Supramolecular amphiphiles based on cyclodextrin and hydrophobic drugs

Sun, Tao; Wang, Qingbing; Bi, Yunke; Xin-li, Chen; Li, Lisha; Ruan, Chunhui; Zhao, Zhifeng; Jiang, Chen

doi:10.1039/c6tb03272a

Cited by 33 publications

(30 citation statements)

References 55 publications

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“…[49][50][51] The lipophilic drug (DIT) was loaded in the hydrophobic inner cavity of β-CDs via host-guest interactions. 40,41 The drug EE of DIT was 94.7%, indicating that DIT was highly exhibited in these NPs and the corresponding DL reached to 3.48%.…”

Section: Synthesis and Characterization Of β-Cds-capped Ceo 2 Npsmentioning

confidence: 95%

“…Furthermore, the porous nanostructures with unique hydrophobic β-CDs cavity could be used as a promising drug carrier for hydrophobic molecules by supra-molecular inclusion. 40,41 In the present study, we investigated the drug-loading ability and anti-psoriasis activity of β-CDs/CeO 2 NPs on IMQ-induced psoriasis-like mouse model by using DIT as the lipophilic model drug.…”

Section: Introductionmentioning

confidence: 99%

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Cyclodextrin-Modified CeO2 Nanoparticles as a Multifunctional Nanozyme for Combinational Therapy of Psoriasis

Wu¹,

Liu²,

Wang³

et al. 2020

IJN

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Reactive oxygen species (ROS)-induced oxidative stress plays a key role in the pathogenesis and progression of psoriasis by causing inflammation. Antioxidative strategies eradicating ROS may serve as effective and easy treatment options for psoriasis, while nanozymes with intrinsic antioxidant enzyme-like activity have not been explored for psoriasis treatment. The aim of this study is to fabricate β-cyclodextrins (β-CDs)-modified ceria nanoparticles (β-CDs/CeO 2 NPs) with drug-loaded and multimimic-enzyme activities for combinational psoriasis therapy. Methods: The β-CDs/CeO 2 NPs were synthesized by a hydrothermal method using unmodified β-CDs as a protecting agent. The structure, size and morphology were analyzed by dynamic light scattering, transmission electron microscopy (TEM), X-ray photoelectron spectroscopy (XPS) and Fourier transform infrared (FTIR) spectroscopy. Considering the superoxide dismutase (SOD)-and catalase-mimetic activities, the in vitro antioxidant activity of the β-CDs/CeO2 NPs was investigated. After dithranol (DIT) was loaded, the drug-loading capacity and release profile were determined by UV-visible light spectrophotometer and high-performance liquid chromatography. The anti-psoriatic efficacy was studied in the imiquimod (IMQ)-induced mouse model on the basis of morphological evaluation, psoriasis area and severity index calculation (PASI), and inflammatory cytokine expression. Results: The average particle size of the blank β-CDs/CeO 2 NPs was 60.89±0.32 nm with a polydispersity index (PDI) of 0.12, whereas that of the DIT-loaded NPs was 79.38±1.06 nm with a PDI of 0.27. TEM results showed the as-prepared NPs formed a uniform quasispherical shape with low polydispersity. XPS indicates synthesized NPs have a mixed Ce 3 + /Ce 4+ valence state. FTIR spectroscopy confirmed the presence of β-CDs and DIT in the NPs. Inhibition of superoxide anion rate by NPs could be reached to 79.4% in the presence of 200 µg/mL, and elimination of H 2 O 2 efficiency reached about 50% in the presence of 40 µg/ mL, demonstrating excellent superoxide dismutase-and catalase-mimicking activities, thereby providing remarkable cryoprotection against ROS-mediated damage. Furthermore, β-CDs on the surface endowed the NPs with drug-loading function via host-guest interactions. The entrapment efficiency and drug loading of DIT are 94.7% and 3.48%, respectively. The in vitro drug release curves revealed a suitable release capability of DIT@β-CDs/CeO 2 NPs under physiological conditions. In IMQ-induced psoriatic model, the DIT@β-CDs/CeO 2 NPs exhibited excellent therapeutic effect. Conclusion: This study may pave the way for the application of nanozyme β-CDs/CeO 2 NPs as a powerful tool for psoriasis therapy.

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Section: Synthesis and Characterization Of β-Cds-capped Ceo 2 Npsmentioning

confidence: 95%

Section: Introductionmentioning

confidence: 99%

Cyclodextrin-Modified CeO2 Nanoparticles as a Multifunctional Nanozyme for Combinational Therapy of Psoriasis

Wu¹,

Liu²,

Wang³

et al. 2020

IJN

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“…The guest molecule containing azobenzene and disulfide bonds was included in the β‐CD cavity to form light‐ and redox‐responsive supramolecular vesicles that greatly promoted drug release under UV light irradiation or reduction . Hydrophobic drugs such as 7‐ethyl‐10‐hydroxycamptothecin (SN‐38), doxorubicin (DOX), phenytoin, and aliskiren could be linked to the guest molecule with an azobenzene moiety via the disulfide bond for the construction of light‐ and redox‐responsive supramolecular vesicles . This group synthesized a hydrophobically modified β‐CD with an azobenzene moiety, which formed an inclusion complex with α‐CD to further self‐assemble UV‐ and pH‐responsive supramolecular vesicles .…”

Section: Cd‐based Light‐responsive Supramolecular Systemsmentioning

confidence: 99%

Recent Advances in Cyclodextrin‐Based Light‐Responsive Supramolecular Systems

Zhang

Wang

et al. 2018

Macromol. Rapid Commun.

