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Synolite as a base resin for dental composites and related biomaterials
Krishnan, V. K., L. H. Mair, et al. (1993), Clin Mater 12(3): 149-52.
Abstract: Synolite resin was analysed using FTIR, NMR and HPLC to determine its components and purity. The resin was found to be predominantly BIS-GMA containing traces of its two isomers. The analysis indicated that there was no unreacted methacrylic acid or other impurities.

Synthesis and characterization of a novel chitosan-gelatin bioconjugate with fluorescence emission
Mi, F. L. (2005), Biomacromolecules 6(2): 975-87.
Abstract: Polysaccharide-protein conjugations have generated increasing interests for biomedical applications in recent years. A naturally occurring cross-linking reagent, genipin, which has been used in herbal medicine, was employed to cross-link chitosan and gelatin for the preparation of a novel chitosan-gelatin conjugate. The primary amine groups on chitosan and gelatin were covalently linked with genipin, leading to the formation of a chitosan-gelatin conjugate with nitrogen-containing heterocycle units, the pyrindine-like derivatives. The FT-IR and UV-vis studies revealed that chitosan could react with genipin via a nucleophilic ring-opening reaction to construct more sufficient and extensive cross-link networks, as compared with its gelatin counterpart. The UV-vis absorption properties of the chitosan-gelatin conjugates were strongly related to the chitosan-to-gelatin weight ratio in the compositions. It is worth noting that the conjugation process endows the special emission properties of the chitosan-gelatin conjugates, which depends on the cross-linking reaction and the formation of hydrogen bonding involved chitosan-gelatin complex. Fluorescence quenching or enhancement was observed from the chitosan-gelatin conjugates upon coordinated with a wide variety of heavy metal ions (Ag+, Cu2+, Fe2+, and Co2+). This study also examined the possibility of covalent coupling the capture chelator (chitosan) with bioactive protein (e.g., albumin, alpha-globulin, and fibrinogen) to create fluorescence emission. These findings may provide a novel way to deliver therapeutic radionuclides for immuno-targeting purposes in the future.

Synthesis and characterization of biocompatible thermo-responsive gelators based on ABA triblock copolymers
Li, C., Y. Tang, et al. (2005), Biomacromolecules 6(2): 994-9.
Abstract: The synthesis of biocompatible, thermo-responsive ABA triblock copolymers in which the outer A blocks comprise poly(N-isopropylacrylamide) and the central B block is poly(2-methacryloyloxyethyl phosphorylcholine) is achieved using atom transfer radical polymerization with a commercially available bifunctional initiator. These novel triblock copolymers are water-soluble in dilute aqueous solution at 20 degrees C and pH 7.4 but form free-standing physical gels at 37 degrees C due to hydrophobic interactions between the poly(N-isopropylacrylamide) blocks. This gelation is reversible, and the gels are believed to contain nanosized micellar domains; this suggests possible applications in drug delivery and tissue engineering.

Synthesis and characterization of mPEG-PLA prodrug micelles
Hans, M., K. Shimoni, et al. (2005), Biomacromolecules 6(5): 2708-17.
Abstract: Polymeric prodrugs of mPEG-PLA-haloperidol (methoxypoly(ethylene glycol)-b-poly(lactic acid)) can self-assemble into nanoscale micelle-like structures in aqueous solutions. mPEG-PLA-haloperidol was prepared and characterized using 1H and 13C NMR. The conjugation efficiency was found to be 64.8 +/- 21%. Micelles that form spontaneously upon solubilization of the mPEG-PLA and the polymeric prodrugs in water were characterized using a variety of techniques. The mPEG-PLA and prodrug micelles were found to have diameters of 28.73 +/- 1.45 and 49.67 +/- 4.29 nm, respectively, using dynamic light scattering (DLS). The micelle size and polydispersity were also evaluated with cryogenic transmission electron microscopy (cryo-TEM) and were consistent with the DLS results. Cryo-TEM and proton NMR confirmed that the micelles were spherical in shape. DLS was also used to determine the aggregation numbers of the micelles. The aggregation numbers ranged from 351 to 603. The change in aggregation number was dependent on the total drug incorporation into the micelle core. Critical micelle concentrations were determined for the various micelle/drug formulations and found to range from 3 to 14 microg/mL. Finally, drug was incorporated into the micelle core using the conjugate, free drug with a saturated aqueous phase during production, or a combination of both techniques. Drug incorporation could be increased from 3% to 20% (w/w) using the different formulations.

