Hydrophilic polymethacrylates containing cholic acid-ethylene glycol derivatives as pendant groups

Benrebouh, Amina; Zhang, Yuehua; Zhu, Xiaoxia

doi:10.1002/1521-3927(20000601)21:10<685::aid-marc685>3.0.co;2-e

Cited by 30 publications

(23 citation statements)

References 20 publications

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“…The nanoparticles prepared from amphiphilic polymers find significant applications in life sciences as clinical diagnostic assays, drug delivery systems and so forth. In recent years, nanoparticles composed of bile acids have attracted considerable interest 1–8. Bile acids (BA)s are natural compounds consisting of a facially amphiphilic steroid nucleus with a hydrophobic β‐side and a hydrophilic α‐side 2.…”

Section: Introductionmentioning

confidence: 99%

“…The amphiphilicity, structure rigidity and acid–base characteristics of the BA molecules make them useful building blocks in biomedical applications. Various polymers with BA residues on the main chain,3, 4, 9 as the pendant groups1, 2, 5, 10 and as the chain‐end groups11 have been synthesized. Due to the biological origin of BA, the inclusion of BA residues into polymers can lead usually to great improvement in the polymers' biocompatibility which is very important for biomedical applications.…”

Section: Introductionmentioning

confidence: 99%

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Self‐aggregated nanoparticles composed of periodate‐oxidized dextran and cholic acid: preparation, stabilization and in‐vitro drug release

Yuan

Zhu

et al. 2006

J of Chemical Tech & Biotech

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A novel method was used to synthesize cholic acid hydrophobic-modified dextrans (CAH-Dex) which form nanoparticles in aqueous solution. The stabilization and drug-loading of the formed nanoparticles were investigated. Dextran was oxidized by sodium periodate to dextran dialdehyde which was then conjugated with cholic acid hydrazide through an acyl hydrazone linkage. The self-aggregation behavior of the resulting conjugates was investigated using nuclear magnetic resonance, fluorescence and photo correlation spectrometry. The conjugates were found to have low critical aggregate concentrations (CAC) (0.46-0.96 × 10 −2 mg mL −1 ) which is characteristic, depending on both the oxidization and substitution degrees. Above the CAC the conjugates tend to form nanoparticle aggregates with inner hydrophobic environment. The diameters of the nanoparticles rely on the pH of the medium due to the aldo-enol transition of the dextran dialdehyde. By crosslinking the aldehyde groups located on the surface using adipic dihydrazide, the nanoparticles were obviously stabilized. The drug-loading and release behavior of the nanoparticles was investigated using indomethacin as a hydrophobic model drug.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Self‐aggregated nanoparticles composed of periodate‐oxidized dextran and cholic acid: preparation, stabilization and in‐vitro drug release

Yuan

Zhu

et al. 2006

J of Chemical Tech & Biotech

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“…It is well known that processability may be improved by the addition of flexible chains to the polyamide backbone, which enhance the molecular mobility, providing better solubility and reducing T g 8–11. For this particular purpose, ethylene oxide units have been extensively incorporated into polymers 12–15. Additionally, the ether linkages can form hydrogen bonds with water, which a priori should improve their water uptake.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization, and water sorption properties of new aromatic polyamides containing benzimidazole and ethylene oxide moieties

Ayala

Maya

García

et al. 2004

J. Polym. Sci. A Polym. Chem.

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New polyamides, containing a benzimidazole side group and ethylene oxide moieties in the structural repeat unit, were synthesized by low‐temperature polycondensation. The aim of this design was to obtain polyamides that were more soluble in common organic solvents and hence had better processability than benzimidazole polyamides while maintaining the water sorption properties characteristic of the latter. The results showed that the number of ether linkages of the repeat unit played an important role in the glass‐transition temperature and in the water sorption properties, the polyamides with one or two ethylene oxide units being more hydrophilic than benzimidazole polyamides. However, the length of the ethylene oxide chain played a minor role in the solubility because the second member of the series, with two ether linkages (i.e., one ethylene oxide unit), reached the same level of solubility as those polyamides with more ethylene oxide moieties. No crystallinity was observed by X‐ray and calorimetric measurements for the new polymers. © 2004 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 43: 112–121, 2005

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“…A series of cholic acid polymer derivatives have been used for drug delivery systems, molecular recognition, dental fillings, and bone repairing materials [23–25]. It is now recognized that the incorporation of a bio-compound such as cholic acid into polymers can improve biological compatibility, activity and safety for biomedical applications [26, 27]. We thus hypothesize that such amphiphilic star-shaped CA(PEG) 4 polymers may be useful for coating RBC before blood transfusion or for intravenous injection in the treatment of elevated RBC aggregation, thus providing rheological benefits similar to Pluronic F68 and PEG.…”

Section: Introductionmentioning

confidence: 99%

Effects of amphiphilic star-shaped poly(ethylene glycol) polymers with a cholic acid core on human red blood cell aggregation

Janvier¹,

Zhu²,

Armstrong³

et al. 2013

Journal of the Mechanical Behavior of Biomedical Materials

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Elevated red blood cell (RBC) aggregation increases low-shear blood viscosity and is closely related to several pathophysiological diseases such as atherosclerosis, thrombosis, diabetes, hypertension, cancer, and hereditary chronic hemolytic conditions. Non-ionic linear polymers such as poly(ethylene glycol) (PEG) and Pluronic F68 have shown inhibitory effects against RBC aggregation. However, hypersensitivity reactions in some individuals, attributed to a diblock component of Pluronic F68, have been reported. Therefore, we investigated the use of an amphiphilic star-shaped PEG polymer based on a cholic acid core as a substitute for Pluronics to reduce RBC aggregation. Cholic acid is a natural bile acid produced in the human liver and therefore should assure biocompatibility. Cholic acid based PEG polymers, termed CA(PEG)4, were synthesized by anionic polymerization. Size exclusion chromatography indicated narrow mass distributions and hydrodynamic radii less than 2 nm were calculated. The effects of CA(PEG)4 on human RBC aggregation and blood viscosity were investigated and compared to linear PEGs by light transmission aggregometry. Results showed optimal reduction of RBC aggregation for molar masses between 10–16 kDa of star-shaped CA(PEG)4 polymers. Cholic acid based PEG polymers affect the rheology of erythrocytes and may find applications as alternatives to linear PEG or Pluronics to improve blood fluidity.

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Hydrophilic polymethacrylates containing cholic acid-ethylene glycol derivatives as pendant groups

Cited by 30 publications

References 20 publications

Self‐aggregated nanoparticles composed of periodate‐oxidized dextran and cholic acid: preparation, stabilization and in‐vitro drug release

Self‐aggregated nanoparticles composed of periodate‐oxidized dextran and cholic acid: preparation, stabilization and in‐vitro drug release

Synthesis, characterization, and water sorption properties of new aromatic polyamides containing benzimidazole and ethylene oxide moieties

Effects of amphiphilic star-shaped poly(ethylene glycol) polymers with a cholic acid core on human red blood cell aggregation

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