Applications of π-π stacking interactions in the design of drug-delivery systems

Zhuang, Wan-Ru; Wang, Yi; Cui, Pengfei; Liu, Xing; Lee, Jaiwoo; Kim, Dong-Yoon; Jiang, Hu‐Lin; Oh, Yu‐Kyoung

doi:10.1016/j.jconrel.2018.12.014

Cited by 314 publications

(191 citation statements)

References 114 publications

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“…Also, because the drug structure is not chemically altered, drug molecules released from such delivery systems are expected to exert their predicted pharmacological effects. Many clinically used chemical drugs possess aromatic rings, such as DOX, playing the π-π stacking interactions the major role in drug delivery systems [83]. It is known that the loading efficiency for DOX decreases when using CNTs with higher levels of PEGylation, due to the increased hydrophilicity of the surface.…”

Section: Discussionmentioning

confidence: 99%

Toxicity of Carbon Nanomaterials and Their Potential Application as Drug Delivery Systems: In Vitro Studies in Caco-2 and MCF-7 Cell Lines

et al. 2020

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Carbon nanomaterials have attracted increasing attention in biomedicine recently to be used as drug nanocarriers suitable for medical treatments, due to their large surface area, high cellular internalization and preferential tumor accumulation, that enable these nanomaterials to transport chemotherapeutic agents preferentially to tumor sites, thereby reducing drug toxic side effects. However, there are widespread concerns on the inherent cytotoxicity of carbon nanomaterials, which remains controversial to this day, with studies demonstrating conflicting results. We investigated here in vitro toxicity of various carbon nanomaterials in human epithelial colorectal adenocarcinoma (Caco-2) cells and human breast adenocarcinoma (MCF-7) cells. Carbon nanohorns (CNH), carbon nanotubes (CNT), carbon nanoplatelets (CNP), graphene oxide (GO), reduced graphene oxide (GO) and nanodiamonds (ND) were systematically compared, using Pluronic F-127 dispersant. Cell viability after carbon nanomaterial treatment followed the order CNP < CNH < RGO < CNT < GO < ND, being the effect more pronounced on the more rapidly dividing Caco-2 cells. CNP produced remarkably high reactive oxygen species (ROS) levels. Furthermore, the potential of these materials as nanocarriers in the field of drug delivery of doxorubicin and camptothecin anticancer drugs was also compared. In all cases the carbon nanomaterial/drug complexes resulted in improved anticancer activity compared to that of the free drug, being the efficiency largely dependent of the carbon nanomaterial hydrophobicity and surface chemistry. These fundamental studies are of paramount importance as screening and risk-to-benefit assessment towards the development of smart carbon nanomaterial-based nanocarriers.

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Section: Discussionmentioning

confidence: 99%

Toxicity of Carbon Nanomaterials and Their Potential Application as Drug Delivery Systems: In Vitro Studies in Caco-2 and MCF-7 Cell Lines

et al. 2020

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“…In a self‐assembly process, different molecular interactions including electrostatic interaction, hydrophobic interaction, hydrogen bonding, and π ‐ π stacking play a vital role in the formation of nanotubular structures [37] . Non‐polar amino acids including aromatic and aliphatic amino acids, are mainly responsible for hydrophobic aggregation through π ‐ π stacking and hydrophobic interactions [38] . However, regarding the polar amino acids, self‐assembly process is the result of electrostatic interactions or hydrogen bonding depending on their charged residues [39] .…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Characterization of Phenylalanine Nanotubes as Green pH‐Responsive Drug Nanocarriers

