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Volume 62, Issue 1
Displaying 1-20 of 20 articles from this issue
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Review
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Kenzo Yahata, Hiromichi Fujioka2014 Volume 62 Issue 1 Pages 1-11
Published: January 01, 2014
Released on J-STAGE: January 01, 2014
JOURNAL FREE ACCESS FULL-TEXT HTMLRecent progress in selective transformation of carbonyl groups using in situ protection methodology is described. These techniques which enable reversing reactivity of functional groups have potential usefulness because they can remove complicated protection–deprotection sequences. In this review, we discuss various in situ protection strategies and their synthetic applications.View full abstractDownload PDF (1932K) Full view HTML
Regular Articles
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Cristina Rîmbu, Ramona Danac, Aurel Pui2014 Volume 62 Issue 1 Pages 12-15
Published: January 01, 2014
Released on J-STAGE: January 01, 2014
JOURNAL FREE ACCESS FULL-TEXT HTMLPalladium(II) complexes with Schiff bases ligands derived from salicylaldehyde and amino acids (Ala, Gly, Met, Ser, Val) have been synthesized and characterized by Fourier transform (FT)-IR, UV-Vis and 1H-NMR spectroscopy. The electrospray mass spectrometry (ES-MS) spectrometry confirms the formation of palladium(II) complexes in 1/2 (M/L) molar ratio. All the Pd(II) complexes 1, [Pd(SalAla)2]Cl2; 2, [Pd(SalGly)2]Cl2; 3, [Pd(SalMet)2]Cl2; 4, [Pd(SalSer)2]Cl2; 5, [Pd(SalVal)2]Cl2; have shown antibacterial activity against Gram-positive bacteria Staphylococcus aureus and Gram-negative bacteria Escherichia coli.View full abstractDownload PDF (752K) Full view HTML -
Rodolfo González-Chávez, Roberto Martínez, María Eugenia Torre-Bouscou ...2014 Volume 62 Issue 1 Pages 16-24
Published: January 01, 2014
Released on J-STAGE: January 01, 2014
JOURNAL FREE ACCESS FULL-TEXT HTML
Supplementary materialThe development of antifungal drugs that inhibit lanosterol 14-α-demethylase (CYP51) via non-covalent ligand interactions is a strategy that is gaining importance. A series of novel tetraindol-4-one derivatives with 1- and 2-(2,4-substituted phenyl) side chains were designed and synthesized based on the structure of CYP51 and fluconazole. The antifungal activities of these derivatives against eight human pathogenic filamentous fungi and yeast strains were evaluated in vitro by measuring the minimal inhibitory concentrations. Nearly all tested compounds 8a–g displayed activity against Candida tropicalis, Candida guilliermondii and Candida parapsilosis with a minimum inhibitory concentration (MIC) value until 8 µg mL−1, on the other hand compounds 7a–g showed activity against Aspergillus fumigatus with a MIC value of 31.25 µg mL−1. A molecular modeling study of the binding interactions between compounds 6, 7d, 8g and the active site of MtCYP51 was conducted based on the computational docking results.View full abstractDownload PDF (804K) Full view HTML -
Mohammed Ibrahim El-Gamal, Chang-Hyun Oh2014 Volume 62 Issue 1 Pages 25-34
Published: January 01, 2014
Released on J-STAGE: January 01, 2014
JOURNAL FREE ACCESS FULL-TEXT HTMLA series of diarylureas and diarylamides possessing pyrrolo[2,3-d]pyrimidine scaffold was designed and synthesized. The in vitro antiproliferative activities of a selected group of the target compounds against NCI-60 cell line panel were tested and compared with Sorafenib and Imatinib as reference compounds. Most of the compounds showed strong and broad-spectrum antiproliferative activities. Compounds IVa, IVb, and IVd with benzamido moiety at position 4 of the pyrrolo[2,3-d]pyrimidine nucleus, para-disubstituted phenyl ring at N1-position of pyrrolo[2,3-d]pyrimidine scaffold, and urea linker showed strong and broad-spectrum anticancer results with high potencies and efficacies. In addition, the amide derivatives Vb and Vc demonstrated one-digit nanomolar IC50 values over two and one cell line(s), respectively. Amid all the target compounds, compound