Hydroxypropyl cyclic β-(1→2)-d-glucans and epichlorohydrin β-cyclodextrin dimers as effective carbohydrate-solubilizers for polycyclic aromatic hydrocarbons

Choi, Jae Min; Jeong, Dae‐Yong; Piao, Jinglan; Kim, Kyoungtea; Nguyen, Andrew Bao Loc; Kwon, Nak‐Jung; Lee, Mi-Kyung; Lee, Im Soon; Yu, Jae‐Hyuk; Jung, Seunho

doi:10.1016/j.carres.2014.10.025

Cited by 8 publications

(6 citation statements)

References 32 publications

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“…β -CD can interact with PAHs in its hydrophobic cavity and form various host–guest complexes 26 35 36 37 38 . Unlike native CDs, dimeric β -CDs exhibit significantly enhanced binding and recognition of target materials due to cooperative binding of two neighboring CDs 27 28 29 30 .…”

Section: Resultsmentioning

confidence: 99%

β-CD Dimer-immobilized Ag Assembly Embedded Silica Nanoparticles for Sensitive Detection of Polycyclic Aromatic Hydrocarbons

Hahm

Jeong

Geun

et al. 2016

Sci Rep

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We designed a β-CD dimer on silver nanoparticles embedded with silica nanoparticles (Ag@SiO2 NPs) structure to detect polycyclic aromatic hydrocarbons (PAHs). Silica NPs were utilized as a template for embedding silver NPs to create hot spot structures and enhance the surface-enhanced Raman scattering (SERS) signal, and a thioether-bridged dimeric β-CD was immobilized on Ag NPs to capture PAHs. The assembled Ag NPs on silica NPs were confirmed by TEM and the presence of β-CD dimer on Ag@SiO2 was confirmed by UV-vis and attenuated total reflection-Fourier transform infrared spectroscopy. The β-CD dimer@Ag@SiO2 NPs were used as SERS substrate for detecting perylene, a PAH, directly and in a wide linearity range of 10−7 M to 10−2 M with a low detection limit of 10−8 M. Also, the β-CD dimer@Ag@SiO2 NPs exhibited 1000-fold greater sensitivity than Ag@SiO2 NPs in terms of their perylene detection limit. Furthermore, we demonstrated the possibility of detecting various PAH compounds using the β-CD dimer@Ag@SiO2 NPs as a multiplex detection tool. Various PAH compounds with the NPs exhibited their distinct SERS bands by the ratio of each PAHs. This approach of utilizing the assembled structure and the ligands to recognize target has potential for use in sensitive analytical sensors.

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Section: Resultsmentioning

confidence: 99%

β-CD Dimer-immobilized Ag Assembly Embedded Silica Nanoparticles for Sensitive Detection of Polycyclic Aromatic Hydrocarbons

Hahm

Jeong

Geun

et al. 2016

Sci Rep

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“…In addition, non-steroidal anti-inflammatory agents, paclitaxel, ergosterol, flavonoids were solubilized by the supramolecular complex with cyclic b-(1,2) glucans [20,23,26,48,119]. Then, various modified structures such as carboxymethyl, butyryl, succinyl, and methyl derivatives have also been utilized as shown in Table 1, and in particular hydroxyl modifications show the successful solubility enhancement on relatively large non-polar drugs such as polycyclic aromatic hydrocarbons and anaphtoflavone [30,104]. The bioavailability enhancement is also shown via increasing the solubility or stability [29,105].…”

Section: Solubilization Technologymentioning

confidence: 98%

“…With the same motivation, butyrylation was performed by adding butyryl chloride in dimethylformaide and pyridine [103]. For the additional space for larger compounds, hydroxypropyl groups could be attached, where the different ratio of propylene oxide and cyclic b-(1,2) glucans determined the DS [30,104]. In addition, oligomerization of cyclic b-(1,2) glucans was designed and carried out with epichlorohydrin to improve the complexation capability [105,106].…”

Section: Natural and Chemical Derivatizationmentioning

confidence: 99%

“…In fact, various bulky compounds such as amphotericin B, paclitaxel, indomethacin, reserpine, steroids, and vitamins have formed inclusion complexes with cyclic b-(1,2) glucans [22][23][24][25][26]. Recent study has also shown some results induced by the complexing ability of cyclic b-(1,3)-b-(1,6) and cyclic b-(1,2)-a-(1,6) glucans as well as the chemically derivatized cyclic b-(1,2) glucans [27][28][29][30][31].…”