Synthesis and characterization of nano-biomaterials with potential osteological applications
Phillips, M. J., J. A. Darr, et al. (2003), J Mater Sci Mater Med 14(10): 875-82.
Abstract: The manufacture of high-surface area, un-agglomerated nano-sized (1-100 nm) bioceramic particles are of interest for many applications including injectable/controlled setting bone cements, high strength porous/non-porous synthetic bone grafts, and the reinforcing phase in nano-composites that attempt to mimic the complex structure and superior mechanical properties of bone. In the present study, we report on the manufacture of nano-particle hydroxyapatite powders by several wet chemical methods, which incorporate a freeze-drying step. In particular, it was found that the emulsion-based syntheses yielded powders with high surface areas and small primary particle sizes. Freeze drying rather than oven drying of powders prepared by conventional wet chemical synthesis yielded a nano-sized powder with a comparatively higher surface area of 113 m(2)/g. All powders were calcined in air in a furnace at 900 degrees C to investigate the effects of synthesis method on phase purity and surface area. The materials were characterized by a range of analytical methods including Fourier-transform infrared spectroscopy employing the photo acoustic (PAS-FTIR) sampling technique, BET surface area analysis, X-ray powder diffraction (XRD), and the particles were examined using a transmission electron microscope (TEM).

Synthesis and characterization of novel blood-compatible soluble chemically cross-linked polyurethanes with excellent mechanical performance for biomedical applications
Liu, Z., X. Wu, et al. (2005), Biomacromolecules 6(3): 1713-21.
Abstract: A controlled cross-linking polymerization system was designed, and soluble chemically cross-linked polyurethane was synthesized using laurylamine, n-octylamine, n-pentylamine, and ethylenediamine chain extenders. The mechanical analysis showed that the polyurethane materials synthesized in this paper have very excellent mechanical properties with a breaking elongation of 1914% and a tensile strength of 4303 N/cm(2). Such good mechanical properties must enable it to have good longevity when used as biomaterials. The polyurethane materials with n-pentylamine and n-octylamine chain extenders show reduced platelet adhesion than that with an ethylenediamine chain extender after sustaining 200 000 times of load cycles, indicating that polyurethanes introduced with an alkyl side chain onto the hard segments keep good antithrombogenic properties after sustaining load cycles. This might be because the hard segments are shielded by the alkyl side chain when the micro-phase-separation structure is destroyed in the repeated deformation of the polyurethane materials. The present investigation reveals that the influence of introducing long alkyl side chains into the backbone of the polyurethane macromolecule has been shown to reduce platelet deposition and to enhance in vitro albumin adsorption. However, in this paper, it has been observed that the polyurethane material introduced with a proper-length alkyl side chain onto the hard segment has the best antithrombogenic properties after the fatigue test.

Synthesis and characterization of polyanhydride for local BCNU delivery carriers
Kim, M. S., K. S. Seo, et al. (2005), Biomed Mater Eng 15(3): 229-38.
Abstract: p-Carboxyphenoxy propane (CPP) prepolymer consisting of 4 units and sebacic acid (SA) prepolymer consisting of about 10 units were synthesized by reacting CPP and SA in the presence of excess acetic anhydride, respectively. Polyanhydride, poly(CPP-SA) copolymers were copolymerized by a melt polycondensation process with a mixture of CPP and SA prepolymer. Copolymers of average molecular weight up to 110,000 g/mol were achieved. The crystallinity of poly(CPP-SA) copolymers was decreased by the addition of the CPP homopolymer segment to SA homopolymer. Poly(CPP-SA) copolymers gradually degraded for period of 10 days. No large difference of weight loss observed according to molecular weight variation of poly(CPP-SA) copolymers. BCNU release from wafers fabricated by poly(CPP-SA) showed a sustained release pattern with no initial burst and delay of drug release.

