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Advances in Biodegradable Polymers

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A special issue of Molecules (ISSN 1420-3049).

Deadline for manuscript submissions: closed (31 July 2018) | Viewed by 58549

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Prof. Dr. Marek M. Kowalczuk

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1. Wolverhampton School of Biology, Chemistry and Forensic Science, Faculty of Science and Engineering, University of Wolverhampton, Wolverhampton WV1 1LY, UK
2. Centre of Polymer and Carbon Materials, Polish Academy of Sciences, 41-800 Zabrze, Poland
Interests: biocompatible and biodegradable polymer systems; polymer mass spectrometry; bioactive oligomers; controlled drug delivery systems; ring-opening polymerization; forensic engineering of advanced polymeric materials
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Special Issue Information

Dear Colleagues,

Biodegradable polymers have become materials of hope for the future, and knowledge on the relationships among their structure, properties and functions is essential for prospective safe applications of such materials in the areas of human health and the environment. Unfortunately, most plastics produced by the petrochemical industry are not biodegradable and, therefore, accumulate in the environment. This continues to pose a growing challenge for authorities at both the local and national levels; hence, there is a demand for biodegradable polymers. Applying novel biotechnological and chemical approaches enable design of macromolecules with high added value and new biodegradable and bioactive polymers or oligomers for diverse applications in medicine, the cosmetic industry and agriculture are recently developed.

At the initial stages of the development of biodegradable polymers, research was focused on the effect of macromolecular architecture on final biodegradable properties. Unfortunately, aspects such as bio-safety of biodegradable polymers or nano-safety of their composites were, and still are, frequently neglected. In an effort to make biodegradable polymers safe, methodology of forensic engineering of advanced polymeric materials (FEAPM) is currently being developed, which should help to define and minimize potential failure of novel polymer products.

The aim of this Special Issue is to present a contemporary overview of recent developments in the field of biodegradable polymers. Reviews, full papers, and short communications, covering the aspects of the current trends in expansion of such polymeric materials are all welcome.

Prof. Dr. Marek M. Kowalczuk
Guest Editor

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Keywords

synthesis of biodegradable polymers
structure-property relationships of biodegradable polymers
novel analytical approaches for characterization of biodegradable polymers
chemical modification of biodegradable polymers
biosafety of biodegradable polymeric materials
commercial applications of biodegradable polymers

Published Papers (10 papers)

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Research

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13 pages, 4695 KiB

Open AccessArticle

Melt Viscoelastic Assessment of Poly(Lactic Acid) Composting: Influence of UV Ageing

by Vincent Verney, Audrey Ramoné, Florence Delor-Jestin, Sophie Commereuc, Marek Koutny, Geoffrey Perchet and Julien Troquet

Molecules 2018, 23(10), 2682; https://doi.org/10.3390/molecules23102682 - 18 Oct 2018

Cited by 6 | Viewed by 3131

Abstract

This study is devoted to the degradation pathway (bio, photo degradation and photo/bio) of Poly(Lactic acid) PLA polymers by means of melt viscoelasticity. A comparison was made between three PLA polymers with different microstructures (L, D stereoisomers). Biodegradability was determined during composting by burying the polymer films in compost at 58 °C. Melt viscoelasticity was used to assess the molecular evolution of the materials during the composting process. Viscoelastic data were plotted in the complex plane. We used this methodology to check the kinetics of the molecular weight decrease during the initial stages of the degradation, through the evolution of Newtonian viscosity. After a few days in compost, the Newtonian viscosity decreased sharply, meaning that macromolecular chain scissions began at the beginning of the experiments. However, a double molar mass distribution was also observed on Cole–Cole plots, indicating that there is also a chain recombination mechanism competing with the chain scission mechanism. PLA hydrolysis was observed by infra-red spectroscopy, where acid characteristic peaks appeared and became more intense during experiments, confirming hydrolytic activity during the first step of biodegradation. During UV ageing, polymer materials undergo a deep molecular evolution. After photo-degradation, lower viscosities were measured during biodegradation, but no significant differences in composting were found. Full article

