Hydrolytic Degradation of Poly(ester amides) Derived from Carbohydrates

Martı́nez, Manuel Bueno; Pinilla, Inmaculada Molina; Mata, Francisca Zamora; Pérez, Juan Manuel Sánchez

doi:10.1021/ma961476z

Cited by 39 publications

(13 citation statements)

References 17 publications

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“…21 In a more detailed study, Makino et al also found that the salt concentration in buffer solutions accelerated ester bond cleavage by converting acidic degradation products into neutral salts. 22 Similar phenomena have been observed with other degradable polymers of the polyamide type 23 and the aliphatic polyester type derived from lactic and glycolic acids (PLAGA). 15 Differences in crystallinity may also explain these differences, as hydrolytic degradation of aliphatic polyesters is known to be faster in amorphous domains than in crystalline ones.…”

Section: Discussionsupporting

confidence: 70%

Mechanism and rate of degradation of polyhydroxyoctanoate films in aqueous media: A long-termin vitro study

Marois

Zhang

Vert

et al. 2000

J. Biomed. Mater. Res.

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The present study investigated the in vitro mechanism and degradation rate of polyhydroxyoctanoate (PHO). Solution-cast PHO films were incubated in either water or isoosmotic phosphate-buffered saline (PBS) for periods ranging from 1 to 24 months. Physical characterization included weight loss, water absorption, pH change, tensile strength, and scanning electron microscopy (SEM) studies. Analytical investigations including electron spectroscopy for chemical analysis, Fourier transform infrared (FTIR) spectroscopy, differential scanning calorimetry (DSC), wide-angle X-ray diffraction, and size exclusion chromatography were also performed to assess chemical and morphological changes to the structure of the PHO. The results show that the PHO-cast films incubated in either water or isoosmotic PBS underwent a simple hydrolytic degradation process characterized by water absorption, gradual molecular weight decrease, and negligible mass loss after 24 months of incubation. DSC results suggest that degradation occurred in the amorphous zone, followed by an attack in the crystalline domain. An increase in the vibration stretching of OH after 24 months of incubation, as revealed by FTIR, may indicate that the degradation process began internally, moving outwardly toward the surface of the PHO films. This process was more rapid in the films incubated in PBS than in those incubated in water. However, no significant changes in the morphology of the films were detected by SEM. This study demonstrated that the in vitro degradation of PHO in water or in PBS is a very slow hydrolytic process, exceeding 2 years. Our findings also suggest that the internal degradation mechanism is faster in PBS because of the ionic strength of the medium and that this internal process surface moves gradually toward the surface.

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Section: Discussionsupporting

confidence: 70%

Mechanism and rate of degradation of polyhydroxyoctanoate films in aqueous media: A long-termin vitro study

Marois

Zhang

Vert

et al. 2000

J. Biomed. Mater. Res.

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“…It is important to study the degradation of these polymers in different mileu since these polymers are intended to be implanted inside the body for different biomedical applications. It has also been proven that amides are not cleaved while only esters contribute for hydrolytic degradation of PEAs . Esters are cleaved at a higher rate in basic pH .…”

