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Volume 59, Issue 10
Displaying 1-20 of 20 articles from this issue
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Regular Articles
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Saied Saeed Hosseiny Davarani, Majid Kalate Bojdi, Ali MehdiniaArticle type: Regular Article
2011 Volume 59 Issue 10 Pages 1209-1213
Published: October 01, 2011
Released on J-STAGE: October 01, 2011
JOURNAL FREE ACCESSElectrochemical oxidation of hydroquinone (1a) and 2,3-dimethylhydroquinone (1b) have been studied in the presence of 2-aminophenol (3a) and 2-amino-4-chlorophenol (3b), as nucleophiles in phosphate buffer solution (pH 7.2) using cyclic voltammetry and controlled potential coulometry. We proposed different mechanisms for the electrode process. The products were derived with good yield and purity using controlled-potential electrochemical oxidation of 1a, b in the presence of 3a and 3b at the graphite electrode in an undivided cell.View full abstractDownload PDF (999K) -
Keita Kondo, Toshiyuki Niwa, Yuichi Ozeki, Masaki Ando, Kazumi DanjoArticle type: Regular Article
2011 Volume 59 Issue 10 Pages 1214-1220
Published: October 01, 2011
Released on J-STAGE: October 01, 2011
JOURNAL FREE ACCESSIn this study, in order to address the problems with manufacturing orally rapidly disintegrating tablets (ODT) containing functional (taste masking or controlled release) coated particles, such as the low compactability of coated particles and the rupture of coated membrane during compression, a novel ODT containing taste-masked coated particles (TMP) in the center of the tablets were prepared using one-step dry-coated tablets (OSDrC) technology. As a reference, physical-mixture tablets (PM) were prepared by a conventional tableting method, and the properties of the tablets and the effect of compression on the characteristics of TMP were evaluated. OSDrC was found to have higher tensile strength and far lower friability than PM, but the oral disintegration time of OSDrC is slightly longer than that of PM following high compression pressure. Consequently, OSDrC approaches the target tablet properties of ODT, whereas PM does not. The deformation of TMP in OSDrC due to compression is slight, and the release rate of acetaminophen (AAP) from OSDrC is the same as from TMP. However, TMP on the surface of PM are considerably deformed, and the release rate of AAP from PM is faster than from TMP. These findings suggest that OSDrC technology is a useful approach for preparing ODT containing functional coated particles. Furthermore, we demonstrate that the elastic recovery of tablets can affect differences in the properties of OSDrC, PM and placebo tablets (PC).View full abstractDownload PDF (2468K) -
Mamoru Fukuda, Akinori GotoArticle type: Regular Article
2011 Volume 59 Issue 10 Pages 1221-1226
Published: October 01, 2011
Released on J-STAGE: October 01, 2011
JOURNAL FREE ACCESSA novel floating sustained release tablet having a cavity in the center was developed by utilizing the physicochemical properties of L-menthol and the penetration of molten hydrophobic polymer into tablets. A dry-coated tablet containing famotidine as a model drug in outer layer was prepared with a L-menthol core by direct compression. The tablet was placed in an oven at 80°C to remove the L-menthol core from tablet. The resulting tablet was then immersed in the molten hydrophobic polymers at 90°C. The buoyancy and drug release properties of tablets were investigated using United States Pharmacopeia (USP) 32 Apparatus 2 (paddle 100 rpm) and 900 ml of 0.01 N HCl. The L-menthol core in tablets disappeared completely through pathways in the outer layer with no drug outflows when placed in an oven for 90 min, resulting in a formation of a hollow tablet. The hollow tablets floated on the dissolution media for a short time and the drug release was rapid due to the