(This article belongs to the Special Issue Advances in Biodegradable Polymers)

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19 pages, 5535 KiB

Open AccessArticle

Poly-Gamma-Glutamic Acid (γ-PGA)-Based Encapsulation of Adenovirus to Evade Neutralizing Antibodies

by Ibrahim R. Khalil, Martin P. Khechara, Sathishkumar Kurusamy, Angel L. Armesilla, Abhishek Gupta, Barbara Mendrek, Tamara Khalaf, Mariastella Scandola, Maria Letizia Focarete, Marek Kowalczuk and Iza Radecka

Molecules 2018, 23(10), 2565; https://doi.org/10.3390/molecules23102565 - 08 Oct 2018

Cited by 31 | Viewed by 5595

Abstract

In recent years, there has been an increasing interest in oncolytic adenoviral vectors as an alternative anticancer therapy. The induction of an immune response can be considered as a major limitation of this kind of application. Significant research efforts have been focused on the development of biodegradable polymer poly-gamma-glutamic acid (γ-PGA)-based nanoparticles used as a vector for effective and safe anticancer therapy, owing to their controlled and sustained-release properties, low toxicity, as well as biocompatibility with tissue and cells. This study aimed to introduce a specific destructive and antibody blind polymer-coated viral vector into cancer cells using γ-PGA and chitosan (CH). Adenovirus was successfully encapsulated into the biopolymer particles with an encapsulation efficiency of 92% and particle size of 485 nm using the ionic gelation method. Therapeutic agents or nanoparticles (NPs) that carry therapeutics can be directed specifically to cancerous cells by decorating their surfaces using targeting ligands. Moreover, in vitro neutralizing antibody response against viral capsid proteins can be somewhat reduced by encapsulating adenovirus into γ-PGA-CH NPs, as only 3.1% of the encapsulated adenovirus was detected by anti-adenovirus antibodies in the presented work compared to naked adenoviruses. The results obtained and the unique characteristics of the polymer established in this research could provide a reference for the coating and controlled release of viral vectors used in anticancer therapy. Full article

(This article belongs to the Special Issue Advances in Biodegradable Polymers)

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15 pages, 2042 KiB

Open AccessArticle

Structural Architectural Features of Cyclodextrin Oligoesters Revealed by Fragmentation Mass Spectrometry Analysis

by Cristian Peptu, Maksym Danchenko, Ľudovít Škultéty and Jaroslav Mosnáček

Molecules 2018, 23(9), 2259; https://doi.org/10.3390/molecules23092259 - 05 Sep 2018

Cited by 14 | Viewed by 4153

Abstract

Cyclodextrins (CDs) were used in the present study for the ring-opening oligomerization (ROO) of l-lactide (LA) in order to synthesize biodegradable products with possible applications in pharmaceutical and medical fields. The practical importance of ROO reactions may reside in the possibility of synthesizing novel CD derivatives with high purity due to the dual role played by CDs, the role of the initiator through the hydroxylic groups, and the role of the catalyst by monomer inclusion in the CD cavity. The analyzed compounds were CDs modified with oligolactides obtained through ROO reactions of l-lactide in dimethylformamide. The resulting CD isomeric mixtures were investigated using classical characterization techniques such as gel permeation chromatography and nuclear magnetic resonance. Moreover, advanced mass spectrometry (MS) techniques were employed for the determination of the average number of monomer units attached to the cyclodextrin and the architecture of the derivatives (if the monomer units were attached as a single chain or as multiple chains). Thus, fragmentation studies effectuated on two different instruments (ESI Q-TOF and MALDI TOF) allowed us to correlate the size of the oligolactide chains attached to the CD with the observed fragmentation patterns. Full article

