Near-infrared light-responsive, diselenide containing core-cross-linked micelles prepared by the Diels–Alder click reaction for photocontrollable drug release application

Salma, Sabrina Aufar; Patil, Maheshkumar Prakash; Kim, Dong Woo; Le, Cuong Minh Quoc; Ahn, Byung-Hyun; Kim, Gun‐Do; Lim, Kwon Taek

doi:10.1039/c8py00961a

Cited by 38 publications

(25 citation statements)

References 28 publications

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“…55 ± 1.88 nm), which is consistent with previous reports [36,52]. The obvious D h difference observed between NCMs and CCMs may be attributed to the intramicellar covalent Se-Se network formation and concomitant shrinkage in the interface between the hydrophobic and hydrophilic portion of the mPEG-P(LA-DSeDEA)-PCL copolymer resulting in a more compact micellar structure [27,33,34]. Both NCMs and CCMs experienced suitable ζ-potentials for cellular attachment and internalization, −9.68 ± 3.03 and −13.1 ± 1.17, respectively.…”

Section: Self-assembly and Preparation Of Core Crosslinked Polymeric supporting

confidence: 90%

“…The diselenide-bearing CCMs demonstrated reasonable stability in physiological conditions with appreciable redox-responsive camptothecin (CPT) and doxorubicin (DOX) release in tumor tissue [23]. Indocyanine green (ICG) and DOX-loaded CCMs (DOX@CCMs) were prepared by a [4+2] cycloaddition reaction between PEO-b-PFMA and diselenide containing a bismaleimide crosslinker [33]. The micelles exhibited near-infrared (NIR) triggered Se-Se bond cleavage and rapid release of DOX, leading to enhanced apoptosis in HepG2 cells.…”

Section: Introductionmentioning

confidence: 99%

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Fabrication of Core Crosslinked Polymeric Micelles as Nanocarriers for Doxorubicin Delivery: Self-Assembly, In Situ Diselenide Metathesis and Redox-Responsive Drug Release

et al. 2020

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Polymeric micelles (PMs) have been used to improve the poor aqueous solubility, slow absorption and non-selective biodistribution of chemotherapeutic agents (CAs), albeit, they suffer from disassembly and premature release of payloads in the bloodstream. To alleviate the thermodynamic instability of PMs, different core crosslinking approaches were employed. Herein, we synthesized the poly(ethylene oxide)-b-poly((2-aminoethyl)diselanyl)ethyl l-aspartamide)-b-polycaprolactone (mPEG-P(LA-DSeDEA)-PCL) copolymer which self-assembled into monodispersed nanoscale, 156.57 ± 4.42 nm, core crosslinked micelles (CCMs) through visible light-induced diselenide metathesis reaction between the pendant selenocystamine moieties. The CCMs demonstrated desirable doxorubicin (DOX)-loading content (7.31%) and encapsulation efficiency (42.73%). Both blank and DOX-loaded CCMs (DOX@CCMs) established appreciable colloidal stability in the presence of bovine serum albumin (BSA). The DOX@CCMs showed redox-responsive drug releasing behavior when treated with 5 and 10 mM reduced glutathione (GSH) and 0.1% H2O2. Unlike the DOX-loaded non-crosslinked micelles (DOX@NCMs) which exhibited initial burst release, DOX@CCMs demonstrated a sustained release profile in vitro where 71.7% of the encapsulated DOX was released within 72 h. In addition, the in vitro fluorescent microscope images and flow cytometry analysis confirmed the efficient cellular internalization of DOX@CCMs. The in vitro cytotoxicity test on HaCaT, MDCK, and HeLa cell lines reiterated the cytocompatibility (≥82% cell viability) of the mPEG-P(LA-DSeDEA)-PCL copolymer and DOX@CCMs selectively inhibit the viabilities of 48.85% of HeLa cells as compared to 15.75% of HaCaT and 7.85% of MDCK cells at a maximum dose of 10 µg/mL. Overall, all these appealing attributes make CCMs desirable as nanocarriers for the delivery and controlled release of DOX in tumor cells.

