Enzymatic Poly(octamethylene suberate) Synthesis by a Two-Step Polymerization Method Based on the New Greener Polymer-5B Technology

Pfluck, Ana C. D.; Barros, Dragana P.C. de; Oliva, Abel; Fonseca, Luís P.

doi:10.3390/pr10020221

Cited by 3 publications

(4 citation statements)

References 33 publications

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“…A heating treatment (60 or 80°C) was applied to the as‐obtained wet POS together with immobilized CALB without stirring, achieving a 1.7‐ and 1.8‐fold M w increase (in‐water and in‐miniemulsion synthesized POS respectively). Incubation of isolated wet polymers (without catalyst) under heat did not lead to any changes, confirming that thermal polymerization does not occur 53 …”

Section: Post‐reaction Strategies For Mw Increasementioning

confidence: 61%

“…Incubation of isolated wet polymers (without catalyst) under heat did not lead to any changes, confirming that thermal polymerization does not occur. 53 On the other hand, for LA/GA polymerization, M n values did increase with thermal treatment. The assays were performed on PLGAs prepared in isopropyl ether with different composition (M n < 1000 Da), under vacuum at 190 C, during 20 h. Final molecular weights ranged between 8400 (LA/GA = 25/75) and 10,129 Da (LA/GA = 50/50).…”

Section: Post-reaction Strategies For Mw Increasementioning

confidence: 93%

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Evaluation of biocatalytic pathways in the synthesis of polyesters: Towards a greener production of surgical sutures

Nicolás

Lassalle

Ferreira

2022

Polymers for Advanced Techs

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This review presents an updated and alternative perspective on enzymatic synthesis to obtain polyesters, with a focus on the precursor materials for absorbable sutures: poly‐lactic, poly‐glycolic, and poly‐lactic‐co‐glycolic acids. Currently, the profitable path towards the industrial synthesis of polyesters is ring‐opening polymerization (ROP) of lactones, which is an experimentally complex process and implies a hazardous environmental impact due to the need for energy consumption, use of large volumes of toxic organic solvents and of non‐biocompatible metal‐based catalysts. On the contrary, enzymatically driven reactions may be performed under mild conditions in simple reactors. Mechanistic and experimental issues of the two major biocatalyzed strategies ‐direct condensation and ROP‐ were analyzed from a green chemistry perspective. These enzyme‐catalyzed poly‐esterifications often return low yield and/or low final molecular weight (Mw). Considering all the analyzed published data available, possible strategies to overcome these limitations were postulated: implementation of aqueous biphasic reaction systems, use of ultrasound agitation and sequential addition of reactants or co‐solvents. To promote Mw increment, post‐reaction treatments can be carried out such as thermally induced short‐chain polymerization under vacuum and incorporation of glycols as chain extenders.

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Section: Post‐reaction Strategies For Mw Increasementioning

confidence: 61%

Section: Post-reaction Strategies For Mw Increasementioning

confidence: 93%

Evaluation of biocatalytic pathways in the synthesis of polyesters: Towards a greener production of surgical sutures

Nicolás

Lassalle

Ferreira

2022

Polymers for Advanced Techs

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“…Although poly(alkylene dicarboxylate)s have been broadly studied [ 10 , 21 , 22 , 23 ], there is a lack of data on using 1,8-octane diol polyesters as nanocarriers. Nevertheless, this group of esters’ synthesis, crystallization behaviour, and good mechanical properties have been reported [ 23 , 24 , 25 , 26 , 27 ].…”

Section: Introductionmentioning

confidence: 99%

“…We previously demonstrated the preparation of poly(octamethylene suberate) (POS), biodegradable AP using enzymatic polymerization in a miniemulsion system and water as a reaction media using Polymer-5B technology [ 23 , 24 , 25 ]. The impact of polymer degradation products on cells and tissue is crucial for applying biodegradable polymers [ 28 ].…”