(This article belongs to the Special Issue Advances in Biodegradable Polymers)

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16 pages, 4146 KiB

Open AccessFeature PaperArticle

Molecular Level Structure of Biodegradable Poly(Delta-Valerolactone) Obtained in the Presence of Boric Acid

by Khadar Duale, Magdalena Zięba, Paweł Chaber, Dany Jeanne Di Fouque, Antony Memboeuf, Cristian Peptu, Iza Radecka, Marek Kowalczuk and Grażyna Adamus

Molecules 2018, 23(8), 2034; https://doi.org/10.3390/molecules23082034 - 14 Aug 2018

Cited by 13 | Viewed by 6978

Abstract

In this study, low molecular weight poly(δ-valerolactone) (PVL) was synthesized through bulk-ring openings polymerization of δ-valerolactone with boric acid (B(OH)₃) as a catalyst and benzyl alcohol (BnOH) as an initiator. The resulting homopolymer was characterized with the aid of nuclear magnetic resonance (NMR) and mass spectrometry (MS) techniques to gain further understanding of its molecular structure. The electrospray ionization mass spectrometry (ESI-MS) spectra of poly(δ-valerolactone) showed the presence of two types of homopolyester chains—one terminated by benzyl ester and hydroxyl end groups and one with carboxyl and hydroxyl end groups. Additionally, a small amount of cyclic PVL oligomers was identified. To confirm the structure of PVL oligomers obtained, fragmentation of sodium adducts of individual polyester molecules terminated by various end groups was explored in ESI-MSⁿ by using collision induced dissociation (CID) techniques. The ESI-MSⁿ analyses were conducted both in positive- and negative ion mode. The comparison of the fragmentation spectra obtained with proposed respective theoretical fragmentation pathways allowed the structure of the obtained oligomers to be established at the molecular level. Additionally, using matrix-assisted laser desorption ionization time-of-flight mass spectrometry (MALDI-TOF-MS), it was proven that regardless of the degree of oligomerization, the resulting PVL samples were a mixture of two types of linear PVL oligomers differing in end groups and containing just a small amount of cyclic oligomers that tended to be not visible at higher molar masses. Full article

(This article belongs to the Special Issue Advances in Biodegradable Polymers)

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17 pages, 2217 KiB

Open AccessArticle

Surface Response Methodology-Based Mixture Design to Study the Influence of Polyol Blend Composition on Polyurethanes’ Properties

by Said Arévalo-Alquichire, Maria Morales-Gonzalez, Luis E. Diaz and Manuel F. Valero

Molecules 2018, 23(8), 1942; https://doi.org/10.3390/molecules23081942 - 03 Aug 2018

Cited by 5 | Viewed by 3486

Abstract

Polyurethanes are materials with a strong structure-property relationship. The goal of this research was to study the effect of a polyol blend composition of polyurethanes on its properties using a mixture design and setting mathematic models for each property. Water absorption, hydrolytic degradation, contact angle, tensile strength hardness and modulus were studied. Additionally, thermal stability was studied by thermogravimetric analysis. Area under the curve was used to evaluate the effect of polyol blend composition on thermal stability and kinetics of water absorption and hydrolytic degradation. Least squares were used to calculate the regression coefficients. Models for the properties were significant, and lack of fit was not (p < 0.05). Fit statistics suggest both good fitting and prediction. Water absorption, hydrolytic degradation and contact angle were mediated by the hydrophilic nature of the polyols. Tensile strength, modulus and hardness could be regulated by the PE content and the characteristics of polyols. Regression of DTG curves from thermal analysis showed improvement of thermal stability with the increase of PCL and PE. An ANOVA test of the model terms demonstrated that three component influences on bulk properties like water absorption, hydrolytic degradation, hardness, tensile strength and modulus. The PEG*PCL interaction influences on the contact angle, which is a surface property. Mixture design application allowed for an understanding of the structure-property relationship through mathematic models. Full article

