mol creatinine and also mean UT for controls was found to be a 2.75 +/- 1.78 mmol SH-/mol creatinine. The mean +/- SD/cell values of SCE frequency in peripheral lymphocytes from the workers and controls were 6.20 +/- 1.56 and 5.23 +/- 1.23, respectively. The mean +/- SD frequencies (%o) of MN in the exposed and control groups were 1.98 +/- 0.50 and 2.09 +/- 0.35, respectively. Significant effects of work-related exposure were detected in the UT excretion and SCEs analyzed in peripheral blood lymphocytes (p < 0.05 and p < 0.01, respectively). The MN frequency in lymphocytes from the styrene-exposed group did not differ from that in the controls (p > 0.05). Effect of smoking, age and duration of exposure on the genotoxicity parameters analyzed were also evaluated. In conclusion, although our data do not demonstrate a dose-response relationship, they do suggest that styrene exposure was evident and that this styrene exposure may contribute to the observed genotoxic damage in furniture workers.

Adult↗
PubMedDate not supplied

Polyester dendritic systems for drug delivery applications: design, synthesis, and characterization.

Attachment of drugs to high molecular weight polymers can significantly improve both tumor targeting and therapeutic efficacy due to the enhanced permeability and retention effect observed in tumor tissue. However, the commercial availability of well-defined water-soluble polymeric systems with narrow polydispersities that are biocompatible, nontoxic, and nonimmunogenic is rather limited. To address this need, we have investigated dendritic polymers as promising scaffolds for the preparation of new soluble polymeric drug carriers due to their well-defined molecular architecture and their multiplicity of surface sites. Herein we show the design and synthesis of dendritic polyester systems based on the monomer unit 2,2-bis(hydroxymethyl)propanoic acid as a possible versatile drug carrier. The potent anticancer drug doxorubicin was attached via a pH-sensitive linkage to one of the carriers presented, demonstrating the feasibility of using these polyester dendritic structures to prepare a viable polymer-drug conjugate.

Antibiotics, Antineoplastic↗
PubMedDate not supplied

Self-assembling nanocomplexes from insulin and water-soluble branched polyesters, poly[(vinyl-3-(diethylamino)- propylcarbamate-co-(vinyl acetate)-co-(vinyl alcohol)]-graft- poly(L-lactic acid): a novel carrier for transmucosal delivery of peptides.

The design of carriers for protein delivery that provide protection against enzymatic degradation and facilitate protein transport across epithelial surfaces, thus avoiding parenteral administration, remains a challenge. Self-assembling nanoscale protein/polymer complexes might present a promising approach. We synthesized water-soluble, amphiphilic polyesters, poly[(vinyl-3-(diethylamino)-propylcarbamate-co-(vinyl acetate)-co-(vinyl alcohol)]-graft-poly(L-lactic acid), containing a positively charged backbone, and studied the spontaneous formation of nanocomplexes (NC) with insulin. NC were characterized using dynamic light scattering, zeta-potential measurements, and atomic force microscopy (AFM). Insulin loading was determined with HPLC, and the binding constants were obtained by isothermal titration calorimetry (ITC). The NC formation was followed using nephelometric and light scattering techniques. Water-soluble, positively charged, branched polyesters with amphiphilic properties were obtained in a three-step polymer-analogous reaction. The degree of amine substitution, DS, in the PVAL backbone was varied between 0.04 and 0.5, and grafting this backbone with L-lactide increased the molecular weight from 18 kDa to 81 kDa. The polymer composition was optimized to facilitate NC formation with insulin resulting in a DS of 0.09 and a poly(L-lactide) side chain substitution of 0.5 with an average chain length of two lactic acids. Depending on polymer composition, stable NC of 200-500 nm diameter were formed with insulin, and the binding constants ranged from 4.7 x 10(5) to 9.5 x 10(6) M(-1). Positively charged surface charges ranging from +5 to +35mV and an insulin loading up to 98% of 33 IU/mL were obtained. The NC visualized by AFM revealed spheroidal particles with an entangled internal structure. It was demonstrated that this class of multifunctional polymers is capable of self-assembly with a peptidic substrate. The resulting nanosized complexes offer the potential for mucosal insulin/protein delivery and merit further investigations under in vivo conditions.

Biological Transport↗
PubMed2001

Convenient synthesis of aliphatic polyesters by distannoxane-catalyzed polycondensation.