Section: Resultsmentioning

confidence: 99%

Poly(ester amide)s from Soybean Oil for Modulated Release and Bone Regeneration

Natarajan

Dasgupta

Shetty

et al. 2016

ACS Appl. Mater. Interfaces

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Designing biomaterials for bone tissue regeneration that are also capable of eluting drugs is challenging. Poly(ester amide)s are known for their commendable mechanical properties, degradation, and cellular response. In this regard, development of new poly(ester amide)s becomes imperative to improve the quality of lives of people affected by bone disorders. In this framework, a family of novel soybean oil based biodegradable poly(ester amide)s was synthesized based on facile catalyst-free melt-condensation reaction. The structure of the polymers was confirmed by FTIR and (1)H -NMR, which indicated the formation of the ester and amide bonds along the polymer backbone. Thermal analysis revealed the amorphous nature of the polymers. Contact angle and swelling studies proved that the hydrophobic nature increased with increase in chain length of the diacids and decreased with increase in molar ratio of sebacic acid. Mechanical studies proved that Young's modulus decreased with decrease in chain lengths of the diacids and increase in molar ratio of sebacic acid. The in vitro hydrolytic degradation and dye release demonstrated that the degradation and release decreased with increase in chain lengths of the diacids and increased with increase in molar ratio of sebacic acid. The degradation followed first order kinetics and dye release followed Higuchi kinetics. In vitro cell studies showed no toxic effects of the polymers. Osteogenesis studies revealed that the polymers can be remarkably efficient because more than twice the amount of minerals were deposited on the polymer surfaces than on the tissue culture polystyrene surfaces. Thus, a family of novel poly(ester amide)s has been synthesized, characterized for controlled release and tissue engineering applications wherein the physical, degradation, and release kinetics can be tuned by varying the monomers and their molar ratios.

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“…47 Amides are cleaved only in the presence of enzymes. 48 Therefore, ester hydrolysis is the contributing factor for the hydrolytic degradation of PEAs. Basic pH accelerates the degradation of the esters.…”

Section: Resultsmentioning

confidence: 99%

“…Digestive system exhibits acidic pH, whereas wound sites in chronic inflammation possess basic pH . Amides are cleaved only in the presence of enzymes . Therefore, ester hydrolysis is the contributing factor for the hydrolytic degradation of PEAs.…”

Section: Results and Discussionmentioning

confidence: 99%

Poly(ester amide)s from Poly(ethylene terephthalate) Waste for Enhancing Bone Regeneration and Controlled Release

Natarajan

Madras

Chatterjee

2017

ACS Appl. Mater. Interfaces

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The present study elucidates the facile synthesis and exceptional properties of a family of novel poly(ester amide)s (PEAs) based on bis(2-hydroxy ethylene) terephthalamide that was obtained from the poly(ethylene terephthalate) waste. Fourier transform infrared and H NMR were used to verify the presence of ester and amide in the polymer backbone. Differential scanning calorimetry data showed that the glass transition temperature decreased with as the chain length of dicarboxylic acids increased. Dynamic mechanical analysis and contact angle studies proved that the modulus values and hydrophobicity increased with as the chain lengths of dicarboxylic acids increased. In vitro hydrolytic degradation and dye release studies demonstrated that the degradation and release decreased with as the chain lengths of dicarboxylic acids increased. Modeling these data illustrated that degradation and release follow first-order degradation and zero-order release, respectively. The in vitro cytocompatibility studies confirmed the minimal toxicity characteristic of these polymers. Osteogenic studies proved that these polymers can be highly influential in diverting the cells toward osteogenic lineage. Alizarin red staining evinced the presence of twice the amount of calcium phosphate deposits by the cells on these polymers when compared to the control. The observed result was also corroborated by the increased expression of alkaline phosphatase. These findings were further validated by the markedly higher mRNA expressions for known osteogenic markers using real time polymerase chain reaction. Therefore, these polymers efficiently promoted osteogenesis. This study demonstrates that the physical properties, degradation, and release kinetics can be altered to meet the specific requirements in organ regeneration as well as facilitate simultaneous polymer resorption through control of the chain length of the monomers. The findings of this study have significant implications for designing cost-effective biodegradable polymers for tissue engineering.

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Hydrolytic Degradation of Poly(ester amides) Derived from Carbohydrates

Cited by 39 publications

References 17 publications

Mechanism and rate of degradation of polyhydroxyoctanoate films in aqueous media: A long-termin vitro study

Mechanism and rate of degradation of polyhydroxyoctanoate films in aqueous media: A long-termin vitro study

Poly(ester amide)s from Soybean Oil for Modulated Release and Bone Regeneration

Poly(ester amide)s from Poly(ethylene terephthalate) Waste for Enhancing Bone Regeneration and Controlled Release

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