Chemical & pharmaceutical bulletin最新文献

{"title":"Electrochemical Characterization of a Novel Organoelectrocatalyst, 7-Azabicyclo[2.2.1]heptan-7-ol (ABHOL), and Its Application to Electrochemical Sensors","authors":"Masaki Toda, Kyoko Sugiyama, Fumiya Sato, Yusuke Sasano, Tsutomu Fujimura, Yoshiharu Iwabuchi, Katsuhiko Sato","doi":"10.1248/cpb.c23-00710","DOIUrl":"https://doi.org/10.1248/cpb.c23-00710","url":null,"abstract":"</p><p>Electrochemical enzyme sensors are suitable for simple monitoring methods, for example, as glucose sensors for diabetic patients; however, they have several disadvantages arising from the properties of the enzyme. Therefore, non-enzymatic electrochemical sensors using functional molecules are being developed. In this paper, we report the electrochemical characterization of a new hydroxylamine compound, 7-azabicyclo[2.2.1]heptan-7-ol (ABHOL), and its application to glucose sensing. Although the cyclic voltammogram for the first cycle was unstable, it was reproducible after the second cycle, enabling electrochemical analysis of ethanol and glucose. In the first cycle, ABHOL caused complex reactions, including electrochemical oxidation and comproportionation with the generated oxoammonium ions. The electrochemical probe performance of ABHOL was more efficient than the typical nitroxyl radical compound, 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO), and had similar efficiency to 9-azabicyclo[3.3.1]nonane <i>N</i>-oxyl (ABNO), which is activated by the bicyclic structure. The results demonstrated the advantages of ABHOL, which can be synthesized from inexpensive materials <i>via</i> simple methods.</p>\u0000<p></p>\u0000<img alt=\"\" src=\"https://www.jstage.jst.go.jp/pub/cpb/72/3/72_c23-00710/figure/72_c23-00710.png\"/>\u0000<span style=\"padding-left:5px;\">Fullsize Image</span>","PeriodicalId":9773,"journal":{"name":"Chemical & pharmaceutical bulletin","volume":"2 1","pages":""},"PeriodicalIF":1.7,"publicationDate":"2024-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140018993","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Electrochemical Analysis for Total Alkalinity of Water by the Measurement of Cathodic Prepeak of Quinone Caused by Surplus Acid","authors":"Akira Kotani, Miyu Sakazume, Koichi Machida, Kazuhiro Yamamoto, Hideki Hakamata","doi":"10.1248/cpb.c23-00752","DOIUrl":"https://doi.org/10.1248/cpb.c23-00752","url":null,"abstract":"</p><p>In this study, an electrochemical analysis, coupled with the concept of back neutralization titration and the voltammetric determination of surplus acid, is proposed for determining the total alkalinity of water samples. When linear sweep voltammetry of 3,5-di-<i>tert</i>-butyl-1,2-benzoquinone (DBBQ) with H₂SO₄ in a water and ethanol (44 : 56, v/v) mixture was carried out using a bare glassy carbon working electrode, a cathodic prepeak of DBBQ caused by H₂SO₄ was observed on the voltammogram at a more positive potential than when compared with the original cathodic peak of DBBQ. When similar voltammetry was carried out in the presence of Na₂CO₃ and H₂SO₄, the cathodic prepeak height of DBBQ was decreased with an increase in the Na₂CO₃ concentration. The decrease of the cathodic prepeak height of DBBQ was found to be linearly related to the Na₂CO₃ concentration ranging from 0.025 to 2.5 mM (<i>r</i>² = 0.998). The total equivalent concentrations of inorganic bases in samples of mineral water and tap water were determined, and then the results were converted to the total alkalinities of the water samples (mg/L CaCO₃). The total alkalinities of the water samples determined by the present electrochemical analysis were essentially the same compared with those by the neutralization titration method. From these results, we were able to demonstrate that the present electrochemical analysis with accuracy and precision could be applied to determine the total alkalinity, which is one of the indicators to examine water quality. The present electrochemical analysis would contribute to achieving the sustainable development goals (SDGs) of #6 and #14.