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PubMed2003

Preparation and characterization of polypseudorotaxanes based on block-selected inclusion complexation between poly(propylene oxide)-poly(ethylene oxide)-poly(propylene oxide) triblock copolymers and alpha-cyclodextrin.

A series of new polypseudorotaxanes were synthesized in high yields when the middle poly(ethylene oxide) (PEO) block of poly(propylene oxide)-poly(ethylene oxide)-poly(propylene oxide) (PPO-PEO-PPO) triblock copolymers was selectively recognized and included by alpha-cyclodextrin (alpha-CD) to form crystalline inclusion complexes (ICs), although the middle PEO block was flanked by two thicker PPO blocks, and a PPO chain had been previously thought to be impenetrable to alpha-CD. X-ray diffraction studies demonstrated that the IC domains of the polypseudorotaxanes assumed a channel-type structure similar to the necklace-like ICs formed by alpha-CD and PEO homopolymers. Solid-state CP/MAS (13)C NMR studies showed that the alpha-CD molecules in the polypseudorotaxanes adopted a symmetrical conformation due to the formation of ICs. The compositions and stoichiometry of the polypseudorotaxanes were studied using (1)H NMR, and a 2:1 (ethylene oxide unit to alpha-CD) stoichiometry was found for all polypseudorotaxanes although the PPO-PEO-PPO triblock copolymers had different compositions and block lengths, suggesting that only the PEO block was closely included by alpha-CD molecules, whereas the PPO blocks were uncovered. The hypothesis was further supported by the differential scanning calorimetry (DSC) studies of the polypseudorotaxanes. The glass transitions of the PPO blocks in the polypseudorotaxanes were clearly observed because they were uncovered by alpha-CD and remained amorphous, whereas the glass-transition temperatures increased, because the molecular motion of the PPO blocks was restricted by the hard crystalline phases of the IC domains formed by alpha-CD and the PEO blocks. The thermogravimetric analysis (TGA) revealed that the polypseudorotaxanes had better thermal stability than their free components due to the inclusion complexation. Finally, the kinetics of the threading process of alpha-CD onto the copolymers was also studied. The findings reported in this article suggested interesting possibilities in designing other cyclodextrin ICs and polypseudorotaxanes with block structures.

Cyclodextrins↗
PubMed1994

Surface modification of poly(lactide-co-glycolide) nanospheres by biodegradable poly(lactide)-poly(ethylene glycol) copolymers.

The modification of surface properties of biodegradable poly(lactide-co- glycolide) (PLGA) and model polystyrene nanospheres by poly(lactide)-poly(ethylene glycol) (PLA:PEG) copolymers has been assessed using a range of in vitro characterization methods followed by in vivo studies of the nanospheres biodistribution after intravenous injection into rats. Coating polymers with PLA:PEG ratio of 2:5 and 3:4 (PEG chains of 5000 and 2000 Da. respectively) were studied. The results reveal the formation of a PLA:PEG coating layer on the particle surface resulting in an increase in the surface hydrophilicity and decrease in the surface charge of the nanospheres. The effects of addition of electrolyte and changes in pH on stability of the nanosphere dispersions confirm that uncoated particles are electrostatically stabilized, while in the presence of the copolymers, steric repulsions are responsible for the stability. The PLA:PEG coating also prevented albumin adsorption onto the colloid surface. The evidence that this effect was observed for the PLA:PEG 3:4 coated nanospheres may indicate that a poly(ethylene glycol) chain of 2000 Da can provide an effective repulsive barrier to albumin adsorption. The in vivo results reveal that coating of PLGA nanospheres with PLA:PEG copolymers can alter the biodistribution in comparison to uncoated PLGA nanospheres. Coating of the model polystyrene nanospheres with PLA:PEG copolymers resulted in an initial high circulation level, but after 3 hours the organ deposition data showed values similar to uncoated polystyrene spheres. The difference in the biological behaviour of coated PLGA and polystyrene nanospheres may suggest a different stability of the adsorbed layers on these two systems.(ABSTRACT TRUNCATED AT 250 WORDS)

Animals↗
PubMed2000

Structure of poly (dT).poly (dA).poly (dT).

