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Volume 63, Issue 7
Displaying 1-12 of 12 articles from this issue
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Communication to the Editor
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Tokutaro Ogata, Tomoyo Yoshida, Manami Tanaka, Chie Fukuhara, Maki Shi ...2015 Volume 63 Issue 7 Pages 485-488
Published: July 01, 2015
Released on J-STAGE: July 01, 2015
JOURNAL FREE ACCESS FULL-TEXT HTMLA new type of O-alkylation of 2-hydroxy-1,4-naphthoquinone with alkoxymethyl chlorides is described. The reaction course can be controlled by the choice of base and yields O-alkylated or O-alkoxymethylated products in high yield with high selectivity.Graphical Abstract Fullsize ImageView full abstractDownload PDF (495K) Full view HTML
Regular Articles
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Shin-ichi Kondo, Yuna Asano, Natsumi Koizumi, Kenjiro Tatematsu, Yuka ...2015 Volume 63 Issue 7 Pages 489-494
Published: July 01, 2015
Released on J-STAGE: July 01, 2015
JOURNAL FREE ACCESS FULL-TEXT HTMLWe fabricated polymeric micelles containing 5-fluorouracil (5-FU) or fluorescein using the amphiphilic block copolymer, poly-4-vinylpyridine-b-6-O-methacryloyl galactopyranose. Although the polymeric micelles were stable at pH 7.4, they readily decomposed at pH 5, resulting in near complete release of 5-FU. Uptake of polymeric micelles containing fluorescein by HepG2 and HCT116 cells was also investigated. With both cell types, strong fluorescence was observed after a 12-h incubation, but the fluorescence weakened after 24 h of incubation. The fluorescein incorporated into the polymeric micelles was released into acidic organelles (endosome and/or lysosome), from which it diffused throughout the cell. The cytotoxicity of polymeric micelles containing 5-FU was evaluated against HepG2 cells using a CCK-8 assay. The results suggest that polymeric micelles containing 5-FU are more cytotoxic to HepG2 cells than free 5-FU.Graphical Abstract Fullsize ImageView full abstractDownload PDF (3410K) Full view HTML -
Nadia Hanafy Metwally, Mohamed Ahmed Badawy, Doha Samir Okpy2015 Volume 63 Issue 7 Pages 495-503
Published: July 01, 2015
Released on J-STAGE: July 01, 2015
JOURNAL FREE ACCESS FULL-TEXT HTMLThe knöevenagel condensation of 3-phenyl-4-thioxo-2-thiazolidinone (1) with 1-phenyl-3-aryl-1H-pyrazole-4-carbaldehydes 2a–d in refluxing glacial acetic acid or in polyethylene glycol-400 (PEG-400) at room temperature without catalyst, afforded the corresponding 5-hetarylmethylene derivatives 3a–d. [4+2]Cycloaddition reaction of compounds 3 with N-arylmaleimides, acrylonitrile and ethyl acrylate afforded thiopyrano[2,3-d]thiazole derivatives 5a–p. The anticancer activity of some of the newly synthesized compounds was investigated against different human cancer cell lines (MCF7 and HEPG2) and confirmed by molecular docking. Moreover, the structure for one representative example of the new products was confirmed by X-ray crystallography. The structure of all the newly synthesized compounds was established by elemental and spectral data.Graphical Abstract Fullsize ImageView full abstractDownload PDF (1067K) Full view HTML -
Su Yang Jeong, Hye Mi Kim, Kyu Ha Lee, Kyu Yeob Kim, Dae Sun Huang, Jo ...2015 Volume 63 Issue 7 Pages 504-511
Published: July 01, 2015
Released on J-STAGE: July 01, 2015
Advance online publication: May 01, 2015
JOURNAL FREE ACCESS FULL-TEXT HTML
Supplementary materialAlthough Danggui is the root of Angelica gigas NAKAI in the Korean Pharmacopoeia, it is determined that Danggui is also the root of Angelica sinensis (OLIV.) DIELS in China and Hong Kong, as well as the root of Angelica acutiloba KITAGAWA in Japan. Accordingly, we tried to develop an identification method using the main compounds in A. gigas, A. sinensis, and A. acutiloba through HPLC/diode-array detector (DAD). This method was fully validated for linearity, accuracy, precision, recovery, and robustness. Multivariate analysis was also implemented after pattern analysis and monitoring. As a result, each compound pattern of A. gigas, A. sinensis, and A. acutiloba was identified, making it possible to distinguish them from each other.Graphical Abstract Fullsize ImageView full abstractDownload PDF (724K) Full view HTML -
