Design of smart polyacrylates showing thermo-, pH-, and CO<sub>2</sub>-responsive features

Huang, Jianbing; Qin, Herong; Wang, Biyun; Tan, Qinglan; Lu, Jiang

doi:10.1039/c9py01410a

Cited by 21 publications

(29 citation statements)

References 37 publications

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“…Many release mechanisms have been explored, ranging from simple diffusion of the drugs from the carrier to more sophisticated stimuli-responsive polymeric micelles 1 − 5 that can release the drug on demand in response to specific stimuli. These include changes in temperature 6 − 11 and pH, 12 − 18 irradiation with UV–vis light, 19 − 25 or the presence of analytes such as thiols. 26 − 29 Among the various types of stimuli, enzymatic activation or degradation may offer great potential due to the overexpression of specific enzymes in different diseases.…”

Section: Introductionmentioning

confidence: 99%

Using High Molecular Precision to Study Enzymatically Induced Disassembly of Polymeric Nanocarriers: Direct Enzymatic Activation or Equilibrium-Based Degradation?

Slor

Amir

2021

Macromolecules

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Enzyme-responsive polymers and their assemblies offer great potential to serve as key materials for the design of drug delivery systems and other biomedical applications. However, the utilization of enzymes to trigger the disassembly of polymeric amphiphiles, such as micelles, also suffers from the limited accessibility of the enzyme to moieties that are hidden inside the assembled structures. In this Perspective, we will discuss examples for the utilization of high molecular precision that dendritic structures offer to study the enzymatic degradation of polymeric amphiphiles with high resolution. Up to date, several different amphiphilic systems based on dendritic blocks have all shown that small changes in the hydrophobicity and amphiphilicity strongly affected the degree and rate of enzymatic degradation. The ability to observe the huge effects due to relatively small variations in the molecular structure of polymers can explain the limited enzymatic degradation that is often observed for many reported polymeric assemblies. The observed trends imply that the enzymes cannot reach the hydrophobic core of the micelles, and instead, they gain access to the amphiphiles by the unimer–micelle equilibrium, making the unimer exchange rate a key parameter in tuning the enzymatic degradation rate. Several approaches that are aimed at overcoming the stability–responsiveness challenge are discussed as they open the way to the design of stable and yet enzymatically responsive polymeric nanocarriers.

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Section: Introductionmentioning

confidence: 99%

Using High Molecular Precision to Study Enzymatically Induced Disassembly of Polymeric Nanocarriers: Direct Enzymatic Activation or Equilibrium-Based Degradation?

Slor

Amir

2021

Macromolecules

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“…Aza‐Michael addition reaction followed by amidation with acryloyl chloride provides a facile pathway for synthesizing many specific functional monomers with ester, ether, amide, and amine functionality. [ 2,3,7–9 ] Recently, using this protocol, we have reported the synthesis of a N ‐(3‐(hexylamino)‐ N ‐(3‐(isopropylamino)‐3‐oxopropyl) acrylamide monomer (Mn, n = 6 (hexyl)) via Aza‐Michael addition reaction between N ‐isopropyl acrylamide (NIPAM) and n ‐hexyl amine, followed by a nucleophilic substitution reaction with acryloyl chloride and polymerized this monomer via RAFT polymerization method using O ‐propynyl 2‐( N , N ‐diphenylcarbamothioylthio) propanoate (PDPCP) as a RAFT agent. [ 10 ] We have also studied the properties the polyM6 polymer formed using different techniques gel permeation chromatography (GPC), 1 H NMR, 13 C NMR, Fourier transform infra red spectroscopy (FTIR), UV–vis, contact angle measurement, thermo‐gravimetry‐differential thermal analysis (TG‐DTA), differential scanning calorimetry (DSC), and X‐ray diffraction analysis (XRD).…”

Section: Introductionmentioning

confidence: 99%

Effect of n‐Alkyl Side Chain Length on the Thermal and Rheological Properties of PolyN‐(3‐(alkylamino)‐N‐(3‐(isopropylamino)‐3‐oxopropyl)acrylamide) Homopolymers

