Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
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Volume 56, Issue 6
Displaying 1-30 of 30 articles from this issue
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Regular Articles
  • Electrochemical Oxidation of Luteolin at a Glassy Carbon Electrode and Its Application in Pharmaceutical Analysis
    Ailin Liu, Shaobo Zhang, Liying Huang, Yangyuan Cao, Hong Yao, Wei Che ...
    Article type: Regular Article
    2008 Volume 56 Issue 6 Pages 745-748
    Published: June 01, 2008
    Released on J-STAGE: June 01, 2008
    DOIhttps://doi.org/10.1248/cpb.56.745
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    Luteolin is a flavonoid reported to occur widely in many medicinal plants. The electrochemical behavior of luteolin was studied in phosphate buffer solution (PBS) of pH 4.0 at a glassy carbon electrode (GCE) by cyclic voltammetry (CV) and differential pulse voltammetric method (DPV). The results indicated the well-defined redox peak of luteolin which was involving two electrons and two protons was observed and the electrode process is adsorption-controlled. The charge transfer coefficient (α) was calculated as 0.66. The relationships between oxidation peak current and the concentration of luteolin are linear in the range of 1.0×10−8—1.0×10−6 M by DPV method. The detection limit had been estimated as 5.0×10−9 M. The facile and rapid method has been successfully applied to the detection of luteolin in tablets.
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  • Electro-Organic Synthesis and Characterization of New Dihydroxybenzene Dinitrile Derivatives with Fluorescent Properties
    Abdolmajid Bayandori Moghaddam, Mohammad Reza Ganjali, Rassoul Dinarva ...
    Article type: Regular Article
    2008 Volume 56 Issue 6 Pages 749-752
    Published: June 01, 2008
    Released on J-STAGE: June 01, 2008
    DOIhttps://doi.org/10.1248/cpb.56.749
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    Novel fluorescent molecules were synthesized by designing an environmentally friendly method involving the bulk electrolysis technique. This electrochemical treatment process helps protect the environment by minimizing the toxic waste component of effluent. The electrochemical oxidation of 3,6-dihydroxybenzene-1,2-dinitrile (DBD) in the presence of benzenesulfinic acids was studied in an aqueous solution (H2O : AN, 90 : 10), which included an acetate buffer (pH=5.0). This research utilized a variety of experimental techniques, including cyclic voltammetry, controlled-potential electrolysis as well as spectroscopic identification of compounds produced as products. In addition, our fluorescent studies offered results in line with existing findings. At the wavelength of 205 nm, DBD and compound (6) were excited and their fluorescent emissions were monitored.
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  • Miniaturized Membrane Sensors for the Determination of Rivastigmine Hydrogen Tartrate
    Amira Mabrouk El-Kosasy, Maissa Yacoub Salem, Mohamed Galal El-Bardicy ...
    Article type: Regular Article
    2008 Volume 56 Issue 6 Pages 753-757
    Published: June 01, 2008
    Released on J-STAGE: June 01, 2008
    DOIhttps://doi.org/10.1248/cpb.56.753
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    Novel miniaturized polyvinyl chloride (PVC) membrane sensors in all-solid state graphite and platinum wire supports were developed, electrochemically evaluated and used for the assay of rivastigmine hydrogen tartrate drug (RIV). The RIV sensors are based on the formation of an ion-association complex between the drug cation and tetrakis(4-chlorophenyl)borate (TpClPB) anionic exchanger as electroactive material dispersed in a PVC matrix. Linear responses of 10−2—10−5 M and 10−2—10−4 M with cationic slopes of 56.4 mV and 53.6 mV over the pH range 4—7 were obtained by using the RIV-coated graphite (sensor 1) and platinum wire (sensor 2) membrane sensors, respectively. The proposed method displays useful analytical characteristics for the determination of RIV in Exelon® capsules with average recoveries of 100.01±0.835, 100.09±0.896, and in plasma with average recoveries of 99.47±0.97, 99.58±0.82, and in rat brain homogenate with average recoveries of 98.16±1.62, 99.02±1.57, for sensors 1 and 2, respectively. The methods were also used to determine the intact drug in the presence of its degradation product and thus could be used as stability indicating methods. The results obtained by the proposed procedures were statistically analyzed and compared with those obtained by using a reported method. No significant difference for both accuracy and precision was observed.