The molecular structure of poly (dT).poly (dA).poly (dT) has been determined and refined using the continuous x-ray intensity data on layer lines in the diffraction pattern obtained from an oriented fiber of the DNA. The final R-value for the preferred structure is 0.29 significantly lower than that for plausible alternatives. The molecule forms a 12-fold right-handed triple-helix of pitch 38.4 A and each base triplet is stabilized by a set of four Crick-Watson-Hoogsteen hydrogen bonds. The deoxyribose rings in all the three strands have C2'-endo conformations. The grooveless cylindrical shape of the triple-helix is consistent with the lack of lateral organization in the fiber.

DNA↗
PubMed2000

Structure of Poly (U).poly (A).poly (U).

The molecular structure of poly (U).poly (A).poly (U) has been determined and refined using the continuous x-ray intensity data on layer lines in the diffraction pattern obtained from an oriented fiber of the RNA. The final R-value for the preferred structure is 0.24, far lower than that for the plausible alternatives. The polymer forms an 11-fold right-handed triple-helix of pitch 33.5A and each base triplet is stabilized by Crick-Watson-Hoogsteen hydrogen bonds. The ribose rings in the three strands have C3'-endo, C2'-endo and C2'-endo conformations, respectively. The helix derives additional stability through systematic interchain hydrogen bonds involving ribose hydroxyls and uracil bases. The relatively grooveless cylindrical shape of the triple-helix is consistent with the lack of lateral organization.

DNA↗
PubMed2000

Structure of poly (I).poly (A).poly (I).

The molecular structure of poly (I).poly (A).poly (I) has been determined and refined using the continuous intensity data on layer lines in the x-ray diffraction pattern obtained from an oriented fiber of this polymorphic RNA complex. The polymer forms a 12-fold right-handed triple-helix of pitch 39.7A and each base-triplet is stabilized by quasi Crick-Watson-Hoogsteen hydrogen bonds. The ribose rings in all the three strands have C3'-endo conformations. The final R-value for this best structure is 0.24 and the x-ray fit is significantly superior to all the alternative structures where the different chains might have different furanose conformations. This all-purine triple-helix, counter-intuitively, has a diameter roughly 3A shorter than that of DNA and RNA triple-helices containing a homopurine and two complementary homopyrimidine strands. Its compact, grooveless cylindrical shape is consistent with the lack of lateral organization.

Adenine↗
PubMed1979

Serological analysis of antigen-specific helper factors specific for poly-L(Tyr, Glu)-poly-DLAla--poly-LLys [(T, G)-A--L] and L Glu60-LAla30-LTyr10 (GAT).

In vitro prepared antigen-specific helper factors reactive to the synthetic polypeptide antigens poly-L(Tyr, Glu)-poly-DLAla--poly-LLys [(T, G)-A--L] or LGlu60-LAla30-LTyr10 (GAT) and bearing Ia determinants were analyzed serologically to determine the nature of the Ia determinants they expressed. I subregion-specific mouse anti-Ia antisera were used, and showed that (T, G)-A--L-specific helper factor (HF) contains I-A subregion-controlled determinants, whereas GAT-specific HF carries I-J subregion-controlled antigens. This unexptected finding was confirmed in both the H-2k and H-2 b haplotypes, using a variety of anti-I-J antisera. Rabbit anti-Ia antisera also reacted with both HF which raised the possibility that the Ia determinants on HF may be carbohydrate in nature. The fact that HF has a low molecular weight and yet contains Ia determinants, antigen-binding capacity and idiotypic markers is compatible with this interpretation.

Adsorption↗
PubMed1981

Enhancing effect of murine anti-idiotypic serum on the proliferative response specific for poly(LTyr, LGlu)-poly(DLAla)--poly(LLys)[(T,G)-A--L].