IVa demonstrated the best results in both one-dose and five-dose testing modes. It showed 109.18% mean % inhibition over the NCI-60 cancer cell line panel at 10 µM concentration, submicromolar 50% inhibitory concentration (IC50) values over eight cell lines of eight different cancer types, and high efficacy with total growth inhibition (TGI) and 50% lethal concentration (LC50) values less than 4.22 µM over three colon, ovarian, and prostate cancer cell lines. It showed superior potency and efficacy to Sorafenib and Imatinib over most of the tested cell lines.View full abstractDownload PDF (1319K) Full view HTML -
Shuo-Guo Li, Xiao-Jun Huang, Man-Mei Li, Mei Wang, Rui-Bing Feng, Wei ...2014 Volume 62 Issue 1 Pages 35-44
Published: January 01, 2014
Released on J-STAGE: January 01, 2014
Advance online publication: October 22, 2013JOURNAL FREE ACCESS FULL-TEXT HTML
Supplementary materialEight new bisdesmosidic triterpenoid saponins, clematiunicinosides A–H (1–8), along with eleven known ones (9–19), were isolated from the roots of Clematis uncinata. Their structures were elucidated on the basis of spectroscopic analysis and chemical evidence. All the isolated saponins were tested for their cytotoxic activities on human caski cervical cancer (Caski) cells, and compounds 13, 17 and 19 exhibited inhibitory effect on Caski cells.View full abstractDownload PDF (527K) Full view HTML -
Yuanyuan Jia, Daiying Zuo, Zengqiang Li, Hanmo Liu, Zhengning Dai, Jia ...2014 Volume 62 Issue 1 Pages 45-53
Published: January 01, 2014
Released on J-STAGE: January 01, 2014
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Supplementary materialDoxorubicin (DOX) is a widely used antitumor drug whose application is seriously limited by its cardiotoxicity. Mitochondria-mediated cardiomyocyte apoptosis plays a critical role in DOX-induced cardiotoxicity (DIC). The aim of the present study was to investigate the protective effect of astragaloside IV (3-O-beta-D-xylopyranosyl-6-O-beta-D-glucopyranosyl-cycloastragenol, AS-IV), a pure saponin isolated from Astragalus membranaceus, against DOX-induced cardiomyocyte apoptosis in primary cultured neonatal rat cardiomyocytes. Immunocytochemistry and Microculture Tetrazolium (MTT) assays showed that AS-IV significantly reduced DOX-induced cardiomyocyte loss. Additionally, AS-IV markedly ameliorated DOX-caused cardiomyocyte dysfunction via restoring the beating cell ratio and beating rate in cardiomyocytes. Furthermore, AS-IV substantially reduced the mitochondrial reactive oxygen species (ROS) production and lactate dehydrogenase (LDH), creatine kinase-MB isoenzyme (CK-MB) and cytochrome c (CytC) release, and restored the reduced ATP level, succinate dehydrogenase (SDH) and ATP synthase activities induced by DOX, suggesting that AS-IV significantly attenuated DOX-induced mitochondrial damage and dysfunction. It was further observed that DOX-induced cardiomyocyte apoptosis, as qualitatively evaluated by Hoechst 33258 staining and accurately quantified by flow cytometry, was markedly inhibited by AS-IV. Western blot analysis manifested that AS-IV significantly inhibited the activation of mitochondrial apoptotic pathway (MAP) via inducing the phosphorylation of Akt and Bad. Furthermore, phosphatidylinositol 3-kinase (PI3K) inhibitor 2-(4-morpholinyl)-8-phenyl-1(4H)-benzopyran-4-one hydrochloride (LY294002) remarkably inhibited the anti-apoptotic effect of AS-IV. Moreover, AS-IV didn’t compromise the antitumor activity of DOX. Taken together, our findings indicate that AS-IV ameliorates DIC, and this beneficial effect appears to be dependent on the activation of the PI3K/Akt pathway. Thus, AS-IV may hold promise as an efficient cardioprotective agent against DIC.View full abstractDownload PDF (3491K) Full view HTML -
Yasunori Miyazaki, Kaoru Miyawaki, Tomonobu Uchino, Yoshiyuki Kagawa2014 Volume 62 Issue 1 Pages 54-57
Published: January 01, 2014
Released on J-STAGE: January 01, 2014
