Microstructure analysis of biocompatible phosphoester copolymers

Steinbach, Tobias; Schröder, Romina; Ritz, Sandra; Wurm, Frederik R.

doi:10.1039/c3py00563a

Cited by 54 publications

(49 citation statements)

References 44 publications

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“…As in our previous studies, 2‐(benzyloxy)ethanol was used as an initiator to enable calculation of the molecular weight of the polymer by 1 H NMR spectroscopy . Aromatic signals at ≈7.5 ppm were compared with the signals of the polyphosphate backbone at 4 ppm (see the Supporting Information for details).…”

Section: Resultsmentioning

confidence: 99%

Reversible Bioconjugation: Biodegradable Poly(phosphate)‐Protein Conjugates

Steinbach

Becker

Spiegel

et al. 2016

Macromolecular Bioscience

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Protein-polymer conjugates are widely used to improve the pharmacokinetic properties of therapeutic proteins. Commercially available conjugates employ poly(ethylene glycol) (PEG) as the protective polymer; however, PEG has a number of shortcomings, including non-biodegradability and immunogenicity, that call for the development of alternatives. Here, the synthesis of biodegradable poly(phosphate), that is, poly(ethyl ethylene phosphate) (PEEP), by organo-catalyzed anionic ring-opening polymerization exhibiting dispersity values Ð < 1.3 is reported. Polymers with molecular weights between 2000 and 33 200 g mol are then ω-functionalized with a succinimidyl carbonate group and subsequently conjugated to model proteins. These are the first conjugates based on polyphosphates which degraded upon exposure to phosphodiesterase. As is the case for PEGylated therapeutics, residual in vitro activity of the PPEylated conjugates depends on the extent of protein modification. These results suggest that PEEP exhibits the desired properties of a biopolymer for use in next generation, fully degradable drug delivery systems.

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Section: Resultsmentioning

confidence: 99%

Reversible Bioconjugation: Biodegradable Poly(phosphate)‐Protein Conjugates

Steinbach

Becker

Spiegel

et al. 2016

Macromolecular Bioscience

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“…[1][2][3] While many types of hydrogels [4][5][6] have been studied in detail, the rarity of phosphodiester-based materials [7][8][9] is remarkable given their prevalence in nature. Phosphotriesters [10][11][12][13][14][15][16][17] enjoy widespread use and can be purified and synthesized via conventional synthetic techniques, but lack the biomimetic advantages that the ionic phosphodiesters have to offer.…”

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confidence: 99%

Phosphodiester Hydrogels for Cell Scaffolding and Drug Release Applications

Dera

Diliën

Billen

et al. 2019

Macromolecular Bioscience

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Given the major structural role phosphodiesters play in the organism it is surprising they have not been more widely adopted as a building block in sophisticated biomimetic hydrogels and other biomaterials. The potential benefits are substantial: phosphoester‐based materials show excellent compatibility with blood, cells, and a remarkable resistance to protein adsorption that may trigger a foreign‐body response. In this work, a novel class of phosphodiester‐based ionic hydrogels is presented which are crosslinked via a phosphodiester moiety. The material shows good compatibility with blood, supports the growth and proliferation of tissue and presents opportunities for use as a drug release matrix as shown with fluorescent model compounds. The final gel is produced via base‐induced elimination from a phosphotriester precursor, which is made by the free‐radical polymerization of a phosphotriester crosslinker. This crosslinker is easily synthesized via multigram one‐pot procedures out of common laboratory chemicals. Via the addition of various comonomers the properties of the final gel may be tuned leading to a wide range of novel applications for this exciting class of materials.

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“…In order to avoid metal contamination without any special purification steps, the organocatalytic approach has emerged as a powerful metal-free polymerization process in recent years. 7 Considerable effort has been directed toward the evaluation of various types of both organic acids/bases for the ROP of cyclic esters, 7-37 cyclic carbonates, [38][39][40][41][42][43] epoxides, [44][45][46][47] lactams, 48 cyclic (carbo)siloxanes, 49 cyclic phosphates, [50][51][52][53][54] etc. Regarding the ROP of cyclic esters, organic Brønsted acids, e.g., methane sulfonic acid (MSA) and triflimide, were found to be suited for the polymerization of lactones, [8][9][10][11][12][13][14][15][16][17][18][19] whereas organic bases, e.g., 1,8-diazadicyclo [5.4.0]undec-7-ene (DBU) and 4-dimethylaminopyridine (DMAP), were effective for the ROP of the lactide (LA).…”

Section: Introductionmentioning

confidence: 99%

Organophosphate-catalyzed bulk ring-opening polymerization as an environmentally benign route leading to block copolyesters, end-functionalized polyesters, and polyester-based polyurethane

et al. 2015

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Abstract. The ring-opening polymerizations (ROPs) of ε-caprolactone (ε-CL), -varelolactone, 1,5-dioxepan-2-one, trimethylene carbonate, and L-lactide were performed in the bulk using an organophosphate, such as diphenyl phosphate, bis(4-nitrophenyl)phosphate, and di(2,6-xylyl)phosphate, as the catalyst. The ROPs proceeded in a well-controlled manner even in the bulk condition to afford well-defined aliphatic polyesters, polyester-ether, and polycarbonate with relatively low dispersities. Notably, the amount of the loaded catalyst was successfully reduced when compared to the conventional organophosphate-catalyzed ROP in solution. A kinetic study revealed the controlled/living nature of the present bulk ROP system, which allowed us to produce the block copolymers composed of polyesters, polyester-ether, and polycarbonate in one-pot. Syntheses of the end-functionalized poly(ε-caprolactone)s (PCLs) and poly(trimethylene carbonate) were successfully demonstrated using alcohol initiators possessing highly reactive functional groups. Furthermore, the α,ω-dihydroxy telechelic PCL-diol as well as the three-and four-armed star-shaped PCL-polyols were also easily obtained by using the polyols as an initiator. Finally, the one-pot synthesis of polyurethane via the ROP of ε-CL and subsequent urethane forming reaction was demonstrated by taking advantage of the dual catalytic abilities of the organophosphate for both the ROP and polyurethane synthesis.

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Microstructure analysis of biocompatible phosphoester copolymers

Cited by 54 publications

References 44 publications

Reversible Bioconjugation: Biodegradable Poly(phosphate)‐Protein Conjugates

Reversible Bioconjugation: Biodegradable Poly(phosphate)‐Protein Conjugates

Phosphodiester Hydrogels for Cell Scaffolding and Drug Release Applications

Organophosphate-catalyzed bulk ring-opening polymerization as an environmentally benign route leading to block copolyesters, end-functionalized polyesters, and polyester-based polyurethane

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