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Section: Self-assembly and Preparation Of Core Crosslinked Polymeric supporting

confidence: 90%

Section: Introductionmentioning

confidence: 99%

Fabrication of Core Crosslinked Polymeric Micelles as Nanocarriers for Doxorubicin Delivery: Self-Assembly, In Situ Diselenide Metathesis and Redox-Responsive Drug Release

et al. 2020

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“…In a similar approach, Lim and co‐workers used redox‐responsive dithio‐containing bismaleimides as crosslinking agent via DA reaction, to prepare redox‐responsive core‐crosslinked micelles for doxorubicin loading . In subsequent studies, the authors furthermore introduced a diselenide containing bismaleimide crosslinker to obtain a sensitive crosslinking agent in the presence of a reductive‐oxidative medium …”

Section: Click Chemistry For Functionalization Of Reactive Particlesmentioning

confidence: 99%

Reactive Precursor Particles as Synthetic Platform for the Generation of Functional Nanoparticles, Nanogels, and Microgels

Gruber

Navarro

Klinger

2019

Adv Materials Inter

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Precise control of the chemical functionality of polymer nanoparticles is a key requirement in tailoring their (dynamic) colloidal properties toward advanced applications. However, current synthetic techniques are still limited in the versatility of chemical design and preparation of such functional colloidal nanomaterials. Two major challenges remain: First, various particle preparation methods are restricted in their functional group tolerance, thus hindering certain combinations of polymer backbones with specific functional groups. Second, the preparation of particles with different functionalities requires the synthesis of different particle batches. But this often results in a simultaneous variation of colloidal features. As a result, the accurate determination of important structure–property relations is still hindered. To address these restrictions, postmodification of preformed reactive particles is gaining more attention. This technique has evolved from polymer synthesis, where postpolymerization functionalization enables the introduction of a plethora of functional groups without changing the degree of polymerization and the molecular weight distribution. Similarly, modifying precursor particles enables the introduction of functional groups into particles while reducing variations in colloidal features, e.g., particle size and size distribution. This powerful synthetic method complements established procedures for functionalization of particle surfaces, thereby enabling the facile preparation of (multi‐)functional particle libraries, which will allow precise investigations of structure–property relations.

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“…Polymers 2020, 12, x 2 of 11 whose fluorescence switch was driven by a combination of poly(N-isopropylacrylamide) (PNIPAm) and the AIE effect [23]. Selenium-containing polymers showed versatile responsive behaviors to multiple stimuli, such as oxidation, reduction, and irradiation [24][25][26][27][28][29], which make them potentially useful as bio-building blocks. Redox responsiveness is an important property of diselenide-containing polymers [30][31][32][33].…”

Section: Introductionmentioning

confidence: 99%

Novel AIEgen-Functionalized Diselenide-Crosslinked Polymer Gels as Fluorescent Probes and Drug Release Carriers

et al. 2020

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Stimuli-responsive functional gels have shown significant potential for application in biosensing and drug release systems. In this study, aggregation-induced emission luminogen (AIEgen)-functionalized, diselenide-crosslinked polymer gels were synthesized via free radical copolymerization. A series of polymer gels with different crosslink densities or tetraphenylethylene (TPE) contents were synthesized. The diselenide crosslinker in the gels could be fragmented in the presence of H2O2 or dithiothreitol (DTT) due to its redox-responsive property. Thus, the TPE-containing polymer chains were released into the aqueous solution. As a result, the aqueous solution exhibited enhanced fluorescence emission due to the strong hydrophobicity of TPE. The degradation of polymer gels and fluorescence enhancement in an aqueous solution under different H2O2 or DTT concentrations were studied. Furthermore, the polymer gels could be used as drug carriers, suggesting a visual drug release process under the action of external redox agents. The AIEgen-functionalized, diselenide-crosslinked polymer gels hold great potential in the biomedical area for biosensing and controlled drug delivery.

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Near-infrared light-responsive, diselenide containing core-cross-linked micelles prepared by the Diels–Alder click reaction for photocontrollable drug release application

Abstract: We report a facile and efficient preparation of a NIR-triggered micelle system for a drug vehicle.

Cited by 38 publications

References 28 publications

Fabrication of Core Crosslinked Polymeric Micelles as Nanocarriers for Doxorubicin Delivery: Self-Assembly, In Situ Diselenide Metathesis and Redox-Responsive Drug Release

Fabrication of Core Crosslinked Polymeric Micelles as Nanocarriers for Doxorubicin Delivery: Self-Assembly, In Situ Diselenide Metathesis and Redox-Responsive Drug Release

Reactive Precursor Particles as Synthetic Platform for the Generation of Functional Nanoparticles, Nanogels, and Microgels

Novel AIEgen-Functionalized Diselenide-Crosslinked Polymer Gels as Fluorescent Probes and Drug Release Carriers

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