JOURNAL FREE ACCESS FULL-TEXT HTMLWe introduced the application of a planetary centrifugal mixer to dispensing powdered medicines to prevent from individual variation in the skills of pharmacists with a manual blending. The blending performance of the mixer was explored in terms of four operational variables, namely, operation speed (400–1000 rpm), operation time (10–60 s), charging rate in vessel (20–50%), and size of vessel (35, 58, 125, 550 mL), using colored lactose and crystalline lactose as the principle model medicine and diluent, respectively. The blending degree was assessed by image analysis, so the extent of uniformity was expressed as the relative standard deviation of the color difference signal Cb value of YCrCb color space. Application of the mixer to blending three commercial medicines with diluents was carried out. Sufficient blending was achieved at 10 s using a 20% charging rate and 35 mL vessel irrespective of operation speed. As the charging rate was increased, a higher operation speed was needed to obtain uniform blending. A larger sized vessel also required a higher operation speed. Uniform blending was achieved in all of the mixtures of colored lactose and crystalline lactose at the weight ratio of 1 : 9–9 : 1. In the application studies using Adona®, Anginal® and Neophylline® powder, the blending performance of the mixer was equivalent to that of the manual blending method, showing relative standard deviations of 2.2–3.3% and 1.8–3.8%, respectively. These results revealed that the planetary centrifugal mixer was suitable for blending powdered medicine.View full abstractDownload PDF (374K) Full view HTML -
Hiroki Kitayama, Yuki Takechi, Nobutake Tamai, Hitoshi Matsuki, Chikak ...2014 Volume 62 Issue 1 Pages 58-63
Published: January 01, 2014
Released on J-STAGE: January 01, 2014
JOURNAL FREE ACCESS FULL-TEXT HTMLBy combination of differential scanning calorimetry (DSC) and fluorescence spectroscopy of 6-propionyl-2-(dimethylamino)naphthalene (Prodan), we elucidated the thermotropic phase behavior of hydrogenated soybean phosphatidylcholine (HSPC)–cholesterol binary liposome membrane which has similar lipid composition to Doxil®, the widely used liposome product in treatment of various tumors. We found that the characteristic points at cholesterol mole fraction (Xch)=0.023 and 0.077 correspond to the hexagonal lattice, in which cholesterol molecules are considered to be regularly distributed in all regions of HSPC lipid bilayer with 1 : 42 and 1 : 12 units, respectively, as static averaged structures. Apparent endothermic peak disappeared at Xch=0.40 in the DSC thermograms, indicating the existence of single liquid ordered phase at Xch>0.40. In addition, fluorescence measurements of Prodan and its lauroyl derivative in poly(ethylene glycol) (PEG)-modified liposomes indicated that PEG modification has a negligible effect on the phase behavior of HSPC–cholesterol binary liposome membrane. These results may provide useful information in developing novel liposome products whose stability and encapsulated drug release are controlled.View full abstractDownload PDF (1123K) Full view HTML -
Atsushi Fujihira, Nobuaki Shimizu2014 Volume 62 Issue 1 Pages 64-71
Published: January 01, 2014
Released on J-STAGE: January 01, 2014
JOURNAL FREE ACCESS FULL-TEXT HTMLWe evaluated the effects of internal phase and receptor solution pH on the rate of drug release from water-in-oil emulsions using methylene blue as a model drug. The water-in-oil emulsions were prepared using an aqueous solution of methylene blue, squalene, and a non-ionic-lipophilic surfactant. The methylene blue release rate was strongly dependent on both internal phase and receptor solution pH. Methylene blue dissolved in squalene in the presence of a surfactant. The water–squalene distribution of methylene blue changed with pH, whereas its ionic state did not. The pH dependence of the methylene blue release rate may have been due to this distribution change. We also investigated the pH dependence in terms of the mobility of water molecules using time-domain NMR. The mobility of water in water-in-oil emulsions was also dependent on the internal phase