Hydrogen-bonded supramolecular micelle-mediated drug delivery enhances the efficacy and safety of cancer chemotherapy

Cheng, Chih Chia; Sun, Ya Ting; Lee, Ai Wei; Huang, Shan; Fan, Wen Lu; Chiao, Yu‐Hsuan; Chiu, Chih Wei; Lai, Juin Yih

doi:10.1039/d0py00082e

Cited by 22 publications

(13 citation statements)

References 52 publications

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“…Targeted nano-drug delivery systems with small sizes (10 to 100 nm) enhance permeation through the newborn blood vessels of tumor tissues with slower clearance due to the lack of lymph 12 . These drug nanocarriers including micelles 13,14 , polymersomes 15 , liposomes 16 , dendrimers 17 , carbon nanotubes 18 , magnetic nanoparticles 19 and silica nanoparticles 20,21 are of high importance because of their higher permeability, detection of target cells, accumulation at cancer sites, less side effects, and more efficient treatment 4,5,22 .…”

Section: Introductionmentioning

confidence: 99%

One Pot Doxorubicin Partitioning and Encapsulation on Silica Nanoparticle, Applying Aqueous Two Phase System for Preparation of pH-Responsive Nanocarriers

Baghbanbashi¹,

Pazuki²,

Khoee³

2021

Preprint

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Providing an efficient system for drug delivery and chemotherapy has always been an important issue. Modification of the surface of silica nanoparticles (SiO2) provides an opportunity for achieving stimulus-sensitive drug delivery system. Here, we have modified the surface of SiO2 using hydrogen bonding interactions by employing an aqueous two-phase system (ATPS) based on polyethylene glycol and lysine. This novel biocompatible ATPS provides an environment for simultaneous drug encapsulation, SiO2 modification, and drug partitioning in one pot. Addition of SiO2 to ATPS increased the partitioning of doxorubicin (DOX) as an anti-cancer drug from 47.92 in the absence of nanoparticles to 92.33 due to the interactions between drug and nanoparticles. The formation of nanoformulation and its characteristics were investigated applying microscopy, spectroscopy and thermal analysis. Drug release study demonstrated that DOX is loaded on nanoformulations efficiently with an encapsulation efficiency of 63.84% and shows lower release in physiological environment compared to the unmodified nanoparticles. While in acidic conditions of pH 5.5, significant increase was observed in the release profile. MTT assay on MCF-7 cancer cells confirmed that the nanoformulations were non-toxic and DOX-loaded nanocarrier showed anti-cancer behavior. These results indicate that the prepared nanoformulations are promising nanocarriers for controlled drug release purposes.

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Section: Introductionmentioning

confidence: 99%

One Pot Doxorubicin Partitioning and Encapsulation on Silica Nanoparticle, Applying Aqueous Two Phase System for Preparation of pH-Responsive Nanocarriers

Baghbanbashi¹,

Pazuki²,

Khoee³

2021

Preprint

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“…First, propargyl-ended difunctional PEG [number-average molecular weight ( M n ), 3000–4000 g/mol] is reacted with azide-functionalized aminopyridinyl amide (DAP) via an azide–alkyne cycloaddition reaction. High-quality DAP-end terminated difunctional PEG (BDAP-PEG) is obtained after purification and dialysis. Subsequently, BDAP-PEG is reacted with uracil via a high-yielding Michael addition reaction to generate BU-DPy-PEG (yield = 90%).…”

Section: Resultsmentioning

confidence: 92%

“…BDAP-PEG was synthesized via a previously described one-step synthetic route . BDAP-PEG (5.00 g, 1.43 mmol) and pyridine (0.24 g, 3.00 mmol) were dissolved in anhydrous tetrahydrofuran (THF, 50 mL) and cooled in an ice-salt bath.…”

Section: Methodsmentioning

confidence: 99%

“…BDAP-PEG was synthesized via a previously described one-step synthetic route. 35 BDAP-PEG (5.00 g, 1.43 mmol) and pyridine (0.24 g, 3.00 mmol) were dissolved in anhydrous tetrahydrofuran (THF, 50 mL) and cooled in an ice-salt bath. An anhydrous THF (10 mL) solution of acryloyl chloride (0.27 g, 3.00 mmol) was added dropwise over 30 min at 0 °C, and the mixture was continuously stirred at 25 °C overnight.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

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Self-Assembled Supramolecular Micelles with pH-Responsive Properties for More Effective Cancer Chemotherapy

Cheng

Sun

Lee

et al. 2020

ACS Biomater. Sci. Eng.

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pH-Responsive hydrogen-bonded supramolecular micelles, composed of a water-soluble poly(ethylene glycol) polymer with two terminal sextuple hydrogen bonding groups, can spontaneously organize in aqueous media to give well-defined, uniformly sized spherical micelles. The supramolecular micelles exhibit a number of unique physical characteristics, such as interesting amphiphilic behavior, desirable micellar size and nanospherical morphology, excellent biocompatibility, tailorable drug-loading capacities, and high structural stability in media containing serum or red blood cells. In addition, the drug release kinetics of drug-loaded micelles can be easily manipulated to achieve the desired release profile by regulating the environmental pH, thus these micelles are highly attractive candidates as an intelligent drug carrier system for cancer therapy. Cytotoxicity assays showed that the drug-loaded micelles induced pH-dependent intracellular drug release and exerted strong antiproliferative and cytotoxic activities toward cancer cells. Importantly, cellular uptake and flow cytometric analyses confirmed that a mildly acidic intracellular environment significantly increased cellular internalization of the drug-loaded micelles and subsequent drug release in the cytoplasm and nucleus of cancer cells, resulting in more effective induction of apoptotic cell death. Thus, this system may provide an efficient route toward achieving the fundamental properties and practical realization of pHsensitive drug-delivery systems for chemotherapy.

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“…A large number of studies have demonstrated that the drug loading system based on hydrogen bonds not only had high drug loading capacity and excellent stability but also could intelligently release loaded drugs due to the pH responsiveness of hydrogen bonds. 14–16…”

Section: Introductionmentioning

confidence: 99%

Hydrogen-bond super-amphiphile based drug delivery system: design, synthesis, and biological evaluation

Chen

Huang

et al. 2022

RSC Adv.

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Hydrogen-bonded supramolecular micelle-mediated drug delivery enhances the efficacy and safety of cancer chemotherapy

Abstract: Multiple hydrogen-bonded supramolecular polymers tend to form stable spherical micelles with oppositely charged anticancer drugs in biological environments, which improves cellular drug uptake and more effectively induces apoptosis in cancer cells.

Cited by 22 publications

References 52 publications

One Pot Doxorubicin Partitioning and Encapsulation on Silica Nanoparticle, Applying Aqueous Two Phase System for Preparation of pH-Responsive Nanocarriers

One Pot Doxorubicin Partitioning and Encapsulation on Silica Nanoparticle, Applying Aqueous Two Phase System for Preparation of pH-Responsive Nanocarriers

Self-Assembled Supramolecular Micelles with pH-Responsive Properties for More Effective Cancer Chemotherapy

Hydrogen-bond super-amphiphile based drug delivery system: design, synthesis, and biological evaluation

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