Synthesis and characterization of polypyrrole-hyaluronic acid composite biomaterials for tissue engineering applications
Collier, J. H., J. P. Camp, et al. (2000), J Biomed Mater Res 50(4): 574-84.
Abstract: New tissue engineering technologies will rely on biomaterials that physically support tissue growth and stimulate specific cell functions. The goal of this study was to create a biomaterial that combines inherent biological properties which can specifically trigger desired cellular responses (e.g., angiogenesis) with electrical properties which have been shown to improve the regeneration of several tissues including bone and nerve. To this end, composites of the biologically active polysaccharide hyaluronic acid (HA) and the electrically conducting polymer polypyrrole (PP) were synthesized and characterized. Electrical conductivity of the composite biomaterial (PP/HA) was measured by a four-point probe technique, scanning electron microscopy was used to characterize surface topography, X-ray photoelectron spectroscopy and reflectance infrared spectroscopy were used to evaluate surface and bulk chemistry, and an assay with biotinylated hyaluronic acid binding protein was used to determine surface HA content. PP/HA materials were also evaluated for in vitro cell compatibility and tissue response in rats. Smooth, conductive, HA-containing PP films were produced; these films retained HA on their surfaces for several days in vitro and promoted vascularization in vivo. PP/HA composite biomaterials are promising candidates for tissue engineering and wound-healing applications that may benefit from both electrical stimulation and enhanced vascularization.

Synthesis and characterization of porous beta-tricalcium phosphate blocks
Bohner, M., G. H. van Lenthe, et al. (2005), Biomaterials 26(31): 6099-105.
Abstract: Porous beta-tricalcium phosphate (beta-TCP) blocks with four different macropore sizes (pore larger than 50 microm were synthesized using "calcium phosphate emulsions", and characterized by optical, geometrical, gravimetric, and radiological methods. The reproducibility of the synthesis method was excellent. Moreover, the macropore size could be easily controlled without modifying the microporosity (pore smaller than 50 microm) or the total porosity (microporosity+macroporosity). Based on the initial composition of the blocks and their final apparent density, the microporosity, macroporosity, and the total block porosity were calculated to be close to 21%, 54%, and 75%, respectively. These values were confirmed by microcomputed tomography (microCT). The mean macropore diameters were close to 150, 260, 510 and 1220 microm, as measured optically. Consistently lower values (25% lower) were obtained by microCT, but the linear correlation between microCT and optical method was high (r(2)>0.97). The macropore size distribution calculated from microCT scans appears to be narrow and normally distributed. The very good correlation between the results of the various methods and the possibility to determine the pore size distribution suggest that microCT is an ideal tool to non-destructively characterize macroporous calcium phosphate bone substitutes.

Synthesis and characterization of surface-functionalized conducting polyaniline-chitosan nanocomposite
Cheng, D., H. Xia, et al. (2005), J Nanosci Nanotechnol 5(3): 466-73.
Abstract: We describe in this paper an easy route to the synthesis of a novel surface-functionalized conducting polyaniline-chitosan nanocomposite. A stable colloidal dispersion was prepared when aniline was polymerized in the presence of chitosan as the steric stabilizer. TEM study shows that these surface-functionalized polyaniline-chitosan nanoparticles have rice-grain morphologies. The effect of reaction parameters on the mean size of the polyaniline-chitosan nanoparticles was studied. The steric electrostatic interaction between segments of these two polymers explains the excellent storage stability of the polyaniline-chitosan dispersion. Reaction parameters were optimized in order to get stable polyaniline-chitosan dispersion. The chemical structures of polyaniline-chitosan nanocomposite were characterized. FT-IR spectra of the polyaniline-chitosan nanocomposite show that there exist a certain interaction between polyaniline and chitosan. X-ray photoelectron spectroscopy spectra show that chitosan is largely present at the surface of polyaniline-chitosan nanoparticles. The electrical conductivity of the polyaniline-chitosan nanocomposite increases with increasing the amount of polyaniline to a high value of 0.25 S/cm.

