Biodegradable Aromatic–Aliphatic Poly(ester–amides) from Monolignol-Based Ester Dimers

Upton, Brianna M.; Kasko, Andrea M.

doi:10.1021/acssuschemeng.7b03784

Cited by 14 publications

(17 citation statements)

References 38 publications

(65 reference statements)

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“…The synthesis of the p-coumaroyl tert-butyl ester (2a), feruloyl tert-butyl ester (2b) and sinapoyl tert-butyl ester (2c) were previously reported. 20 Silica gel 60 (230−400 mesh, Fisher) was used for column chromatography. Thin layer chromatography (TLC) was conducted with silica gel 60-F245 plates and visualized with a hand-held UV lamp.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Biomass-Derived Poly(ether-amide)s Incorporating Hydroxycinnamates

Upton

Kasko

2019

Biomacromolecules

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Lignin-derived chemicals have great potential as feedstock to produce polymeric materials, due to the low cost and high abundance of lignin biomass. Lignin is one of the few nonpetroleum sources of aromatic carbon, a desirable moiety in high-performance polymers. Herein we describe the synthesis and characterization of a series of 21 poly(ether-amide)s that incorporate hydroxycinnamates derived from lignin. Three different hydroxycinnamates (coumaric acid, ferulic acid, sinapinic acid) were incorporated into dimers, and then copolymerized with a series of seven aliphatic and aromatic diamines via interfacial polymerization. The resultant polymers exhibited poor solubility in standard organic solvents (excluding DMF), but exhibited moderate glass transition temperatures and moderate thermal stabilities. Additionally, the polymers exhibit excellent resistance to hydrolysis. The modularity of this synthetic approach could be used to rapidly generate diverse polymers with a broad range of well-tuned properties.

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Section: ■ Experimental Sectionmentioning

confidence: 99%

Biomass-Derived Poly(ether-amide)s Incorporating Hydroxycinnamates

Upton

Kasko

2019

Biomacromolecules

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“…Among the available bioresources, l -amino acids provide a unique opportunity due to their natural abundance as well as their direct relevance to the biological system under physiological conditions . Synthetic polypeptides from l -amino acids and their di- and triblock copolymers were reported for diverse biomedical applications. − Recently, l -amino acid based nonpeptide polymer analogues, such as poly(ester–amide)s, − polyurethanes, polycarbonates, − poly(ester-urea-urethane)s, functional polyesters, − poly(ester-urethanes)s, − etc., were reported. Nanoassemblies of these polymers have a unique ability to undergo biodegradation at the intracellular level to deliver loaded cargoes such as genes and drugs. , Wu et al reported coumarin and the Nile red based FRET probes in GSH redox cleavable l -cysteine based poly(ester–amide) nanocarrier for bioimaging in cancer cells .…”

Section: Introductionmentioning

confidence: 99%

Enzyme-Responsive Theranostic FRET Probe Based on l-Aspartic Amphiphilic Polyester Nanoassemblies for Intracellular Bioimaging in Cancer Cells

Saxena

Pradeep

Jayakannan

2019

ACS Appl. Bio Mater.

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The present study reports one of the first attempts on the design and development of an enzymatic-biodegradable theranostic fluorescence resonance energy transfer (FRET) probe constructed on l-amino acid polymer nanoassemblies and demonstrates the proof-of-concept in live cell bioimaging. l-Aspartic acid was converted into amide or carbamate pendants containing bis-carboxylic acid ester monomers, and they were subjected to melt polymerization along with commercial diols to produce amphiphilic aliphatic polyesters. Nanoparticles of size <200 nm were obtained because of self-assembly of these amphiphilic polyesters in an aqueous medium. These nanoparticles exhibited excellent encapsulation capability for green-fluorescent anti-inflammatory drug curcumin (CUR) and highly luminescent red-fluorophore Nile red (NR) to yield a CUR-NR theranostic FRET probe. Detailed photophysical studies were carried out to demonstrate photoexcitation energy transfer from CUR to NR for the occurrence of the FRET phenomena. The theranostic FRET probe was found to be very stable at extracellular environment and underwent biodegradation at the intracellular regions for delivery of the loaded cargoes. As a result, the theranostic FRET probe functioned as turn-on at the extracellular level and became turn-off at the intracellular level under lysosomal enzyme-responsiveness. The polymer nanoparticle was nontoxic to cells, whereas its CUR encapsulated nanoparticle showed relatively good cytotoxicity in breast cancer cell lines. Live cell confocal microscopy studies using lysotracker staining confirmed the colocalization of CUR as well as NR within the polymer nanoparticles in the lysosomes for enzymatic-biodegradation. Selective photoexcitation experiments in the confocal microscope were carried out to study the FRET probe action in cancer cells. Time-dependent FRET imaging directly supported the occurrence of FRET at the intracellular level and enabled the real-time drug release studies. The present approach opens natural resource-based biodegradable theranostic FRET probes for bioimaging application.

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“…In this review, monomers derived from plant biomass such as glucose are called “phytomonomers”. , The phenolic phytomonomers are used for the synthesis of biobased polymers. , The following sections have been classified into polyesters , and polyamides. , Some of the biobased heterocyclic polymers introduced in this review have higher performance than all the reported neat polymers. The aforementioned approaches allow the establishment of a new class of high-performance materials beyond biobased polymers which will contribute to the industrial polymer materials field in the future.…”

Section: Introductionmentioning

confidence: 99%

Syntheses of Aromatic/Heterocyclic Derived Bioplastics with High Thermal/Mechanical Performance

Ali

Kaneko

2019

Ind. Eng. Chem. Res.

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Biobased plastics derived from renewable starting materials are indispensable for the establishment of low-carbon green-sustainable society. However, aromatic biobased plastics are hardly developed although they are expected to show very high thermal/mechanical performance. The cinnamates are one of the aromatic biobased renewable materials, and cinnamatesbased photofunctional polyesters were prepared which showed high thermomechanical properties. On the other hand, environmentally degradable heterocyclic polyamides including aliphatic/aromatic components derived from itaconic acid showed higher performance than conventional aliphatic polyamides. The heterocyclic polyamides showed UV-triggered solubilization in water which can be expected to apply to a fishing line that is gradually solubilized in seawater under the sunlight. In addition, heterocyclic biobased PAs derived from cinnamate-photodimer derivatives have a significant impact due to their excellent thermal stability, as well as transparency. Considering the cost/performance of biobased polymer, performance should give higher values and the higher possibility to materialize in industry. In this viewpoint, the aromatic biobased polymers are excellent candidates. Further exploration of biobased monomers and the development of cinnamate-derivative production as well as new monomer design present an outstanding prospect to meet the new and advanced horizons of polymer chemistry.

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Biodegradable Aromatic–Aliphatic Poly(ester–amides) from Monolignol-Based Ester Dimers

Cited by 14 publications

References 38 publications

Biomass-Derived Poly(ether-amide)s Incorporating Hydroxycinnamates

Biomass-Derived Poly(ether-amide)s Incorporating Hydroxycinnamates

Enzyme-Responsive Theranostic FRET Probe Based on l-Aspartic Amphiphilic Polyester Nanoassemblies for Intracellular Bioimaging in Cancer Cells

Syntheses of Aromatic/Heterocyclic Derived Bioplastics with High Thermal/Mechanical Performance

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