Synthesis and solution behaviour of dual light- and temperature-responsive poly(triethylene glycol-<i>co</i>-spiropyran) copolymers and block copolymers

Grimm, Oliver; Maßmann, Sarina C.; Schacher, Felix H.

doi:10.1039/c9py00458k

Cited by 18 publications

(26 citation statements)

References 69 publications

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“…SP-incorporating poly (oligo (ethylene glycol) acrylate)-based copolymers have been synthesized by nitroxide mediated polymerization with varying amounts of SP (from 0 to 16 mol%). The visible light irradiation of the copolymer dissolved in pH 8 TRIS buffer resulted in a decrease in its cloud point temperature by 30 K at 16 mol% SP content, as previously detected by UV/Vis spectroscopy [45].…”

Section: Introductionsupporting

confidence: 76%

Controlling Growth of Poly (Triethylene Glycol Acrylate-Co-Spiropyran Acrylate) Copolymer Liquid Films on a Hydrophilic Surface by Light and Temperature

et al. 2021

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A quartz crystal microbalance with dissipation monitoring (QCM-D) was employed for in situ investigations of the effect of temperature and light on the conformational changes of a poly (triethylene glycol acrylate-co-spiropyran acrylate) (P (TEGA-co-SPA)) copolymer containing 12–14% of spiropyran at the silica–water interface. By monitoring shifts in resonance frequency and in acoustic dissipation as a function of temperature and illumination conditions, we investigated the evolution of viscoelastic properties of the P (TEGA-co-SPA)-rich wetting layer growing on the sensor, from which we deduced the characteristic coil-to-globule transition temperature, corresponding to the lower critical solution temperature (LCST) of the PTEGA part. We show that the coil-to-globule transition of the adsorbed copolymer being exposed to visible or UV light shifts to lower LCST as compared to the bulk solution: the transition temperature determined acoustically on the surface is 4 to 8 K lower than the cloud point temperature reported by UV/VIS spectroscopy in aqueous solution. We attribute our findings to non-equilibrium effects caused by confinement of the copolymer chains on the surface. Thermal stimuli and light can be used to manipulate the film formation process and the film’s conformational state, which affects its subsequent response behavior.

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Section: Introductionsupporting

confidence: 76%

Controlling Growth of Poly (Triethylene Glycol Acrylate-Co-Spiropyran Acrylate) Copolymer Liquid Films on a Hydrophilic Surface by Light and Temperature

et al. 2021

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“…[ 15 ] PNIPAM can be made to have light and temperature dual sensitive properties by incorporating photosensitive groups or molecules such as azobenzenes, stilbenes, spiropyrans (SPA), spirooxazines fulgides, and diarylethenes into the end groups or side chains of PNIPAM. [ 14,16–18 ] Light‐responsive materials receive particular attention in many research fields including biomedicine as light sources are safe, clean, easy to use, and controlled. [ 19 ] Many researchers reported dual‐/tri‐/multi‐responsive random and/or block copolymers consisting of photo‐responsive SPA and temperature‐, pH‐ and/or CO 2 ‐ sensitive segments because of the quick response rate and reversible isomerization of SPA molecules.…”

Section: Introductionmentioning

confidence: 99%

“…[ 19 ] Many researchers reported dual‐/tri‐/multi‐responsive random and/or block copolymers consisting of photo‐responsive SPA and temperature‐, pH‐ and/or CO 2 ‐ sensitive segments because of the quick response rate and reversible isomerization of SPA molecules. [ 17,18,20,21 ] Cloud point temperature or LCST was influenced by the switching state and the amount of SPA moieties. A very low concentration of SPA molecules showed high‐efficiency light‐controlled drug release, and the release efficiency reached even up to 90–100% under UV light irradiation.…”

Section: Introductionmentioning

confidence: 99%

Temperature and Photo Dual‐Stimuli Responsive Block Copolymer Self‐Assembly Micelles for Cellular Controlled Drug Release