disintegration of tablet. When the hollow tablets were immersed in molten hydrophobic polymers for 1 min, the rapid drug release was drastically retarded due to a formation of wax matrices within the shell of tablets and the tablets floated on the media for at least 6 h. When Lubri wax® was used as a polymer, the tablets showed the slowest sustained release. On the other hand, faster sustained release properties were obtained by using glyceryl monostearate (GMS) due to its low hydrophobic nature. The results obtained in this study suggested that the drug release rate from floating tablets could be controlled by both the choice of hydrophobic polymer and the combined use of hydrophobic polymers.View full abstractDownload PDF (1567K) -
Yi Luo, Xiaoling Li, Xiaochun Huang, Yum-Shing Wong, Tianfeng Chen, Yi ...Article type: Regular Article
2011 Volume 59 Issue 10 Pages 1227-1232
Published: October 01, 2011
Released on J-STAGE: October 01, 2011
JOURNAL FREE ACCESSEpidemiological, preclinical and clinical studies have supported the role of selenocompounds as potential cancer chemopreventive and chemotherapeutic agents. In this study, a novel selenophene-based compound, 1,4-diselenophene-1,4-diketone (DSeD), has been synthesized by Double Friedel–Crafts reaction and identified as a potent antiproliferative agent against a panel of six human caner cell lines. Despite this potency, DSeD was relatively nontoxic toward human normal cells, HS68 fibroblasts and HK-2 kidney cells. These results suggest that DSeD possesses great selectivity between cancer and normal cells. Induction of apoptosis in human melanoma A375 cells by DSeD was evidenced by accumulation of sub-G1 cell population, DNA fragmentation and nuclear condensation. Activation of caspase-9 and depletion of mitochondrial membrane potential indicated the initiation of the mitochondria-mediated apoptosis pathway. Pretreatment of cells with general caspase inhibitor z-VAD-fmk and caspase-9 inhibitor z-LEHD-fmk significantly suppressed the cell apoptosis, demonstrating the important roles of caspase and mitochondria in DSeD-induced apoptotic cell death. Furthermore, DSeD-induced apoptosis was found independent of reactive oxygen species generation. Taken together, our results suggest that DSeD induces caspase-dependent apoptosis in A375 cells through activation of mitochondria-mediated apoptosis pathway.View full abstractDownload PDF (977K) -
Kazuya Otake, Satoru Azukizawa, Masaki Fukui, Michiko Shibabayashi, Hi ...Article type: Regular Article
2011 Volume 59 Issue 10 Pages 1233-1242
Published: October 01, 2011
Released on J-STAGE: October 01, 2011
JOURNAL FREE ACCESSNovel 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid derivatives were synthesized and (S)-7-(2-{2-[(E)-2-cyclopentylvinyl]-5-methyloxazol-4-yl}ethoxy)-2-[(2E,4E)-hexadienoyl]-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (14c) was identified as a peroxisome proliferator-activated receptor (PPAR) α/γ dual agonist. The transactivation activity of 14c was comparable to that of rosiglitazone in human PPARγ (EC50=0.14 μM) and was much higher than in human PPARα (EC50=0.20 μM). In addition, 14c, but not rosiglitazone, showed human protein-tyrosine phosphatase 1B (PTP-1B) inhibitory activity (IC50=1.85 μM). 14c showed about 10-fold stronger hypoglycemic and hypotriglyceridemic effects than rosiglitazone by repeated application for 14 d in male KK-Ay mice. Furthermore, 14c, but not rosiglitazone, increased hepatic peroxisome acyl CoA oxidase activity at 30 mg/kg/d for 7 d in male Syrian hamsters, probably due to its PPARα agonist activity. 14c did not affect plasma volume at 100 mg/kg/d for 14 d in male ICR mice, while rosiglitazone significantly increased it. In conclusion, 14c is a promising candidate for an efficacious and safe anti-diabetic drug with triple actions as a PPARα/γ dual agonist with PTP-1B inhibitory activity.View full abstractDownload PDF (785K) -
