Cationic ring-opening polymerization of protected oxazolidine imines resulting in gradient copolymers of poly(2-oxazoline) and poly(urea)

Leiske, Meike N.; Hartlieb, Matthias; Sobotta, Fabian H.; Paulus, Renzo M.; Görls, Helmar; Bellstedt, Peter; Schubert, Ulrich S.

doi:10.1039/c6py00785f

Cited by 5 publications

(4 citation statements)

References 69 publications

(102 reference statements)

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“…This complies with previously published k p values of the homopolymerizations of the investigated monomers . To gain an insight into the monomer distribution within the polymer chain, the calculation of the reactivity ratios is indispensable and was performed using eq . The reactivity ratios of EtOx and BocOx were found to be similar ( r BocOx = 1.02 ≈ 1 ≈ r EtOx = 0.98), suggesting the formation of random copolymers .…”

Section: Resultssupporting

confidence: 72%

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Comparison of random and gradient amino functionalized poly(2‐oxazoline)s: Can the transfection efficiency be tuned by the macromolecular structure?

Hertz

Leiske

Wloka

et al. 2018

J. Polym. Sci. Part A: Polym. Chem.

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Poly(ethylene imine) can be considered as the gold standard for DNA delivery into cells in vitro, but severe cytotoxic side‐effects and inapplicability for targeted approaches in vivo urgently call for the design of new gene carriers. Since poly(2‐oxazoline)s (P(Ox)s) can be easily synthesized and modified, this polymer class might be ideal for the optimization of polymeric transfection processes. The utilization of 2‐methyl‐2‐oxazoline (MeOx) and 2‐ethyl‐2‐oxazoline (EtOx) is also known to be beneficial because these monomers were suggested to overcome solubility issues, mediate stealth behavior and, consequently, facilitate a reduction of cytotoxicity. A series of amino (AmOx) functionalized P(Ox) copolymers with either MeOx (gradient copolymers) or EtOx (random copolymers) was synthesized, deprotected and biochemically characterized regarding cytotoxicity, polyplex formation ability, cellular uptake, and transfection efficiency. Polymers with percentages of AmOx higher than 35 mol % showed stable polyplex formation and also an increase in cytotoxicity. All elucidated P(Ox)s revealed a poor transfection efficiency in both L929 and Hepa1‐6 cell lines. However, the investigations contribute to the understanding of the influence of stealth units (MeOx and EtOx) and their distribution within the polymer chain on selected properties of polyplexes and describe characteristics of amino functionalized P(Ox)s in different cell lines. © 2018 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2018, 56, 1210–1224

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Section: Resultssupporting

confidence: 72%

“…The monomer conversions after certain reaction times could be determined by the utilization of GC measurements. The polymerization constants ( k p ) of the different monomers were calculated using eqs and …”

Section: Resultsmentioning

confidence: 99%

Comparison of random and gradient amino functionalized poly(2‐oxazoline)s: Can the transfection efficiency be tuned by the macromolecular structure?

Hertz

Leiske

Wloka

et al. 2018

J. Polym. Sci. Part A: Polym. Chem.

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“…In this work, a novel fluorine-containing polyether P(FPO/THF) was synthesized by cationic ring-opening polymerization of 2-(2,2,3,3-tetrafluoro-propoxymethyl)-oxirane (FPO) and tetrahydrofuran (THF) [29,30]. The main chain structure of the polyether structure showed the lower glass transition temperature [31].…”

Section: Introductionmentioning

confidence: 99%

Study of a Novel Fluorine-Containing Polyether Waterborne Polyurethane with POSS as a Cross-Linking Agent