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Cyclodextrins (CDs), one of the host molecules in supramolecular chemistry, can host guest molecules to form inclusion complexes via non-covalent and reversible host-guest interactions. CD-based light-responsive supramolecular systems are typically constructed using CDs and guest molecules with light-responsive moieties, including azobenzene, arylazopyrazole, o-nitrobenzyl ester, pyrenylmethyl ester, coumarin, and anthracene. To date, numerous efforts have been reported on the topic of CD-based light-responsive supramolecular systems, but these have not yet been highlighted in a separated review. This review summarizes the efforts reported over the past ten years. The main text of this review is divided into five sections (vesicles, micelles, gels, capturers, and nanovalves) according to the formation of self-assemblies. This feature article aims to afford a comprehensive understanding of the light-responsive moieties used in the construction of CD-based light-responsive supramolecular systems and to provide a helpful guide for the further design of CD-based light-responsive supramolecular systems.

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“…Furthermore, SCs with ap rocessed amphiphilic nature or responsive properties can self-assemble into different morphologies, such as micelles and vesicles,s ot hat they can be applied in the drug-delivery field. [31][32][33] Aside for the traditional drug-loadeds trategy, the application of supramolecular prodrug self-assemblies with better safety and intelligent behaviorh as recently attracted attention. [31][32][33] Aside for the traditional drug-loadeds trategy, the application of supramolecular prodrug self-assemblies with better safety and intelligent behaviorh as recently attracted attention.…”

Section: Introductionmentioning

confidence: 99%

“…[26][27][28][29][30] Owing to their dynamic reversible nature and various stimuli-responsive properties, SCs have self-assemblya nd drug-release properties that exhibit more intelligent behavior. [31][32][33] Aside for the traditional drug-loadeds trategy, the application of supramolecular prodrug self-assemblies with better safety and intelligent behaviorh as recently attracted attention. For example, Jin and Ji et al [34][35][36] have contributed significantly to the field of supramolecularp rodrug self-assemblies, and they report the use of a-cyclodextrin-hydrazide-doxorubicin (a-CD-hydrazide-DOX)a nd b-CD-hydrazone-DOX as host moieties for the facile construction of differents upramolecular prodrug micelles.…”

Section: Introductionmentioning

confidence: 99%

Photo‐ and pH‐ Dual‐Responsive β‐Cyclodextrin‐Based Supramolecular Prodrug Complex Self‐Assemblies for Programmed Drug Delivery

Bai

Liu

Song

et al. 2018

Chemistry An Asian Journal

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Despite the fact that progress has been made in the application of supramolecular prodrug self-assembliest o enhance the functionality of drug-delivery systems, corresponding research on multi-responsive supramolecular prodrug self-assemblies for programmedd rug delivery is still limited. In this paper,t he synthesis and self-assembly behavior of supramolecularp rodrug complexes( SPCs) with b-cyclodextrin-acylhydrazone-doxorubicin (b-CD-hydrazone-DOX) and the targeting of azobenzene-terminated poly[2-(dimethylamino)ethyl methacrylate] (Azo-PDMA-FA) as a building block were investigated. The obtained SPCs could also form self-assemblies on the basis of their amphiphilic nature. Next, SPC-based multi-compartment vesiclesa nd complex micelles, which were confirmed by transmission electron microscopy and dynamic/static light scattering, were obtained with good reversibility under alternative visible light or UV irradiation. Furthermore, three-stage programmed drug-delivery behavior was observed from dual-re-sponsiveS PC-based self-assemblies by utilizing UV and pH stimuli.S pecifically,t he SPCs first self-assembled into multicompartmental vesicles, which was accompanied by as low releaseo fD OX. Next, UV-light irradiation induced the dissociation of b-CD/Azo,w hich led to morphologyt ransition and as light increaseinthe rate of releaseofDOX. Upon transferring the self-assemblies to phosphate-buffer solution (pH 5.0), the releaser ates increased notably as ar esult of the broken acylhydrazone bond. Finally,b asic cell experiments further demonstrated that the SPC-based self-assemblies could be internalized into cancerc ells, which suggests their promise for applicationsinc ancer therapy.Scheme1.Morphology transition of supramolecular prodrugcomplex self-assemblies and their programmed drug-release behaviorregulated by UV lighta nd pH.

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Supramolecular amphiphiles based on cyclodextrin and hydrophobic drugs

Abstract: Herein we report a novel “supra-prodrug-type” superamphiphile design: via a redox-sensitive self-immolative linker, a hydrophobic drug molecule was labeled with an azobenzene moiety, which was designed to be capped by a hydrophilic cyclodextrin (CD) molecule.

Cited by 33 publications

References 55 publications

<p>Cyclodextrin-Modified CeO<sub>2</sub> Nanoparticles as a Multifunctional Nanozyme for Combinational Therapy of Psoriasis</p>

<p>Cyclodextrin-Modified CeO<sub>2</sub> Nanoparticles as a Multifunctional Nanozyme for Combinational Therapy of Psoriasis</p>

Recent Advances in Cyclodextrin‐Based Light‐Responsive Supramolecular Systems

Photo‐ and pH‐ Dual‐Responsive β‐Cyclodextrin‐Based Supramolecular Prodrug Complex Self‐Assemblies for Programmed Drug Delivery

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