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Volume 59, Issue 12
Displaying 1-22 of 22 articles from this issue
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Review
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Shin MizukamiArticle type: Review
2011 Volume 59 Issue 12 Pages 1435-1446
Published: December 01, 2011
Released on J-STAGE: December 01, 2011
JOURNAL FREE ACCESSMolecular imaging technologies, which enable the visualization of the behaviors or functions of biomolecules in living systems, have received considerable attention from life scientists. Novel imaging technologies that overcome the limitations of current imaging techniques are desired. In this review, two independent technologies that were recently developed by the authors are described. The first technology is for smart 19F magnetic resonance imaging (MRI) probes that were developed for in vivo applications. These probes were developed by exploiting paramagnetic relaxation enhancement in order to detect hydrolase activity. With respect to cellular applications, gene expression in cells was visualized using one of the 19F MRI probes. It was confirmed that this probe design principle is effective for various hydrolases, and broad applications are expected. The second technology is for practical protein labeling. This labeling method is based on a mutant β-lactamase and its specific labeling probes. Since the probe is fluorescence resonance energy transfer (FRET)-based, this labeling method achieves both specific and fluorogenic labeling of target proteins. In addition, derivatization of the probe enabled the labeling of intracellular proteins and the modification of various functional molecules.View full abstractDownload PDF (7037K)
Regular Articles
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Hideko Maeda, Takuma Kusuhara, Mitsutomo Tsuhako, Hirokazu NakayamaArticle type: Regular Article
2011 Volume 59 Issue 12 Pages 1447-1451
Published: December 01, 2011
Released on J-STAGE: December 01, 2011
JOURNAL FREE ACCESSThe phosphorylation of 5′-deoxy-5-fluorouridine (doxifluridine, 5′-DFUR) has been achieved using inorganic cyclo-triphosphate (P3m, Na3P3O9) and monoimido-cyclo-triphosphate (MCTP, Na3P3O8NH) in aqueous solution. In the reaction of 5′-DFUR with P3m, 2′-monophospho-5′-DFUR and 3′-monophospho-5′-DFUR were synthesized with a total yield of more than 95%. In the reaction of 5′-DFUR with MCTP, 2′-diphosphoramidophosphono-5′-DFUR and 3′-diphosphoramidophosphono-5′-DFUR were synthesized with a total yield of more than 40%. The phosphorylated products with P3m and MCTP were stable in neutral and alkaline solutions.View full abstractDownload PDF (846K) -
Naho Furuyama, Susumu Hasegawa, Shuichi Yada, Takeshi Hamaura, Naoki W ...Article type: Regular Article
2011 Volume 59 Issue 12 Pages 1452-1457
Published: December 01, 2011
Released on J-STAGE: December 01, 2011
JOURNAL FREE ACCESSThe surface of amorphous compounds crystallizes faster compared to the bulk. This suggests that molecules at the surface have high molecular mobility. Crystallization behavior is affected by various factors including molecular weight and glass transition temperature (Tg). In this study, we focus on troglitazone which is composed of diastereomers, RR/SS and RS/SR, as model compound, because each diastereomer has the same molecular weight and similar chemical structure. Troglitazone is isolated into each diastereomer, and both amorphous prepared from RR/SS and RS/SR showed similar Tg (around 60°C). The surface relaxation of each amorphous troglitazone prepared from two diastereomers, RR/SS and RS/SR, was determined to compare surface molecular mobility, using inverse gas chromatography under dry conditions. As a result, amorphous prepared from RS/SR, showed the shorter surface relaxation time at 40°C (temperature below Tg), which means it has higher molecular mobility than that from RR/SS at the surface although both have the same molecular weight and similar Tg. Microscopy analysis was conducted to observe the crstallization behavior at the surface of amorphous troglitazone in conditions of high temperature and humidity. Micrographs showed that crystallization area at the surface of amorphous prepared from RS/SR, which showed the shorter surface relaxation time, increased faster than that of the amorphous prepared from RR/SS. Although the reason for the difference in the surface relaxation time of each amorphous troglitazone could not be determined, factors such as the difference of configuration might affect the difference.View full abstractDownload PDF (4022K) -
