The power of the ring: a pH-responsive hydrophobic epoxide monomer for superior micelle stability

Song, J. J.; Palanikumar, L.; Choi, Yeongkyu; Kim, Inhye; Heo, Tae Young; Ahn, Eungjin; Choi, Sang‐Hoon; Lee, Eunji; Shibasaki, Yuji; Ryu, Ja‐Hyoung; Kim, Byeong Su

doi:10.1039/c7py01613a

Cited by 22 publications

(43 citation statements)

References 70 publications

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“…A critical micelle concentration of 0.014 mg mL −1 was determined for PEG 40 ‐ b ‐PEEGE 25 (wt% of EEGE = 66.7%) by using DPH as fluorescent probe ( Figure ) . This value is in good agreement with the CMC value of 0.0103 mg mL −1 which has been determined by using pyrene as fluorescent probe in a recent paper by Song et al for PEG 114 ‐ b ‐PEEGE 60 (wt% of EEGE = 63.2%) . This value is of the same order of magnitude as those of commonly studied PEG‐PCL copolymers, indicating a good stability of the micelles …”

Section: Resultssupporting

confidence: 80%

“…After this work‐up, no phosphazenium traces were detectable on 1 H and 13 C NMR spectra (Figure C and Figure S1, Supporting Information). According to Kim and co‐workers, a EEGE X n of 22 in the PEG‐PEEGE block copolymers provides micelles that are not toxic against HeLa cells, up to 500 µg mL −1 . The polymerization degree ( X n ) of the PEEGE block was set to 25, 15, and 5 to ensure a good biocompatibility of the mPEG‐ b ‐PEEGE micelles.…”

Section: Resultsmentioning

confidence: 99%

“…The use of linear mPEG‐ b ‐PEEGE to encapsulate hydrophobic compounds (Nile Red and Paclitaxel) was reported once by Kim and co‐workers. The fast drug release was revealed at pH = 3 and they suggested similar release kinetics at tumoral or endosomal pH . It should also be emphasized that the self‐assembly properties, hydrophobic compounds encapsulation, and release of amphiphilic PEEGE‐ b ‐PEG dendrimer‐like and PEG‐ b ‐PEEGE block star‐shaped copolymers have been recently studied.…”

Section: Introductionmentioning

confidence: 82%

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pH‐Sensitive Poly(ethylene glycol)/Poly(ethoxyethyl glycidyl ether) Block Copolymers: Synthesis, Characterization, Encapsulation, and Delivery of a Hydrophobic Drug

Illy

Zimbron

Molinié

et al. 2019

Macro Chemistry & Physics

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Curcumin is a natural polyphenolic compound known for its numerous pharmacological properties. However, its low water solubility and instability at neutral pH are serious drawbacks preventing its use as an oral drug. Well‐defined amphiphilic poly(ethylene glycol)‐block‐poly(ethoxyethyl glycidyl ether) (PEG‐b‐PEEGE) block copolymers carrying acid‐labile acetal groups are synthesized by anionic ring‐opening polymerization and investigated as potential pH‐sensitive nano‐carriers for delivery of curcumin to cancer cells. The nanoparticles, resulting from copolymer self‐assembly in aqueous media, are characterized by dynamic light scattering and cryo‐transmission electron microscopy. The nanoparticles’ stabilities are evaluated in three different phosphate buffers (pH = 7.2, 6.4, and 5.3). The stability decreases at lower pH and a complete disappearance of the nanoparticles is noticed after 4 days at pH 5.3. Curcumin is encapsulated in hydrophobic core of mPEG40‐b‐PEEGE25 nanoparticles allowing significant enhancements of curcumin solubility in water and lifetime at neutral pH. In vitro curcumin release is studied at different pH by UV‐spectroscopy and high‐performance liquid chromatography (HPLC). The cytotoxicity of curcumin and curcumin encapsulated in micelles is evaluated by cell viability 3‐(4,5‐Dimethyl‐2‐thiazolyl)‐2,5‐diphenyl‐2H‐tetrazolium bromide (MTT) assay on MDA‐MB‐231 human breast cancer cells.