Makiko Nishida, Hitoshi YoshimitsuArticle type: Regular Article
2011 Volume 59 Issue 10 Pages 1243-1249
Published: October 01, 2011
Released on J-STAGE: October 01, 2011
JOURNAL FREE ACCESSThree new 15-hydroxy-trinor type (1—3), a new tetranor type (4), and two new 3,15,23,24-tetrahydroxy-16-oxo type cycloartane glycosides (5, 6) were isolated from the rhizome of Cimicifuga heracleifolia KOMAROV. Their structures were determined by the use of the 2D-NMR techniques and chemical evidence.View full abstractDownload PDF (756K) -
Xuan-Qin Chen, Yan Li, Kun-Zhi Li, Li-Yan Peng, Juan He, Kou Wang, Zhe ...Article type: Regular Article
2011 Volume 59 Issue 10 Pages 1250-1253
Published: October 01, 2011
Released on J-STAGE: October 01, 2011
JOURNAL FREE ACCESSFour new acylphloroglucinols with an unusual 6/6/5 spirocyclic skeleton, hyperbeanols A—D (1—4), were isolated from the methanol extract of Hypericum beanii along with 16 known compounds. Their structures were established on the basis of spectroscopic and X-ray diffraction analysis. Hyperbeanols A—C were three stereoisomers different only at the relative configuration of C-4 and C-13, which were distinguished by the nuclear Overhauser effect spectroscopy (NOESY) spectroscopic data in combination with the single X-ray analysis of hyperbeanol A (1). The cytotoxic activity of hyperbeanols A—D against the cancer cell lines SK-BR-3, HL-60, SMMC-7721, PANC-1, MCF-7, and K562 was also evaluated.View full abstractDownload PDF (567K) -
MD Iqbal Mahmood, Yuri Matsuo, Saburo Neya, Tyuji HoshinoArticle type: Regular Article
2011 Volume 59 Issue 10 Pages 1254-1262
Published: October 01, 2011
Released on J-STAGE: October 01, 2011
JOURNAL FREE ACCESSImmunological response induced by small amino peptide has attracted much recent attention in the field of immunotherapy. Wilms' tumor (WT1) protein is one of the potent tumor antigens inducing immunological response in mouse and human, because WT1 is over expressed in many types of leukemia and various kinds of solid tumors. A 9-mer peptide encoded in WT1 protein (CMTWNQMNL; amino acid 235—243) is known to serve as antigenic peptide for human leukocyte antigen (HLA)-A*2402 molecule. It was reported that the replacement of the second amino residue, which is deeply responsible for the peptide binding to HLA, induced strong immunological response compared to the natural peptide. In this study, 19 kinds of single amino substitutions were introduced at position 2 of this 9-mer WT1 peptide. We performed molecular dynamics simulation on the complex of each of WT1 epitope peptides and HLA-β2 micro globulin (β2m) molecule, and subsequently estimated the binding affinity using molecular mechanics/generalized-Born surface area method combined with normal mode analysis. Our computation indicated that the peptide containing M2Y or M2W mutation showed high binding affinity to the HLA-β2m molecule as well as the natural peptide. We have also examined the role of the residue at position 2 in peptide binding to HLA-β2m. The calculation showed that van der Waals interaction between the side chain of the residue at position 2 and hydrophobic residues inside B-pocket of HLA are important. These findings will be helpful to search other potent peptides that will enhance strong immunological response specific to HLA-A*2402 molecule.View full abstractDownload PDF (2656K) -
Yuko Shikamura, Akira Ohtori, Kakuji TojoArticle type: Regular Article
2011 Volume 59 Issue 10 Pages 1263-1267
Published: October 01, 2011
Released on J-STAGE: October 01, 2011