Yoshio Nishimura, Yasuko Okamoto, Masaya Ikunaka, Yoshihiko OhyamaArticle type: Regular Article
2011 Volume 59 Issue 12 Pages 1458-1466
Published: December 01, 2011
Released on J-STAGE: December 01, 2011
JOURNAL FREE ACCESSA mixture of alkyl 1,4-dihydro-2-methylthio-4,4,6-trisubstituted pyrimidine-5-carboxylate 1 and its tautomeric isomer, alkyl 1,6-dihydro-2-methylthio-4,6,6-trisubstituted pyrimidine-5-carboxylate 2 is synthesized by the Atwal–Biginelli cyclocondensation reaction of S-methylisothiourea hemisulfate salt 3 with 2-(gem-disubstituted)methylene-3-oxoesters 4 that can be accessed by the Lehnert procedure for the Knoevenagel-type condensation. The structures of the tautomeric products of the Atwal–Biginelli cyclocondensation reaction, 1 and 2, which are inseparable from each other, are determined unambiguously by 1H-NMR spectroscopy at various temperatures and nuclear Overhauser enhancement spectroscopy (NOESY) experiment. Because these dihydropyrimidine products are otherwise inaccessible and thus hitherto unavailable, the synthetic methods established in this study will help to expand the molecular diversity of their related derivatives.View full abstractDownload PDF (1395K) -
Akihito Yokosuka, Yukiko Matsuo, Maki Jitsuno, Kohei Adachi, Yoshihiro ...Article type: Regular Article
2011 Volume 59 Issue 12 Pages 1467-1470
Published: December 01, 2011
Released on J-STAGE: December 01, 2011
JOURNAL FREE ACCESSTwo new lignan glycosides, named larrealignans A (1) and B (2), and a known lignan (3) were isolated from the aerial parts of Larrea tridentata (Zygophyllaceae). The structures of 1 and 2 were determined on the basis of spectroscopic analysis and the results of hydrolytic cleavage. The isolated compounds (1—3) and aglycones (1a, 2a) of 1 and 2 were evaluated for their cytotoxic activities against HL-60 human leukemia cells.View full abstractDownload PDF (494K) -
Jérémy Ricci, Minkyu Kim, Won-Yoon Chung, Kwang-Kyun Par ...Article type: Regular Article
2011 Volume 59 Issue 12 Pages 1471-1475
Published: December 01, 2011
Released on J-STAGE: December 01, 2011
JOURNAL FREE ACCESSNovel artemisinin-glycolipid hybrids were directly synthesized from 12β (C–C)-type deoxoartemisinin and glycolipid and exhibited exceptional in vitro anticancer activity, particularly against the oral carcinoma cancer cell lines, respectively. The artemisinin-glycolipid hybrids, with effective concentrations under 20 μM, demonstrated better anticancer activity than either artemisinin or glycolipid alone and showed five times more anti-oral cancer activity than either cisplatin or paclitaxel.View full abstractDownload PDF (675K) -
Zhi-Bo Xing, Lei Yao, Guo-Qiang Zhang, Xian-Yu Zhang, You-Xue Zhang, D ...Article type: Regular Article
2011 Volume 59 Issue 12 Pages 1476-1480
Published: December 01, 2011
Released on J-STAGE: December 01, 2011
JOURNAL FREE ACCESSRadix Stephaniae tetrandrae, which contains tetrandrine (Tet) and fangchinoline, is traditionally used as an analgesic, antirheumatic, and antihypertensive drug in China. In this study, we investigated its effect on breast cancer cell proliferation and its potential mechanism of action in vitro. Treatment of cells with fangchinoline significantly inhibited MDA-MB-231 cell proliferation in a concentration- and time-dependent manner. To define the mechanism underlying the antiproliferative effects of fangchinoline, we studied its effects on critical molecular events known to regulate the apoptotic machinery. Specifically, we addressed the potential of fangchinoline to induce apoptosis of breast cancer cells. Fangchinoline induced internucleosomal