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Section: Resultssupporting

confidence: 80%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 82%

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pH‐Sensitive Poly(ethylene glycol)/Poly(ethoxyethyl glycidyl ether) Block Copolymers: Synthesis, Characterization, Encapsulation, and Delivery of a Hydrophobic Drug

Illy

Zimbron

Molinié

et al. 2019

Macro Chemistry & Physics

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“…Independently from previous research, our group reported the preparation of TPGE modulate the hydrolysis rate of the acetal linker ( Figure 12 a). [ 26 ] 3,4‐Dihydropyran (a widely utilized protecting group for alcohols) was used to shield the free hydroxyl group of glycidol, which resulted in the TPGE monomer at a high yield. As TPGE is a hydrophobic moiety, amphiphilic polymers can easily be prepared through its block copolymerization initiated with m PEG (Figure 12b).…”

Section: Glycidyl Ethers With An Acetal Moietymentioning

confidence: 99%

“…After the successful introduction of the EEGE monomer, various types of acetal‐based monomers have been employed in the synthesis of polyethers, including 1,2‐isopropylidene glyceryl glycidyl ether (IGG), [ 23 ] catechol acetonide glycidyl ether (CAGE), [ 24 ] 1‐(glycidyloxy)ethyl ethylene glycol ether (GEGE), [ 25 ] tetrahydropyranyl glycidyl ether (TPGE), [ 26 ] tetrahydrofuranyl glycidyl ether (TFGE), [ 26,27 ] and cyclohexyloxy ethyl glycidyl ether (CHGE) [ 28 ] ( Figure 1 ). These monomers not only utilized as protecting groups for hydroxyl groups under AROP conditions but also used as pH‐responsive moieties in biomedical applications, further expanding their utility in the use of functionalized polyethers.…”

Section: Introductionmentioning

confidence: 99%

Acetal‐Based Functional Epoxide Monomers: Polymerizations and Applications

Baek

Kim

Park

et al. 2021

Macromolecular Bioscience

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Protecting group chemistry is essential for various organic transformation and polymerization processes. In particular, conventional anionic ring‐opening polymerization (AROP) often requires proper protecting group chemistry because it is typically incompatible with most functional groups due to the highly basic and nucleophilic conditions. In this context, many functional epoxide monomers with proper protecting groups are developed, including the acetal group as a representative example. Since the early introduction of ethoxyethyl glycidyl ether, there is significant development of acetal‐based monomers in the polyethers. These monomers are now utilized not only as protecting groups for hydroxyl groups under AROP conditions but also as pH‐responsive moieties for biomedical applications, further expanding their utility in the use of functionalized polyethers. Recent progress in this field is outlined from their synthesis, polymerization, and biomedical applications.

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Design of Topology‐Controlled Polyethers toward Robust Cooperative Hydrogen Bonding

Kim

Choi

Baek

et al. 2023

Adv Funct Materials

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Topology control of polymers is critical for determining their physical properties and potential applications; in particular, topologies that incorporate numerous hydrogen bonding (H‐bonding) donors and acceptors along the polymer chains considerably influence the formation of different inter‐ and intramolecular H‐bonding motifs. In this study, the high‐level control of inter‐ and intramolecular H‐bonding is investigated in topology‐controlled poly(glycidoxy carbonyl benzoic acid)s (PGCs). Three types of topology‐controlled PGCs (i.e., linear, hyperbranched, and branched cyclic structures having a similar degree of polymerization) are prepared by introducing aromatic carboxylic acids into the corresponding polyglycidols (PGs) via quantitative post‐polymerization modification with phthalic anhydride. The obtained three types of PGCs demonstrated the high‐level interplay between the inter‐ and intramolecular H‐bonding in polymer chains by exhibiting the pH‐dependent self‐association properties in the solution state and the strong adhesion properties in the bulk state with high transparency. Interestingly, the dramatically enhanced adhesive property by 2.6‐fold is demonstrated by simple mixing of branched cyclic PGC and topology‐controlled PGs to promote the cooperative H‐bonding between polymer chains. The new class of cooperative H‐bonding is anticipated between topology‐controlled polymers to contribute to the development of advanced adhesive and the high potential in biological and biomedical applications due to its excellent biocompatibility.

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The power of the ring: a pH-responsive hydrophobic epoxide monomer for superior micelle stability

Abstract: We developed micelles with superior stability by integrating a novel hydrophobic, pH-responsive epoxide monomer, tetrahydropyranyl glycidyl ether.

Cited by 22 publications

References 70 publications

pH‐Sensitive Poly(ethylene glycol)/Poly(ethoxyethyl glycidyl ether) Block Copolymers: Synthesis, Characterization, Encapsulation, and Delivery of a Hydrophobic Drug

pH‐Sensitive Poly(ethylene glycol)/Poly(ethoxyethyl glycidyl ether) Block Copolymers: Synthesis, Characterization, Encapsulation, and Delivery of a Hydrophobic Drug

Acetal‐Based Functional Epoxide Monomers: Polymerizations and Applications

Design of Topology‐Controlled Polyethers toward Robust Cooperative Hydrogen Bonding

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