JOURNAL FREE ACCESSThe purpose of this study was to analyze drug pharmacokinetics in the posterior eye tissues after topical instillation. For the in vivo study, the concentrations of ofloxacin in rabbit ocular tissues were analyzed by high performance liquid chromatography at 1, 2, and 3 h after instillation. For the in silico simulation, the concentration distribution of ofloxacin in the eye was calculated by the ocular pharmacokinetic model based on the diffusion/partition model. The simulated profiles were then compared with the in vivo experimental findings. In the in vivo study, the drug concentration in the posterior vitreous body initially decreased with time after topical instillation, and thereafter, the concentration increased. The in silico simulation of ocular pharmacokinetics indicated that the drug penetration of the posterior vitreous body was determined by three major pathways: (1) the initial transscleral penetration, (2) the intermediate transcorneal penetration, and (3) the late transretinal penetration. The in vivo findings were well described by a series of contributions by these three pathways. In conclusion, the present in vivo and in silico studies suggest that the instilled drugs initially reached the posterior vitreous body by diffusion through the sclera and then later by corneal penetration and systemic circulation.View full abstractDownload PDF (3805K) -
Masaki Ogino, Seiji Fukui, Yoshihisa Nakada, Ryosuke Tokunoh, Shigekaz ...Article type: Regular Article
2011 Volume 59 Issue 10 Pages 1268-1273
Published: October 01, 2011
Released on J-STAGE: October 01, 2011
JOURNAL FREE ACCESSAcyl-CoA: cholesterol acyltransferase (ACAT) is an intracellular enzyme that catalyzes cholesterol esterification. ACAT inhibitors are expected to be potent therapeutic agents for the treatment of atherosclerosis. A series of potent ACAT inhibitors based on an (4-phenylcoumarin)acetanilide scaffold was identified. Evaluation of the structure–activity relationships of a substituent on this scaffold, with an emphasis on improving the pharmacokinetic profile led to the discovery of 2-[7-chloro-4-(3-chlorophenyl)-6-methyl-2-oxo-2H-chromen-3-yl]-N-[4-chloro-2-(trifluoromethyl)phenyl]acetamide (23), which exhibited potent ACAT inhibitory activity (IC50=12 nM) and good pharmacokinetic profile in mice. Compound 23 also showed regressive effects on atherosclerotic plaques in apolipoprotein (apo)E knock out (KO) mice at a dose of 0.3 mg/kg per os (p.o.).View full abstractDownload PDF (627K) -
Katsuyoshi Matsunami, Hideaki Otsuka, Yoshio TakedaArticle type: Regular Article
2011 Volume 59 Issue 10 Pages 1274-1280
Published: October 01, 2011
Released on J-STAGE: October 01, 2011
JOURNAL FREE ACCESSChemical investigation of the 1-BuOH soluble fraction of the dried fruits of Myrsine seguinii (Myrsinaceae) led to the isolation of five new glycosides, named myrseguinosides A—E (1—5), together with eight known compounds (6—13). The absolute structures of the new glycosides were elucidated by spectroscopic and chemical analyses to be a monoterpene glucoside (1), two flavonol glycosides (2, 3), and two oleanane-type triterpene saponins (4, 5). Myrseguinosides B (2), D (4), and E (5) exhibited 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical-scavenging activity and growth inhibitory activity toward human cancer cells, respectively.View full abstractDownload PDF (937K) -
Sang-Yong Kim, Yoshiki Kashiwada, Kazuyoshi Kawazoe, Kotaro Murakami, ...Article type: Regular Article
2011 Volume 59 Issue 10 Pages 1281-1284
Published: October 01, 2011
Released on J-STAGE: October 01, 2011
JOURNAL FREE ACCESSFour new lindenane sesquiterpenoid dimers, spicachlorantins G—J (1—4), were isolated from the roots of Chloranthus spicatus together with seven known compounds, including chloramultilide A, shizukaol B, shizukaol D, shizukaol F, shizukaol P, chlorahololide D, and cycloshizukaol A. The planar structures of the new compounds were established by 1D-, 2D-NMR, and MS analyses. The absolute configurations of these compounds were determined by analyzing rotating Overhauser enhancement and exchange spectroscopy (ROESY) and circular dichroism (CD) spectra.View full abstractDownload PDF (688K) -
