Redox and pH responsive polymeric vesicles constructed from a water-soluble pillar[5]arene and a paraquat-containing block copolymer for rate-tunable controlled release

Zhong, Jiaxing; Tang, Qiuju; Ju, Yanshan; Lin, Yonghui; Bai, Xiaowen; Zhou, Junyi; Luo, Haipeng; Lei, Zhentao; Tong, Zaizai

doi:10.1080/09205063.2018.1561814

Cited by 12 publications

(10 citation statements)

References 49 publications

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“…pillar [n]arenes, as a new class of macrocycle first synthesized by Ogoshi et al (2008), have recently been widely used in many fields including molecular recognition (Yakimova et al, 2016;Yuan et al, 2017), mechanical interlocking molecules (Chen et al, 2013a;Zhang et al, 2019c), artificial transmembrane channels (Chen et al, 2013b;Xin et al, 2017), metal ion separation (Xia et al, 2017), chemical sensors (Wu et al, 2014;Stepanova et al, 2017;Wei et al, 2017;Hua et al, 2018;Sun et al, 2018), and supramolecular polymers (Strutt et al, 2012;Zhou et al, 2014a;Nierengarten et al, 2016;Zhang et al, 2018). At present, researchers are more focusing on the study of watersoluble pillar [n]arenes (Hu et al, 2016;Yang et al, 2016;Yu et al, 2016;Zhou et al, 2017b;Li et al, 2019;Zhong et al, 2019) because they can effectively bind different types of molecules into their cavities to construct a series of stimulus-responsive supramolecular amphiphiles for the application in DDSs. Among the DDSs, the pillararenes, as building units, are mostly based on the design of negative ion or neutral amphiphilic.…”

Section: Introductionmentioning

confidence: 99%

A pH-Responsive Supramolecular Drug Delivery System Constructed by Cationic Pillar[5]arene for Enhancing Antitumor Activity

Liu

Zhou

et al. 2021

Front. Chem.

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Drug delivery systems have good biocompatibiliy and low side effects for cancer treatment, but overcoming high efficiency of drug-loading and the drug-targeting controlled release still remains challenging. In this work, supramolecular vesicles, with pH-triggering effect, have been successfully constructed for drug delivery, which are fabricated by the complexation between a cationic pillar[5]arene (DAWP5) and a sodium dodecyl sulfonate (SDS) in aqueous solution. Drug-loading and releasing results demonstrated that anticancer drug doxorubicin (DOX) could be loaded efficiently by such cationic vesicles in neutral condition, and the drug release could be controlled in the simulated weak acid environment of tumor cells. Moreover, the vesicles had low cytotoxicity to normal human cell (L02), while the DOX-loaded vesicles could significantly enhance the cytotoxicity of free DOX for normal cell L02 and four tested tumor cells (Hela, HepG2, MGC-803 and T24). Especially for HepG2, after 24 h incubation time, IC50 of DOX-loaded vesicles was only 0.79 μM, about 23% of that of DOX (3.43 μM). These results suggested that such novel vesicles have promising potential to construct nano-drug delivery systems for various biomedical applications.

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Section: Introductionmentioning

confidence: 99%

A pH-Responsive Supramolecular Drug Delivery System Constructed by Cationic Pillar[5]arene for Enhancing Antitumor Activity

Liu

Zhou

et al. 2021

Front. Chem.

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“…To regulate the rate of drug release, in 2018, Zhong and co-workers successfully constructed dual pH-and redox-responses polymer vesicles generated by the host-guest interactions of WP5 and a paraquat-containing block copolymer BCP. 76 These polymeric vesicles loaded with DOX showed modulated drug release rates based on exposure to a single stimulus or a combination of both stimuli. In addition, under the conditions of this study, the DOX-loaded polymeric vesicles showed anticancer activity similar to that of free DOX in vitro, indicating that these vesicles may play important roles in the treatment of cancer as controlled-release drug carriers.…”