Deng

Zhang

et al. 2023

Polymers

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Waterborne polyurethane are more eco-friendly materials due to lower volatile organic compounds (VOCs, mainly isocyanates) content than the alternative materials. However, these rich hydrophilic groups polymers have not yet reached good mechanical properties, durability and hydrophobicity behaviors. Therefore, hydrophobic waterborne polyurethane has become a research hotspot, attracting significant attention. In this work, firstly, a novel fluorine-containing polyether P(FPO/THF) was synthesized by cationic ring-opening polymerization of 2-(2,2,3,3-tetrafluoro-propoxymethyl)-oxirane (FPO) and tetrahydrofuran (THF). Secondly, fluorinated polymer P(FPO/THF), isophorone diisocyanate (IPDI) and hydroxy-terminated polyhedral oligomeric silsesquioxane (POSS-(OH)8) were used to prepare a new fluorinated waterborne polyurethane (FWPU). Hydroxy-terminated POSS-(OH)8 was used as a cross-linking agent, while dimethylolpropionic acid (DMPA) and triethylamine (TEA) were used as a catalyst. Four kinds of waterborne polyurethanes (FWPU0, FWPU1, FWPU3, FWPU5) were obtained by adding different contents of POSS-(OH)8 (0%, 1%, 3%, 5%). The structures of the monomers and polymers were verified by 1H NMR and FT-IR, and the thermal stabilities of various waterborne polyurethanes were analyzed by thermogravimetric analyzer (TGA) and differential scanning calorimetry (DSC). As the results, the thermal analysis showed that the FWPU performed the good thermal stability and the glass transition temperature could reach at about −50 °C. The FWPU1 film exhibited that the elongation at break was 594.4 ± 3.6% and the tensile strength at break was 13.4 ± 0.7 MPa, elucidating that the FWPU1 film developed the excellent mechanical properties relative to the alternative FWPUs. Further, the FWPU5 film performed the promising properties, including the higher surface roughness of FWPU5 film (8.41 nm) obtained by the atomic force microscope (AFM) analysis, and the higher value of water contact angle (WCA) at 104.3 ± 2.7°. Those results illustrated that the novel POSS-based waterborne polyurethane FWPU containing a fluorine element could develop the excellent hydrophobicity and mechanical properties.

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“…Poly(2-oxazoline)s, pseudopeptides having pendent amido groups, are synthesized via ring-opening polymerization of 2-oxazoline [37][38][39][40][41][42][43][44][45][46][47] and are known to show excellent biocompatibility. [48][49][50][51][52][53][54][55][56] We have already reported incorporation of poly(2-oxazoline)s into biosynthesized artificial extracellular matrix protein (CS5-ELF) consisting of a REDV sequence in the cell-binding domain and an elastin-like sequence.…”

Section: Introductionmentioning

confidence: 99%

Preparation of Alginic Acid/Poly(2‐Oxazoline) Hybrid Gels and Their Use in Cell Preservation

Tsurube,

Takasu

2023

Macro Materials & Eng

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A hybrid gel is developed aiming to extend the storage period for cell preservation compared with an alginate gel. The introduction of poly(2‐oxazoline)s into alginic acid promises to improve functional materials by changing their functional groups (e.g., poly(2‐isopropyl‐2‐oxazoline) has the lower critical solution temperature behavior). This study demonstrates chemical modification of a carboxylate of sodium alginate by 1,3‐diaminopropane‐terminated poly(2‐oxazoline)s using 3‐ethylcarbodiimide hydrochloride (EDC) and N‐hydroxy succinimide (NHS) as the condensation reagents for the aminations. The incorporated ratio of poly(2‐oxazoline)s side chains into the carboxylates estimated by 1H NMR is ca. 5–12% and the remaining pendent carboxylates are used for gelation by adding calcium salts (CaCl2). Gelation is observed within 30 min producing 93–99% gel fractions that swell in water. Similar gelation occurs in the cultivation medium of green‐fluorescence protein (GFP)‐encoded and COVID‐19 spike protein‐encoded DNA recombinant E.coli in both the absence and presence of isopropyl β‐D‐1‐thiogalactopyranoside (IPTG). Even in the presence of IPTG, fluorescence ascribed to GFP is not observed while the cells are kept at 25 °C for 3 weeks. After solvation by ethylenediaminetetraacetic acid (EDTA), fluorescence intensity at 508 nm is clearly observed and cell preservation at room temperature is thereby demonstrated.

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Cationic ring-opening polymerization of protected oxazolidine imines resulting in gradient copolymers of poly(2-oxazoline) and poly(urea)

Cited by 5 publications

References 69 publications

Comparison of random and gradient amino functionalized poly(2‐oxazoline)s: Can the transfection efficiency be tuned by the macromolecular structure?

Comparison of random and gradient amino functionalized poly(2‐oxazoline)s: Can the transfection efficiency be tuned by the macromolecular structure?

Study of a Novel Fluorine-Containing Polyether Waterborne Polyurethane with POSS as a Cross-Linking Agent

Preparation of Alginic Acid/Poly(2‐Oxazoline) Hybrid Gels and Their Use in Cell Preservation

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