DNA fragmentation, chromatin condensation, activation of caspases-3, -8, and -9, and cleavage of poly(ADP ribose) polymerase, as well as enhanced mitochondrial cytochrome c release. Furthermore, fangchinoline increased the expression of the proapoptotic protein B cell lymphoma-2 associated X (Bax) and decreased the expression of the antiapoptotic protein B cell lymphoma-2 (Bcl-2). In addition, the proliferation-inhibitory effect of fangchinoline was associated with decreased levels of phosphorylated Akt. Our results indicate that fangchinoline can inhibit breast cancer cell proliferation by inducing apoptosis via the mitochondrial apoptotic pathway and decreasing phosphorylated Akt. Thus fangchinoline may be a novel agent that can potentially be developed clinically to target human malignancies.View full abstractDownload PDF (1555K) -
Makoto Tamaki, Kazumasa Takanashi, Takuji Harada, Kenta Fujinuma, Mits ...Article type: Regular Article
2011 Volume 59 Issue 12 Pages 1481-1484
Published: December 01, 2011
Released on J-STAGE: December 01, 2011
JOURNAL FREE ACCESSTo find candidates with high antimicrobial and low hemolytic activities, many gramicidin S (GS) analogs of various ring sizes have been designed and synthesized. However, syntheses of antimicrobially active analogues of GS having a disordered symmetry structure from C2 have almost never been reported, because the stable, amphiphilic β-sheet structure of GS with C2 symmetry is considered essential for its strong antibacterial activity. In the present studies, novel thirteen cycloundecapeptides 1—13 related to GS were synthesized and examined. Among them, cyclo(-Va11-Orn2-Leu3-D-Phe4-X5-Pro6-Val7-Orn8-Leu9-D-Phe10-Pro11-) (X=Lys (10), Orn (11), Arg (12) and Lys(Lys) (13)) resulted in high antibiotic activity against both Gram-positive and Gram-negative microorganisms tested. In addition, 11 showed low toxicity against sheep blood cells compared with that of GS. Further, circular dichroism (CD) spectra of 10—13 had a curve similar to each other, suggesting that the conformations of these analogues in methanol are similar to each other. However, CD spectra of 10—13 were different from that of GS in the 190—210 nm region. These results suggest that the presences of one added amino acid residue at position 5 of 10—13 might be partially effective through a structural change in the biological activity of 10—13. In addition, the structural modifications at position 5 lower the undesirable hemolytic activity and enhance the desirable antibiotic activity.View full abstractDownload PDF (944K) -
Marianne Alphonse Mahrouse, Ehab Farouk ElkadyArticle type: Regular Article
2011 Volume 59 Issue 12 Pages 1485-1493
Published: December 01, 2011
Released on J-STAGE: December 01, 2011
JOURNAL FREE ACCESSA binary mixture of ciprofloxacin hydrochloride (CIP) and metronidazole (MET) was determined by five simple and accurate methods, without prior separation. In the first method, CIP was determined by second derivative spectrophotometric method (2D) by measuring the amplitude at 282 nm (zero ordinate value of MET). On the other hand, the determination of MET was based on isosbestic point technique, where the total content of the mixture was determined at 294.5 nm (isosbestic point), then the content of MET could be calculated by subtraction. The second method was first derivative ratio spectrophotometric method (1DD) where the total amplitude at 261 and 285 nm and the amplitude at 295.5 nm were selected to simultaneously determine CIP and MET in binary mixture, respectively. The third method was based on dual wavelength analysis, in which two wavelengths were selected, at which the absorbances of the other component were the same. The fourth method depends on using Q-analysis method (absorbance ratio) which involves the formation of Q-absorbance equation using the respective absorptivity values at 294.5 nm (isosbestic point) and 281.5 nm (λmax of CIP). The fifth method is partial least-squares (PLS) chemometric technique for determination of CIP and MET. The developed methods were successfully applied to the analysis of CIP and MET in laboratory prepared mixtures and tablets with good recoveries and their validation was carried out following the International Conference on Harmonization (ICH) guidelines. The results obtained were statistically compared with each other showing no significant difference with respect to accuracy and precision.View full abstractDownload PDF (673K) -
