Preparation of upper critical solution temperature (UCST) responsive diblock copolymers bearing pendant ureido groups and their micelle formation behavior in water

Fujihara, Ami; Shimada, Noritomo; Maruyama, Atsushi; Ishihara, Kazuhíko; Nakai, Keita; Yusa, Shin Ichi

doi:10.1039/c5sm00499c

Cited by 48 publications

(53 citation statements)

References 42 publications

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“…When the temperature decreased, the transparent solution became turbid again. This reversible thermoresponsive behavior is analogous to polymer solutions with an upper critical solution temperature (UCST), above which the assembled polymers will disassemble into free polymers …”

Section: Resultsmentioning

confidence: 99%

“…This reversible thermoresponsive behavior is analogous to polymer solutions with an upper critical solution temperature (UCST), above which the assembled polymers will disassemble into free polymers. [40][41][42][43][44][45][46] Due to the increased hydrophobicity of PEtOx and PnPrOx compared to PMeOx, the transition temperatures of PEtOx2/ TA and PnPrOx2/TA were anticipated to be lower than 90 8C. However, PEtOx2/TA and PnPrOx2/TA solutions were always turbid when the temperature varied from 20 to 80 8C (Fig.…”

Section: Thermoresponsive Properties Investigationmentioning

confidence: 99%

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Thermoresponsive polymeric nanoparticles based on poly(2‐oxazoline)s and tannic acid

Wang

et al. 2018

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

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Hydrogen bonding is widely present and plays a significant role in material science and supramolecular chemistry. This work reports a straightforward strategy for the preparation of polymeric nanoparticles from neutral poly(2‐oxazoline)s (POx) and tannic acid (TA) driven by their intermolecular hydrogen bonding. Dynamic light scattering (DLS) and scanning electron microscope (SEM) measurements showed that POx bearing different substituents, that is, methyl, ethyl and n‐propyl in the 2‐position all could assemble with TA into stable nanoparticles in water or ethanol. The diameter of the assembled nanoparticles could be manipulated by varying parameters such as molecular weight of POx, concentration and ratio of POx, and TA. Interestingly, POx/TA nanoparticles exhibited upper critical solution temperature (UCST)‐type thermoresponsive properties in ethanol or water depending on the molecular weight and substituent in the 2‐position of POx. Increasing or decreasing the temperature at the transition point resulted in the reversible transformation between assembled nanoparticles and disassembled poly(2‐n‐propyl‐2‐oxazoline) (PnPrOx) and TA. In view of the tailored size of the stable nanoparticles and the biocompatibilities of POx and TA, the prepared thermoresponsive nanoparticles are promising candidates as carriers for medicine toward related biomedical applications. © 2018 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2018, 56, 1520–1527

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Section: Resultsmentioning

confidence: 99%

Section: Thermoresponsive Properties Investigationmentioning

confidence: 99%

Thermoresponsive polymeric nanoparticles based on poly(2‐oxazoline)s and tannic acid

Wang

et al. 2018

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

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“…We have reported that temperature induced micelle formation of double hydrophilic block copolymer (PMPC‐ b ‐PUEM) composed of poly(2‐ureidoethylmethacrylate) (PUEM) and biocompatible poly(2‐methacryloyloxyethyl phosphorylcholine) (PMPC) . PMPC‐ b ‐PUEM can dissolve in water as a unimer state above the UCST for the PUEM block.…”

Section: Introductionmentioning

confidence: 99%

Preparation of ureido group bearing polymers and their upper critical solution temperature in water

Fujihara

Itsuki

Shimada

et al. 2016

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

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Poly(2-ureidoethylmethacrylate) (PUEM n ) was synthesized via reversible addition-fragmentation chain transfer (RAFT) radical polymerization and following polymer reaction. We prepared two PUEM n samples with different degrees of polymerization (n 5 100 and 49). The polymers exhibited upper critical solution temperature (UCST) in phosphate-buffered saline (PBS) solution. The phase separation temperature (T p ) in PBS can be controlled ranging from 17 to 55 8C by changing molecular weight of the polymer, polymer concentration, and adding NaCl concentration. The polymers in PBS formed coacervate drops by liquid-liquid phase separations below T p . Results of the dielectric relaxation measurement, the hydration number per monomeric unit was 5 above T p . Based on a fluorescence study, the polymer formed slightly hydrophobic environments below T p . The liquid-liquid phase separation was occurred presumably because of weak hydrophobic interactions and intermolecularly hydrogen bonding interactions between the pendant ureido groups.

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“…39 Moreover, temperature-responsive amphiphilic polymers have been one of the greatest research focuses in recent years as temperature signal can be operated easily in vivo and a large amount of promising biomaterials can be used for hyperthermia-induced drug delivery, smart bioactive surface, protein chromatography and tissue engineering. [57][58][59][60] Among thermoresponsive polymers, poly(N,Ndimethylaminoethyl methacrylate) (PDMAEMA), a typical pHand LCST-type temperature-responsive polymer, has attracted much attention due to its unique role during the transition of LCST-UCST, i.e. the polymer is soluble at low temperature and precipitates at elevated temperatures.…”

Section: Introductionmentioning

confidence: 99%

A star-shaped amphiphilic block copolymer with dual responses: synthesis, crystallization, self-assembly, redox and LCST–UCST thermoresponsive transition

2016

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synthesized by the combination of ring-opening polymerization (ROP), dicyclohexylcarbodiimide (DCC) reaction and atom transfer radical polymerization (ATRP). After the quaternization reaction of the PDMAEMA segment with excess 1,3propane sultone, poly(ε-caprolactone)-SS-poly(3-dimethyl(methacryloyloxyethyl) ammonium propane sulfonate (SPCL-SS-PDMAPS) was obtained. The star-shaped structure of the copolymers and the presence of the amorphous PDMAEMA and PDMAPS in copolymers decreased or even completely suppressed the crystallizability of PCL in copolymers. These copolymers could self-assemble into spherical micelles in water. The thermoresponsive micelle solutions showed transition from a lower critical solution temperature (LCST) of SPCL-SS-PDMAEMA to an upper critical solution temperature (UCST) of SPCL-SS-PDMAPS, indicating that the LCST-UCST transition of the micellar solutions can be accomplished by the transition of PDMAEMA to PDMAPS. Moreover, the redox-responsive investigation showed that the distributions of hydrodynamic radius (Rh) broadened with the emergence of aggregates when DL-dithiothreitol (DTT) was added into the micellar systems, since the DTT would cause the breakage of disulfide bonds linking PCL and the PDMAEMA/PDMAPS blocks in copolymers.The micelles/aggregates that were self-assembled from star-shaped copolymer presented redox-responsive behaviour and LCST-UCST thermoresponsive transition.

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Preparation of upper critical solution temperature (UCST) responsive diblock copolymers bearing pendant ureido groups and their micelle formation behavior in water

Cited by 48 publications

References 42 publications

Thermoresponsive polymeric nanoparticles based on poly(2‐oxazoline)s and tannic acid

Thermoresponsive polymeric nanoparticles based on poly(2‐oxazoline)s and tannic acid

Preparation of ureido group bearing polymers and their upper critical solution temperature in water

A star-shaped amphiphilic block copolymer with dual responses: synthesis, crystallization, self-assembly, redox and LCST–UCST thermoresponsive transition

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