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  • Cinnamyl Derivatives: Synthesis and Factor Xa (FXa) Inhibitory Activities
    Tetsuji Noguchi, Naoki Tanaka, Toyoki Nishimata, Riki Goto, Miho Hayak ...
    Article type: Regular Article
    2008 Volume 56 Issue 6 Pages 758-770
    Published: June 01, 2008
    Released on J-STAGE: June 01, 2008
    DOIhttps://doi.org/10.1248/cpb.56.758
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    To develop a potent and oral anticoagulant, a series of compounds with cinnamyl moiety was synthesized and their factor Xa (FXa) inhibitory activities were examined. As a result, some cinnamyl derivatives showed potent FXa inhibitory activities in vitro. Among them, compounds with substituent at the 3-position on the central benzene ring represented by (N-{4-[1-(acetimidoyl)piperidin-4-yloxy]-3-chlorophenyl}-N-[(E)-3-(3-amidinophenyl)-2-propenyl]sulfamoyl)acetic acid dihydrochloride (45b) and (N-{4-[1-(acetimidoyl)piperidin-4-yloxy]-3-carbamoylphenyl}-N-[(E)-3-(3-amidinophenyl)-2-propenyl]sulfamoyl)acetic acid dihydrochloride (45j) exhibited potent FXa inhibitory activities with IC50 values of less than 10 nM in vitro. These compounds also showed potent anticoagulant activities both in vitro and ex vivo. Furthermore, these compounds exhibited no lethal toxicity (30 mg/kg, i.v.).
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  • Complexes of Chromium(III) with 2,3-Dihydroxynaphthalene-6-sulfonic Acid and 4,5-Dihydroxynaphthalene-2,7-disulfonic Acid in Aqueous Solution
    Mehmet Suat Aksoy
    Article type: Regular Article
    2008 Volume 56 Issue 6 Pages 771-774
    Published: June 01, 2008
    Released on J-STAGE: June 01, 2008
    DOIhttps://doi.org/10.1248/cpb.56.771
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    The chromium(III) complex species formed, in acidic and basic solutions at 25.0±0.1 °C, between Cr(III) and 2,3-dihydroxynaphthalene-6-sulfonic acid (2,3-DHN-6-SA, H2L2−) and 4,5-dihydroxynaphthalene-2,7-disulfonic acid (4,5-DHN-2,7-DSA, H2L−) were determined. Over the acidic pH range, the coordination of 2,3-DHN-6-SA and 4,5-DHN-2,7-DSA to Cr(III) in 1 : 1 mole ratio occurs, and CrL and CrL− type complexes are formed. At near neutral pH, CrL(OH)− and CrL(OH)2− type hydroxo complexes are formed. The acid-dissociation constants of ligands and the formation constants of chromium(III) complexes were determined in 0.1 m KNO3 ionic medium by potentiometric titration using the BEST computer program. Thus, the removing capacities of these ligands could be examined by calculating the equilibrium concentration of Cr(III) that exists in the discharge water of various industries since Cr(III) ions are the main pollutants present during waste water treatment in our city, Bursa.
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  • Synthesis and Antiviral Activity Evaluation of some Novel Acyclic C-Nucleosides
    Nikolaos Lougiakis, Panagiotis Marakos, Nicole Poul, Jan Balzarini
    Article type: Regular Article
    2008 Volume 56 Issue 6 Pages 775-780
    Published: June 01, 2008
    Released on J-STAGE: June 01, 2008
    DOIhttps://doi.org/10.1248/cpb.56.775
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    The preparation of novel 5-amino or 7-hydroxy substituted pyrazolo[4,3-b]pyridine and pyrazolo[3,4-c]pyridine acyclic C-nucleosides is described. Their synthesis was carried out by condensation of suitably substituted lithiated picolines with 2-benzyloxyethoxymethylchloride followed by pyrazole ring annulation. The compounds were evaluated for their antiviral activity against a wide panel of viruses, but were found inactive at subtoxic concentrations.
