Redox-Responsive, Core Cross-Linked Polyester Micelles

Zhang, Zhonghai; Yin, Lichen; Tu, Chunlai; Song, Ziyuan; Zhang, Yanfeng; Xu, Yun‐Xiang; Tong, Rong; Zhou, Qin; Ren, Jie; Cheng, Jianjun

doi:10.1021/mz300522n

Cited by 117 publications

(137 citation statements)

References 63 publications

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“…[43][44][45][46] A typical procedure for the synthesis of mPEGb-poly(Tyr) 25 was as followed: In a glovebox, Tyr(alkynyl)-OCA (246 mg, 1 mmol) in DCM (4 ml) was added into a DCM solution (1 ml) of mPEG5k (200 mg, 0.04 mmol) and DMAP (4.9 mg, 0.04 mmol) at room temperature. The complete monomer consumption was verified by measuring the intensity of the anhydride peak of OCA at 1810 cm -1 by FT-IR.…”

Section: Synthesis Of 2-nitrobenzyl 6-bromohexanoatementioning

confidence: 99%

“…Then, Cheng reported a redox-responsive core cross-linked (CCL) poly(α-hydroxy acids) micelle obtained through ROP of Tyr(alkynyl)-OCA with monomethoxy poly(ethylene glycol) (mPEG) as initiator, followed by cross-linking the alkynyl side chains in the hydrophobic cores with bis(azidoethyl) disulfide. [44] The CCL micelles not only improved the structural stability but also allowed the controlled release of cargo molecules in response to the reducing reagent. [45,46] In this work, we developed a versatile method to prepared photo-responsive poly(α-hydroxy acids) with pendent o-NB ester group.…”

Section: Introductionmentioning

confidence: 99%

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Photo‐responsive amphiphilic poly(α‐hydroxy acids) with pendent o‐nitrobenzyl ester constructed via copper‐catalyzed azide‐alkyne cycloaddition reaction

Liu

Niu

et al. 2015

Polymers for Advanced Techs

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Photo-responsive block copolymer mPEG-b-poly(Tyr)-g-NB was prepared by introduction of o-nitrobenzyl ester group into the side chain of amphiphilic poly(ethylene glycol)-b-poly(α-hydroxy acids) (mPEG-b-poly(Tyr)) containing pendent alkynyl group via copper-catalyzed azide-alkyne cycloaddition reaction. The amphiphilic mPEG-bpoly(Tyr) was synthesized via the ring-opening polymerization of O-carboxyanhydrides, with monomethoxy poly (ethylene glycol) (mPEG) as macroinitiator. The molecular structure, self-assembly, and photo-controlled release of the obtained mPEG-b-poly(Tyr)-g-NB were thoroughly investigated. mPEG-b-poly(Tyr)-g-NB could self-assemble into spherical micelles in water and showed disassembly under UV light irradiation, which was demonstrated by means of UV-vis spectroscopy, scan electron microscopes, and dynamic light scattering measurement. Fluorescence emission measurements demonstrated that Nile red, encapsulated by micelles, can be released upon UV irradiation. This study provides a convenient way to construct smart poly(α-hydroxy acids)-based nanocarriers for controlled release of hydrophobic drugs.

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Section: Synthesis Of 2-nitrobenzyl 6-bromohexanoatementioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Photo‐responsive amphiphilic poly(α‐hydroxy acids) with pendent o‐nitrobenzyl ester constructed via copper‐catalyzed azide‐alkyne cycloaddition reaction

Liu

Niu

et al. 2015

Polymers for Advanced Techs

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“…30 Although many of these micelles have demonstrated good stability and 'stealth' properties, 31 the hydrophobic cores have largely been based on non-degradable polymers such as polyacrylamide or polyacrylate. 32,33 Therefore, analogous micelles composed entirely of biologically inert and/or biodegradable polymers would be better candidates for clinical use. 34 To address these issues, we have synthesized a functional biodegradable and biocompatible block copolymer based on methoxypoly(ethyleneglycol)-b-poly(ε-caprolactone-co-α-azido-ε-caprolactone) (mPEG-b-poly(εCL-co-αN3εCL)) as precursor of reduction sensitive core-crosslinked micelles.…”