Murine anti-idiotypic serum against C3 H.SW anti-poly(LTyr, LGlu)-poly(DLAla)--poly(LLys)[(T,G)-A--L] antibodies was elicited in C57BL/6 mice. The effect of the anti-idiotypes on the proliferation of primed lymph node cells was investigated. The anti-idiotypic serum stimulated the proliferative response of the (T,G)-A--L-specific lymph node cells as well as of nylon wool-enriched T cells. In the presence of suboptimal doses of (T,G)-A--L, the addition of the anti-idiotypes enhanced the proliferation to the levels obtained with the optimal dose of (T,G)-A--L itself. These results suggest the existence of shared idiotypic determinants between antibodies and the (T,G)-A--L-specific proliferative T cells.

Animals↗
PubMed2007

In vitro degradation of biodegradable blending materials based on poly(p-dioxanone) and poly(vinyl alcohol)-graft-poly(p-dioxanone) with high molecular weights.

Amphiphilic biodegradable graft copolymer, poly(vinyl alcohol)-graft-poly(p-dioxanone) (PVA-g-PPDO), was used to prepare a new biodegradable material by blending with poly(p-dioxanone) (PPDO). The in vitro degradation properties of the copolymer and blends with different contents of PVA-g-PPDO were studied in phosphate buffer at 37 degrees C. The degradation processes of the PVA-g-PPDO and its blends with the PPDO were monitored by weight loss, viscosimetry, water uptake, differential scanning calorimetry (DSC), and scanning electron microscopy. The results of inherent viscosity and weight loss reveal that the PVA-g-PPDO has a different in vitro degradation behavior from that of PPDO, and the introducing of copolymer into the blending system may enhance the degradability of PPDO when the contents of copolymer is higher than 5%. The change of the degree of crystallization (Dc) of copolymer and blends derived from the DSC also shows that the copolymer and blends have faster degradation rates than the neat PPDO during the testing period. A degradation mechanism of the blends was postulated based on the results of the weight retention, inherent viscosity measurement, and DSC.

Biocompatible Materials↗
PubMed2002

The effect of salts on the micellization temperature of aqueous poly(ethylene oxide)-b-poly(propylene oxide)-b-poly(ethylene oxide) solutions and the dissolution rate and water diffusion coefficient in their corresponding gels.

Studies were performed to examine the effect of ionic salts on phase transitions, dissolution rates, and diffusion coefficients of water in gels of poly(ethylene oxide)-b-poly(propylene oxide)-b-poly(ethylene oxide) with polymer concentrations ranging from 22 to 32% w/w and salt concentrations ranging from 0 to 1.5% w/w. Salts tested include Na(3)PO(4), Na(2)SO(4), Na(2)HPO(4), NaH(2)PO(4), NaCH(3)CO(2), NaCl, and KI. Micellization transition temperatures were obtained using differential scanning calorimetry. The dissolution rates were obtained by measurement of the surface erosion rates, and diffusion coefficients were obtained by using a method to analyze the intrusion of water into the aqueous gels. It was found that salts had no effect on the dissolution rate of the polymer gels into deionized water. However, when the salt concentration in the aqueous dissolution media was adjusted to match the concentration in the gels, the dissolution rate of the polymer gel decreased with increasing salt concentration. The salts also had a profound effect on the critical micellization temperature (CMT) and the diffusion coefficient of water within the gel. The diffusion coefficient and CMT decreased in the presence of salts. The magnitude of these effects was comparable to their placement on the Hofmeister, or lyotropic series for salts. The effects of polymer and salt concentrations on the CMT were quantified, and a single correlation was proposed to predict the micellization temperatures for a wide range of salt and polymer concentrations.

Diffusion↗
PubMed1996

Self-Assembly in a Mixture of Two Poly(ethylene oxide)-b-poly(propylene oxide)-b-poly(ethylene oxide) Copolymers in Water