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  • Synthesis of New N-Analogous Corollosporine Derivatives with Antibacterial Activity by Laccase-Catalyzed Amination
    Annett Mikolasch, Susanne Hessel, Manuela Gesell Salazar, Helfried Neu ...
    Article type: Regular Article
    2008 Volume 56 Issue 6 Pages 781-786
    Published: June 01, 2008
    Released on J-STAGE: June 01, 2008
    DOIhttps://doi.org/10.1248/cpb.56.781
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    Corollosporine isolated from the marine fungus Corollospora maritima and N-analogous corollosporines are antimicrobial substances. Owing to the basic structure of the N-analogous corollosporines, they have become an attractive target for laccase-catalyzed derivatisation. In this regard we report on the straightforward laccase-catalyzed amination of dihydroxylated arenes with N-analogous corollosporines. In biological assays the obtained amination products are more active than the parent compounds.
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  • Application of Multivariate Methods to the Simultaneous Fourier Transform Infrared (FT-IR) Spectrometric Determination of Stereo-Isomers; Quinine and Quinidine
    Abdel-Aziz Mohamed Wahbi, Marwa Saio Moneeb, Ismail Ibrahim Hewala, Ma ...
    Article type: Regular Article
    2008 Volume 56 Issue 6 Pages 787-791
    Published: June 01, 2008
    Released on J-STAGE: June 01, 2008
    DOIhttps://doi.org/10.1248/cpb.56.787
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    The two stereo-isomers; quinine and quinidine have been determined in their mixtures in the IR region using chemometric multivariate methods, principal component regression (PCR) and partial least squares (PLS). A training set of thirty synthetic binary mixture solutions in the possible combinations containing 0.0—4.0 and 4.0—0.0% w/v quinine and quinidine, respectively in chloroform was used to develop the multivariate calibrations. A validation set containing thirty synthetic binary mixtures of variable ratios in the range of 0.2—4.0 and 4.0—0.2% w/v for quinine and quinidine, respectively in chloroform was used to validate the developed calibrations. The results of analysis of the validation synthetic mixtures were found to be 100.5±0.44% (R.S.D.%=0.44) and 100.5±0.38% (R.S.D.%=0.38) for quinine and 100.1±0.67% (R.S.D.%=0.67) and 100.1±0.68% (R.S.D.%=0.68) for quinidine using PCR and PLS models, respectively.
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  • A Controlled Porosity Osmotic Pump System with Biphasic Release of Theophylline: Influence of Weight Gain on Its in Vivo Pharmacokinetics
    Yueqi Bi, Yunyan Zhang, Junning Zhao, Shengjun Mao, Shixiang Hou
    Article type: Regular Article
    2008 Volume 56 Issue 6 Pages 792-795
    Published: June 01, 2008
    Released on J-STAGE: June 01, 2008
    DOIhttps://doi.org/10.1248/cpb.56.792
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    In our previous work, a controlled porosity osmotic pump system with biphasic release of theophylline, a system composed of a tablet-in-tablet (TNT) core and a controlled porosity coating membrane, was developed for the nocturnal therapy of asthma. Sodium phosphate and sodium chloride were selected as the osmotic agents in inner and outer layer of the TNT core respectively, and CA–PEG400–DEP (54.5%–36.4%–9.1%, w/w) was chosen as coating solution. Formulations with weight gain of 19 mg/T (mg per tablet), 9 mg/T and 6 mg/T were prepared respectively and their pharmacokinetics in beagle dogs were also studied to examine the influence of weight gain on their in vivo pharmacokinetics. Sustained release tablet of theophylline (SRT) was selected as reference to evaluate the in vitro and in vivo difference between conventional sustained release tablets and the developed formulation. Tmax and mean residence time (MRT) of the developed formulations were prolonged compared to that of SRT and a satisfying bioavailability was achieved at weight gain of 6 mg/T. If applied to the chronotherapy of asthma at night, the developed formulation with a weight gain of 6 mg/T might help to reduce the inconvenience brought by too later administration of conventional dosage forms and maintain a relatively high blood drug concentration 7 h after administration.