Fei Liu, Xiaoqing Wang, Zheng Li, Jin Li, Xiaomei Zhuang, Zhenqing Zha ...2015 Volume 63 Issue 7 Pages 512-518
Published: July 01, 2015
Released on J-STAGE: July 01, 2015
JOURNAL FREE ACCESS FULL-TEXT HTMLYQA-14 is a promising agent for treating addiction to cocaine and opioids. However, previous studies have showed there is marked contrast between the relatively small differences in pharmacological action in vivo and the large differences in their respective receptor binding properties in vitro. We hypothesized that the conflict between the in vivo and in vitro outcomes was attributable to poor brain exposure to YQA-14 caused by drug efflux transporters. To address this issue, we investigated the directional flux of YQA-14 across Caco-2 cells at 37°C or 4°C and the bidirectional transport in the presence and absence of transporter chemical inhibitors. These phenomena were further investigated by an in vivo determination of the brain and blood pharmacokinetics (PK) profile of YQA-14 following intraperitoneal administration with and without inhibitor. The efflux ratio of YQA-14 on Caco-2 cell monolayers was 2.39 and the efflux was temperature-dependent. When co-incubated with GF120918 or LY335979, the efflux of YQA-14 was markedly decreased. However, there was no significant difference in the permeability of YQA-14 when the cells were treated with Ko143. In vivo experiments showed that the brain-to-plasma ratio increased by more than 75-fold and 20-fold with co-administration of GF120918 and LY335979, respectively. Use of Ko143 did not change the brain-to-blood ratio of YQA-14. The results indicate that the brain distribution of YQA-14 was restricted because of active efflux transport at the blood brain barrier. In addition, P-glycoprotein (P-gp) played a dominant role in limiting the distribution of YQA-14 to the brain.Graphical Abstract Fullsize ImageView full abstractDownload PDF (664K) Full view HTML -
Yutaka Inoue, Yuka Iwazaki, Yoshinori Onuki, Chiaki Funatani, Isamu Mu ...2015 Volume 63 Issue 7 Pages 519-524
Published: July 01, 2015
Released on J-STAGE: July 01, 2015
Advance online publication: April 16, 2015
JOURNAL FREE ACCESS FULL-TEXT HTMLThe current study used 3 types of carrageenan (denoted here as Car)—κ, ι, and λ—to prepare a jelly vehicle for acetaminophen (AAP), and then compared their usefulness as jelly vehicles. The rheological characteristics of each preparation were assessed and then drug elution from the preparation was assessed using dissolution testing. The behavior of each preparation when immersed in water was also examined using magnetic resonance imaging (MRI) in order to better understand the drug elution behaviour of each preparation. Viscoelasticity measurements revealed that 0.75 w/v%-ι-Car and 1.25 w/v%-λ-Car had viscoelasticity values equivalent to that of 0.5 w/v%-κ-Car. Dissolution testing of these 3 preparations indicated that 100% drug elution took 45 min with 0.5 w/v%-κ-Car while it took only 5 min with 0.75 w/v%-ι-Car and 1.25 w/v%-λ-Car. When deuterium oxide was added to κ-Car 0.5%, the MRI images darkened overall starting immediately after addition. The images revealed that the sample and deuterium oxide quickly mixed. In contrast, images revealed that deuterium oxide gradually penetrated κ-Car 1.0%. MRI images had uniform contrast, and deuterium oxide took 6 h or longer to penetrate the samples overall. These findings suggest that water is less apt to penetrate a jelly with an increased car concentration and a denser 3-dimensional network structure. Differences in the structure of car are said to result in better gelling, with κ having the best gelling characteristics, followed by ι and then λ. Thus, this paper discusses the role that vehicle gelling strength plays in the elution of acetaminophen.Graphical Abstract Fullsize ImageView full abstractDownload PDF (1006K) Full view HTML -