pH. Water-in-oil emulsions that showed high water mobility also released drug more rapidly. These results suggest that methylene blue is released from the water-in-oil emulsion through a reverse micelle mechanism. Methylene blue moves from the internal phase to a soluble reverse micelle of the surfactant, diffuses through the oil phase within this reverse micelle, and is transferred to the receptor solution. It appeared that the reverse micelles could diffuse in oil more freely than water droplets of the water-in-oil emulsion because the micelles were much smaller than the droplets. We found that the drug release rate from a water-in-oil emulsion comprising squalene and a non-ionic surfactant could be controlled by pH optimization.View full abstractDownload PDF (3339K) Full view HTML -
Aoi Miyamoto, Yuko Kitaichi, Kazuo Uchikura2014 Volume 62 Issue 1 Pages 72-76
Published: January 01, 2014
Released on J-STAGE: January 01, 2014
JOURNAL FREE ACCESS FULL-TEXT HTMLLaboratory tests of the decomposition of corticosteroids during activated sludge processing were investigated. Corticosteroid standards were added to activated sludge, and aliquots were regularly taken for analysis. The corticosteroids were extracted from the samples using a solid-phase extraction method and analyzed LC-MS. Ten types of corticosteroids were measured and roughly classified into three groups: 1) prednisolone, triamcinolone, betamethasone, prednisolone acetate, and hydrocortisone acetate, which decomposed within 4 h; 2) flunisolide, betamethasone valerate, and budesonide of which more than 50% remained after 4 h, but almost all of which decomposed within 24 h; and 3) triamcinolone acetonide, and fluocinolone acetonide of which more than 50% remained after 24 h. The decomposed ratio was correlated with each corticosteroid’s Log P, especially groups 2) and 3).View full abstractDownload PDF (665K) Full view HTML -
Yuko Kawasaki, Mitsuhiro Sekiguchi, Masashi Kawasaki, Yutaka Hirakura2014 Volume 62 Issue 1 Pages 77-83
Published: January 01, 2014
Released on J-STAGE: January 01, 2014
Advance online publication: October 29, 2013JOURNAL FREE ACCESS FULL-TEXT HTMLBisphosphonates (BPs) are the drug of choice for treating bone diseases such as osteoporosis, Paget’s disease, and metastatic bone disease. BPs with nitrogen-containing side chains (N-BPs) are known to act as inhibitors for farnesyl pyrophosphate synthase (FPPS), a key enzyme in the mevalonate pathway. In this study, we evaluated the effect of different side chains on the binding affinity of BPs to human FPPS using calorimetric techniques. Differential scanning calorimetry (DSC) was used to determine the thermal unfolding of FPPS in the presence of BPs. The addition of a series of clinically available BPs increased the structural stability of human FPPS by preferential binding, as indicated by an increase in the FPPS unfolding temperature. The magnitude of the increase was correlated with in vivo antiresorptive efficacy, suggesting that the stabilization of FPPS underlies the inhibitory effect of the BPs. Isothermal titration calorimetry (ITC) experiments were performed to evaluate the binding thermodynamics of BPs against human FPPS. Analysis of the binding energetics revealed that over 30 years of optimization practiced by different pharmaceutical companies has enhanced the enthalpic contribution as well as binding affinity of BPs. The larger enthalpic contribution observed for newer, more potent BPs derives from both improved hydrogen bonding interactions and shape complementarity based on comparisons of our results with available structure information.View full abstractDownload PDF (4003K) Full view HTML -
Chisato Mukai, Yasuhito Takahashi, Kumiko Ogawa, Yujiro Hayashi, Fuyuh ...2014 Volume 62 Issue 1 Pages 84-87
Published: January 01, 2014
Released on J-STAGE: January 01, 2014
JOURNAL FREE ACCESS FULL-TEXT HTML