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  • Optimized Preparation of in Situ Forming Microparticles for the Parenteral Delivery of Vinpocetine
    Jizhong Li, Fei Chen, Chanjuan Hu, Ling He, Keshu Yan, Liying Zhou, We ...
    Article type: Regular Article
    2008 Volume 56 Issue 6 Pages 796-801
    Published: June 01, 2008
    Released on J-STAGE: June 01, 2008
    DOIhttps://doi.org/10.1248/cpb.56.796
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    A spherical symmetric design-response surface methodology was applied to optimize the preparation of vinpocetine-loaded poly(D,L-lactide-co-glycolide) PLGA in situ forming microparticles (ISM system). The influence of the ratio of PLGA to vinpocetine (w/w), the concentration of Tween 80 (w/v) and the volume of propylene glycol on the burst release, medium particle diameter and size distribution was evaluated. Scan electron microscopy of the optimized in situ microparticles exhibited spherical shape, and vinpocetine-loading mainly inside the microparticles. The data showed that the release of vinpocetine from in situ microparticles in vitro and in vivo lasted about 40 d. In vivo pharmacokinetic characteristics of the optimized in situ microparticles was assessed after they were intramuscularly injected into rats. HPLC method was used to determine the plasma concentration of vinpocetine. The absolute bioavailability of vinpocetine in the microparticles was 27.6% in rats, which suggested that PLGA in situ microparticles were a valuable system for the delivery of vinpocetine.
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  • Intramolecular Nonbonded S···N Interaction in Rabeprazole
    Kazuhiko Hayashi, Shiho Ogawa, Shigeki Sano, Motoo Shiro, Kentaro Yama ...
    Article type: Regular Article
    2008 Volume 56 Issue 6 Pages 802-806
    Published: June 01, 2008
    Released on J-STAGE: June 01, 2008
    DOIhttps://doi.org/10.1248/cpb.56.802
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    Intramolecular nonbonded S···N interactions in the crystal structures of the derivatives (7a—d) of sodium rabeprazole (1) and an intermolecular nonbonded S···N interaction between ethylmethylsulfoxide and pyridine in a solution were recognized. These results made us estimate that the intramolecular nonbonded S···N interaction existed in 1 and its derivatives in a solution, and formed the 4-membered quasi-ring in 2 (Fig. 1) followed by the increase of the reactivity of 2 to give the putative spiro sulfoxide 3, which is the key intermediate in the reaction cascade of 1 (Chart 1).
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  • Identification and Comparative Determination of Rhodionin in Traditional Tibetan Medicinal Plants of Fourteen Rhodiola Species by High-Performance Liquid Chromatography-Photodiode Array Detection and Electrospray Ionization-Mass Spectrometry
    Tao Li, Hao Zhang
    Article type: Regular Article
    2008 Volume 56 Issue 6 Pages 807-814
    Published: June 01, 2008
    Released on J-STAGE: June 01, 2008
    DOIhttps://doi.org/10.1248/cpb.56.807
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    Using the HPLC/PDA/ESI/MS method, a comparative analysis of rhodionin (RH) was undertaken in order to conduct a qualitative and quantitative study in 38 batches of fourteen species of Rhodiola for quality control purposes. Alongside of this RH analysis, a simultaneous determination of salidroside (SA), tyrosol (TY), and gallic acid (GA) was carried out. Rhodiola plants are a popularly used ethnodrug from the Qinghai-Tibetan plateau of China. The identity of RH was unambiguously determined based on the quasimolecular ions in negative ESI-MS mode. This method was validated in respect to sensitivity, linearity, precision, repeatability and recovery using optimized chromatographic conditions. The linear calibration curve was acquired with R2>0.999, and the limit of detection (S/N=3) was estimated to be 43.75 μg/g. The relative standard deviations (RSDs) of the intra- and inter-day precisions were 0.75% and 0.50%, respectively. The repeatability was evaluated by a replicated analysis of samples with the RSD value found within 0.67%. The recovery rates varied within the range of 98.79—100.08% with RSD less than 1.10%. In the present study, the content of RH was quantified within 0.4192—4.7260 mg/g for 16 batches of R. crenulata. It was also found in eight other species plants. The results demonstrated that RH is a useful characteristic standard compound for quality evaluation and chemical differentiation among species of Rhodiola. The study also indicated that the analytical procedure is precise, reproducible and a potential tool for both quality assessment and species identification.