Raj Kumar Thapa, Sang-Duk Han, Hyoung Geun Park, Miwon Son, Joon Ho Ju ...2015 Volume 63 Issue 7 Pages 525-530
Published: July 01, 2015
Released on J-STAGE: July 01, 2015
Advance online publication: May 09, 2015
JOURNAL FREE ACCESS FULL-TEXT HTMLTopical fungal infections can become severe if left untreated. Efficient treatment modalities for topical fungal infections aid the penetration of antifungal agents deep into viable skin layers. Terbinafine is a fungicidal agent that inhibits ergosterol, an essential fungal component. The main objective of this study was to evaluate skin permeation and retention of a terbinafine-loaded solution containing chitosan as a film former. Comparative assessment of skin permeation and retention was performed using a prepared formulation (DA 5505) and marketed formulations of terbinafine in murine and porcine skin. To mimic fungal infection of skin, keratinized skin was induced in NC/Nga mice. In comparison with the marketed formulations, DA 5505 exhibited significantly better skin permeation. The flux, permeation coefficient, and enhancement ratio of terbinafine were remarkably increased by DA 5505 in comparison with the marketed formulations, and lag time was dramatically reduced. DA 5505 significantly increased cumulative terbinafine retention in viable skin layers in comparison with the marketed solution, suggesting enhanced efficacy. Furthermore, DA 5505 exhibited superior skin permeation in normal skin and keratinized skin. Thus, the DA 5505 formulation has the potential to effectively deliver terbinafine to superficial and deep cutaneous fungal infections.Graphical Abstract Fullsize ImageView full abstractDownload PDF (687K) Full view HTML -
Zbigniew Karczmarzyk, Waldemar Wysocki, Zofia Urbańczyk-Lipkowska, Prz ...2015 Volume 63 Issue 7 Pages 531-537
Published: July 01, 2015
Released on J-STAGE: July 01, 2015
JOURNAL FREE ACCESS FULL-TEXT HTMLA series of sulfur 1,2,4-triazine derivatives were prepared and evaluated as anticancer compounds for two human breast cancer cell lines (MCF-7, MDA-MB-231) with some of them acting as low micromolar inhibitors. Evaluation of the cytotoxicity using a 3-(4,5-dimethylthiazol-2-yl)-3,5-diphenyltetrazolium bromide (MTT) assay, the inhibition of [3H]thymidine incorporation into DNA, and collagen synthesis inhibition demonstrated that these products exhibit cytotoxic effects on these breast cancer cell lines in vitro. The most effective were disulfide and sulfenamide compounds with two valence sulfur atoms. A structure–activity relationship study was performed using X-ray analysis and theoretical calculations at an ab initio density functional theory (DFT) level.Graphical Abstract Fullsize ImageView full abstractDownload PDF (781K) Full view HTML -
Kenta Mizoi, Yu Mashima, Yuya Kawashima, Masato Takahashi, Seisuke Mim ...2015 Volume 63 Issue 7 Pages 538-545
Published: July 01, 2015
Released on J-STAGE: July 01, 2015
JOURNAL FREE ACCESS FULL-TEXT HTMLWe discovered that a reagent comprising a combination of PhBCl2 and nitriles was useful for syntheses of both 3-acylindoles and 1-(1H-indol-3-yl)alkylamine from indoles. The reaction proceeded selectively at the 3-position of indoles providing 3-acylindoles in moderate to high yields on treatment with the above reagent. Furthermore, the reaction provided the corresponding amine products in moderate to high yields after the intermediate imine was reduced by NaBH3CN. These reactions proceeded under mild conditions and are applicable to the formation of indoles functionalized at the 3-position.Graphical Abstract Fullsize ImageView full abstractDownload PDF (563K) Full view HTML -
