The fabrication of hybrid micelles with enhanced permeability for drug delivery <i>via</i> a diethoxymethylsilyl-based crosslinking strategy

Zhang, Xianshuo; Liu, Fangjun; Li, Xiaochen; Tian, Yunfei; Ma, Liang; Yu, Cui‐Yun; Wei, Hua

doi:10.1039/c9py00810a

Cited by 5 publications

(4 citation statements)

References 37 publications

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“…Hence, it is most likely that for the micelle-based drug delivery systems, the promoted drug release due to the loss of micelle stability outperforms enhanced drug encapsulation and compromised drug diffusion because of the formation of hydrophobic aggregates. The increased cumulative drug release because of the loss of micelle stability was previously observed as well. , …”

Section: Resultsmentioning

confidence: 99%

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Folate-Targeted Anticancer Drug Delivery via a Combination Strategy of a Micelle Complex and Reducible Conjugation

Wang

Long

Zhang

et al. 2020

ACS Biomater. Sci. Eng.

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Conjugation of various active targeting ligands to the surface of nanocarriers to realize specific recognition by the corresponding receptors localized on the membrane of the cancer cells has provided a powerful means toward enhanced cancer therapy. Folic acid (FA) is one of the most used targeting ligands due to the overexpressed FA receptors in many cancer cell lines. However, conjugation of hydrophobic FA to the surface of nanocarriers usually alters the hydrophilic/hydrophobic balance of the stabilized nanoparticles, leading to their thermodynamic instability and subsequent formation of aggregates, which apparently compromises the in vivo long circulation and minimized side effects of nanocarriers. The currently leading strategy to overcome this issue is to incorporate a protecting hydrophilic stealth that can be deshielded to expose the targeting ligand at the desired tumor site, which generally involves multistep chemical modifications, conjugations, and purifications. To develop a simple alternative toward FA-mediated enhanced anticancer drug delivery, a combination strategy of micelle complex and reducible conjugation was reported in this study. FA was first conjugated to the terminus of the hydrophilic block of a reduction-sensitive miktoarm star-shaped amphiphilic copolymer, PCL3-SS-POEGMA1, with the previously optimized star structure by click coupling via a reducible disulfide link. The resulting PCL3-SS-POEGMA1-SS-FA was further mixed with the parent PCL3-SS-POEGMA1 to afford a micelle complex with both reducibly conjugated and relatively low amount of FA-targeting ligands toward excellent FA-mediated targeted drug delivery without compromised salt stability in vitro and in vivo. Therefore, the combined strategy developed herein provides a simple and powerful means to promote FA-mediated anticancer drug delivery.

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Section: Resultsmentioning

confidence: 99%

“…The increased cumulative drug release because of the loss of micelle stability was previously observed as well. 34,35 In Vitro Cellular Uptake and Competition Study. FAmediated cellular uptake was further quantified in HeLa cells (folate receptor (FR)+) using flow cytometry (FCM) analysis (Figure 7).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Folate-Targeted Anticancer Drug Delivery via a Combination Strategy of a Micelle Complex and Reducible Conjugation

Wang

Long

Zhang

et al. 2020

ACS Biomater. Sci. Eng.

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“…Esterification of 2-hydroxyethyl disulfide with acyl chloride, acyl bromide, and carboxylic acid has been reported to generate various bioreducible agents as promising monomers, 27,28 crosslinking agents, 29,30 initiator, 31 and chain transfer reagents [28][29][30][31][32] for the construction of valuable biomaterials. Therefore, 2-hydroxyethyl disulfide was used as a precursor to prepare a glutathione (GSH)-responsive HSEMA-g-PCL macromonomer in this study (Scheme S1 †).…”

Section: Synthesis and Characterization Of The Hsema-g-pcl Macromonomermentioning

confidence: 99%

Facile synthesis and self-assembly behaviors of biodegradable amphiphilic hyperbranched copolymers with reducible poly(caprolactone) grafts

Zhang

Wang

et al. 2022

Polym. Chem.

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“…Of the reported stimuli approaches, the application of GSH-sensitive polymers containing disulfide bridges is of particular importance owing to the distinct difference in the GSH levels between normal cells (≈2 mm) and specific tumor cells (≈10 mm). [36] The previously fabricated disulfide bridges-contained organic/inorganic hybrid nanomedicines [37,38] and hyperbranched nanomedicines [39] showed that the intracellular cleavage of disulfide links promotes the destabilization of nanomedicine and subsequently intracellular drug release in tumor cells for enhanced therapeutic efficiency.…”

Section: Introductionmentioning

confidence: 99%

Fabrication of GSH‐Responsive Poly(Tertiary Amine‐Oxide)‐Based Nanomedicines for Enhanced Anticancer Drug Release

Zhang,

Ma,

Wang

et al. 2023

Macro Chemistry & Physics

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Poly(tertiary amine‐oxide)‐based polymeric nanocarriers have showed more functionalities than stealthy PEG‐based analogs due to the structure of phospholipid affinitive N‐oxides groups, which has attracted considerable attention to the synthesis of various zwitterionic copolymers with tertiary amine‐oxide grafts for enhanced anticancer drug delivery. However, poly(tertiary amine‐oxide)‐based amphiphilic copolymers with tumor intracellular microenvironment sensitivities, to the knowledge, have been rarely reported likely due to the lack of a controlled synthetic strategy. Herein, a reducible zwitterionic copolymer, poly(ε‐caprolactone)25‐SS‐poly(2‐(N‐oxide‐N,N‐diethylamino)ethyl methacrylate)30 (PCL25‐SS‐OPDEA30) is designed and synthesized successfully via combination of controlled polymerization techniques and post polymerization modification. Specifically, postoxidation of poly(tertiary amine) is confirmed to be a better synthetic strategy toward a well‐defined polymer structure relative to direct polymerization of N,N‐diethylaminoethyl methacrylate (ODEA). The effect of disulfide bridges on the self‐assembly behaviors, in vitro drug loading and drug release properties is investigated in detail. Notablely, the resulting micelles self‐assembled from PCL25‐SS‐OPDEA30 show much greater colloidal stability, higher drug loading content (DLC), and better in vitro tumor cell inhibition than the reduction‐insensitive counterparts. Overall, this study reports a robust strategy toward zwitterionic nanomedicines for on‐demand anticancer drug delivery.

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The fabrication of hybrid micelles with enhanced permeability for drug delivery via a diethoxymethylsilyl-based crosslinking strategy

Abstract: A novel reducible silica monomer, DESSPMA with diethoxysilyl groups for in situ crosslinking to give a lower crosslinking density and greater permeability than the triethoxysilyl-based TESSPMA was developed to realize enhanced therapeutic efficiency.

Cited by 5 publications

References 37 publications

Folate-Targeted Anticancer Drug Delivery via a Combination Strategy of a Micelle Complex and Reducible Conjugation

Folate-Targeted Anticancer Drug Delivery via a Combination Strategy of a Micelle Complex and Reducible Conjugation

Facile synthesis and self-assembly behaviors of biodegradable amphiphilic hyperbranched copolymers with reducible poly(caprolactone) grafts

Fabrication of GSH‐Responsive Poly(Tertiary Amine‐Oxide)‐Based Nanomedicines for Enhanced Anticancer Drug Release

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