et al. 2020

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The present study is aiming to investigate the potential of phenylalanine amino acid nanotubes (PhNTs) synthesized by a self‐assembly process as an efficient and pH‐responsive green drug nanocarrier for the treatment of oral disease. Phenylalanine was used for the preparation of solutions with three different concentrations (0.1, 0.5 and 2.5 mg/ml). Scanning electron microscopy (SEM) and Field emission scanning electron microscopy (FESEM) images showed that low and high concentrations of phenylalanine solution creates nanospheres and nanowires, respectively rather than tubular‐shaped nanostructures. In contrast, phenylalanine nanotubes were synthesized by medium concentration (0.5 mg/ml). The tubular shape and nanoscale diameter of the synthesized PhNTs were characterized by FESEM, Transmission Electron microscopy (TEM), Dynamic Light Scattering (DLS) and Fourier Transform Infrared Spectroscopy (FTIR). These characterization tests confirmed the synthesis of PhNTs with a tubular shape and nanoscale diameter. In the second stage, metronidazole was loaded into the phenylalanine‐based nanostructures as an effective drug for oral disorders. The results indicated that nanospheres and nanowires show drug loading efficiency of 49 % and 58 %, respectively, after 48 h of incubation time. Whereas, the drug loading efficiency for nanotubes was 91 %. The results from the FTIR analysis and UV‐vis spectroscopy verified the presence of metronidazole into the hollow structure of PhNT. While a burst drug release was observed for nanospheres and nanowires, PhNTs showed a well‐controlled release of metronidazole up to 95 % at oral pH, which is best fitted to the Weibull model. Subsequently, the cell viability of phenylalanine‐based nanostructures was assessed by MTT test on L929 fibroblast cell line.

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“…Disulfide, as a chemically sensitive bond, can be hydrolyzed in the presence of reductive substances such as dithiothreitol (DTT) and GSH. [ 9,16 ] Herein, we further evaluated the reduction sensitivity of three nanodrug particles. When incubated with 10 × 10 −3 m DTT, the diameter of these particles gradually increased and accompanied by nonuniform distribution (Figure S8a–c, Supporting Information).…”

Section: Resultsmentioning

confidence: 99%

GLUT1‐Targeting and GSH‐Responsive DOX/L61 Nanodrug Particles for Enhancing MDR Breast Cancer Therapy

Wang

Qin

et al. 2020

Part & Part Syst Charact

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Efficient targeting to tumor tissues and subsequent rapid drug release in cancer cells remains a major challenge for nanodrug delivery systems. Herein, smart nanodrug particles with reduction‐sensitive and active tumor‐targeting ability are constructed based on the nanoprecipitation of glucosamine‐grafted pluronic L61 (GA‐L61) and disulphide‐linked doxorubicin dimer (DOXSSDOX) to overcome tumor multidrug resistance (MDR). These nanoparticles show proper size and excellent stability under neutral conditions, while quickly release DOX due to the breakage of disulfide bonds under reductive medium. In vitro cellular uptake and drug efflux demonstrate that L61 can efficiently increase DOX concentration in MCF/ADR resistant cells by inhibiting the function of drug resistance proteins. In vivo biodistribution reveals that glucose transporter 1 (GLUT1)‐mediated tumor‐targeting significantly improves tumor accumulation of the glucosamine‐contained nanoparticles. Finally, the combination of GLUT1‐targeting, glutathione (GSH)‐responsive, and MDR‐reversal effects in nanoparticles achieve superior antitumor effects, which can provide an efficient, safe, and economic approach for drug delivery and cancer chemotherapy.

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Applications of π-π stacking interactions in the design of drug-delivery systems

Cited by 314 publications

References 114 publications

Toxicity of Carbon Nanomaterials and Their Potential Application as Drug Delivery Systems: In Vitro Studies in Caco-2 and MCF-7 Cell Lines

Toxicity of Carbon Nanomaterials and Their Potential Application as Drug Delivery Systems: In Vitro Studies in Caco-2 and MCF-7 Cell Lines

Synthesis and Characterization of Phenylalanine Nanotubes as Green pH‐Responsive Drug Nanocarriers

GLUT1‐Targeting and GSH‐Responsive DOX/L61 Nanodrug Particles for Enhancing MDR Breast Cancer Therapy

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