</p>\u0000<p></p>\u0000<img alt=\"\" src=\"https://www.jstage.jst.go.jp/pub/cpb/72/3/72_c23-00752/figure/72_c23-00752.png\"/>\u0000<span style=\"padding-left:5px;\">Fullsize Image</span>","PeriodicalId":9773,"journal":{"name":"Chemical & pharmaceutical bulletin","volume":"32 1","pages":""},"PeriodicalIF":1.7,"publicationDate":"2024-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140003254","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Unusual Enzymatic C–C Bond Formation and Cleavage Reactions during Natural Product Biosynthesis","authors":"Richiro Ushimaru","doi":"10.1248/cpb.c23-00889","DOIUrl":"https://doi.org/10.1248/cpb.c23-00889","url":null,"abstract":"</p><p>Natural products from plants and microorganisms provide a valuable reservoir of pharmaceutical compounds. C–C bond formation and cleavage are crucial events during natural product biosynthesis, playing pivotal roles in generating diverse and intricate chemical structures that are essential for biological functions. This review summarizes our recent findings regarding biosynthetic enzymes that catalyze unconventional C–C bond formation and cleavage reactions during natural product biosynthesis.</p>\u0000<p></p>\u0000<img alt=\"\" src=\"https://www.jstage.jst.go.jp/pub/cpb/72/3/72_c23-00889/figure/72_c23-00889.png\"/>\u0000<span style=\"padding-left:5px;\">Fullsize Image</span>","PeriodicalId":9773,"journal":{"name":"Chemical & pharmaceutical bulletin","volume":"75 1","pages":""},"PeriodicalIF":1.7,"publicationDate":"2024-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140003414","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Construction of Biosensing System for Glycated Albumin Using an Electron Transfer Peptide-Modified Protein Probe","authors":"Michiru Ito, Kazuharu Sugawara","doi":"10.1248/cpb.c23-00702","DOIUrl":"https://doi.org/10.1248/cpb.c23-00702","url":null,"abstract":"</p><p>Glycated albumin (GA) is one of the proteins that replaces several sugar moieties and can be used as an indicator of diabetes mellitus. We developed a sensing system that uses GA in the early detection of diabetes mellitus. In this study, H₆Y₄C acetylated (Ac-) at the N-terminals of the peptide was combined with wheat germ agglutinin (WGA) to recognize glucose moieties. The Ac-H₆Y₄C-WGA was constructed as a GA-sensing probe. The tyrosine residues of Y₄C exhibited an oxidation peak, and His-tag moieties were introduced to separate Ac-H₆Y₄C-WGA in the synthesis of the probe. The Ac-H₆Y₄C-WGA probe binds with the 1–2 molecules of Ac-H₆Y₄C per WGA using matrix assisted laser desorption/ionization-time of flight (MALDI-TOF)-MS. Next, the functions of Ac-H₆Y₄C-WGA were evaluated using voltammetry. The number of electron-transfers was calculated based on the relationship between the peak potential and logarithm of scan rate and was 3.03. In the electrochemical measurements with mannose and bovine serum albumin, the peak currents were similar to that of GA alone. By contrast, a decrease in the peak current was suppressed when glucose was added to the solution containing the probe. As a result, Ac-H₆Y₄C-WGA was selectively bound to the glucose moieties of GA. The calibration curve <i>via</i> differential pulse voltammetry was proportional to the concentrations of GA and ranged from 1.0 × 10⁻¹² to 2.0 × 10⁻¹¹ M with a detection limit of 3.3 × 10⁻¹³ M.</p>\u0000<p></p>\u0000<img alt=\"\" src=\"https://www.jstage.jst.go.jp/pub/cpb/72/3/72_c23-00702/figure/72_c23-00702.png\"/>\u0000<span style=\"padding-left:5px;\">Fullsize Image</span>","PeriodicalId":9773,"journal":{"name":"Chemical & pharmaceutical bulletin","volume":"3 1","pages":""},"PeriodicalIF":1.7,"publicationDate":"2024-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140018991","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Development of a Water Soluble Self-assembling Analogue of Vizantin","authors":"Mayo Nakano, Kyohei Sakamoto, Naoto Yamasaki, Yui Asano, Masataka Oda, Hironobu Takahashi, Takashige Kawakami, Masahisa Inoue, Hirofumi Yamamoto","doi":"10.1248/cpb.c23-00716","DOIUrl":"https://doi.org/10.1248/cpb.c23-00716","url":null,"abstract":"</p><p>Vizantin, 6,6′-bis-<i>O</i>-(3-nonyldodecanoyl)-α,α′-trehalose, has been developed as a safe immunostimulator on the basis of a structure–activity relationship study with trehalose 6,6′-dicorynomycolate. Our recent study indicated that vizantin acts as an effective Toll-like receptor-4 (TLR4) partial agonist to reduce the lethality of an immune shock caused by lipopolysaccharide (LPS). However, because vizantin has low solubility in water, the aqueous solution used in <i>in vivo</i> assay systems settles out in tens of minutes. Here, vizantin was chemically modified in an attempt to facilitate the preparation of an aqueous solution of the drug. This paper describes the concise synthesis of a water-soluble vizantin analogue in which all the hydroxyl groups of the sugar unit were replaced by sulfates. The vizantin derivative displayed micelle-forming ability in water and potent TLR-4 partial agonist activity.