A convenient synthesis of aliphatic polyesters by the distannoxane-catalyzed polycondensation of aliphatic dicarboxylic acids and aliphatic diols in solvents under azeotropic conditions was developed. To determine the optimum conditions for polycondensation of succinic acid with 1,4-butandiol, the effect of various types of catalyst and their concentration was investigated. By choosing the appropriate solvent, the polymerization was made to proceed in a two-phase system of solvent and molten polymer, and in the presence of 0.001 mol % of 1-chloro-3-hydroxy-1,1,3,3-tetrabutyldistannoxane (CHTD), poly(butylene succinate) (PBS) with a weight-average molecular weight of 277,000 was obtained. This method was then successfully applied to the synthesis of various aliphatic polyesters, such as poly(ethylene succinate), poly(1,4-cyclohexanedimethylene succinate), and poly(ethylene sebacate).

Biodegradation, Environmental↗
PubMedDate not supplied

Biocatalytic synthesis of fluorinated polyesters.

The biocatalytic synthesis of fluorinated polyesters from activated diesters and fluorinated diols has been investigated. The effects of time, continuous enzyme addition, enzyme concentration, and diol chain length were studied to determine the factors that would limit chain extension, such as enzyme inactivation, enzyme specificity, the equilibrium position for the reaction, hydrolytic side reactions, and polymer precipitation. An enzyme screen demonstrated that only Novozym 435, an immobilized lipase from Candida antarctica, was effective in producing the fluorinated polyester. Molecular weight and polydispersity analyses were performed by means of gel permeation chromatography. End group analysis was accomplished through the use of matrix-assisted laser desorption/ionization time-of-flight mass spectroscopy. Polymer molecular weight steadily increased and then leveled off after approximately 30 h, with a weight average molecular weight of approximately 1773. The majority of the polymer chains were terminated with either hydroxyl or vinyl groups. Polymers that were synthesized from bulk monomers had higher molecular weights, but high enzyme concentrations were required. Enzyme specificity toward shorter chain fluorinated diols appeared to be the governing factor in limiting chain growth. However, polymer molecular weight increased further (M(w) = 8094) when a fluorinated diol that contained an additional methylene spacer between the fluorine atoms and hydroxyl groups was used.

Biotechnology↗
PubMed2002

Designing macromolecules for therapeutic applications: polyester dendrimer-poly(ethylene oxide) "bow-tie" hybrids with tunable molecular weight and architecture.

The design and preparation of new polyester dendrimer, poly(ethylene oxide) hybrid systems for drug delivery and related therapeutic applications, are described. These systems consist of two covalently attached polyester dendrons, where one dendron provides multiple functional handles for the attachment of therapeutically active moieties, while the other is used for attachment of solubilizing poly(ethylene oxide) chains. By varying the generation of the dendrons and the mass of the poly(ethylene oxide) chains, the molecular weight, architecture, and drug loading can be readily controlled. The "bow-tie" shaped dendritic scaffold was synthesized using both convergent and divergent methods, with orthogonal protecting groups on the periphery of the two dendrons. Poly(ethylene oxide) was then attached to the periphery of one dendron using an efficient coupling procedure. A small library of eight carriers with molecular weights ranging from about 20 kDa to 160 kDa were prepared and characterized by various techniques, confirming their well-defined structures.

Drug Delivery Systems↗
PubMed2002

Degradation of aliphatic polyester films by commercially available lipases with special reference to rapid and complete degradation of poly(L-lactide) film by lipase PL derived from Alcaligenes sp.

Commercial lipases were examined for their degradation efficiency of aliphatic polyester films. In 100 days immersion of polyester films in lipase solutions at 37 degrees C at pH 7.0, Lipase Asahi derived from Chromobacterium viscosum degraded polybutylene succinate-co-adipate (PBSA), poly (e-caprolactone) (PCL) and polybutylene succinate (PBS), and Lipase F derived from Rhizopus niveus degraded PBSA and PCL during 4-17 days. Lipase F-AP15 derived from Rhizopus orizae could degrade PBSA in 22 days. In these cases, PBS and PBSA were mainly degraded to dimers, whereas PCL was mainly degraded to monomers. Only poly(3-hydroxybutyrate-co-3-hydroxyvalerate) (PHB/V) and poly (L-lactide) (PLA) were not degraded in the experiments. However, PLA degraded completely at 55 degrees C, pH 8.5 with Lipase PL during 20 days. This result could be explained with the sequential reactions of the chemical hydrolysis of the polymer to oligomers at higher pH and temperature, and the succeeding enzymatic hydrolysis of oligomers to the monomers.