U Min Seo, Bing Tian Zhao, Won Il Kim, Eun Kyoung Seo, Jae Hyun Lee, B ...2015 Volume 63 Issue 7 Pages 546-553
Published: July 01, 2015
Released on J-STAGE: July 01, 2015
Advance online publication: May 14, 2015
JOURNAL FREE ACCESS FULL-TEXT HTMLThe flower bud of Tussilago farfara L., called Farfarae Flos, has traditionally been used in Oriental medicine for the treatment of bronchitis and asthma. To establish a standard for quality control as well as the reliable identification of Farfarae Flos, the contents of five standards, rutin (1), isoquercetin (2), 3,5-dicaffeoylquinic acid (3), tussilagone (4), and tussilagonone (5), were determined by quantitative high-performance liquid chromatography (HPLC)/photodiode array (PDA) analysis. The five standards were separated on a YoungJinBioChrom Aegispak C18-L (250-mm×4.6-mm, 5-µm) column by gradient elution using 0.03% trifluoroacetic acid in water (A), with acetonitrile (B) as the mobile phase. The flow rate was 1.0 mL/min, and the UV detector wavelength was set at 220 nm. The method was successfully used in the analysis of Farfarae Flos from different geographic origins with relatively simple conditions and procedures, and the results demonstrated satisfactory linearity, recovery, precision, accuracy, stability, and robustness. The HPLC analytical method for pattern recognition analysis was validated by repeated analysis of 62 Farfarae Flos samples. This result indicated that the established HPLC/PDA method is suitable for quantitation and pattern recognition analyses for the quality evaluation of Farfarae Flos.Graphical Abstract Fullsize ImageView full abstractDownload PDF (561K) Full view HTML
Notes
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Kwan-Chul Kim, Ik-Soo Lee, Ick-Dong Yoo, Byung-Jo Ha2015 Volume 63 Issue 7 Pages 554-557
Published: July 01, 2015
Released on J-STAGE: July 01, 2015
JOURNAL FREE ACCESS FULL-TEXT HTMLTwo new sesquiterpene derivatives (1 and 2), ramarin A (1) and ramarin B (2), together with three known compounds (3–5) were isolated from the fruiting bodies of Ramaria formosa. The structures of the two sesquiterpenes were established by extensive spectroscopic studies and chemical evidence. The inhibitory activity of the isolated compounds (1–5) against human neutrophil elastase (HNE) was evaluated in vitro. All compounds tested inhibited HNE by 35–30% at the highest concentration used (100 µM), whereas the positive control, epigallocatechin gallate (EGCG), exhibited 60% inhibition at 100 µM.Graphical Abstract Fullsize ImageView full abstractDownload PDF (530K) Full view HTML -
Nguyen Huu Toan Phan, Nguyen Thi Dieu Thuan, Ninh Thi Ngoc, Nguyen Phu ...2015 Volume 63 Issue 7 Pages 558-564
Published: July 01, 2015
Released on J-STAGE: July 01, 2015
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Supplementary materialFive new tirucallane saponins, paramignyosides A–E (1–5), were isolated from the water fraction of the Paramignya scandens stem and leaves. Their structures were elucidated on the basis of spectroscopic evidence including high-resolution electrospray ionization mass spectrometry (HR-ESI-MS) and one dimensional (1D)- and 2D-NMR. The effects of isolated compounds on pro-inflammatory cytokines were evaluated by measuring the production of interleukin (IL)-12 p40, IL-6, and tumor necrosis factor-α (TNF-α) in lipopolysaccharide (LPS)-stimulated bone marrow-derived dendritic cells (BMDCs). Paramignyoside C (3) exhibited selective and potent inhibitory effect (IC50=5.03±0.19 µM) on the production of IL-12 p40 comparable to that of the positive control, SB203580 (IC50=5.00±0.16 µM). Further studies are required to confirm efficacy in vivo and the mechanism of anti-inflammatory effects.Graphical Abstract Fullsize ImageView full abstractDownload PDF (665K) Full view HTML
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