Tohru Kambe, Toru Maruyama, Atsushi Naganawa, Masaki Asada, Akiteru Se ...Article type: Regular Article
2011 Volume 59 Issue 12 Pages 1494-1508
Published: December 01, 2011
Released on J-STAGE: December 01, 2011
JOURNAL FREE ACCESSFor the purpose of discovering an orally available EP4 subtype-selective agonist, a series of 8-aza prostaglandin E1 (PGE1) analogs were synthesized and evaluated for their affinity for PGE2 receptor subtypes. Additionally, the structure–activity relationships of these compounds were studied. Among the tested compounds, the 8-aza PGE1 analog 6 and 8-aza-5-thiaPGE1 analog 12 had highly potent EP4 receptor affinity, good functional activity, and excellent subtype-selectivity. Furthermore, these analogs demonstrated good stability in human liver microsomes. As a result, we concluded that these two series of 8-aza PGE1 analogs could be promising chemical leads for an orally available EP4 subtype-selective agonist.View full abstractDownload PDF (1085K) -
Adivireddy Padmaja, Akkarapalli Muralikrishna, Chittoor Rajasekhar, Ve ...Article type: Regular Article
2011 Volume 59 Issue 12 Pages 1509-1517
Published: December 01, 2011
Released on J-STAGE: December 01, 2011
JOURNAL FREE ACCESSA new class of pyrrolyl/pyrazolyl arylaminosulfonylmethyl 1,3,4-oxadiazoles, 1,3,4-thiadiazoles, and 1,2,4-triazoles were prepared and tested for antimicrobial activity. Amongst the tested compounds, 5c displayed high antimicrobial activity.View full abstractDownload PDF (1379K) -
Development of a Novel Tablet Machine for a Tiny Amount of Powder and Evaluation of Capping TendencyHideya Nakamura, Yui Sugino, Tomohiro Iwasaki, Satoru WatanoArticle type: Regular Article
2011 Volume 59 Issue 12 Pages 1518-1522
Published: December 01, 2011
Released on J-STAGE: December 01, 2011
JOURNAL FREE ACCESSA novel single punch tablet machine was developed for a tiny amount of powder sample. This tablet machine mainly consists of upper and lower punches, single die, and conical powder feeder equipped with micro-vibrators. By using the powder feeder, mass of discharged powder can be maintained constant even if a tiny amount of powder having poor flowability is used. Motions of both upper and lower punches can be set arbitrarily. Thus, this machine enables us to prepare tablets with a tiny amount of powder sample under the same compression mechanism as conventional rotary tablet machines. Performance of the developed tablet machine was evaluated in a continuous direct tableting using a model powder with poor flowability. Thirty-four tablets (195 mg×34) having acceptable properties can be successfully prepared using no more than 10.0 g of a powder sample. We then proposed a novel in-die evaluation method of capping tendency. A new phase diagram consisting of the elastic recovery energy and the plastic deformation energy was proposed. These energies were calculated from a force-displacement profile, continuously monitored by the developed tablet machine. The results indicate that by using the new diagram the capping tendency of tablets prepared from various model powders can be well discriminated. The developed tablet machine and proposed evaluation method can contribute to a significant cost reduction and speeding up of formulation studies of oral dosage form.View full abstractDownload PDF (1004K) -
Tohru Kambe, Toru Maruyama, Masayuki Nakano, Yoshiyuki Yamaura, Tomoyu ...Article type: Regular Article
2011 Volume 59 Issue 12 Pages 1523-1534
Published: December 01, 2011
Released on J-STAGE: December 01, 2011