The self-assembly behavior in water of a mixture of two poly (ethylene oxide)-b-poly(propylene oxide)-b-poly(ethylene oxide) copolymers, (EO)13(PO)30(EO)13 (L64) and (EO)37(PO)58(EO)37 (P105), was explored at 25°C. The phase boundaries were established using 2H-NMR and inspection under polarized light; the structure of the various lyotropic liquid crystalline (LLC) phases was determined with small-angle X-ray scattering, while viscosity and differential scanning calorimetry measurements were used to probe the isotropic water-rich solution region. Isotropic regions, similar to the neat polymers, are stable at high polymer content. The addition of water induces structure in the amphiphilic block copolymer system. An extended lamellar (D) LLC phase is formed at 20-25% water content; a hexagonal (E) and a cubic (I) LLC phases supersede D at higher water contents. In addition to the above, a narrow isotropic region (L') is observed on the L64-water binary axis, in equilibrium with the E and the D phases. The hexagonal and lamellar LLC phases extended all the way from the L64-rich to the P105-rich side of the ternary L64-P105-water phase diagram; the characteristic hexagonal and lamellar structural dimensions varied linearly with P105 content in the L64-P105 mixture at a constant water concentration. An isotropic (micellar) solution phase (L1) dominates the high-water content corner of the ternary phase diagram. Viscosity measurements in this region provided evidence for increased interactions between the micelles as the boundary to the LLC phases was approached.

Journal Article↗
PubMed2006

The use of poly(sodium N-undecanoyl-L-leucylvalinate), poly(sodium N-undecanoyl-L-leucinate) and poly(sodium N-undecanoyl-L-valinate) surfactants as chiral selectors for determination of enantiomeric composition of samples by multivariate regression modeling of fluorescence spectral data.

Steady-state fluorescence spectroscopy was employed to investigate the use of chiral polymeric surfactants as chiral selectors in chiral analysis by multivariate regression modeling of spectral data. Partial-least-squares regression modeling (PLS-1) was used to correlate changes in the fluorescence spectral data of 1,1'-bi-2-naphthol (BOH), 1,1'-binaphthyl-2,2'-diamine (BNA), or 2,2,2-trifluoroanthrylethanol (TFA) in the presence of poly(sodium N-undecanoyl-L-leucylvalinate), poly(sodium N-undecanoyl-L-leucinate) or poly(sodium N-undecanoyl-L-valinate) as the enantiomeric composition of the chiral analytes was varied. The regression models produced from the spectral data were validated by determining the enantiomeric composition of independently prepared test solutions. The ability of the model to correctly predict the enantiomeric composition of future samples was evaluated using the root-mean-square percent-relative error (RMS%RE) of prediction. In terms of RMS%RE, the ability of the model to accurately predict the enantiomeric composition of future samples was dependent on the chiral analyte, the polymeric surfactant used, and the surfactant medium, and ranged between 1.57 and 6.10%. Chiral analyte concentrations as low as 5 x 10(-6) M were found to give regression models with good predictability.

Anthracenes↗
PubMed1977

Physicochemical studies of a branched polypeptide antigen: poly(L-Tyr,L-Glu)-poly(DL-Ala)--poly(L-Lys).

The synthesis of a branched polypeptide, poly(L-Tyr,L-Glu)-poly(DL-Ala)--poly(L-Lys), is described. Physicochemical investigations of the polymer by means of hydrogen-deuterium exchange, potentiometric titrations, and viscosity measurements indicate a non-ordered, flexible conformation in aqueous solution, depending on pH and salt concentration. A hysteresis phenomenon observed in the titrations is tentatively ascribed to interactions between the sidechains, and in accordance with observations from the infrared spectrum of the polymer it is suggested that rather slow conformational changes of the polymer molecules occur in aqueous solutions. The immunochemical implications of the physiochemical findings are discussed with special reference to the concept of sequential and conformational determinants.

Alanine↗
PubMed1996

Stability study of nanoparticles of poly(epsilon-caprolactone), poly(D,L-lactide) and poly(D,L-lactide-co-glycolide).

The objective was to evaluate the stability of nanoparticles prepared with poly(epsilon-caprolactone), poly(D,L-lactide) and poly(D,L-lactide-co-glycolide) polymers and stored at different temperatures and in different media. The stability parameters studied were molecular weight and crystallinity of the polymer, nanoparticle size and pH. The results show that the stability of polymeric nanoparticles depends on (i) the type of polymers with the following increasing order of polymer stability: PLA25GA50 < PLA37.5GA25 < PLA50 = PCL, (ii) the storage temperature: PCL and PLA50 nanoparticles can be kept at 4 degrees C and RT during one year, while PLA37.5GA25 and PLA25GA50 nanoparticles have to be stored at 4 degrees C, and (iii) the storage conditions: buffering or freeze-drying nanoparticles improves stability.

