Backbone‐Based LCST‐Type Hyperbranched Poly(oligo(ethylene glycol)) with CO<sub>2</sub>‐Reversible Iminoboronate Linkers

Yu, Jiabao; Chao, Huan Ping; Guo, Li; Tang, Rupei; Liu, Zhao‐Tie; Jiang, Jinqiang

doi:10.1002/macp.201800346

Cited by 6 publications

(5 citation statements)

References 34 publications

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“…The clear-turbid phase transition occurred before and after cloud point temperature (T cp ) [19][20][21][22][23]. The polymer hydration is thus wrapped by water molecules and dissolves when the temperature is lower than T cp .…”

Section: Introductionmentioning

confidence: 99%

Precise Synthesis and Thermoresponsive Property of Poly(ethyl glycidyl ether) and Its Block and Statistic Copolymers with Poly(glycidol)

Wang

Narumi

et al. 2021

Polymers

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In this paper, we describe a comprehensive study of the thermoresponsive properties of statistic copolymers and multiblock copolymers synthesized by poly(glycidol)s (PG) and poly(ethyl glycidyl ether) (PEGE) with different copolymerization methods. These copolymers were first synthesized by ring-opening polymerization (ROP), which was initiated by tert-butylbenzyl alcohol (tBBA) and 1-tert-butyl-4,4,4-tris(dimethylamino)-2,2-bis[tris(dimethylamino)phosphoranylidenamino]-2Λ5,4Λ5-catenadi(phosphazene) (t-Bu-P4) as the catalyst, and then the inherent protective groups were removed to obtain the copolymers without any specific chain end groups. The thermoresponsive property of the statistic copolymer PGx-stat-PEGEy was compared with the diblock copolymer PGx-b-PEGEy, and the triblock copolymers were compared with the pentablock copolymers. Among them, PG-stat-PEGE, PG-b-PEGE-b-PG-b-PEGE-b-PG, and PEGE-b-PG-b-PEGE-b-PG-b-PEGE, and even the specific ratio of PEGE-b-PG-b-PEGE, exhibited LCST-type phase transitions in water, which were characterized by cloud point (Tcp). Although the ratio of x to y affected the value of the Tcp of PGx-stat-PEGEy, we found that the disorder of the copolymer has a decisive effect on the phase-transition behavior. The phase-transition behaviors of PG-b-PEGE, part of PEGE-b-PG-b-PEGE, and PG-b-PEGE-b-PG copolymers in water present a two-stage phase transition, that is, firstly LCST-type and then the upper critical solution temperature (UCST)-like phase transition. In addition, we have extended the research on the thermoresponsive properties of EGE homopolymers without specific α-chain ends.

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Section: Introductionmentioning

confidence: 99%

Precise Synthesis and Thermoresponsive Property of Poly(ethyl glycidyl ether) and Its Block and Statistic Copolymers with Poly(glycidol)

Wang

Narumi

et al. 2021

Polymers

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“…The target polymer was synthesized via an iminoboronate multicomponent reaction: [ 34,35 ] TAPA (0.47 g, 2.50 mmol), FPBA (1.31 g, 8.75 mmol), Diols‐OEG (1.88 g, 4.38 mmol), and HQ‐TAPA (0.28 g, 0.63 mmol) were dissolved in 8.0 mL anhydrous ethanol with mild stirring and then refluxed in the system under nitrogen in a Schlenk tube (25 mL) for 24 h. The crude product was concentrated via a rotary evaporation, and then washed three times with diethyl ether and dried in vacuum overnight. Yield: 92.3%.…”

Section: Methodsmentioning

confidence: 99%

Iminoboronate Backbone‐Based Hyperbranched Polymeric Micelles with Fenton‐Like Enhanced ROS Response