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  • Aroylethenesulfonylacetic Acid Methyl Ester—A Synthon for Novel Sulfone Linked Bis Heterocycles
    Venkatapuram Padmavathi, Annaji Venkata Nagendra Mohan, Konda Mahesh, ...
    Article type: Regular Article
    2008 Volume 56 Issue 6 Pages 815-820
    Published: June 01, 2008
    Released on J-STAGE: June 01, 2008
    DOIhttps://doi.org/10.1248/cpb.56.815
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    Novel sulfone linked bis heterocycles containing two different heterocyclic rings viz., pyrazoline in combination with thiadiazole, oxadiazole and triazole were synthesized and studied their antimicrobial activity.
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  • Glass-State Amorphous Salt Solids Formed by Freeze-Drying of Amines and Hydroxy Carboxylic Acids: Effect of Hydrogen-Bonding and Electrostatic Interactions
    Saori Kadoya, Ken-ichi Izutsu, Etsuo Yonemochi, Katsuhide Terada, Chik ...
    Article type: Regular Article
    2008 Volume 56 Issue 6 Pages 821-826
    Published: June 01, 2008
    Released on J-STAGE: June 01, 2008
    DOIhttps://doi.org/10.1248/cpb.56.821
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    We studied effect of molecular interactions on the physical properties of binary freeze-dried solids and frozen aqueous solutions using model chemicals containing various functional groups (amino, carboxyl, hydroxyl). Thermal analysis of frozen solutions containing alkyl diamines and hydroxy di- or tricarboxylic acids showed thermal transitions (Tg′: glass transition of maximally freeze-concentrated phase) at temperatures higher than those of the individual solutes. A binary frozen solution containing 80 mM 1,3-diamino-2-hydroxypropane (single-solute Tg′<−60 °C) and 120 mM citric acid (single-solute Tg′: −55.0 °C) made the transition at −30.8 °C. The molecular weight of the solutes had smaller effects on the transition temperatures of the frozen mixture component solutions. Lyophilization of some high Tg′ mixture frozen solutions (e.g., 1,3-diamino-2-hydroxypropane and citric acid) resulted in cake-structure amorphous solids with glass transition temperatures (Tg) higher than those of the individual components. Networking of intense hydrogen-bondings and electrostatic interactions between the heterogeneous molecules through the multiple functional groups was suggested to reduce the component mobility in the amorphous freeze-concentrated phase and the freeze-dried solids. Controlling the interactions should be a key to optimizing the physical properties of multi-component amorphous freeze-dried pharmaceutical formulations.
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Notes
Communicatins to the Editor
  • Morphology and Surface States of Colloidal Probucol Nanoparticles Evaluated by Atomic Force Microscopy
    Kunikazu Moribe, Chalermphon Wanawongthai, Jyutaro Shudo, Kenjirou Hig ...
    Article type: Communications to the Editor
    2008 Volume 56 Issue 6 Pages 878-880
    Published: June 01, 2008
    Released on J-STAGE: June 01, 2008
    DOIhttps://doi.org/10.1248/cpb.56.878
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    Morphology and surface states of colloidal probucol nanoparticles after dispersion of probucol/polyvinylpyrrolidone (PVP)/sodium dodecyl sulphate (SDS) ternary ground mixture into water were investigated by atomic force microscopy (AFM). The observed particles had core-shell structure, i.e. drug nanocrystals were covered with PVP and SDS complex. The AFM phase image and the force curve analyses indicated that probucol nanoparticles with PVP K17 showed layer structure, compared to those with PVPK12. The structural difference was explainable in terms of the molecular states of PVP-SDS complex on the particle surface. These findings support not only the mechanism of drug nanoparticle formation but also the in vivo absorption results with the almost same particle size of ca. 40 nm.
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