Section: Introductionmentioning

confidence: 99%

Bioreducible cross-linked core polymer micelles enhance in vitro activity of methotrexate in breast cancer cells

et al. 2017

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Polymer micelles have emerged as promising carriers for controlled release applications, however, several limitations of micelle-based drug delivery have also been reported. To address these issues, we have synthesized a functional biodegradable and cytocompatible block copolymer based on methoxypoly(ethyleneglycol)-b-poly(ε-caprolactone-co-α-azido-ε-caprolactone) (mPEG-b-poly(εCL-co-αN3εCL)) as a precursor of reduction sensitive core-crosslinked micelles. The synthesized polymer was formulated as micelles using a dialysis method and loaded with the anti-inflammatory and anticancer drug methotrexate (MTX). The micellar cores were subsequently crosslinked at their pendant azides by a redoxresponsive bis(alkyne). The size distributions and morphology of the polymer micelles were assessed using dynamic light scattering (DLS) and transmission electron microscopy, and drug release assays were performed under simplified (serum free) physiological and reductive conditions. Cellular uptake studies in human breast cancer cells were performed using Oregon-green loaded core-crosslinked micelles. The MTX-loaded core-crosslinked micelles were assessed for their effects on metabolic activity in human breast cancer (MCF-7) cells by evaluating the reduction of the dye MTT 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide. The apoptosis inducing potential of MTX-loaded core-crosslinked micelles was analysed using Hoechst/propidium iodide (PI) and annexin-V/PI assays. The data from these experiments indicated that drug release from these cross-linked micelles can be controlled and that the redox-responsive micelles are more effective carriers for MTX than non-crosslinked analogues and the free drug in the cell-lines tested.

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“…[8][9][10] Environmentally, responsive technologies (eg, those based on pH sensitivity, thermal sensitivity, and redox sensitivity), combined with covalent cross-linking, have exhibited outstanding performance in the controlled release of encapsulated drugs. [11][12][13][14][15] In addition, ionic cross-linking, namely the electrostatic interaction between the positive and negative charges of the hydrophobic polymer blocks, is also a good choice in the micellar core. 16 On the other hand, weakly acidic interstitial fluid (pH 6.75-7.23) in solid tumors and acidic endosomes/ lysosomes (pH 4.0-5.5) in cells possess the characteristic acidic environment.…”

Section: Introductionmentioning

confidence: 99%

Acid-triggered core cross-linked nanomicelles for targeted drug delivery and magnetic resonance imaging in liver cancer cells

Li¹,

Li²,

Yi³

et al. 2013

IJN

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Purpose:To research the acid-triggered core cross-linked folate-poly(ethylene glycol)-b-poly [N-(N′,N′-diisopropylaminoethyl) glutamine] (folated-PEG-P[GA-DIP]) amphiphilic block copolymer for targeted drug delivery and magnetic resonance imaging (MRI) in liver cancer cells. Methods:As an appropriate receptor of protons, the N,N-diisopropyl tertiary amine group (DIP) was chosen to conjugate with the side carboxyl groups of poly(ethylene glycol)-b-poly (L-glutamic acid) to obtain PEG-P(GA-DIP) amphiphilic block copolymers. By ultrasonic emulsification, PEG-P(GA-DIP) could be self-assembled to form nanosized micelles loading doxorubicin (DOX) and superparamagnetic iron oxide nanoparticles (SPIONs) in aqueous solution. When PEG-P(GA-DIP) nanomicelles were combined with folic acid, the targeted effect of folated-PEG-P(GA-DIP) nanomicelles was evident in the fluorescence and MRI results. Results: To further increase the loading efficiency and the cell-uptake of encapsulated drugs (DOX and SPIONs), DIP (pK a ≈6.3) groups were linked with ∼50% of the side carboxyl groups of poly(L-glutamic acid) (PGA), to generate the core cross-linking under neutral or weakly acidic conditions. Under the acidic condition (eg, endosome/lysosome), the carboxyl groups were neutralized to facilitate disassembly of the P(GA-DIP) blocks' cross-linking, for duly accelerating the encapsulated drug release. Combined with the tumor-targeting effect of folic acid, specific drug delivery to the liver cancer cells and MRI diagnosis of these cells were greatly enhanced. Conclusion: Acid-triggered and folate-decorated nanomicelles encapsulating SPIONs and DOX, facilitate the targeted MRI diagnosis and therapeutic effects in tumors.

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Redox-Responsive, Core Cross-Linked Polyester Micelles

Cited by 117 publications

References 63 publications

Photo‐responsive amphiphilic poly(α‐hydroxy acids) with pendent o‐nitrobenzyl ester constructed via copper‐catalyzed azide‐alkyne cycloaddition reaction

Photo‐responsive amphiphilic poly(α‐hydroxy acids) with pendent o‐nitrobenzyl ester constructed via copper‐catalyzed azide‐alkyne cycloaddition reaction

Bioreducible cross-linked core polymer micelles enhance in vitro activity of methotrexate in breast cancer cells

Acid-triggered core cross-linked nanomicelles for targeted drug delivery and magnetic resonance imaging in liver cancer cells

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