Zhang

Guo

Liu

et al. 2020

Macro Chemistry & Physics

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is widespread in tumor cells, even clinical studies revealed that the concentration of H 2 O 2 in cancerous tissues is many times higher (ranging from 100 × 10 −6 to 1 × 10 −3 m) compared to that in normal tissues (35 × 10 −6 m). [15,16] The differentiated ROS level in different regions inspires the development of ROS-responsive micelles for targeted drug delivery. [17][18][19] Motifs such as thioether, thioketal, ferrocene, tellurium, selenium, and boronic ester are introduced to the structures of the polymers to endow the self-assembled micelles with ROS-responsiveness. [20][21][22][23][24] However, current designs always allow the micelles to exhibit responsive drug delivery at relatively high concentrations of ROS, which is the main obstacle to limit their further uses. Therefore, it is highly pressing to improve the sensitivity of the ROS-responsive polymeric nanocarriers.Zhu and co-workers reported a cinnamaldehyde-encapsulated nanomicellar system based on H 2 O 2 -responsive hyperbranched polyglycerols with thioether-linked anticancer drug of 7-ethyl-10-hydroxy-camptothecin (SN38). [25] The in vitro study proposed that the preferentially released cinnamaldehyde (CA) could effectively induce intracellular ROS generation and accelerate the micellar degradation to release SN38 for an enhanced cancer therapy. Ge and co-workers fabricated a novel ROS-responsive polyprodrug polymersome loaded with ultrasmall iron oxide nanoparticles and glucose oxidase. The tumor acidity-activable Fenton reaction can efficiently produce ·OH to trigger camptothecin (CPT) release for high-efficient cooperative cancer therapy. [26] Such strategies involve locally catalyzingtriggered chemical reactions to generate abundant and special products only inside tumor tissues and therefore provide a highly efficient tumor-specific theranostic effects. Cancer tissues are usually featured with mild acidic conditions and high ROS levels due to the fast metabolism-induced overproduction of metabolic products. [17][18][19][20][21][22][23][24][25][26][27][28][29] In addition, the concentration of Cu(II) ions in cancer cells is 2-3 times higher than that within normal cells (0.98 µg mL −1 ), while the concentrations of Zn(II), Fe(III), and Se(II) are significantly lower in cancer tissues. [30] It should be noted that a Fenton-like reaction may occur for the polyphenols and Cu(II) complexed system to quickly generate a variety of reactive oxygen species. [31] Therefore, cancer tissues are more subject to electron transfer between Cu(II) ions and polyphenols to generate ROS. Such Cu-complexed Fenton-like reaction can also effectively induce the tumor-specific therapy Compared to normal cells, there is a relatively high level of reactive oxygen species (ROS) in tumor cells caused by defecting ROS scavenging systems. To this issue, developing ROS-responsive nanocarriers has been a promising way to cancer therapy. However, it is always difficult for a certain ROSresponsive nanocarrier to be perfectly triggered due to the complexity of cancerous tissue...

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“…[112,116] CO2-responsive iminoboronate poly(oligo(ethylene glycol)) polymers have also been reported by Jiang and co-workers, with bubbling of CO2 reversibly producing carbonic acid that triggers IBE bond hydrolysis to trigger depolymerisation processes that can be reversed by purging with N2 gas. [120] This CO2dependent behaviour has been demonstrated in multiple systems (vide infra) using both 1 H NMR and fluorescence assays to measure the fragmentation/re-complexation of IBE systems upon sequential CO2/N2 bubbling.…”

Section: Dynamic Self-healing and Stimuli-responsive Polymers And Hyd...mentioning

confidence: 96%

The Bull-James assembly: Efficient iminoboronate complex formation for chiral derivatization and supramolecular assembly

Groleau

James

Bull

2021

Coordination Chemistry Reviews

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Backbone‐Based LCST‐Type Hyperbranched Poly(oligo(ethylene glycol)) with CO₂‐Reversible Iminoboronate Linkers

Cited by 6 publications

References 34 publications

Precise Synthesis and Thermoresponsive Property of Poly(ethyl glycidyl ether) and Its Block and Statistic Copolymers with Poly(glycidol)

Precise Synthesis and Thermoresponsive Property of Poly(ethyl glycidyl ether) and Its Block and Statistic Copolymers with Poly(glycidol)

Iminoboronate Backbone‐Based Hyperbranched Polymeric Micelles with Fenton‐Like Enhanced ROS Response

The Bull-James assembly: Efficient iminoboronate complex formation for chiral derivatization and supramolecular assembly

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Backbone‐Based LCST‐Type Hyperbranched Poly(oligo(ethylene glycol)) with CO2‐Reversible Iminoboronate Linkers

Cited by 6 publications

References 34 publications

Precise Synthesis and Thermoresponsive Property of Poly(ethyl glycidyl ether) and Its Block and Statistic Copolymers with Poly(glycidol)

Precise Synthesis and Thermoresponsive Property of Poly(ethyl glycidyl ether) and Its Block and Statistic Copolymers with Poly(glycidol)

Iminoboronate Backbone‐Based Hyperbranched Polymeric Micelles with Fenton‐Like Enhanced ROS Response

The Bull-James assembly: Efficient iminoboronate complex formation for chiral derivatization and supramolecular assembly

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Backbone‐Based LCST‐Type Hyperbranched Poly(oligo(ethylene glycol)) with CO₂‐Reversible Iminoboronate Linkers