</p>\u0000<p></p>\u0000<img alt=\"\" src=\"https://www.jstage.jst.go.jp/pub/cpb/72/2/72_c23-00716/figure/72_c23-00716.png\"/>\u0000<span style=\"padding-left:5px;\">Fullsize Image</span>","PeriodicalId":9773,"journal":{"name":"Chemical & pharmaceutical bulletin","volume":"4 1","pages":""},"PeriodicalIF":1.7,"publicationDate":"2024-02-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139979223","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Enhanced Physical Stability of L-Ascorbic Acid in an Ionic Liquid.","authors":"Takeshi Oshizaka, Issei Takeuchi, Katsuya Mukae, Kenji Mori, Kenji Sugibayashi","doi":"10.1248/cpb.c23-00861","DOIUrl":"10.1248/cpb.c23-00861","url":null,"abstract":"<p><p>Ionic liquid (IL) technology was used to enhance the stability of L-ascorbic acid (AA). Pyridoxine was selected as the counter cation for anionic AA in IL. After AA was dissolved in water at 40 °C, its ratio decreased to 3.2% after 7 d. In contrast, the IL formulation showed negligible degradation, with almost no loss of AA even after 28 d. These results suggest that the use of IL enhances the stability of AA.</p>","PeriodicalId":9773,"journal":{"name":"Chemical & pharmaceutical bulletin","volume":" ","pages":"209-212"},"PeriodicalIF":1.7,"publicationDate":"2024-02-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139569540","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Effect of Ag and Ni-Doped Cerium Oxide Nanoparticles on the Formation of ROS and Evaluation as an Alternative Physical Sunscreen Material","authors":"Agnes Giovanni Marsius, Satria Hidayat, Damar Rastri Adhika, Akhmad Zein Eko Mustofa, Veinardi Suendo, Heni Rachmawati","doi":"10.1248/cpb.c23-00512","DOIUrl":"https://doi.org/10.1248/cpb.c23-00512","url":null,"abstract":"</p><p>CeO₂ nanoparticles (nanoceria) were proposed as an alternative physical sunscreen agent with antioxidant properties and comparable UV absorption performance. Green synthesis of nanoceria with Ag and Ni dopants resulted in doped nanoceria with lower catalytic activity and biologically-safe characteristics. The doped nanoceria was characterized using X-ray diffraction (XRD), transmission electron microscopy (TEM), Rancimat Instrument, and UV-Vis Spectrophotometer for SPF (Sun Protection Factor) determination. XRD and TEM analysis showed that nanoceria had been successfully formed in nanoscale-sized with a change in crystallite size due to the crystal defect phenomenon caused by dopant addition. While the Rancimat test and band gap energy analysis were conducted to evaluate the oxidative stability and reactive oxygen species formation, it was confirmed that dopant addition could decrease catalytic activity of material, resulting in Ni-doped Ce with a longer incubation time (11.81 h) than Ag-doped Ce (10.58 h) and non-doped Ce (10.30 h). <i>In-vitro</i> SPF value was measured using the thin layer technique of sunscreen prototype with Virgin Coconut Oil (VCO)-based emulsion, which yielded 10.862 and 5.728 SPF values for 10% Ag-doped Ce and 10% Ni-doped Ce, respectively. The dopant addition of nanoceria could reduce catalytic activity and give a decent <i>in vitro</i> UV-shielding performance test; thus, Ag and Ni-doped nanoceria could be seen as promising candidates for alternative physical sunscreen agents.</p>\u0000<p></p>\u0000<img alt=\"\" src=\"https://www.jstage.jst.go.jp/pub/cpb/72/2/72_c23-00512/figure/72_c23-00512.png\"/>\u0000<span style=\"padding-left:5px;\">Fullsize Image</span>","PeriodicalId":9773,"journal":{"name":"Chemical & pharmaceutical bulletin","volume":"184 1","pages":""},"PeriodicalIF":1.7,"publicationDate":"2024-02-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139910106","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Antiproliferative Activities of Cynaropicrin and Related Compounds against Cancer Stem Cells","authors":"Kousuke Araki, Minami Hara, Shohei Hamada, Takahiro Matsumoto, Seikou Nakamura","doi":"10.1248/cpb.c23-00811","DOIUrl":"https://doi.org/10.1248/cpb.c23-00811","url":null,"abstract":"</p><p>Glioblastoma (GBM) has a high mortality rate despite the availability of various cancer treatment options. Although cancer stem cells (CSCs) have been associated with poor prognosis and metastasis, and play an important role in the resistance to existing anticancer drugs and radiation; no CSC-targeting drugs are currently approved in clinical practice. Therefore, the development of antiproliferative agents against CSCs is urgently required. In this study, we evaluated the antiproliferative activities of 21 sesquiterpenoids against human GBM U-251 MG