Supplementary materialThe [RhCl(CO)2]2-catalyzed [2+2+1] cycloaddition of bis(allene)s, which have a substituent at the allenic terminus, produced the 8-substituted bicyclo[5.3.0]deca-1(10),6-dien-9-one frameworks. The synthesis of 8,10-dimethylbicyclo[5.3.0]deca-1(10),6-dien-9-one could also be achieved from the bis(1,1,3-trisubstituted-allene).View full abstractDownload PDF (493K) Full view HTML
Notes
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Noriko Okumura, Shiori Wakamatsu, Bunji Uno2014 Volume 62 Issue 1 Pages 88-91
Published: January 01, 2014
Released on J-STAGE: January 01, 2014
JOURNAL FREE ACCESS FULL-TEXT HTMLThis study demonstrated that the electro-chemical analysis of hydrophobic quinones can be performed in liposome suspension systems. We prepared and analyzed liposome suspensions containing lapachol, which is a quinone-based anti-tumor activity compound. In this suspension system, a simple one redox couple of lapachol is observed. These results are quite different from those obtained in organic solvents. In addition, the pH dependence of redox behaviors of lapachol could be observed in multilamellar vesicle (MLV) suspension system. This MLV suspension system method may approximate the electrochemical behavior of hydrophobic compounds in aqueous conditions. A benefit of this liposome suspension system for electrochemical analysis is that it enables to observe water-insoluble compounds without using organic solvents.View full abstractDownload PDF (876K) Full view HTML -
Minpei Kuroda, Takaaki Shizume, Yoshihiro Mimaki2014 Volume 62 Issue 1 Pages 92-96
Published: January 01, 2014
Released on J-STAGE: January 01, 2014
JOURNAL FREE ACCESS FULL-TEXT HTMLFive new triterpene glycosides, namely lonicerosides F–J (1–5), together with five known ones, were isolated from the stems and leaves of Lonicera japonica. Based on extensive spectroscopic analysis, including two-dimensional (2D)-NMR experiments, and the results of hydrolysis, the structures of the new compounds were determined to be 3β-[(β-D-glucopyranosyl)oxy]-23-hydroxyolean-12-en-28-oic acid O-β-D-glucopyranosyl-(1→6)-[α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranosyl ester (loniceroside F), 3β-[(β-D-glucopyranosyl)oxy]-23-hydroxyolean-12-en-28-oic acid O-(3-O-acetyl-β-D-xylopyranosyl)-(1→6)-[α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranosyl ester (loniceroside G), 3β-[(β-D-glucopyranosyl)oxy]-23-hydroxyolean-12-en-28-oic acid O-(4-O-acetyl-β-D-xylopyranosyl)-(1→6)-[α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranosyl ester (loniceroside H), 3β-[(α-L-arabinopyranosyl)oxy]-23-hydroxyolean-12-en-28-oic acid O-(3-O-acetyl-β-D-xylopyranosyl)-(1→6)-[α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranosyl ester (loniceroside I), and 3β-[(α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl)oxy]-olean-12-en-28-oic acid O-α-L-rhamnopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→6)]-β-D-glucopyranosyl ester (loniceroside J).View full abstractDownload PDF (404K) Full view HTML -
Masateru Ono, Ayako Takigawa, Yukiyo Kanemaru, Gen Kawakami, Kiyotaka ...2014 Volume 62 Issue 1 Pages 97-105
Published: January 01, 2014
Released on J-STAGE: January 01, 2014
JOURNAL FREE ACCESS FULL-TEXT HTMLFive new resin glycosides having macrolactone structures (jalapins), named calysolins V–IX (1–5), were isolated from the leaves, stems, and roots of Calystegia soldanella ROEM. et SCHULT. (Convolvulaceae). Their structures were determined on the basis of spectroscopic data as well as chemical evidence. The isolated compounds could be classified into two macrolactone types—one having a 22-membered ring (1–4) and the other with a 27-membered ring (5). The sugar moieties of 1–5 were found to exist in partially acylated forms comprising 2S-methylbutyric acid and tiglic acid. Compounds 4 and 5 are the first representatives of the calysolic acid C as the component glycosidic acid. Additionally, the antiviral activity of 1–5, together with calysolins I–IV and soldanelline B, which are previously isolated jalapins from this plant, toward herpes simplex virus type 1 was evaluated. All the compounds showed antiviral activity.View full abstractDownload PDF (873K) Full view HTML -