Synthesis and characterization of thermosensitive chitosan copolymer as a novel biomaterial
Lee, J. W., M. C. Jung, et al. (2004), J Biomater Sci Polym Ed 15(8): 1065-79.
Abstract: Novel water-soluble thermosensitive chitosan copolymers were prepared by graft polymerization of N-isopropylacrylamide (NIPAAm) onto chitosan using cerium ammonium nitrate (CAN) as an initiator. The physicochemical properties of the resulting chitosan-g-NIPAAm copolymers were characterized by Fourier transform infrared (FT-IR) spectroscopy, 1H-nuclear magnetic resonance, X-ray diffraction measurement, thermogravimetric analysis (TGA) and solubility test. Sol-gel transition behavior was investigated by the cloud point measurement of the chitosan-g-NIPAAm aqueous solution. The gelling temperature was examined using the vial inversion method. The percentage of grafting (%) and efficiency of grafting (%) were investigated according to concentrations of monomer and initiator. The maximum grafted chitosan copolymer was obtained with 0.4 M NIPAAm and 6 x 10(-3) M CAN. Water-soluble chitosan-g-NIPAAm copolymers were prepared successfully and they formed thermally reversible hydrogel, which exhibits a lower critical solution temperature (LCST) around 32 degrees C in aqueous solutions. A preliminary in vitro cell study showed nontoxic and biocompatible properties. These results suggest that chitosan-g-NIPAAm copolymer could be very useful in biomedical and pharmaceutical applications as an injectable material for cell and drug delivery.

Synthesis and in vitro drug release behavior of amphiphilic triblock copolymer nanoparticles based on poly (ethylene glycol) and polycaprolactone
Zhang, Y. and R. X. Zhuo (2005), Biomaterials 26(33): 6736-42.
Abstract: Novel BAB type amphiphilic triblock copolymers consisting of poly (ethylene glycol) (PEG) (B) as hydrophilic segment and poly (epsilon-caprolactone) (PCL) (A) as hydrophobic block were prepared by coupling reaction using L-lysine methyl ester diisocyanate (LDI) as the chain extender. The triblock copolymers obtained were characterized by FT-IR, 1H NMR, GPC, and DSC. Core-shell type nanoparticles were prepared by nanoprecipitation method and below 100 nm nanoparticles were obtained due to their specific structure. Transmission electron microscopy image demonstrated that these nanoparticles were spherical in shape. Stability of the nanoparticles in biological media was evaluated. Poorly water-soluble anticancer drug 4'-demethyl-epipodophyllotoxin (DMEP) was chosen for controlled drug release because it was easily encapsulated into polymeric nanoparticles via hydrophobic interaction. In vitro release behavior of DMEP from polymeric nanoparticles was investigated, the results showed that the drug release rate can be modulated by the variation of the copolymer composition.

Synthesis and mesomorphic properties of glycosyl dialkyl- and diacyl-glycerols bearing saturated, unsaturated and methyl branched fatty acid and fatty alcohol chains. Part I. Synthesis
Milkereit, G., S. Gerber, et al. (2005), Chem Phys Lipids 135(1): 1-14.
Abstract: Glycosyl dialkyl- and diacyl-glycerols bearing saturated, unsaturated or chiral methyl branched chains in the tail and disaccharide and trisaccharide carbohydrate headgroups were synthesised. Standard procedures were used for the preparation of the educts and the glyco lipids: trichloracetimidate procedure for the preparation of long-chained compounds, glycosylation using the beta-peracetate and boron trifluoride etherate was successful for the preparation of lipids with a medium-alkyl chain length. Preparation of the ester was afforded in a multi-step synthesis according to published procedures. Thus, several lipids were synthesised in a few synthetic steps in good yields. The introduction of unsaturated or methyl branched chains lead to liquid crystallinity at ambient temperature, because these compounds will be used as model compounds for biological systems. The biophysical properties of these compounds will be reported in a following paper.

