Supramolecular Complex of Methyl-β-cyclodextrin with Adamantane-Grafted Hyaluronic Acid as a Novel Antitumor Agent

Elamin, Khaled M.; Yamashita, Yūki; Higashi, Taishi; Motoyama, Keiichi; Arima, Hisatomi

doi:10.1248/cpb.c17-00824

Cited by 13 publications

(11 citation statements)

References 44 publications

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“…In this study, we demonstrated that MβCD is a potential enhancer of the BITC-induced antiproliferation in human colorectal cancer cells. MβCD is accepted as an effective agent to remove the plasma membrane cholesterol [20] and reported to induce cholesterol efflux in HCT-116 cells [26], consistent with the present result Figure 1. The non-toxic concentration of MβCD (2.5 mM) enhanced the BITCinduced antiproliferation (Figure 2(b)) and apoptosis induction (Figure 3(b)) without change in the BITC accumulation (Figure 1(c)).…”

Section: Discussionsupporting

confidence: 90%

Methyl-β-cyclodextrin potentiates the BITC-induced anti-cancer effect through modulation of the Akt phosphorylation in human colorectal cancer cells

Yang

Miyagawa

Liu

et al. 2018

Bioscience, Biotechnology, and Biochemistry

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Methyl-β-cyclodextrin (MβCD) is an effective agent for the removal of plasma membrane cholesterol. In this study, we investigated the modulating effects of MβCD on the antiproliferation induced by benzyl isothiocyanate (BITC), an ITC compound mainly derived from papaya seeds. We confirmed that MβCD dose-dependently increased the cholesterol level in the medium, possibly through its removal from the plasma membrane of human colorectal cancer cells. The pretreatment with a non-toxic concentration (2.5 mM) of MβCD significantly enhanced the BITC-induced cytotoxicity and apoptosis induction, which was counteracted by the cholesterol supplementation. Although BITC activated the phosphoinositide 3-kinase (PI3K)/Akt pathway, MβCD dose-dependently inhibited the phosphorylation level of Akt. On the contrary, the treatment of MβCD enhanced the phosphorylation of mitogen activated protein kinases, but did not potentiate their BITC-induced phosphorylation. These results suggested that MβCD might potentiate the BITC-induced anti-cancer by cholesterol depletion and thus inhibition of the PI3K/Akt-dependent survival pathway. Abbreviations: CDs: cyclodextrins; MβCD: methyl-β-cyclodextrin; ITCs: isothiocyanates; BITC: benzyl isothiocyanate; PI3K: phosphoinositide 3-kinase; PDK1: phosphoinositide-dependent kinase-1; MAPK: mitogen activated protein kinase; ERK1/2: extracellular signal-regulated kinase1/2; JNK: c-Jun N-terminal kinase; PI: propidium iodide; FBS: fatal bovine serum; TLC: thin-layer chromatography; PBS(-): phosphate-buffered saline without calcium and magnesium; MEK: MAPK/ERK kinase; PIP2: phosphatidylinositol-4,5-bisphosphate; PIP3: phosphatidylinositol-3,4,5-trisphosphate.

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Section: Discussionsupporting

confidence: 90%

Methyl-β-cyclodextrin potentiates the BITC-induced anti-cancer effect through modulation of the Akt phosphorylation in human colorectal cancer cells

Yang

Miyagawa

Liu

et al. 2018

Bioscience, Biotechnology, and Biochemistry

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“…Methyl-b-cyclodextrin (MbCD) has been mainly applied as a drug carrier in the pharmaceutical field (Loftsson and Duchene 2007) and as a cholesterol-depleting reagent in cell biological studies on lipid rafts (Ashrafzadeh and Parmryd 2015). It has also been reported that MbCD has potential antitumor efficacy and has the possibility of recruiting as an antitumor drug (Grosse et al 1998a;1998b;Gotoh et al 2014;Resni et al 2015;Elamin et al 2018). Recently, accumulating evidence supports that cyclodextrins also have an anti-atherosclerotic efficacy (Zimmer et al 2016;Ao et al 2016a;Pilely et al 2019;Wang et al 2019;Kim et al 2020).…”

Section: Discussionmentioning

confidence: 99%

Methyl-β-cyclodextrin suppresses the monocyte-endothelial adhesion triggered by lipopolysaccharide (LPS) or oxidized low-density lipoprotein (oxLDL)

Chen

Zhou

Zhang

et al. 2021

Pharmaceutical Biology

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“…The smaller nanogels were taken up by two kinds of tumor cells (HeLa and HepG2) (Choi et al, ). Adamantane‐grafted hyaluronic acid can work as carrier for methyl‐β‐cyclodextrin through supramolecular assembly and proved to be a potential antitumor agent (Elamin, Yamashita, Higashi, Motoyama, & Arima, ).…”

Section: Polysaccharidesmentioning

confidence: 99%

Carbohydrate‐based nanomaterials for biomedical applications

Gim

Zhu

Seeberger

et al. 2019

WIREs Nanomed Nanobiotechnol

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Carbohydrates are abundant biomolecules, with a strong tendency to form supramolecular networks. A host of carbohydrate-based nanomaterials have been exploited for biomedical applications. These structures are based on simple monoor disaccharides, as well as on complex, polymeric systems. Chemical modifications serve to tune the shapes and properties of these materials. In particular, carbohydrate-based nanoparticles and nanogels were used for drug delivery, imaging, and tissue engineering applications. Due to the reversible nature of the assembly, often based on a combination of hydrogen bonding and hydrophobic interactions, carbohydrate-based materials are valuable substrates for the creations of responsive systems. Herein, we review the current research on carbohydratebased nanomaterials, with a particular focus on carbohydrate assembly. We will discuss how these systems are formed and how their properties are tuned. Particular emphasis will be placed on the use of carbohydrates for biomedical applications.

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Supramolecular Complex of Methyl-β-cyclodextrin with Adamantane-Grafted Hyaluronic Acid as a Novel Antitumor Agent

Abstract: Methyl-β-cyclodextrin (M-β-CyD) exhibits cytotoxic activity, and has the potentials as an antitumor agent. However, a tumor-selectivity of M-β-CyD is low, leading to low antitumor activity and the adverse effects.

Cited by 13 publications

References 44 publications

Methyl-β-cyclodextrin potentiates the BITC-induced anti-cancer effect through modulation of the Akt phosphorylation in human colorectal cancer cells

Methyl-β-cyclodextrin potentiates the BITC-induced anti-cancer effect through modulation of the Akt phosphorylation in human colorectal cancer cells

Methyl-β-cyclodextrin suppresses the monocyte-endothelial adhesion triggered by lipopolysaccharide (LPS) or oxidized low-density lipoprotein (oxLDL)

Carbohydrate‐based nanomaterials for biomedical applications

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