Li-Chai Chen, Shin-Hun Juang, Ken-Ming Chang, Cherng-Chyi Tzeng, Jih-J ...2014 Volume 62 Issue 1 Pages 106-111
Published: January 01, 2014
Released on J-STAGE: January 01, 2014
JOURNAL FREE ACCESS FULL-TEXT HTMLCertain amide-containing anthraquinone, xanthone, and carbazole derivatives have been synthesized and evaluated in vitro for their antiproliferative activities against a panel of human cancer cell lines including nasopharyngeal carcinoma (NPC-TW01), lung carcinoma (NCI-H661), and leukemia (Jurkat). Among them, 2-(9,10-dioxo-9,10-dihydroanthracen-2-yloxy)-N-(naphthalen-2-yl)acetamide (13) was the most active against NPC-TW01 with an IC50 value of 2.62 µM while its xanthone and dibenzofuran counterparts, 14 and 15, were inactive with an IC50 value of 16.10 and 11.09 µM, respectively. Studies on NPC-TW01 cell cycle distribution revealed that compound 13 inhibited proliferation of NPC-TW01 by the alteration of cell division and the accumulation of cells in G0/G1 phase.View full abstractDownload PDF (446K) Full view HTML -
Xiangduan Tan, Panfeng Wang, Siyun Nian, Guoping Wang2014 Volume 62 Issue 1 Pages 112-117
Published: January 01, 2014
Released on J-STAGE: January 01, 2014
Advance online publication: October 25, 2013JOURNAL FREE ACCESS FULL-TEXT HTMLIn this study, a series of amide derivatives were synthesized and evaluated for their S-adenosyl-L-homocysteine hydrolase (SAHase) inhibitory activities. The results demonstrated that most of compounds displayed potent SAHase inhibitory activities. Interestingly, compounds 11 and 14 exhibited more potent inhibitory effects than the aristeromycin, one of the most potent SAHase inhibitors known so far. Compounds 12, 13, 15 and 17 exhibited a moderate effect (IC50<10.0 µM). The structure–activity relationship found that compounds with substituted indazole-5-yl group at Ar position and ethylamino group at the side chain showed better SAHase inhibitory activities.View full abstractDownload PDF (558K) Full view HTML -
Zhao-Yuan Wu, Wei Fang, Li-Qiao Shi, Zhong-Yi Wan, Yong Min, Kai-Mei W ...2014 Volume 62 Issue 1 Pages 118-121
Published: January 01, 2014
Released on J-STAGE: January 01, 2014
JOURNAL FREE ACCESS FULL-TEXT HTMLFour new alkylated anthraquinone analogues (1–4) were isolated from a soil actimomycete Streptomyces sp. WS-13394. The structures of compounds 1–4 were elucidated to be 1,4,6-trihydroxy-8-alkylanthraquinones by means of spectroscopic methods, including UV, one dimensional (1D), 2D-NMR and MS spectrometry. All compounds showed activities against BGC-823 and MCF-7 with IC50 from 0.99 to 3.54 µg/mL, while 2 exhibited cytotoxicity against HepG2, A875, BGC-823 and MCF-7 with IC50 2.29, 4.90, 0.99, and 1.66 µg/mL, respectively.View full abstractDownload PDF (347K) Full view HTML -
Miwa Kubo, Yuhong Liu, Mami Ishida, Kenichi Harada, Yoshiyasu Fukuyama2014 Volume 62 Issue 1 Pages 122-124
Published: January 01, 2014
Released on J-STAGE: January 01, 2014
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Supplementary materialA new spiroindene pigment, phelliribsin A, was isolated from the medicinal fungus Phellinus ribis, and its structure was determined by two dimensional (2D)-NMR methods. Phelliribsin A is an unprecedented spiroindene compound, and was found to have cytotoxic activity against PC12 cells at a concentration of 30 µM.View full abstractDownload PDF (461K) Full view HTML -
Kousuke Akiyama, Kazutaka Yamamoto, Tomoko Mineno, Masafumi Okawa, Jun ...2014 Volume 62 Issue 1 Pages 125-133
Published: January 01, 2014
Released on J-STAGE: January 01, 2014
JOURNAL FREE ACCESS FULL-TEXT HTMLThree new acylated methyl glycosides and two new acylated glycosidic acid methyl esters were isolated after treatment of the crude ether-insoluble resin glycoside (convolvulin) fraction from seeds of Quamoclit pennata BOJER (Convolvulaceae) with indium(III) chloride in methanol. Their structures were elucidated on the basis of spectroscopic data and chemical conversions.View full abstractDownload PDF (621K) Full view HTML
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