Section: Introductionmentioning

confidence: 97%

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Properties and current applications of bacterial cyclic β-glucans and their derivatives

Cho

Jeong

Choi

et al. 2016

J Incl Phenom Macrocycl Chem

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Cyclic b-glucans are unique constituents that are found in the periplasmic space and extracellular media of Agrobacterium, Rhizobium, Bradyrhizobium, Rhodobacter, Xanthomonas, and Ralstonia species. Based on their glycosidic linkages, they are classified into three groups composed of cyclic b-(1,2), b-(1,3)-b-(1,6), and b-(1,2)-a-(1,6) linked glucans. Their degrees of polymerization vary ranging from 10 to 40 glucose residues, and the backbone structure can be modified with non-sugar moieties. Since the macrocyclic oligosaccharides possess their own characteristics such as inherent three-dimensional structures, hydrogen bonding, and complex-forming abilities, various possible applications would be of interest in the field of green chemistry, separation science, pharmaceutical, and food industries. In this review, we have addressed the properties and current applications of bio-sourced cyclic bglucans and their derivatives.

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“…However, the rigid structure and poor water solubility of cyclodextrins limit their further application. Compared with cyclodextrins, the advantages of β-glucans over cyclodextrins mainly involve their higher water solubility; additionally, β-glucans also exhibit high viscosities at very low concentrations (1%) and are stable with a wide range of pH levels [ 13 ]. Peter et al reported that the oral delivery of β-glucan was bound by intestinal epithelial and gut-associated lymphoid tissue (GALT) cells and pointed to the promotion of the systemic levels of the drug candidate [ 14 ].…”

Section: Introductionmentioning

confidence: 99%

Cryo-Milled β-Glucan Nanoparticles for Oral Drug Delivery

Chen,

Liu,

Svirskis

et al. 2024

Pharmaceutics

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Gemcitabine is a nucleoside analog effective against a number of cancers. However, it has an oral bioavailability of less than 10%, due to its high hydrophilicity and low permeability through the intestinal epithelium. Therefore, the aim of this project was to develop a novel nanoparticulate drug delivery system for the oral delivery of gemcitabine to improve its oral bioavailability. In this study, gemcitabine-loaded β-glucan NPs were fabricated using a film-casting method followed by a freezer-milling technique. As a result, the NPs showed a small particle size of 447.6 ± 14.2 nm, and a high drug entrapment efficiency of 64.3 ± 2.1%. By encapsulating gemcitabine into β-glucan NPs, a sustained drug release profile was obtained, and the anomalous diffusion release mechanism was analyzed, indicating that the drug release was governed by diffusion through the NP matrix as well as matrix erosion. The drug-loaded NPs had a greater ex vivo drug permeation through the porcine intestinal epithelial membrane compared to the plain drug solution. Cytotoxicity studies showed a safety profile of the β-glucan polymers, and the IC50s of drug solution and drug-loaded β-glucan NPs were calculated as 228.8 ± 31.2 ng·mL−1 and 306.1 ± 46.3 ng·mL−1, respectively. Additionally, the LD50 of BALB/c nude mice was determined as 204.17 mg/kg in the acute toxicity studies. Notably, pharmacokinetic studies showed that drug-loaded β-glucan NPs could achieve a 7.4-fold longer T1/2 and a 5.1-fold increase in oral bioavailability compared with plain drug solution. Finally, in vivo pharmacodynamic studies showed the promising capability of gemcitabine-loaded β-glucan NPs to inhibit the 4T1 breast tumor growth, with a 3.04- and 1.74-fold reduction compared to the untreated control and drug solution groups, respectively. In conclusion, the presented freezer-milled β-glucan NP system is a suitable drug delivery method for the oral delivery of gemcitabine and demonstrates a promising potential platform for oral chemotherapy.

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Hydroxypropyl cyclic β-(1→2)-d-glucans and epichlorohydrin β-cyclodextrin dimers as effective carbohydrate-solubilizers for polycyclic aromatic hydrocarbons

Cited by 8 publications

References 32 publications

β-CD Dimer-immobilized Ag Assembly Embedded Silica Nanoparticles for Sensitive Detection of Polycyclic Aromatic Hydrocarbons

β-CD Dimer-immobilized Ag Assembly Embedded Silica Nanoparticles for Sensitive Detection of Polycyclic Aromatic Hydrocarbons

Properties and current applications of bacterial cyclic β-glucans and their derivatives

Cryo-Milled β-Glucan Nanoparticles for Oral Drug Delivery

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