JOURNAL FREE ACCESSAnalogs 8-aza-16-aryl prostaglandin E1 (PGE1) and 8-aza-5-thia-16-arylPGE1 were synthesized and evaluated with respect to their subtype receptor affinity and EP4 agonist activity for the purposes of identifying subtype-selective EP4 agonists that demonstrate oral efficacy. Using an inhibition assay of lipopolysaccharide (LPS)-induced tumor necrosis factor (TNF)-α production in rats, representative compounds were evaluated for their pharmacokinetic profiles and in vivo efficacy. Structure–activity relationships (SARs) were characterized and presented. Of the compounds tested, several demonstrated better oral exposure and/or in vivo efficacy compared with the previously reported analog 2a.View full abstractDownload PDF (923K) -
Megumi Furukawa, Hideya Suzuki, Mitsuko Makino, Shoujiro Ogawa, Takash ...Article type: Regular Article
2011 Volume 59 Issue 12 Pages 1535-1540
Published: December 01, 2011
Released on J-STAGE: December 01, 2011
JOURNAL FREE ACCESSTwo flavanones, 5,2′,6′-trihydroxy-7,8-dimethoxyflavanone (1), 5,2′,6′-trihydroxy-6,7,8-trimethoxyflavanone (2) and their 2′-O-β-D-glucosides (3, 4), and a neoclerodane-type diterpene, 15-demethoxyscupolin I (5), together with twenty-eight known compounds were isolated from the extracts of Lagochilus leiacanthus. The structures of the new compounds were determined by spectroscopic means. The two new flavanones and some known flavonoids showed the inhibitory activity on the release of β-hexosaminidase from RBL-2H3 cells.View full abstractDownload PDF (755K)
Notes
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Han-Lin Ge, De-Wu Zhang, Li Li, Dan Xie, Jian-Hua Zou, Yi-Kang Si, Jun ...Article type: Note
2011 Volume 59 Issue 12 Pages 1541-1544
Published: December 01, 2011
Released on J-STAGE: December 01, 2011
JOURNAL FREE ACCESSTwo new terpenoids, (+)-(3S,6S,7R,8S)-periconone A (1) and (−)-(1R,4R,6S,7S)-2-caren-4,8-olide (2), have been isolated from an endophytic fungus Periconia sp., which was collected from the plant Annona muricata. Their structures were elucidated on the basis of extensive spectroscopic analyses. In the in vitro assays, the two compounds showed low cytotoxic activities against six human tumor cell lines (HCT-8, Bel-7402, BGC-823, A549, A2780 and MCF-7) with IC50>10−5 M.View full abstractDownload PDF (717K) -
Noriyuki Kogure, Noriko Katsuta, Mariko Kitajima, Hiromitsu TakayamaArticle type: Note
2011 Volume 59 Issue 12 Pages 1545-1548
Published: December 01, 2011
Released on J-STAGE: December 01, 2011
JOURNAL FREE ACCESSTwo new alkaloids (1, 2) were isolated from the whole plants of Crinum asiaticum var. sinicum together with seven known alkaloids. The structures of the new alkaloids were elucidated by spectroscopic analyses and chemical conversions from known alkaloids. New alkaloid 1 was isolated for the first time as a natural product, although it has been prepared as a synthetic product.View full abstractDownload PDF (763K) -
Mopuru Vijaya Bhaskar Reddy, Shih-Shun Chen, Meng-Liang Lin, Hsiu-Hui ...Article type: Note
2011 Volume 59 Issue 12 Pages 1549-1554
Published: December 01, 2011
Released on J-STAGE: December 01, 2011
JOURNAL FREE ACCESSThe chalcone basic skeleton is a unique template which is associated with widespread biological activities. In the present study, a series of novel bichalcones linked with a 1,4-dimethylenepiperazine moiety was prepared through Mannich reaction and Clasien–Schmidt condensation. The synthetic analogs 2—16 were subjected into the cytotoxicity examinations using a panel of 25 human tumor cell lines. Among the tested compounds, 3 and 4 which possessed the 3-pyridyl and phenyl groups as the substructure, respectively, displayed significant cytotoxicity against all the tumor cell lines. The results suggested that these bichalcones were potential to be the anticancer lead drugs.View full abstractDownload PDF (542K) -
Yosuke Kanemaru, Yumi Momiki, Saori Matsuura, Tatsufumi Horikawa, Jin ...Article type: Note
2011 Volume 59 Issue 12 Pages 1555-1558
Published: December 01, 2011
Released on J-STAGE: December 01, 2011