Synthesis and mesomorphic properties of glycosyl dialkyl- and diacyl-glycerols bearing saturated, unsaturated and methyl branched fatty acid and fatty alcohol chains. Part II. Mesomorphic properties
Milkereit, G., K. Brandenburg, et al. (2005), Chem Phys Lipids 135(1): 15-26.
Abstract: The biophysical properties of a series of glycosyl dialkyl- and diacyl-glycerols bearing unsaturated or chiral methyl branched chains in the tail, and di- and trisaccharide carbohydrate headgroups are described. Thermotropism was investigated by polarising microscopy, the lyotropism was investigated by small angle X-ray diffraction and by the contact preparation method, and the gel to liquid crystalline phase transition by FT-IR-spectroscopy. The compounds displayed thermotropic Smectic A (SmA), cubic and columnar phases, whereas in the lyotropic phase diagram lamellar, hexagonal and cubic phases are found. The introduction of unsaturated or methyl branched chains leads to liquid crystallinity at ambient temperature. The difference between the 1,3-oleyl-glycerol maltoside and the corresponding 1,2-oleoyl-glycerol maltoside is small.

Synthesis and properties of crosslinked recombinant pro-resilin
Elvin, C. M., A. G. Carr, et al. (2005), Nature 437(7061): 999-1002.
Abstract: Resilin is a member of a family of elastic proteins that includes elastin, as well as gluten, gliadin, abductin and spider silks. Resilin is found in specialized regions of the cuticle of most insects, providing low stiffness, high strain and efficient energy storage; it is best known for its roles in insect flight and the remarkable jumping ability of fleas and spittle bugs. Previously, the Drosophila melanogaster CG15920 gene was tentatively identified as one encoding a resilin-like protein (pro-resilin). Here we report the cloning and expression of the first exon of the Drosophila CG15920 gene as a soluble protein in Escherichia coli. We show that this recombinant protein can be cast into a rubber-like biomaterial by rapid photochemical crosslinking. This observation validates the role of the putative elastic repeat motif in resilin function. The resilience (recovery after deformation) of crosslinked recombinant resilin was found to exceed that of unfilled synthetic polybutadiene, a high resilience rubber. We believe that our work will greatly facilitate structural investigations into the functional properties of resilin and shed light on more general aspects of the structure of elastomeric proteins. In addition, the ability to rapidly cast samples of this biomaterial may enable its use in situ for both industrial and biomedical applications.

Synthesis and properties of hydroxyapatite/poly-L-lactide composite biomaterials
Ignjatovic, N., S. Tomic, et al. (1999), Biomaterials 20(9): 809-16.
Abstract: Calcium hydroxyapatite (HAp) and poly-L-lactide (PLLA) were synthesized chemically. The obtained HAp was of high purity and, after special thermal treatment, of high crystallinity as well. Synthesis of PLLA was performed using L-lactide as a monomer and nontoxic initiator. In this way a polymer of large molar weight (about 400,000) was obtained. The HAp and PLLA obtained were used as constituents of the HAp/PLLA composite biomaterial, a potential material for implants. The composite was obtained by mixing completely dissolved PLLA with granules of HAp. The composite was compacted by cold and hot pressing at pressures of 49.0-490.5 MPa and temperatures of 20-184 degrees C. The material obtained at optimum process parameters had a density of 99.6% and compressive strength of 93.2 MPa.

Synthesis and properties of melt-processable hyaluronan esters
Zhang, M. and S. P. James (2005), J Mater Sci Mater Med 16(6): 587-93.
Abstract: A series of melt-processable hyaluronan (HA) esters were synthesized for potential biomedical applications (e.g., hot molding with thermoplastic ultra high molecular weight polyethylene for total joint replacements or molding tissue engineering scaffold). A silylated complex of HA with cetyltrimethylammonium cations (silyl HA-CTA) was used as the starting material. The reactions were performed with acid chlorides as the acylation agents in xylenes or no solvent other than the acid chloride. The disappearance of all characteristic FT-IR vibration bands associated with the -OSi(CH3)3 groups and the appearance of the strong ester carbonyl peak at 1753 cm-1 demonstrated the success of esterification. Thermoplasticity was achieved when the length of aliphatic chains in the HA esters was equal to or greater than 10 carbon atoms. It was found that the longer the ester chain, the lower the melting point; thus, to meet various needs different melting temperatures can be obtained by adjusting the acid chloride chain length.

