Biobased polymers derived from itaconic acid bearing clickable groups with potent antibacterial activity and negligible hemolytic activity

Chiloeches, Alberto; Funes, A.; Cuervo-Rodríguez, Rocío; López-Fabal, Fátima; Echeverría, Coro; Muñoz‐Bonilla, Alexandra

doi:10.1039/d1py00098e

Cited by 19 publications

(21 citation statements)

References 35 publications

(40 reference statements)

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“…This value is comparable with other antimicrobial compounds such as MSI-78, a derivative of the natural host-defense peptide magainin, with a selectivity of ~16 for MRSA strain [ 39 ]. However, this value is far from other antimicrobial polymers designed to have low cytotoxicity, for instance using biobased derivatives, by controlling hydrophobic/hydrophilic balance, incorporating PEG or by glycosylation [ 17 , 26 , 35 , 40 ]. In contrast, in Figure 4 b no hemolysis was observed (values well-below 5%) for the low molecular weight degradation product within the tested concentration range (up to 10 mg mL −1 ).…”

Section: Resultsmentioning

confidence: 99%

“…Hemolysis studies were carried out to evaluate the cytotoxicity of the cationic polymer and of the degradation product as previously described [ 26 , 35 ]. Fresh human blood was collected from healthy donors directly into blood collecting tubes containing EDTA to prevent coagulation.…”

Section: Methodsmentioning

confidence: 99%

“…The biodegradability of the polymers can be achieved by the presence or incorporation of labile chemical linkages such as ester, amide and carbonate bonds. Biodegradable polyesters including polylactic acid (PLA), polysaccharides and polyitaconate derivatives have been chemically modified to add antimicrobial moieties in their structures [ 25 , 26 , 27 , 28 , 29 ]. Other strategies involve the incorporation of degradable linkages in the structure of antimicrobial polymers.…”

Section: Introductionmentioning

confidence: 99%

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Antibacterial Polymers Based on Poly(2-hydroxyethyl methacrylate) and Thiazolium Groups with Hydrolytically Labile Linkages Leading to Inactive and Low Cytotoxic Compounds

2021

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Herein, we develop a well-defined antibacterial polymer based on poly(2-hydroxyethyl methacrylate) (PHEMA) and a derivative of vitamin B1, easily degradable into inactive and biocompatible compounds. Hence, thiazole moiety was attached to HEMA monomer through a carbonate pH-sensitive linkage and the resulting monomer was polymerized via reversible addition-fragmentation chain transfer (RAFT) polymerization. N-alkylation reaction of the thiazole groups leads to cationic polymer with thiazolium groups. This polymer exhibits excellent antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA) with an MIC value of 78 µg mL−1, whereas its degradation product, thiazolium small molecule, was found to be inactive. Hemotoxicity studies confirm the negligible cytotoxicity of the degradation product in comparison with the original antibacterial polymer. The degradation of the polymer at physiological pH was found to be progressive and slow, thus the cationic polymer is expected to maintain its antibacterial characteristics at physiological conditions for a relative long period of time before its degradation. This degradation minimizes antimicrobial pollution in the environment and side effects in the body after eradicating bacterial infection.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Antibacterial Polymers Based on Poly(2-hydroxyethyl methacrylate) and Thiazolium Groups with Hydrolytically Labile Linkages Leading to Inactive and Low Cytotoxic Compounds

2021

Self Cite

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“…Itaconic acid was mentioned as one of the promising compounds, among other 12 bio-based products from biorefinery carbohydrates, by the US Department of Energy in 2004 [187]. Its application for innovative polymers (e.g., itaconic-derived antimicrobial polymer [188]) is growing, and the compound market is expected to reach USD 117.1 million by 2026 [189]. Itaconic acid is known to be produced from filamentous fungi, Aspergillus terreus [190].…”

Section: Itaconic Acidmentioning

confidence: 99%

Contribution of Fermentation Technology to Building Blocks for Renewable Plastics