Biopolymers↗
PubMed2004

Synthesis of a novel structural triblock copolymer of poly(gamma -benzyl-l-glutamic acid)-b-poly(ethylene oxide)-b-poly(epsilon-caprolactone).

A novel structural triblock copolymer of poly(gamma-benzyl-l-glutamic acid)-b-poly(ethylene oxide)-b-poly(epsilon-caprolactone) (PBLG-PEO-PCL) was synthesized by a new approach in the following three steps: (1) sequential anionic ring opening polymerization (ROP) of ethylene oxide and epsilon-caprolactone with an acetonitrile/potassium naphthalene initiator system to obtain a diblock copolymer CN-PEO-PCL with a cyano end-group; (2) conversion of the CN end-group into NH2 end-group by hydrogenation to obtain NH2-PEO-PCL; (3) ROP of gamma-benzyl-l-glutamate-N-carboxyanhydrides (Bz-l-GluNCA) with NH2-PEO-PCL as macroinitiator to obtain the target triblock copolymer. The structures from CN-PEO precursor to the triblock copolymers were confirmed by FT-IR and 1H NMR spectroscopy, and their molecular weights were measured by gel permeation chromatography. The monomer of Bz-l-GluNCA can react almost quantitatively with the amino end-groups of NH2-PEO-PCL macroinitiator by ROP.

Biocompatible Materials↗
PubMed2005

Cytotoxicity of thermosensitive polymers poly(N-isopropylacrylamide), poly(N-vinylcaprolactam) and amphiphilically modified poly(N-vinylcaprolactam).

Thermosensitive polymers poly(N-isopropylacrylamide) (PNIPAM), poly(N-vinylcaprolactam) (PVCL) and PVCL grafted with amphiphilic poly(ethylene oxide) (PEO) chains (PVCL-graft-C11EO42) were prepared and characterized and their putative cytotoxicity was evaluated. The cytotoxicity of these thermosensitive polymers and their monomers was investigated as a function of polymer concentration, incubation time and incubation temperature by using 3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) and lactate dehydrogenase (LDH) cytotoxicity tests in Caco-2 and Calu-3 cell cultures. Also, the influence of the chain end functionality on toxicity was examined. Viability (MTT) and cellular damage (LDH) of the cells were shown to be dependent on the surface properties of the polymers, hydrophilicity or hydrophobicity. Hydrophilic PVCL and PVCL-graft-C11EO42 were well tolerated at all polymer concentrations (0.1-10.0 mg/ml) after 3 h of incubation at room temperature and at physiological temperature (37 degrees C). The more hydrophobic PNIPAM induced more clear cellular cytotoxicity at 37 degrees C. The monomers N-isopropylacrylamide and vinylcaprolactam and PEO-macromonomer showed dramatically higher cytotoxicity values with respect to the corresponding polymers. Cell damage was directly dependent on concentration, temperature and incubation time.

Acrylic Resins↗
PubMed2006

Biodegradability and biocompatibility of a pH- and thermo-sensitive hydrogel formed from a sulfonamide-modified poly(epsilon-caprolactone-co-lactide)-poly(ethylene glycol)-poly(epsilon-caprolactone-co-lactide) block copolymer.