Pillaiyar Thanigaimalai, Ki-Cheul Lee, Vinay Kumar Sharma, Niti Sharma ...Article type: Regular Article
2011 Volume 59 Issue 10 Pages 1285-1288
Published: October 01, 2011
Released on J-STAGE: October 01, 2011
JOURNAL FREE ACCESSBased on the hits, 3,4-dihydroquinazoline-2-thione (1) and benzimidazole-2-thione (2), a series of indole-2-thione (3) and indole-2-thiol inhibitors (4) of melanogenesis were designed, synthesized and evaluated in melanoma B16 cells under the stimulant of α-melanocyte stimulating hormone (α-MSH). The indole-2-thione compounds (3a—g) exhibited an effective inhibitory activity on melanin synthesis. The Structure–Activity Relationship (SAR) studies of 2 have revealed that in potent inhibitor 3a (>100% inhibition at 30 μM, IC50=1.40 μM) the role of nitrogen (3-N) at 3-position is insignificance. In addition, the hydrophobic substituents of 3 were better than the hydrophilic one. However, conversion of thione (–C=S, 3) to thiol (–C–SH, 4) led to decrease in the potency.View full abstractDownload PDF (526K) -
Mitsuaki Yamashita, Kazunori Ueda, Koichi Sakaguchi, Harukuni Tokuda, ...Article type: Regular Article
2011 Volume 59 Issue 10 Pages 1289-1293
Published: October 01, 2011
Released on J-STAGE: October 01, 2011
JOURNAL FREE ACCESSIn this paper, a concise one-pot method for the construction of benzo[f]indole-4,9-dione motifs is described. These transformations proceed via a sequential palladium- and copper-catalyzed coupling reaction of 1,4-naphthoquinones with terminal acetylenes, followed by a copper-catalyzed intramolecular cyclization reaction of the resulting coupling product.View full abstractDownload PDF (711K)
Notes
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Seif-Eldin Nasr Ayyad, Khalid Omar Al-Footy, Walied Mohamed Alarif, Ta ...Article type: Note
2011 Volume 59 Issue 10 Pages 1294-1298
Published: October 01, 2011
Released on J-STAGE: October 01, 2011
JOURNAL FREE ACCESSThe petroleum ether extract of the red alga Laurencia obtusa afforded three new C15 acetogenins (cyclic ether enyne): (12Z)-cis-maneonene-D (1), (12E)-cis-maneonene-E (2), and (12Z)-trans-maneonene-C (3), along with one known cis-maneonene-A (4). Blood neutrophils were prepared, cultured, and incubated for 24, 48, and 72 h in medium with and without isolated compounds. Blood neutrophils were prepared, cultured, and incubated for 24, 48 and 72 h in medium with and without the isolated compounds. Both morphology and DNA fragmentation methods assessed the percentage of neutrophils apoptosis in each culture. In the present study, several observations have been made concerning the apoptosis-inducing or inhibiting effect of 1 and 2. Both compounds had no inhibition of apoptosis but apoptosis was enhanced significantly by aging. However, 1 stimulated apoptosis of normal only at the initial 24 h. After that there was no significant difference in apoptosis with or without compound 1, while 2 stimulated apoptosis at all the times. The apoptosis induced by these two compounds was demonstrated by DNA fragmentation assay and microscopic observation. These observations suggest that compounds 1 and 2 may be involved in regulation of programmed death in the initiation and propagation of inflammatory responses.View full abstractDownload PDF (654K) -
Yutaka Inoue, Nana Hasegawa, Yuichi Tozuka, Etsuo Yonemochi, Toshio Og ...Article type: Note
2011 Volume 59 Issue 10 Pages 1299-1302
Published: October 01, 2011
Released on J-STAGE: October 01, 2011