(This article belongs to the Special Issue Advances in Biodegradable Polymers)

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15 pages, 7399 KiB

Open AccessArticle

Oligo-Alginate with Low Molecular Mass Improves Growth and Physiological Activity of Eucomis autumnalis under Salinity Stress

by Piotr Salachna, Monika Grzeszczuk, Edward Meller and Marcin Soból

Molecules 2018, 23(4), 812; https://doi.org/10.3390/molecules23040812 - 02 Apr 2018

Cited by 54 | Viewed by 6526

Abstract

Biopolymers have become increasingly popular as biostimulators of plant growth. One of them, oligo-alginate, is a molecule that regulates plant biological processes and may be used in horticultural practice as a plant growth regulator. Biostimulators are mainly used to improve plant tolerance to abiotic stresses, including salinity. The aim of the study was to assess the effects of salinity and oligo-alginate of various molecular masses on the growth and physiological activity of Eucomis autumnalis. The species is an ornamental and medicinal plant that has been used for a long time in the traditional medicine of South Africa. The bulbs of E. autumnalis were coated using depolymerized sodium alginate of molecular mass 32,000; 42,000, and 64,000 g mol⁻¹. All of these oligo-alginates fractions stimulated plant growth, and the effect was the strongest for the fraction of 32,000 g mol⁻¹. This fraction was then selected for the second stage of the study, when plants were exposed to salt stress evoked by the presence of 100 mM NaCl. We found that the oligo-alginate coating mitigated the negative effects of salinity. Plants treated with the oligomer and watered with NaCl showed smaller reduction in the weight of the above-ground parts and bulbs, pigment content and antioxidant activity as compared with those not treated with the oligo-alginate. The study demonstrated for the first time that low molecular mass oligo-alginate may be used as plant biostimulator that limits negative effects of salinity in E. autumnalis. Full article

(This article belongs to the Special Issue Advances in Biodegradable Polymers)

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18 pages, 3268 KiB

Open AccessArticle

Development of Antimicrobial Biocomposite Films to Preserve the Quality of Bread

by Kelly J. Figueroa-Lopez, Margarita María Andrade-Mahecha and Olga Lucía Torres-Vargas

Molecules 2018, 23(1), 212; https://doi.org/10.3390/molecules23010212 - 19 Jan 2018

Cited by 33 | Viewed by 5001

Abstract

This study focused on the development of gelatin-based films with incorporation of microcrystalline cellulose as reinforcement material. Clove (Syzygium aromaticum), nutmeg (Myristica fragrans), and black pepper (Piper nigrum) oleoresins containing antimicrobial compounds of natural origin were incorporated into the films. The mechanical, thermal, optical, and structural properties, as well as color, seal strength and permeability to water vapor, light, and oil of the films were determined. Adding oleoresins to the gelatin matrix increased the elongation of the material and significantly diminished its permeability to water vapor and oil. Evaluation of the potential use of films containing different oleoresins as bread packaging material was influenced by the film properties. The biocomposite film containing oleoresin from black pepper was the most effective packaging material for maintaining bread’s quality characteristics. Full article

(This article belongs to the Special Issue Advances in Biodegradable Polymers)

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Review

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15 pages, 2976 KiB

Open AccessReview

Polymeric Nanocarriers for the Delivery of Antimalarials

by Zandile Mhlwatika and Blessing Atim Aderibigbe

Molecules 2018, 23(10), 2527; https://doi.org/10.3390/molecules23102527 - 02 Oct 2018

