Variation in structure and properties of poly(glycerol adipate) via control of chain branching during enzymatic synthesis

Taresco, Vincenzo; Creasey, Rhiannon; Kennon, Jeremy Thomas; Mantovani, Giuseppe; Alexander, Cameron; Burley, Jonathan C.; Garnett, Martin C.

doi:10.1016/j.polymer.2016.02.036

Cited by 82 publications

(121 citation statements)

References 36 publications

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“…Further investigations were performed using poly(glycerol‐adipate) (PGA) and some of its modifications ( Figure a) as a polymeric platform. PGA is an amphiphilic polymer, which can be enzymatically synthesized from divinyl adipate and glycerol, with a tunable amount of branches along the main backbone . Due to its intrinsically nontoxic amphiphilic nature, this kind of polyester has been further functionalized to engineer new polymeric platforms for nanotechnology in the healthcare field.…”

Section: Resultsmentioning

confidence: 99%

High‐Throughput Miniaturized Screening of Nanoparticle Formation via Inkjet Printing

Styliari

Conte

Pearce

et al. 2018

Macro Materials & Eng

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The self‐assembly of specific polymers into well‐defined nanoparticles (NPs) is of great interest to the pharmaceutical industry as the resultant materials can act as drug delivery vehicles. In this work, a high‐throughput method to screen the ability of polymers to self‐assemble into NPs using a picoliter inkjet printer is presented. By dispensing polymer solutions in dimethyl sulfoxide (DMSO) from the printer into the wells of a 96‐well plate, containing water as an antisolvent, 50 suspensions are screened for nanoparticle formation rapidly using only nanoliters to microliters. A variety of polymer classes are used and in situ characterization of the submicroliter nanosuspensions shows that the particle size distributions match those of nanoparticles made from bulk suspensions. Dispensing organic polymer solutions into well plates via the printer is thus shown to be a reproducible and fast method for screening nanoparticle formation which uses two to three orders of magnitude less material than conventional techniques. Finally, a pilot study for a high‐throughput pipeline of nanoparticle production, physical property characterization, and cytocompatibility demonstrates the feasibility of the printing approach for screening of nanodrug delivery formulations. Nanoparticles are produced in the well plates, characterized for size and evaluated for effects on metabolic activity of lung cancer cells.

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Section: Resultsmentioning

confidence: 99%

High‐Throughput Miniaturized Screening of Nanoparticle Formation via Inkjet Printing

Styliari

Conte

Pearce

et al. 2018

Macro Materials & Eng

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“…40,41 The physical properties of glycerol-derived polyesters are also known to be sensitive to their microstructure: for example, the hydrophilicity and glass transition temperature of poly(glycerol adipate) depend on the degree of branching. 42 The need for selective access to linear, glycerol-derived polyesters has motivated the development of new synthetic methods. Ring-opening polymerization of glycidyl esters provides macromolecules with low degrees of branching, albeit using synthetic, relatively high-value monomers.…”

Section: Introductionmentioning

confidence: 99%

“…43,44 Lipases have also been used to prepare linear polyesters of glycerol via polycondensation with dicarboxylic acids 45,46 or their bis-vinyl ester derivatives. 47–49 The degrees of polymerization obtained using these enzymatic protocols have been limited due to thermal and shear-induced catalyst degradation, 42,50 issues that could be alleviated using synthetic catalysts. Other potential advantages of using ‘small-molecule’ catalysts in this context include their tolerance of a variety of solvents and reagents, and the possibilities for systematic structural variation.…”

Section: Introductionmentioning

confidence: 99%

Catalyst-controlled polycondensation of glycerol with diacyl chlorides: linear polyesters from a trifunctional monomer

Slavko

Taylor

2017

Chem. Sci.

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“…[258] Similarly,t he lipase of Burkholderia cepacia immobilizedo n diatomaceous earth exhibited an optimal activity at 80 8Cf or the transesterification of dimethyl itaconate, 12-hydroxystearate, and 1,4-BDOi nt oluene. [260] Uyama et al demonstrated that the CALB-catalyzed reaction of divinyl adipate with glycerolw as perfectlyc ontrolled at 45 8Ct og ive ap olyester exclusively based on 1,3-disubstituted units (i.e.,linear polymer). [243] The molar mass decreased at higher temperatures (e.g.,1 00 8C) due to al oss of activitya saresult of CALB denaturationa th ight emperatures.…”

Section: Influence Of Reaction Temperaturementioning

confidence: 99%

Biotic and Abiotic Synthesis of Renewable Aliphatic Polyesters from Short Building Blocks Obtained from Biotechnology

2018

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Biobased polymers have seen their attractiveness increase in recent decades thanks to the significant development of biorefineries to allow access to a wide variety of biobased building blocks. Polyesters are one of the best examples of the development of biobased polymers because most of them now have their monomers produced from renewable resources and are biodegradable. Currently, these polyesters are mainly produced by using traditional chemical catalysts and harsh conditions, but recently greener pathways with nontoxic enzymes as biocatalysts and mild conditions have shown great potential. Bacterial polyesters, such as poly(hydroxyalkanoate)s (PHA), are the best example of the biotic production of high molar mass polymers. PHAs display a wide variety of macromolecular architectures, which allow a large range of applications. The present contribution aims to provide an overview of recent progress in studies on biobased polyesters, especially those made from short building blocks, synthesized through step-growth polymerization. In addition, some important technical aspects of their syntheses through biotic or abiotic pathways have been detailed.

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Variation in structure and properties of poly(glycerol adipate) via control of chain branching during enzymatic synthesis

Cited by 82 publications

References 36 publications

High‐Throughput Miniaturized Screening of Nanoparticle Formation via Inkjet Printing

High‐Throughput Miniaturized Screening of Nanoparticle Formation via Inkjet Printing

Catalyst-controlled polycondensation of glycerol with diacyl chlorides: linear polyesters from a trifunctional monomer

Biotic and Abiotic Synthesis of Renewable Aliphatic Polyesters from Short Building Blocks Obtained from Biotechnology

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