A pH- and thermo-sensitive block copolymer was synthesized by adding pH-sensitive sulfamethazine oligomers (SMOs) to either end of a thermo-sensitive poly(epsilon-caprolactone-co-lactide)-poly(ethylene glycol)-poly(epsilon-caprolactone-co-lactide) (PCLA-PEG-PCLA) block copolymer. The resulting pH- and thermo-sensitive SMO-PCLA-PEG-PCLA-SMO block copolymer solution did not form a gel at high pH (pH 8.0) or at increased temperatures (ca. 70 degrees C), but did form a stable gel under physiological conditions (pH 7.4 and 37 degrees C). The degradation rate of the pH- and thermo-sensitive block copolymer decreased substantially compared with the control block copolymer of PCLA-PEG-PCLA, due to the buffering effect of the SMO-PCLA-PEG-PCLA-SMO sulfonamide groups on the acidic monomer-induced rapid degradation of PCLA-PEG-PCLA. This suitable sol-gel transition and sustained biodegradability of the pH- and thermo-sensitive SMO-PCLA-PEG-PCLA-SMO block copolymer resolves two of the major drawbacks associated with thermo-sensitive block copolymers, namely premature gelation and rapid degradation. Interestingly, SMO-PCLA-PEG-PCLA-SMO showed no evidence of cytotoxicity in vitro. However, subcutaneous injection of the pH- and thermo-sensitive block copolymer solution (20wt% in PBS at pH 8.0) into Sprague-Dawley (SD) rats resulted in rapid, stable gel formation, with the injected hydrogel being completely degraded in vivo in just 6 weeks. The injected hydrogel in vivo presented a typical acute inflammation within 2 weeks, although chronic inflammation was not observed during the first 6-week period. As such, the pH- and thermo-sensitive hydrogel of the SMO-PCLA-PEG-PCLA-SMO block copolymer is a suitable candidate for use in drug delivery systems and cell therapy.

Animals↗
PubMed2006

Dynamics of micelles of the triblock copolymers poly(ethylene oxide)-poly(propylene oxide)-poly(ethylene oxide) in aqueous solution.

A number of results reported on the kinetics of exchange of triblock copolymers poly(ethylene oxide)-poly(propylene oxide)-poly(ethylene oxide), PEO-PPO-PEO, between micelles and the intermicellar aqueous solution are reviewed and analyzed to extract the rate constants k(+) for the entry of a copolymer into a micelle and k(-) for the exit of a copolymer from a micelle. Contrary to what is generally observed for conventional surfactants, the rate constant for the entry of a copolymer into a micelle is slower to much slower than for a diffusion-controlled process and decreases as the degree of polymerization of the PO block, n(PO), increases. The effect of the degree of polymerization of the EO block, n(EO), on the two rate constants is significant only for low values of n(EO). The variation of k(-) with n(PO) strongly suggests that the free copolymer molecule adopts a conformation where the PO block is tightly coiled with little contact with water and not a fully extended and hydrated conformation, in contrast to what is commonly assumed when analyzing the dependence of the cmc on the polymerization degree of the hydrophobic block.

Journal Article↗
PubMed2004

Effects of poly(ethylene oxide)-poly(propylene oxide)-poly(ethylene oxide) triblock copolymers on structure and stability of liposomal dioleoylphosphatidylethanolamine.

The effects caused by poly(ethylene oxide)-poly(propylene oxide)-poly(ethylene oxide) (PEO-PPO-PEO; Pluronic) copolymers on the structure and stability of dioleoylphosphatidylethanolamine (DOPE) liposomes were studied by means of turbidity, leakage, and cryo-transmission electron microscopy investigations. The results show that by inclusion of Pluronics in the DOPE dispersion it is possible to stabilize the lamellar Lalpha phase and to produce liposomes that are stable and nonleaky at low pH (pH 5). The stabilizing capacity was observed to depend critically on the molecular composition of the Pluronics. Block copolymers with comparably long PPO and PEO segment lengths, such as F127 and F108, most effectively protected DOPE liposomes prepared at high pH from aggregation and subsequent structural rearrangements induced by acidification. A sufficiently long PPO block was found to be the most decisive parameter in order to obtain adequate coverage of the liposome surface at low Pluronic concentrations. Upon increasing the copolymer concentration, however, Pluronics with comparably short PPO and PEO segment lengths, such as F87 and P85, could also be used to stabilize the DOPE liposomes. Essentially the same trends were observed when the Pluronics were added to preformed DOPE liposomes instead of being included in the preparation mixture. In this case the least effective copolymers failed, however, to completely prevent the DOPE liposomes from releasing encapsulated hydrophilic markers.

Cryoelectron Microscopy↗