Redox-Responsive, Core-Cross-Linked Micelles Capable of On-Demand, Concurrent Drug Release and Structure Disassembly

Wang, Hua; Tang, Li; Tu, Chunlai; Song, Ziyuan; Yin, Qian; Yin, Lichen; Zhang, Zhonghai; Cheng, Jianjun

doi:10.1021/bm401086d

Cited by 162 publications

(146 citation statements)

References 61 publications

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“…In the last decade, a versatile method to prepare side-chain functionalized PAHAs was established via the ring-opening polymerization (ROP) of Ocarboxyanhydrides (OCAs), a class of five-membered ring compounds derived from amino acids. [39][40][41][42][43][44][45][46] Well-controlled poly (α-hydroxy acids) featuring pendant carboxylic acid groups were obtained via ROP of OCAs derived from glutamic acid or malic acid, followed by deprotection of the benzyl ester side groups. [40,41] In 2012, Cheng reported the synthesis of Tyr (alkynyl)-OCA, an OCA bearing alkynyl group derived from tyrosine.…”

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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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: 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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“…Therefore, if one can crosslink and stabilize the nanoparticles after forming in vitro, it can be expected to maintain the desired nanostructures after administrated into circulation. Wang etc developed camptothecin-conjugated, core-cross-linked micelles with built-in disulfide bonds, which can be broken down and rapidly release CPT in reducing environment (50). The crosslinking was achieved via the azide-alkyne click chemistry after the coprecipitation CPT-poly(tyrosine(alkynyl)-OCA) conjugate and monomethoxy poly(ethyleneglycol)-b-poly(tyrosine(alkynyl)-OCA) (Figure 3b).…”

Section: Nanoparticles From Self-assembly Of Polymersmentioning

confidence: 99%

Nanosized Camptothecin Conjugates for Single and Combined Drug Delivery

Chen¹,

Sun²,

Wang³

et al. 2016

Eur J Bio Med Res

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Camptothecin (CPT), a natural DNA topoisomerase 1 inhibitor, is commonly used as a model hydrophobic compound for anticancer drug delivery research. Nanoparticle loaded with active drugs has the potential to selectively deliver the therapeutic agents into tumor cells without affecting the normal tissues, and hence is attracting tremendous attention from biomedical scientists. Nanoparticles can benefit from the enhanced permeability and retention effect (EPR) of the tumor tissues that allows nanoparticles to be transported through the leaky blood vessels and retained for a longer time compared with traditional small molecule drugs. In particular, covalent camptothecin conjugates are of extensive interest due to their robust stability by covalent chemical bonding. In this mini-review, recent progress of nanosized camptothecin conjugates will be discussed with the focus on the difference of delivery materials as well as their potential of combined drug delivery for the therapy of cancer.

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“…28 Although shell crosslinked micelles can offer better stability along with higher drug loading, however, a challenge in preparation of shell-crosslinked micelles is the need for highly dilute conditions to circumvent undesired inter-micellar crosslinking, therefore making this route difficult for large-scale micellar preparation. 29 Moreover, the inter-micellar crosslinking in shell cross-linked micelles may also cause the agglomeration of nanocarriers into larger particles leading to system instability and poor pharmacokinetic properties. To overcome these limitations, reduction sensitive corecrosslinked micelles have been developed.…”

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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Redox-Responsive, Core-Cross-Linked Micelles Capable of On-Demand, Concurrent Drug Release and Structure Disassembly

Cited by 162 publications

References 61 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

Nanosized Camptothecin Conjugates for Single and Combined Drug Delivery

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

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