Lomwongsopon

Varrone

2022

Fermentation

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Large-scale worldwide production of plastics requires the use of large quantities of fossil fuels, leading to a negative impact on the environment. If the production of plastic continues to increase at the current rate, the industry will account for one fifth of global oil use by 2050. Bioplastics currently represent less than one percent of total plastic produced, but they are expected to increase in the coming years, due to rising demand. The usage of bioplastics would allow the dependence on fossil fuels to be reduced and could represent an opportunity to add some interesting functionalities to the materials. Moreover, the plastics derived from bio-based resources are more carbon-neutral and their manufacture generates a lower amount of greenhouse gasses. The substitution of conventional plastic with renewable plastic will therefore promote a more sustainable economy, society, and environment. Consequently, more and more studies have been focusing on the production of interesting bio-based building blocks for bioplastics. However, a coherent review of the contribution of fermentation technology to a more sustainable plastic production is yet to be carried out. Here, we present the recent advancement in bioplastic production and describe the possible integration of bio-based monomers as renewable precursors. Representative examples of both published and commercial fermentation processes are discussed.

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“… 1 − 5 Most reported AMPs contain positive charges, whose antimicrobial mechanism largely relies on their ionic interactions with negatively charged bacterial membranes. 6 − 9 However, many ionic AMPs suffer from undesirable water solubility, eco-toxicity, poor compatibility with nonionic matrix materials, and fouling potential, 10 − 15 which could limit their biomedical applications. Nonionic AMPs have potential to resolve these limitations, so they can form a new class of desirable coatings for various biomedical applications.…”

Section: Introductionmentioning

confidence: 99%

Hyperbranched Polyesters Based on Indole- and Lignin-Derived Monomeric Aromatic Aldehydes as Effective Nonionic Antimicrobial Coatings with Excellent Biocompatibility

Xiao

Sathiyaraj

et al. 2021

Biomacromolecules

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This research aims to investigate nonionic hyperbranched polyesters (HBPs) derived from indole and lignin resources as new nontoxic antimicrobial coatings. Three nonionic HBPs with zero to two methoxy ether substituents on each benzene ring in the polymer backbones were synthesized by melt-polycondensation of three corresponding AB 2 monomers. The molecular structures and thermal properties of the obtained HBPs were characterized by gel permeation chromatography, nuclear magnetic resonance spectroscopy, Fourier transform infrared spectroscopy, thermogravimetric analysis, and differential scanning calorimetry analyses. These HBPs were conveniently spin-coated on a silicon substrate, which exhibited significant antibacterial effect against Gram-negative ( Escherichia coli and Pseudomonas aeruginosa ) and Gram-positive bacteria ( Staphylococcus aureus and Enterococcus faecalis ). The presence of methoxy substituents enhanced the antimicrobial effect, and the resulting polymers showed negligible leakage in water. Finally, the polymers with the methoxy functionality exhibited excellent biocompatibility according to the results of hemolysis and MTT assay, which may facilitate their biomedical applications.

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Biobased polymers derived from itaconic acid bearing clickable groups with potent antibacterial activity and negligible hemolytic activity

Abstract: Herein, we report, for the first time, the synthesis of clickable polymers derived from biobased itaconic acid, which was then, employed for the preparation via click chemistry of novel cationic...

Cited by 19 publications

References 35 publications

Antibacterial Polymers Based on Poly(2-hydroxyethyl methacrylate) and Thiazolium Groups with Hydrolytically Labile Linkages Leading to Inactive and Low Cytotoxic Compounds

Antibacterial Polymers Based on Poly(2-hydroxyethyl methacrylate) and Thiazolium Groups with Hydrolytically Labile Linkages Leading to Inactive and Low Cytotoxic Compounds

Contribution of Fermentation Technology to Building Blocks for Renewable Plastics

Hyperbranched Polyesters Based on Indole- and Lignin-Derived Monomeric Aromatic Aldehydes as Effective Nonionic Antimicrobial Coatings with Excellent Biocompatibility

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