Zhou

Zhang

Chen

et al. 2020

Macromolecular Bioscience

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To well adapt to the complicated physiological environments, it is necessary to engineer dual‐ and/or multi‐stimuli responsive drug carriers for more effective drug release. For this, a novel temperature responsive lateral chain photosensitive block copolymer, poly[(N‐isopropylacrylamide‐co‐N,N‐dimethylacrylamide) ‐block‐propyleneacylalkyl‐4‐azobenzoate] (P(NIPAM‐co‐DMAA)‐b‐PAzoHPA), is synthesized by atom transfer radical polymerization. The structure is characterized by 1H nuclear magnetic resonance spectrometry and laser light scattering gel chromatography system. The self‐assembly behavior, morphology, and sizes of micelles are investigated by fluorescence spectroscopy, transmission electron microscope, and laser particle analyzer. Dual responsiveness to light and temperature is explored by ultraviolet–visible absorption spectroscopy. The results show that the copolymer micelles take on apparent light and temperature dual responsiveness, and its lower critical solution temperature (LCST) is above 37 °C, and changes with the trans‐/cis‐ isomerization of azobenzene structure under UV irradiation. The blank copolymers are nontoxic, whereas the paclitaxel (PTX)‐loaded counterparts possessed comparable anticancer activities to free PTX, with entrapment efficiency of 83.7%. The PTX release from the PTX‐loaded micelles can be mediated by changing temperature and/or light stimuli. The developed block copolymers can potentially be used for cancer therapy as drug controlled release carriers.

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“…A range of water-soluble acrylic polymers based on ethylene glycol side chains were first synthesized: (i) homopolymers of triethylene glycol methyl ether acrylate (PmTEGA) and (ii) copolymers of diethylene glycol ethyl ether acrylate and oligoethylene glycol methyl ether acrylate (P(eDEGA-co-mOEGA)). PmTEGA is water-soluble in the useful temperature range of PPCs (< 55-70 8C) [25][26][27][28] and may impart a stealth character and improved solubility to proteins. P(eDEGA-co-mOEGA)s exhibit a lower critical solution temperature (LCST), which depends on the exact comonomer ratio, [29,30] and will lead to thermoresponsive PPCs at possibly useful temperatures.…”

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confidence: 99%

Hetero‐Diels–Alder Cycloaddition with RAFT Polymers as Bioconjugation Platform

et al. 2020

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We introduce the bioconjugation of polymers synthesized by RAFT polymerization, bearing no specific functional end group, by means of hetero-Diels-Alder cycloaddition through their inherent terminal thiocarbonylthio moiety with a diene-modified model protein. Quantitative conjugation occurs over the course of a few hours, at ambient temperature and neutral pH, and in the absence of any catalyst. Our technology platform affords thermoresponsive bioconjugates, whose aggregation is solely controlled by the polymer chains.

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Synthesis and solution behaviour of dual light- and temperature-responsive poly(triethylene glycol-co-spiropyran) copolymers and block copolymers

Abstract: We herein report on the synthesis and characterization of materials featuring a dual-responsive copolymer segment consisting of photo-responsive spiropyran (SPA) and temperature-responsive triethylene glycol acrylate (TEGA).

Cited by 18 publications

References 69 publications

Controlling Growth of Poly (Triethylene Glycol Acrylate-Co-Spiropyran Acrylate) Copolymer Liquid Films on a Hydrophilic Surface by Light and Temperature

Controlling Growth of Poly (Triethylene Glycol Acrylate-Co-Spiropyran Acrylate) Copolymer Liquid Films on a Hydrophilic Surface by Light and Temperature

Temperature and Photo Dual‐Stimuli Responsive Block Copolymer Self‐Assembly Micelles for Cellular Controlled Drug Release

Hetero‐Diels–Alder Cycloaddition with RAFT Polymers as Bioconjugation Platform

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