Hydrogels with multiple clickable anchor points: synthesis and characterization of poly(furfuryl glycidyl ether)-<i>block</i>-poly(ethylene glycol) macromonomers

Adatia, Karishma K.; Keller, Stefan; Götz, Tobias; Tovar, Günter E. M.; Southan, Alexander

doi:10.1039/c9py00755e

Cited by 6 publications

(3 citation statements)

References 80 publications

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“…The intensity counts of each gray scale (8 bit = 256 different possible values) were multiplied by the gray scale value to correlate the integral of the resulting curve with the amount of fluorophore-labeled azides. The integrals of both coatings ( click ECM and biotinylated click ECM) were then compared, and the resulting differences were statistically evaluated …”

Section: Methodsmentioning

confidence: 99%

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Azide-Functional Extracellular Matrix Coatings as a Bioactive Platform for Bioconjugation

Keller

Wörgötter

Liedek

et al. 2020

ACS Appl. Mater. Interfaces

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In recent years, the development and application of decellularized extracellular matrices (ECMs) for use as biomaterials have grown rapidly. These cellderived matrices (CDMs) represent highly bioactive and biocompatible materials consisting of a complex assembly of biomolecules. Even though CDMs mimic the natural microenvironment of cells in vivo very closely, they still lack specifically addressable functional groups, which are often required to tailor a biomaterial functionality by bioconjugation. To overcome this limitation, metabolic glycoengineering has emerged as a powerful tool to equip CDMs with chemical groups such as azides. These small chemical handles are known for their ability to undergo bioorthogonal click reactions, which represent a desirable reaction type for bioconjugation. However, ECM insolubility makes its processing very challenging. In this contribution, we isolated both the unmodified ECM and azide-modified clickECM by osmotic lysis. In a first step, these matrices were concentrated to remove excessive water from the decellularization step. Next, the hydrogellike ECM and clickECM films were mechanically fragmentized, resulting in easy to pipette suspensions with fragment sizes ranging from 7.62 to 31.29 μm (as indicated by the mean d 90 and d 10 values). The biomolecular composition was not impaired as proven by immunohistochemistry. The suspensions were used for the reproducible generation of surface coatings, which proved to be homogeneous in terms of ECM fragment sizes and coating thicknesses (the mean coating thickness was found to be 33.2 ± 7.3 μm). Furthermore, they were stable against fluid-mechanical abrasion in a laminar flow cell. When primary human fibroblasts were cultured on the coated substrates, an increased bioactivity was observed. By conjugating the azides within the clickECM coatings with alkyne-coupled biotin molecules, a bioconjugation platform was obtained, where the biotin−streptavidin interaction could be used. Its applicability was demonstrated by equipping the bioactive clickECM coatings with horseradish peroxidase as a model enzyme.

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Section: Methodsmentioning

confidence: 99%

“…The integrals of both coatings (clickECM and biotinylated clickECM) were then compared, and the resulting differences were statistically evaluated. 42 2.1.14. Conjugation of Biotinylated clickECMs with a Fluorophore-Linked Streptavidin Molecule.…”

Section: Materials Instruments and Methodsmentioning

confidence: 99%

Azide-Functional Extracellular Matrix Coatings as a Bioactive Platform for Bioconjugation

Keller

Wörgötter

Liedek

et al. 2020

ACS Appl. Mater. Interfaces

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“…Different strategies have been followed to form covalently bonded reversibly crosslinked polymers and include (i) the introduction of cleavable linkages into monomers 38–40 and (ii) the utilization of monomers bearing functional groups such as cyclopentadiene, 41 anthracene, 42 paraformaldehyde‐diamine, 43 fulvenes, 44 triazolinedione‐indole 45 or furan–maleimide, 46 which can be cleaved effectively by the application of external stimuli. Of these, furan and maleimide functional groups are of great interest and have found wider applicability as the presence of pendent furyl and maleimido groups offers opportunities not only for crosslinking reactions but also for reversible functionalization using appropriate reagents 47–51 . To synthesize thermally reversible crosslinked polymers, the furan–maleimide reaction is highly desirable because the reaction proceeds at ambient temperature forming a cyclic adduct and breaking of the bonds occurs in the temperature range 90–150 °C regenerating furan and maleimide 46,52 .…”