Section: Dovepressmentioning

confidence: 99%

“…75 In 2018, Zhong and coworkers successfully synthesized a water-soluble amphiphilic WP5-modified by carboxyl groups, and constructed pH and redox dual-responsive polymer vesicles based on host-guest interactions of their modified WP5 with a paraquat-containing block copolymer (BCP). 76 This same year, Zhou et al synthesized a water-soluble amphiphilic pillar [5]arene modified by a carboxyl group, and CO 2enhanced bola-type supramolecular amphiphiles were successfully constructed using CO 2 responsive borosilicate GH2 driven by host-guest complexation with a positively charged ammonium salt. Finally, they successfully demonstrated the effective controlled release of selfassembled vesicles consisting of bola-type supramolecular amphiphiles containing calcein.…”

Section: Synthesis Of Anionic Amphiphilic Pillar[n] Arenesmentioning

confidence: 99%

<p>Supramolecular Vesicles Based on Amphiphilic Pillar[n]arenes for Smart Nano-Drug Delivery</p>

Hua¹,

Chen²,

Hou³

et al. 2020

IJN

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Supramolecular vesicles are the most popular smart nano-drug delivery systems (SDDs) because of their unique cavities, which have high loading carrying capacity and controlled-release action in response to specific stimuli. These vesicles are constructed from amphiphilic molecules via host-guest complexation, typically with targeted stimuli-responsive units, which are particularly important in biotechnology and biomedicine applications. Amphiphilic pillar[n]arenes, which are novel and functional macrocyclic host molecules, have been widely used to construct supramolecular vesicles because of their intrinsic rigid and symmetrical structure, electron-rich cavities and excellent properties. In this review, we first explain the synthesis of three types of amphiphilic pillar[n]arenes: neutral, anionic and cationic pillar[n]arenes. Second, we examine supramolecular vesicles composed of amphiphilic pillar[n] arenes recently used for the construction of SDDs. In addition, we describe the prospects for multifunctional amphiphilic pillar[n]arenes, particularly their potential in novel applications.

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“…Yang et al [23] used a water-soluble pillar [5]arene to increase biocompatibility in antibacterial polymeric materials based on cationic polyaspartamide derivatives with different side-chain lengths by creating host-guest complexes to produce new antibacterial materials with pH-sensitive characteristics. Tong et al [24] showed stimulus-responsive polymer vesicles consisting of water-soluble pillar [5]arenes with carboxylate fragments and paraquat-containing block copolymers in water. Vesicles are formed due to the formation of inclusion complexes between the pillar [5]arene and fragments of paraquats included in the structure of polymers.…”

Section: Introductionmentioning

confidence: 99%

Towards Universal Stimuli-Responsive Drug Delivery Systems: Pillar[5]arenes Synthesis and Self-Assembly into Nanocontainers with Tetrazole Polymers

et al. 2021

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In this work, we have proposed a novel universal stimulus-sensitive nanosized polymer system based on decasubstituted macrocyclic structures—pillar[5]arenes and tetrazole-containing polymers. Decasubstituted pillar[5]arenes containing a large, good leaving tosylate, and phthalimide groups were first synthesized and characterized. Pillar[5]arenes containing primary and tertiary amino groups, capable of interacting with tetrazole-containing polymers, were obtained with high yield by removing the tosylate and phthalimide protection. According to the fluorescence spectroscopy data, a dramatic fluorescence enhancement in the pillar[5]arene/fluorescein/polymer system was observed with decreasing pH from neutral (pH = 7) to acidic (pH = 5). This indicates the destruction of associates and the release of the dye at a pH close to 5. The presented results open a broad range of opportunities for the development of new universal stimulus-sensitive drug delivery systems containing macrocycles and nontoxic tetrazole-based polymers.

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Redox and pH responsive polymeric vesicles constructed from a water-soluble pillar[5]arene and a paraquat-containing block copolymer for rate-tunable controlled release

Cited by 12 publications

References 49 publications

A pH-Responsive Supramolecular Drug Delivery System Constructed by Cationic Pillar[5]arene for Enhancing Antitumor Activity

A pH-Responsive Supramolecular Drug Delivery System Constructed by Cationic Pillar[5]arene for Enhancing Antitumor Activity

<p>Supramolecular Vesicles Based on Amphiphilic Pillar[n]arenes for Smart Nano-Drug Delivery</p>

Towards Universal Stimuli-Responsive Drug Delivery Systems: Pillar[5]arenes Synthesis and Self-Assembly into Nanocontainers with Tetrazole Polymers

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