Kumari

Vishwakarma

Mitra

et al. 2021

Macro Chemistry & Physics

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Four new N‐isopropylacrylamide‐ and N‐n‐alkyl amine‐based acrylamide monomers, N‐(3‐(alkylamino)‐N‐(3‐(isopropylamino)‐3‐oxopropyl) acrylamide (Mn) (n = 4, 8, 10, 12) are successfully synthesized and polymerized via reversible addition‐fragmentation chain‐transfer polymerization (polyMn, n = 4, 8, 10, and 12), which are characterized by gel permeation chromatography, 1H NMR, Fourier transform infra red spectroscopy, thermo‐gravimetry‐differential thermal analysis, differential scanning calorimetry (DSC), and rheology. All polymers are thermally stable and undergo a two‐step degradation process at ≈280 and ≈375 °C. Glass transition temperature (Tg)s of these polymers decrease gradually from 99.6 to 52.5 °C with increasing n‐alkyl side chain length. The rheology of these polymers in melt state agrees to a typical Rouse‐melt behavior and allows for confirming the Tg determined from DSC. Benzyl alcohol solution rheology proves a weak structural build‐up, in particular for polyM12. Comparison of the quantum chemical calculations of polyMns with n = 4–8 reveals increase in backbone helicity with increasing n‐alkyl side chain length.

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“…Other examples of triple‐stimuli‐responsive polymeric materials are pH,thermo,ionic strength triple‐stimuli polymers 121 ; pH,thermo,CO 2 triple‐stimuli polymers 122,123 ; pH,photo,redox triple‐stimuli polymers 124 ; and pH,glucose,redox triple‐stimuli polymers 125 …”

Section: Multi‐stimuli‐responsive Polymersmentioning

confidence: 99%

pH‐sensitive polymers: Classification and some fine potential applications

Ofridam

Tarhini

Lebaz

et al. 2021

Polymers for Advanced Techs

172

111

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Stimuli‐responsive materials in general and pH‐responsive polymers in particular have gained increasing interest during the last two decades. Their unique properties, which arise from their ability to exhibit sharp and reversible changes in response to environmental pH conditions, have made them suitable for various applications such as drug delivery and specific body‐site targeting, sensing and actuation, membrane functionalization, separation techniques, as well as in agriculture and food industry and even chemical industries. In the present review, the focus is on the general characteristics of pH‐responsive polymers in terms of their origin, chemical composition, and preparation. Moreover, some of the important and recent applications are reported and discussed.

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Design of smart polyacrylates showing thermo-, pH-, and CO₂-responsive features

Abstract: A novel acrylate monomer was synthesized by facile sequential two-step reactions and polymerized using RAFT polymerization to yield a well-defined thermo-, pH- and CO2-responsive homopolymer.

Cited by 21 publications

References 37 publications

Using High Molecular Precision to Study Enzymatically Induced Disassembly of Polymeric Nanocarriers: Direct Enzymatic Activation or Equilibrium-Based Degradation?

Using High Molecular Precision to Study Enzymatically Induced Disassembly of Polymeric Nanocarriers: Direct Enzymatic Activation or Equilibrium-Based Degradation?

Effect of n‐Alkyl Side Chain Length on the Thermal and Rheological Properties of PolyN‐(3‐(alkylamino)‐N‐(3‐(isopropylamino)‐3‐oxopropyl)acrylamide) Homopolymers

pH‐sensitive polymers: Classification and some fine potential applications

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Design of smart polyacrylates showing thermo-, pH-, and CO2-responsive features

Abstract: A novel acrylate monomer was synthesized by facile sequential two-step reactions and polymerized using RAFT polymerization to yield a well-defined thermo-, pH- and CO2-responsive homopolymer.

Cited by 21 publications

References 37 publications

Using High Molecular Precision to Study Enzymatically Induced Disassembly of Polymeric Nanocarriers: Direct Enzymatic Activation or Equilibrium-Based Degradation?

Using High Molecular Precision to Study Enzymatically Induced Disassembly of Polymeric Nanocarriers: Direct Enzymatic Activation or Equilibrium-Based Degradation?

Effect of n‐Alkyl Side Chain Length on the Thermal and Rheological Properties of PolyN‐(3‐(alkylamino)‐N‐(3‐(isopropylamino)‐3‐oxopropyl)acrylamide) Homopolymers

pH‐sensitive polymers: Classification and some fine potential applications

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Design of smart polyacrylates showing thermo-, pH-, and CO₂-responsive features