Section: Introductionmentioning

confidence: 99%

Partially bio‐based furyl‐functionalized organosoluble poly(ether ether ketone)s

Kuhire

Talanikar

Tawade

et al. 2020

Polymer International

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A new series of partially bio‐based (co)poly(ether ether ketone)s bearing pendent furyl groups was synthesized by nucleophilic aromatic substitution polycondensation of varying molar proportions of 4,4′‐(furan‐2‐ylmethylene)bis(2‐methoxyphenol) and bisphenol‐A with 4,4′‐difluorobenzophenone. The chemical structures, compositions and random nature of (co)poly(ether ether ketone)s were confirmed by NMR spectroscopy. Inherent viscosities and number‐average molecular weights of the (co)poly(ether ether ketone)s were in the range 0.74–2.90 dL g−1 and 33 500–46 300 g mol−1, respectively, indicating the formation of reasonably high molecular weight polymers. (Co)poly(ether ether ketone)s were readily soluble in common organic solvents and could be cast into tough, transparent and flexible films from chloroform solutions. (Co)poly(ether ether ketone)s exhibited 10% weight loss and glass transition temperatures in the range 429–464 and 152–156 °C, respectively. A representative copoly(ether ether ketone) was crosslinked with 1,1′‐(methylenedi‐1,4‐phenylene)bismaleimide via Diels–Alder reaction to form a crosslinked polymer which showed improved mechanical properties and was recycled twice without significant loss of mechanical properties. Diels–Alder/retro Diels–Alder reaction was demonstrated by studies of sol–gel transformation, solubility tests, DSC and stress–strain measurements. © 2020 Society of Chemical Industry

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Coumarin‐4‐ylmethyl‐ and p‐Hydroxyphenacyl‐Based Photoacid Generators with High Solubility in Aqueous Media: Synthesis, Stability and Photolysis

et al. 2020

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(Coumarin‐4‐yl)methyl (c4m) and p‐hydroxyphenacyl (pHP)‐based compounds are well known for their highly efficient photoreactions, but often show limited solubility in aqueous media. To circumvent this, we synthesized and characterized the two new c4m and pHP‐based photoacid generators (PAGs), 7‐[bis(carboxymethyl)amino]‐4‐(acetoxymethyl)coumarin (c4m‐ac) and p‐hydroxyphenacyl‐2,5,8,11‐tetraoxatridecan‐13‐oate (pHP‐t), and determined their solubilities, stabilities and photolysis in aqueous media. The two compounds showed high solubilities in water of 2.77 mmol L−1±0.07 mmol L−1 (c4m‐ac) and 124.66 mmol L−1±2.1 mmol L−1 (pHP‐t). In basic conditions at pH 9, solubility increased for c4m‐ac to 646.46 mmol L−1±0.63 mmol L−1, for pHP‐t it decreased to 34.68 mmol L−1±0.62 mmol L−1. Photochemical properties of the two PAGs, such as the absorption maxima, the maximum molar absorption coefficients and the quantum yields, were found to be strongly pH‐dependent. Both PAGs showed high stabilities s24h ≥95 % in water for 24 h, but decreasing stability with increasing pH value due to hydrolysis. The present study contributes to a clearer insight into the synthesis, solubilities, stabilities, and photolysis of c4m and pHP‐based PAGs for further photochemical applications when high PAG concentrations are required, such as in polymeric foaming.

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Hydrogels with multiple clickable anchor points: synthesis and characterization of poly(furfuryl glycidyl ether)-block-poly(ethylene glycol) macromonomers

Abstract: Functional polyacrylamide hydrogels containing multiple furfuryl anchor points for Diels–Alder reactions were prepared employing new macromonomers.

Cited by 6 publications

References 80 publications

Azide-Functional Extracellular Matrix Coatings as a Bioactive Platform for Bioconjugation

Azide-Functional Extracellular Matrix Coatings as a Bioactive Platform for Bioconjugation

Partially bio‐based furyl‐functionalized organosoluble poly(ether ether ketone)s

Coumarin‐4‐ylmethyl‐ and p‐Hydroxyphenacyl‐Based Photoacid Generators with High Solubility in Aqueous Media: Synthesis, Stability and Photolysis

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