Adipates↗
PubMed2004

Degradation of microbial polyesters.

Microbial polyhydroxyalkanoates (PHAs), one of the largest groups of thermoplastic polyesters are receiving much attention as biodegradable substitutes for non-degradable plastics. Poly(D-3-hydroxybutyrate) (PHB) is the most ubiquitous and most intensively studied PHA. Microorganisms degrading these polyesters are widely distributed in various environments. Although various PHB-degrading microorganisms and PHB depolymerases have been studied and characterized, there are still many groups of microorganisms and enzymes with varying properties awaiting various applications. Distributions of PHB-degrading microorganisms, factors affecting the biodegradability of PHB, and microbial and enzymatic degradation of PHB are discussed in this review. We also propose an application of a new isolated, thermophilic PHB-degrading microorganism, Streptomyces strain MG, for producing pure monomers of PHA and useful chemicals, including D-3-hydroxycarboxylic acids such as D-3-hydroxybutyric acid, by enzymatic degradation of PHB.

3-Hydroxybutyric Acid↗
PubMed2004

Design of amine-modified graft polyesters for effective gene delivery using DNA-loaded nanoparticles.

PURPOSE: The purpose of this study was the design of a polymeric platform for effective gene delivery using DNA-loaded nanoparticles. METHODS: The polymers were synthesized by carbonyldiimidazole (CDI)-mediated coupling of diamines diethylaminopropylamine (DEAPA), dimethylaminopropylamine (DMAPA) or diethylaminoethylamine (DEAEA) to poly(vinyl alcohol) (PVA) with subsequent grafting of D,L-lactide and glycolide (1:1) in the stoichiometric ratios of 1:10 and 1:20 (free hydroxyl groups/monomer units). The polymers were characterized by 1H-NMR, gel permeation chromatography-multiple-angle laser-light-scattering, and differential scanning calorimetry. DNA-loaded nanoparticles prepared by a modified solvent displacement method were characterized with regard to their zeta (zeta)-potential and size. The transfection efficiency was assessed with the plasmid DNA pCMV-luc in L929 mouse fibroblasts. RESULTS: The polymers were composed of highly branched, biodegradable cationic polyesters exhibiting amphiphilic properties. The amine modification enhanced the rapid polymer degradation and resulted in the interaction with DNA during particle preparation. The nanoparticles exhibited positive zeta-potentials up to +42 mV and high transfection efficiencies, comparable to polyethylenimine (PEI) 25 kDa/DNA complexes at a nitrogen to phosphate ratio of 5. CONCLUSIONS: The polymers combined amine-functions and short poly(D,L-lactic-co-glycolic acid) (PLGA) chains resulting in water-insoluble polymers capable of forming biodegradable DNA nanoparticles through coulombic interactions and polyester precipitation in aqueous medium. The high transfection efficiency was based on fast polymer degradation and the conservation of DNA bioactivity.

Animals↗
PubMed2002

Identification of sensitizing diethyleneglycol maleate in a two-component polyester cement.

Unsaturated polyester (UP) cement caused allergic contact dermatitis in car repair work. The resin was a condensate of polyols and maleic anhydride with reactive solvent, auxiliary substances, and inorganic reinforcement substances. To identify the causative chemicals, the cement was tested on a sensitized patient. For analysis, samples of the resin were eluted with acetone and eluted with hexane to precipitate inorganic material and large polyester molecules. The eluate was evaporated. The remainder, dissolved in acetone, was separated into fractions on silica plates by thin layer chromatography (TLC). On the developed (hexane/chloroform, 15/85) plates, 20 bands were obtained under UV-light at 254 nm. Samples of the bands were scraped and used for patch testing. The scraping at a retention factor (Rf) of 0.24 caused a skin reaction. The bands at this retention were removed from six plates, combined, eluted with acetone and purified again by TLC. The purified fraction mixed in petrolatum in the dilution series was used for conclusive patch testing on the patient. An allergic reaction was induced at down to 0.003% wt/wt. According to MS and IR analyses, the isolated compound was diethyleneglycol maleate (DEGM, MW204). In addition to the resin part, the sanding dust also contained this monomer.

Dermatitis, Allergic Contact↗
PubMed1989

Thermal degradation of polyester coating powders: 1,4-dicyanobenzene as an occupational marker compound.