JOURNAL FREE ACCESSNuclear factor-κB (NF-κB) is an inducible transcription factor activated by a variety of cytokines, and promotes the transcription of genes involved in cancer, inflammation, autoimmune disease, and viral infection, among others. Because of its involvement in numerous disease processes, considerable research has focused on NF-κB as a potential drug target. We previously reported that cupric ion (Cu2+) blocks NF-κB activation. However, Cu2+ is unsuitable for drug applications. The copper complex of an artificial peptide HPH-Pep (HPH-Pep-Cu2+) was a promising alternative, but it did not easily cross the cell membrane. We report the development of a NF-κB inhibiting Cu2+ complex with improved cell-penetrating activity arising from the coupling of a Tat peptide to HPH-Pep-Cu2+.View full abstractDownload PDF (667K) -
Takunori Matsumoto, Tsuyoshi Hosoya, Hiroshi Tomoda, Motoo Shiro, Hide ...Article type: Note
2011 Volume 59 Issue 12 Pages 1559-1561
Published: December 01, 2011
Released on J-STAGE: December 01, 2011
JOURNAL FREE ACCESSTwo new antimicrobial chlorinated cyclopentenones, palmaenones A (1) and B (2) were isolated from the culture broth of discomycete Lachnum palmae (NBRC-106495), and the structures of 1 and 2 were elucidated by spectroscopic data and the stereochemistry of 1 was directly determined by a single-crystal X-ray diffraction analysis. Palmaenones A (1) and B (2) are cyclopentenones containing three chlorines. Compound 1 exhibited potent antimicrobial activity against Micrococcus luteus, Mycobacterium smegmatis, Escherichia coli, Xanthomonas campestris, and Mucor racemosus, while the activities of compound 2 were weaker than 1.View full abstractDownload PDF (675K) -
Zhuo Hu, Rui Zhan, Xue Du, Jia Su, Xiao-Nian Li, Jian-Hong Yang, Hai-B ...Article type: Note
2011 Volume 59 Issue 12 Pages 1562-1566
Published: December 01, 2011
Released on J-STAGE: December 01, 2011
JOURNAL FREE ACCESSFive new ent-kaurane diterpenoids, isodonhenrins A—E (1—5), together with thirteen known ones were isolated from the aerial parts of Isodon henryi. Their structures were identified by means of extensive spectroscopic analysis, and the absolute configurations of 1 were determined by single-crystal X-ray diffraction. Most of the diterpenoids were evaluated for their cytotoxicity against HL-60, SMMC-7721, A-549, MCF-7, and SW480 cell lines. Compound 17 showed significant inhibitory effects on five cell lines, and compounds 6, 9, 10, 11, 12 and 16 exhibited selective activity.View full abstractDownload PDF (751K) -
Akihiro Daikonya, Susumu KitanakaArticle type: Note
2011 Volume 59 Issue 12 Pages 1567-1569
Published: December 01, 2011
Released on J-STAGE: December 01, 2011
JOURNAL FREE ACCESSA new flavonoid, (2R,3R)-3,7,4′-trihydroxy-3′,5′-dimethoxyflavanone, named sophorayunnanol (1), together with eight known polyphenols (2—9), were isolated from the roots of Sophora yunnanensis C.Y.MA (Leguminosae). The structure including absolute stereochemistry of 1 was determined by spectroscopic (high resolution (HR)-MS, 1D- and 2D-NMR, and circular dichroism (CD)) methods. The inhibitory activity of these compounds was examined against nitric oxide (NO) production by lipopolysaccharide (LPS) and interferon (IFN)-γ activated macrophages, RAW264.7 cells. 3,7,3′,5′-Tetrahydroxy-4′-methoxyflavone (6) and piceatannol (9) showed potent inhibitory activity against the production of NO with IC50 values of 14.4±2.5 and 12.9±1.8 μM, respectively. This article is the first report on phytochemical study of S. yunnanensis.View full abstractDownload PDF (506K)
Communication to the Editor
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Masaki Hayashi, Yusuke Sasano, Shota Nagasawa, Masatoshi Shibuya, Yosh ...Article type: Communication to the Editor
2011 Volume 59 Issue 12 Pages 1570-1573
Published: December 01, 2011
Released on J-STAGE: December 01, 2011
JOURNAL FREE ACCESSA highly active organocatalyst for alcohol oxidation has been developed. 9-Azanoradamantane N-oxyl (Nor-AZADO 4), constituting an unhindered, stable nitroxyl radical, exhibits superior catalytic activity to 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) and AZADOs in the oxidation of alcohols to their corresponding carbonyl compounds.View full abstractDownload PDF (833K)
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