Section: Introductionmentioning

confidence: 99%

Design and Biocompatibility of Biodegradable Poly(octamethylene suberate) Nanoparticles to Treat Skin Diseases

de Barros,

Fonseca,

Gonçalves

et al. 2024

Pharmaceutics

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Biodegradable aliphatic polyester formulations as carriers for topical drug delivery show the potential to encapsulate structurally different therapeutic compounds. Poly(octamethylene suberate) (POS) nanoparticles (POS-NPs) were used as a matrix to encapsulate four therapeutic molecules used to treat skin disorders: caffeine (CF), quercetin (QR), hydrocortisone (HC), and adapalene (AD). Hydrophobicity and chemical structure of bioactive compounds (BCs) influenced the physicochemical stability of drug-loaded nanoparticles. The particle size of drug-loaded nanoparticles was between 254.9 nm for the CF-POS-NP and 1291.3 for QR-POS-NP. Particles had a negative charge from −27.6 mV (QR) to −49.2 mV (HC). Drug loading content for all BC-POS-NPs varies between 36.11 ± 1.48% (CF-POS-NP) and 66.66 ± 4.87% (AD-POS-NP), and their entrapment efficiency is relatively high (28.30 ± 1.81% and 99.95 ± 0.04%, respectively). Calorimetric analysis showed the appearance of polymorphism for AD- and HC-loaded systems and the drug’s complete solubilisation into all nanoparticle formulations. FTIR and NMR spectra showed apparent drug incorporation into the polymer matrix of NPs. The encapsulation of BCs enhanced the antioxidative effect. The prepared POS nanoparticles’ cytotoxicity was studied using two dermal cell lines, keratinocyte (HaCaT) cells and fibroblasts (HDFn). The nanoparticle cytotoxic effect was more substantial on HaCaT cell lines. A reconstructed human epidermis (RHE) was successfully used to investigate the penetration of polymeric NPs. Based on permeation and histology studies, HC-POS-NPs and CF-POS-NPs were shown not to be suitable for dermal applications with the explored drug concentrations. AD presents a high permeation rate and no toxic impact on RHE.

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Recent Advances in the Enzymatic Synthesis of Polyester

Wang

Liu²,

Lee

et al. 2022

Polymers

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Polyester is a kind of polymer composed of ester bond-linked polybasic acids and polyol. This type of polymer has a wide range of applications in various industries, such as automotive, furniture, coatings, packaging, and biomedical. The traditional process of synthesizing polyester mainly uses metal catalyst polymerization under high-temperature. This condition may have problems with metal residue and undesired side reactions. As an alternative, enzyme-catalyzed polymerization is evolving rapidly due to the metal-free residue, satisfactory biocompatibility, and mild reaction conditions. This article presented the reaction modes of enzyme-catalyzed ring-opening polymerization and enzyme-catalyzed polycondensation and their combinations, respectively. In addition, the article also summarized how lipase-catalyzed the polymerization of polyester, which includes (i) the distinctive features of lipase, (ⅱ) the lipase-catalyzed polymerization and its mechanism, and (ⅲ) the lipase stability under organic solvent and high-temperature conditions. In addition, this article also focused on the advantages and disadvantages of enzyme-catalyzed polyester synthesis under different solvent systems, including organic solvent systems, solvent-free systems, and green solvent systems. The challenges of enzyme optimization and process equipment innovation for further industrialization of enzyme-catalyzed polyester synthesis were also discussed in this article.

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Enzymatic Poly(octamethylene suberate) Synthesis by a Two-Step Polymerization Method Based on the New Greener Polymer-5B Technology

Cited by 3 publications

References 33 publications

Evaluation of biocatalytic pathways in the synthesis of polyesters: Towards a greener production of surgical sutures

Evaluation of biocatalytic pathways in the synthesis of polyesters: Towards a greener production of surgical sutures

Design and Biocompatibility of Biodegradable Poly(octamethylene suberate) Nanoparticles to Treat Skin Diseases

Recent Advances in the Enzymatic Synthesis of Polyester

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