A method for the determination of emissions in workroom air as a result of the thermal degradation of polyester coating powders is described. The method is based on the determination of certain marker compounds only. Polyester coating powders were degraded thermally in laboratory experiments and 1,4-dicyanobenzene was chosen as the marker compound. An air sampling method and a high-performance liquid chromatographic method for the determination of the marker compound are proposed. The detection limit for a 48-I air sample was 0.4 microgram m-3.

Air Pollutants, Occupational↗
PubMed1999

Tissue reactions to polypyrrole-coated polyesters: A magnetic resonance relaxometry study.

The electrically conductive properties of polypyrrole (PPy) as a coating on polyester material are very attractive for the manufacture of small diameter blood conduits. However, before these PPy-coated materials can be investigated for their capacity to generate endothelialized luminal surfaces, they must first be studied for their innocuousness in a living environment. The specific goal of the present study was to investigate the in vivo interactions of PPy-coated and noncoated woven polyester materials implanted subcutaneously in rats for prescheduled periods of 2, 5, 10, 20, and 30 days. The in vivo magnetic resonance (MR) relaxation times were computed for a small area of muscle tissue adjacent to the implants. A correlation was concurrently attempted with blood monocyte activation studies as well as histological observations of the tissue-material interface. The progressive pattern of the slower transversal relaxation time (T2s) values revealed a more persistent tissue reaction for the most conductive PPy-coated materials and a shorter acute tissue response as the surface resistivity increased. Similarly, the blood monocyte activation studies indicated that the thickness of the PPy coating, which correlated with the conductivity, was directly related to tissue response. Furthermore, both the MR and biological studies showed that the PPy-coated material with a high surface resistivity displayed the lowest tissue reaction over the entire period of implantation. The results obtained from the blood monocyte activation studies and histological observations correlate well with the noninvasive MR measurements of the body's healing process. The conductive materials with high surface resistivities must be further investigated. Finally, the noninvasive nature of MR relaxometry reveals its outstanding potential for future in vivo investigations of the body's tissue interactions with polymers and nonferromagnetic biomaterials.

Animals↗
PubMed2002

Evaluation of cellular affinity and compatibility to biodegradable polyesters and Type-II collagen-modified scaffolds using immortalized rat chondrocytes.

Immortalized rat chondrocytes (IRCs) were employed to evaluate the cytocompatibility of different biodegradable polyester scaffolds for chondrocyte seeding and cartilage tissue engineering in vitro due to the limitation of using freshly harvested chondroctyes. Cells were seeded onto the films and the porous substrates as well as into the three-dimensional scaffolds made of the biodegradable polyesters including poly(l-lactide) (PLLA) and two poly(lactide-co-glycolide)s (PLGAs). The materials were characterized by water contact angle, electron spectroscopy for chemical analysis (ESCA), and microscopy. PLGA50/50, one of the PLGAs, had the largest cell numbers at 24 h and 96 h (close to the tissue culture polystyrene control), possibly due to its lower contact angle, higher oxygen/carbon (O/C) atomic ratio, and larger degradation rate. When the surface was further modified by cross-linked Type-II collagen, cell population was significantly enhanced (two- to fourfold). The adhesion and proliferation behavior of IRCs on different materials was parallel to that of rabbit chondrocytes, but was more reproducible in general. IRCs are thus suitable for evaluation of different polymer scaffolds. Despite the favorable cytocompatibility of PLGA50/50, blending with a small portion of PLLA is required for easy fabrication and collagen modification. Scaffolds made of blended materials by freeze-drying procedure with the surface modified by cross-linked Type-II collagen were demonstrated as the ideal templates for chondrocyte seeding in our study.

Animals↗
PubMed1999

New technique of leukocytapheresis by the use of nonwoven polyester fiber filter for inflammatory bowel disease.

Leukocytapheresis (LCAP) is widely used for the treatment of immunological diseases. We studied a new treatment of LCAP using a nonwoven polyester fiber filter. In a basic study, 30-70% of leukocytes were removed. Also, 30-68% of the leukocyte subsets were removed. Sixteen inflammatory bowel disease (IBD) patients, mainly with ulcerative colitis (UC), were treated by this method. Their cytokine activity was normalized in the filter and in the peripheral blood. Eleven of 12 patients with UC were induced to remission. Four patients with Crohn's disease (CD) exhibited improvement. The LCAP using a nonwoven polyester fiber filter was very efficient for treating the patients with IBD. Also, it will be a very useful treatment for immunological diseases and extracorporeal immunomodulation.

Adult↗