CSCs and U-251 MG non-CSCs. Particularly, the guaianolide sesquiterpene lactone cynaropicrin (<b>1</b>) showed strong antiproliferative activity against U-251 MG CSCs (IC₅₀ = 20.4 µM) and U-251 MG non-CSCs (IC₅₀ = 10.9 µM). Accordingly, we synthesized six derivatives of <b>1</b> and investigated their structure–activity relationships. Most of the guaianolide sesquiterpene lactones with the α-methylene-γ-butyrolactone moiety showed antiproliferative activities against U-251 MG cells. We conclude that the 5,7,5-ring and the α-methylene-γ-butyrolactone moiety are both important for antiproliferative activities against U-251 MG cells. The results of this study suggest that the α,β-unsaturated carbonyl moiety, which has recently become a research hotspot in drug discovery, is the active center of <b>1</b>. Therefore, we consider <b>1</b> as a potential lead for developing novel drugs targeting CSCs.</p>\u0000<p></p>\u0000<img alt=\"\" src=\"https://www.jstage.jst.go.jp/pub/cpb/72/2/72_c23-00811/figure/72_c23-00811.png\"/>\u0000<span style=\"padding-left:5px;\">Fullsize Image</span>","PeriodicalId":9773,"journal":{"name":"Chemical & pharmaceutical bulletin","volume":"79 1","pages":""},"PeriodicalIF":1.7,"publicationDate":"2024-02-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139910107","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Improved Dissolution Properties of Co-amorphous Probucol with Atorvastatin Calcium Trihydrate Prepared by Spray-Drying","authors":"Shinji Oyama, Noriko Ogawa, Kaori Kawai, Kanako Iwai, Toshiya Yasunaga, Hiromitsu Yamamoto","doi":"10.1248/cpb.c23-00673","DOIUrl":"https://doi.org/10.1248/cpb.c23-00673","url":null,"abstract":"</p><p>A co-amorphous model drug was prepared by the spray-drying (SD) of probucol (PC) and atorvastatin calcium trihydrate salt (ATO) as low water solubility and co-former components, respectively. The physicochemical properties of the prepared samples were characterized by powder X-ray diffraction (PXRD) analysis, thermal analysis, Fourier transform infrared spectroscopy (FTIR), and dissolution tests. Stability tests were also conducted under a stress environment of 40 °C and 75% relative humidity. The results of PXRD measurements and thermal analysis suggested that PC and ATO form a co-amorphous system by SD. Thermal analysis also indicated an endothermic peak that followed an exotherm in amorphous PC and a physical mixture (PM) of amorphous PC and ATO; however, no endothermic peak was detected in the co-amorphous system. The dissolution profiles for PC in the co-amorphous sample composed of PC and ATO were improved compared to those for raw PC crystals or the PM. Stability tests indicated that the co-amorphous material formed by PC and ATO can be stored for 35 d without crystallization, whereas amorphous PC became crystallized within a day. Therefore, co-amorphization of PC and ATO prepared by SD is considered to be a useful method to improve the solubility of PC in water.</p>\u0000<p></p>\u0000<img alt=\"\" src=\"https://www.jstage.jst.go.jp/pub/cpb/72/2/72_c23-00673/figure/72_c23-00673.png\"/>\u0000<span style=\"padding-left:5px;\">Fullsize Image</span>","PeriodicalId":9773,"journal":{"name":"Chemical & pharmaceutical bulletin","volume":"96 1","pages":""},"PeriodicalIF":1.7,"publicationDate":"2024-02-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139762447","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Total Synthesis of Marine Polyketide Plakortone Q","authors":"Shinnosuke Okazaki, Kaho Senda, Ayaka Tokuta, Misa Inagaki, Kazuo Kamaike, Koichiro Ota, Hiroaki Miyaoka","doi":"10.1248/cpb.c23-00876","DOIUrl":"https://doi.org/10.1248/cpb.c23-00876","url":null,"abstract":"</p><p>The total synthesis of the natural bicyclo[3.3.0]furanolactone polyketide, plakortone Q, was achieved in 24 steps from (<i>R</i>)-Roche ester. The main feature of this synthetic strategy is the stereoselective construction of a central tetrahydrofuran moiety with four consecutive stereoisomeric centers using the Upjohn dihydroxylation of oxiranyl-substituted alkenes and acid-mediated 5-<i>endo</i>-<i>tet</i> cyclization.</p>\u0000<p></p>\u0000<img alt=\"\" src=\"https://www.jstage.jst.go.jp/pub/cpb/72/2/72_c23-00876/figure/72_c23-00876.png\"/>\u0000<span style=\"padding-left:5px;\">Fullsize Image</span>","PeriodicalId":9773,"journal":{"name":"Chemical & pharmaceutical bulletin","volume":"32 1","pages":""},"PeriodicalIF":1.7,"publicationDate":"2024-02-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139679250","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}