Synthesis and structure of cerium-substituted hydroxyapatite
Feng, Z., Y. Liao, et al. (2005), J Mater Sci Mater Med 16(5): 417-21.
Abstract: The aim of this study was to explore the effect of cerium ions on the formation and structure of hydroxyapatite (HAP). All particles, prepared by hydrothermal method, were synthesized at varied X(Ce) = Ce/(Ca + Ce) (from 0 to 10%) with the atomic ratio (Ce + Ca)/P fixed at 1.67. Their morphology, composition and crystal structure were characterized by TEM, EPMA, XRD and FTIR. The results showed that in this composition range the apatite structure is maintained, Ce3+ ions could enter the crystal lattice of apatite and substitute Ca2+ ions. The doping of Ce3+ ions resulted in the decrease of the crystallite size with increase in X(Ce). The HAP particles without doping were short rods having a diameter from 10 to 20 nm and a length from 30 to 50 nm. They grew into long needles upon increasing X(Ce).

Synthesis and structure of nanocrystalline TiO2 with lower band gap showing high photocatalytic activity
Nagaveni, K., M. S. Hegde, et al. (2004), Langmuir 20(7): 2900-7.
Abstract: Nanocrystalline TiO2 was synthesized by the solution combustion method using titanyl nitrate and various fuels such as glycine, hexamethylenetetramine, and oxalyldihydrazide. These catalysts are active under visible light, have optical absorption wavelengths below 600 nm, and show superior photocatalytic activity for the degradation of methylene blue and phenol under UV and solar conditions compared to commercial TiO2, Degussa P-25. The higher photocatalytic activity is attributed to the structure of the catalyst. Various studies such as X-ray diffraction, Raman spectroscopy, Brunauer-Emmett-Teller surface area, thermogravimetric-differential thermal analysis, FT-IR spectroscopy, NMR, UV-vis spectroscopy, and surface acidity measurements were conducted. It was concluded that the primary factor for the enhanced activity of combustion-synthesized catalyst is a larger amount of surface hydroxyl groups and a lowered band gap. The lower band gap can be attributed to the carbon inclusion into the TiO2 giving TiO(2-2x)C(x) VO2**.

Synthesis of a poly(L-lysine)-calcium phosphate hybrid on titanium surfaces for enhanced bioactivity
Spoerke, E. D. and S. I. Stupp (2005), Biomaterials 26(25): 5120-9.
Abstract: Titanium has been a successful implant material owing to its excellent strength to weight ratio, toughness, and bioinert oxide surface. Significant progress has been made on the improvement of titanium's bioactivity by coating its oxide surface with calcium phosphates and bioactive molecules. Here, we report on the coating of titanium with a poly(L-lysine)-calcium phosphate hybrid material with a nanoscale texture. This hybrid coating was grown by first nucleating seed crystals of calcium phosphate, directly on the Ti surface and then exposing this surface to solutions containing Ca(2+), PO(4)(3-), and poly(L-lysine). The resultant hybrid coating was characterized by electron microscopy, X-ray diffraction, Fourier transform infrared spectroscopy, thermogravimetric analysis, X-ray photoelectron spectroscopy, and elemental analysis. This material contained 14% by weight poly(L-lysine), and this organic component decreased greatly the dimensions of the surface features, thus enhancing surface area relative to the inorganic control. The highly textured hybrid material was more susceptible than the control to acidic and enzymatic degradation. The amino acid cysteine was covalently linked to the hybrid material, demonstrating the potential of this coating for further functionalization. These hybrid coatings may prove useful in enhancing the bioactivity of titanium.

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Last Modified: 8 February 2006