Cited by 39 | Viewed by 4617

Abstract

Malaria is an infectious disease caused by a protozoan parasite which is transmitted by female Anopheles mosquitoes around tropical and sub-tropical regions. Half of the world’s population is at risk of being infected by malaria. This mainly includes children, pregnant women and people living with chronic diseases. The main factor that has contributed to the spread of this disease is the increase in the number of drug-resistant parasites. To overcome drug resistance, researchers have developed drug delivery systems from biodegradable polymers for the loading of antimalarials. The drug delivery systems were characterized by distinct features such as good biocompatibility, high percentage drug encapsulation, reduced drug toxicity and targeted drug delivery. In this review article, we highlight the various types of drug delivery systems developed from polymeric nanocarriers used for the delivery of antimalarials. Full article

(This article belongs to the Special Issue Advances in Biodegradable Polymers)

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14 pages, 3851 KiB

Open AccessReview

Precision Aliphatic Polyesters via Segmer Assembly Polymerization

by Fu-Rong Zeng, Yang Liang and Zi-Long Li

Molecules 2018, 23(2), 452; https://doi.org/10.3390/molecules23020452 - 18 Feb 2018

Cited by 10 | Viewed by 5369

Abstract

Precise structure-property relation of a biodegradable polymer (e.g., aliphatic polyester) is anticipated only if monomer units and chiral centers are arranged in a defined primary sequence as a biomacromolecule. An emerging synthetic methodology, namely segmer assembly polymerization (SAP), is introduced in this paper to reveal the latest progress in polyester synthesis. Almost any periodic polyester envisioned can be synthesized via SAP using a programed linear or cyclic monomer. In this context, the macroscopic properties of a biodegradable polymer are fundamentally determined by microstructural information through a bottom-up approach. It can be highlighted that SAP ideally combines the precision of organic synthesis and the high efficiency of a polymerization reaction. Previously reported strategies including nucleophilic displacement, polyesterification, cross-metathesis polymerization (CMP), ring-opening polymerization (ROP), ring-opening metathesis polymerization (ROMP) and entropy-driven ring-opening metathesis polymerization (ED-ROMP) are critically reviewed in this paper to shed light on precision synthesis of aliphatic polyesters via SAP. Emerging yet challenging, SAP is a paradigm which reflects the convergence of organic and polymer chemistries and is also an efficient pathway to microstructural control. The current status, future challenges and promising trends in this realm are analyzed and discussed in this overview of the state-of-the-art. Full article

(This article belongs to the Special Issue Advances in Biodegradable Polymers)

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20 pages, 629 KiB

Open AccessFeature PaperReview

Biodegradable and Biocompatible Polyhydroxy-alkanoates (PHA): Auspicious Microbial Macromolecules for Pharmaceutical and Therapeutic Applications

by Martin Koller

Molecules 2018, 23(2), 362; https://doi.org/10.3390/molecules23020362 - 08 Feb 2018

Cited by 216 | Viewed by 12403

Abstract

Polyhydroxyalkanoates (PHA) are bio-based microbial biopolyesters; their stiffness, elasticity, crystallinity and degradability are tunable by the monomeric composition, selection of microbial production strain, substrates, process parameters during production, and post-synthetic processing; they display biological alternatives for diverse technomers of petrochemical origin. This, together with the fact that their monomeric and oligomeric in vivo degradation products do not exert any toxic or elsewhere negative effect to living cells or tissue of humans or animals, makes them highly stimulating for various applications in the medical field. This article provides an overview of PHA application in the therapeutic, surgical and tissue engineering area, and reviews strategies to produce PHA at purity levels high enough to be used in vivo. Tested applications of differently composed PHA and advanced follow-up products as carrier materials for controlled in vivo release of anti-cancer drugs or antibiotics, as scaffolds for tissue engineering, as guidance conduits for nerve repair or as enhanced sutures, implants or meshes are discussed from both a biotechnological and a material-scientific perspective. The article also describes the use of traditional processing techniques for production of PHA-based medical devices, such as melt-spinning, melt extrusion, or solvent evaporation, and emerging processing techniques like 3D-printing, computer-aided wet-spinning, laser perforation, and electrospinning. Full article

(This article belongs to the Special Issue Advances in Biodegradable Polymers)

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