JOURNAL FREE ACCESSChanges in molecular states of p-dimethylaminobenzonitrile (DMABN) coground with β-cyclodextrin (β-CD) were examined using solid-state fluorescence measurements. Formation of a DMABN/β-CD inclusion complex by coprecipitation was confirmed by powder X-ray diffraction measurement. The powder X-ray diffraction pattern of the ground mixture was a halo pattern and differed from the pattern of the mixture prepared by coprecipitation. Solid-state fluorescence measurements revealed emission by DMABN crystals in a twisted intermolecular charge-transfer state at 473 nm. DMABN in the DMABN/β-CD coprecipitate had a fluorescence emission peak at 393 nm due to its planar structure. In contrast, DMABN in a DMABN/β-CD ground mixture had an emission peak at 473 nm due to its twisted structure. Grinding time-dependent structural changes in DMABN were evaluated using fluorescence lifetime and relative quantum yield measurements. Structural changes in DMABN in the DMABN/β-CD coprecipitate from a planar to a twisted structure were observed with grinding. DMABN, dispersed in microcrystalline cellulose (CC) molecules in a DMABN/CC ground mixture, had a fluorescence emission peak at 473 nm. However, the excitation spectrum of a DMABN/β-CD ground mixture differed from that of DMABN in CC. These results indicated that the molecular state of DMABN accommodated in the β-CD cavity differs between the coprecipitate and the ground mixture.View full abstractDownload PDF (796K) -
Shin-ichiro Kurimoto, Yoshiki Kashiwada, Susan Lynne Morris-Natschke, ...Article type: Note
2011 Volume 59 Issue 10 Pages 1303-1306
Published: October 01, 2011
Released on J-STAGE: October 01, 2011
JOURNAL FREE ACCESSThree new steroids dyscusins A—C (1—3), including a stigmastane-type sterol and two pregnanes, together with two known steroids were isolated from the leaves of Dysoxylum cumingianum (Meliaceae). Their structures were elucidated on the basis of extensive spectroscopic analyses. In a cytotoxicity assay, compound 1 showed ten-fold enhanced cytotoxicity against multi-drug resistant cancer cells (KB-C2) in the presence of 2.5 μM colchicine as compared with the absence of colchicine. This notable finding indicated that 1 possessed a multi-drug resistant reversal effect.View full abstractDownload PDF (467K) -
Kazusa Nishiyama, Atsushi Yamada, Tomoharu Takeuchi, Yoichiro Arata, K ...Article type: Note
2011 Volume 59 Issue 10 Pages 1307-1310
Published: October 01, 2011
Released on J-STAGE: October 01, 2011
JOURNAL FREE ACCESSUseful segments (1, 2) for chemical probes embedded in a Galβ1→4Fuc unit were designed and prepared for characterizing sugar-binding proteins in Caenorhabditis elegans. Segment 1 with an amino group terminus was used as a recognition unit in affinity chromatography. It was revealed that some proteins (annexins and galectins) in C. elegans have an affinity for Galβ1→4Fuc.View full abstractDownload PDF (614K) -
Agus Trianto, Idam Hermawan, Nicole Joy de Voogd, Junichi TanakaArticle type: Note
2011 Volume 59 Issue 10 Pages 1311-1313
Published: October 01, 2011
Released on J-STAGE: October 01, 2011
JOURNAL FREE ACCESSChemical investigations on a sponge Haliclona sp. found a meroditerpene 1 having a new carbon skeleton. By analyzing spectroscopic data, the structure was elucidated to comprise a substituted hydroquinone, a tetrahydrooxepine, and a cyclohexene, and these components were united with C1 and C2 units. Compound 1 showed moderate cytotoxicity against NBT-T2 cells with IC50 4.8 μg/ml and also antioxidant activity against 1,1-diphenyl-2-picrylhydrazyl (DPPH) with IC50 3.2 μg/ml.View full abstractDownload PDF (608K)
Communication to the Editor
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Yosuke Demizu, Daigo Wakana, Hiroyuki Kamakura, Masaaki Kurihara, Haru ...Article type: Communication to the Editor
2011 Volume 59 Issue 10 Pages 1314-1316
Published: October 01, 2011
Released on J-STAGE: October 01, 2011
JOURNAL FREE ACCESSWe isolated a new illegal sildenafil analogue named mutaprodenafil from a dietary supplement for erectile dysfunction (ED) and proposed that it is an aildenafil derivative containing an imidazole moiety. We subsequently synthesized mutaprodenafil from a thioaildenafil and authenticated its structure.View full abstractDownload PDF (626K)
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