{"title":"Methylene Blue Removal from the Aqueous Phase Using a Magnetic-Calcined Bamboo Composite Adsorbent.","authors":"Fumihiko Ogata, Kazuya Ujita, Yugo Uematsu, Noriaki Nagai, Chalermpong Saenjum, Shigeharu Tanei, Naohito Kawasaki","doi":"10.1248/cpb.c24-00648","DOIUrl":"10.1248/cpb.c24-00648","url":null,"abstract":"<p><p>In the present study, magnetic-calcined bamboo composite adsorbents (MCBC200, MCBC400, MCBC600, MCBC800, and MCBC1000) were prepared, and their physicochemical characteristics (scanning electron microscope images, differential thermogravimetric analysis, Fourier transform-IR, specific surface area, surface functional groups, and point of zero charge [pH<sub>pzc</sub>]) were evaluated. Furthermore, the adsorption capacity of methylene blue (MB, cationic dye) using the prepared adsorbents was assessed. The value of pH<sub>pzc</sub> and the specific surface area of MCBC400 were 7.8 and 50.6 m<sup>2</sup>/g, respectively. The amounts of acidic or basic functional groups of MCBC400 were relatively greater than those of the other adsorbents. The amount of MB adsorbed onto MCBC400 (31.9 mg/g) was higher than that onto other adsorbents. The adsorption of MB using MCBC400 was evaluated in relation to various parameters, including coexistence, solution pH, adsorption temperature, and contact time. The results followed the Langmuir isotherm model and a pseudo-second-order model with correlation coefficients of 0.980-1.000 and 0.996, respectively. MB was selectively adsorbed by MCBC400 in a binary solution system containing anionic dyes. Finally, one of the adsorption mechanisms was determined by analyzing the elemental distribution and the binding energy before and after the adsorption of MB. The current findings provide important information for removing MB with MCBC400 from the aqueous phase.</p>","PeriodicalId":9773,"journal":{"name":"Chemical & pharmaceutical bulletin","volume":"73 3","pages":"205-212"},"PeriodicalIF":1.5,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143613699","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":"Physical Properties for Novel Cilostazol Co-amorphous; Effect of Preparation Method and Molar Ratio on the Co-amorphous.","authors":"Tomoki Takayama, Shun Kaneko, Vasanthi Palanisamy, Makoto Ono, Varin Titapiwatanakun, Kenjirou Higashi, Toshiro Fukami","doi":"10.1248/cpb.c24-00732","DOIUrl":"10.1248/cpb.c24-00732","url":null,"abstract":"<p><p>Co-amorphous materials have gained special attention in the pharmaceutical field due to their high potential to enhance the oral bioavailability of poorly aqueous soluble drugs. In co-amorphous studies, few reports have examined the physical properties and molecular states of different active pharmaceutical ingredients (APIs) : co-amorphous former (CF) molar ratios and preparation methods. Therefore, we investigated the effect of molar ratio and preparation method on the physical properties of a novel co-amorphous system consisting of cilostazol and l-tryptophan, which we identified through screening. Co-amorphous consisting of molar ratios of 1 : 1 (co-milling (CM) 1 : 1), 1 : 1.5 (CM 1 : 1.5), and 1 : 2 (CM 1 : 2) were prepared by the CM method, while samples with a molar ratio of 1 : 1 (spray drying (SD) 1 : 1) were prepared by the spray drying method. CM 1 : 1.5 and CM 1 : 2 showed the highest solubility. Storage stability was excellent for CM 1:1.5, CM 1 : 2, and SD 1 : 1, whereas physical properties were improved by co-amorphization. To investigate the factors responsible for the improved physical properties, the molecular state of the co-amorphous system was evaluated, and it was inferred that hydrogen bonds were formed between cilostazol and l-tryptophan. Solid-state <sup>13</sup>C-NMR showed several new peaks specific to the solid state in the co-milled sample compared to SD 1 : 1 and cilostazol amorphous, suggesting that the molecular state may differ depending on the preparation method. As described above, different physical properties and molecular states were observed in the novel co-amorphous system consisting of cilostazol and l-tryptophan when the molar ratio of APIs and CF, and the preparation method differed.</p>","PeriodicalId":9773,"journal":{"name":"Chemical & pharmaceutical bulletin","volume":"73 4","pages":"318-326"},"PeriodicalIF":1.5,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143771456","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":"Unconventional Synthetic Approaches to Unusual Peptide Derivatives.","authors":"Takeshi Nanjo","doi":"10.1248/cpb.c24-00752","DOIUrl":"10.1248/cpb.c24-00752","url":null,"abstract":"<p><p>Peptides that contain unusual motifs, such as non-proteinogenic amino acids (AAs) and/or macrocyclic substructures, have recently attracted great attention as a new modality in medium-sized-molecule drug discovery. Therefore, it is highly important to develop methods for the chemical synthesis of a wide variety of such unusual peptide derivatives, which are often difficult to prepare via conventional synthetic approaches. In this review, the development of unconventional approaches for the synthesis of unusual peptide derivatives is discussed. Specifically, a novel external-oxidant-mediated decarboxylative condensation of α-ketoacids that can be applied to the synthesis of a wide variety of unusual peptide derivatives is reported. Moreover, an organocatalytic asymmetric Mannich-type addition is discussed that provides chiral β-amino-α-ketoacids, which are required as starting materials for the decarboxylative condensation. In this reaction, the adducts corresponding to various unusual AA side chains are obtained in high yield and excellent stereoselectivity. Furthermore, the \"N-chloropeptide strategy\" is proposed as a new method for the chemical modification of peptides without the need for a reactive AA residue.</p>","PeriodicalId":9773,"journal":{"name":"Chemical & pharmaceutical bulletin","volume":"73 4","pages":"268-282"},"PeriodicalIF":1.5,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143771457","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":"Novel Vial-Inner-Surface Treatment Technology Improves Chemical Durability and Vial-Inner-Surface Uniformity to Reduce Drug Adsorption on the Vial.","authors":"Norikazu Miyamoto, Kenta Ohsugi, Taishi Higashi, Keiichi Motoyama","doi":"10.1248/cpb.c24-00658","DOIUrl":"10.1248/cpb.c24-00658","url":null,"abstract":"<p><p>The pharmaceutical industry relies heavily on the safe and efficient packaging of drugs and injection glass vials play a pivotal role in this regard. Ensuring the quality and consistency of these vials is essential for safeguarding the potency of pharmaceutical formulations. In this study, the recent breakthroughs achieved in the manufacturing of injection glass vials by implementing advanced surface-processing technologies were examined. We developed potential injection glass vials using the novel vial-inner-surface treatment (VIST) technology to homogenize the inner surface of the vials. Compared with common vials, the elution of alkali contents and conductivity of these injection glass vials were reduced because of the VIST technology, resulting in the formation of smooth and homogeneous inner surfaces. In addition, drug adsorption onto the inner surface of the VIST vials was considerably lowered than that onto common vials. These results suggest that VIST vials are of excellent quality and could become the standard injection glass vials.</p>","PeriodicalId":9773,"journal":{"name":"Chemical & pharmaceutical bulletin","volume":"73 2","pages":"94-102"},"PeriodicalIF":1.5,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143406123","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}
Shin Aoki, Tomohiro Tanaka, Kenta Yokoi, Azusa Kanbe, Tomoe Morita, Mayuka Nii, Hidetoshi Satoh, Masaki Kakihana, Shotaro Otaki, Saki Sekiguchi, Koki Nakamura, Toshifumi Tojo, Masanori Baba, Mika Okamoto
{"title":"Design, Synthesis, and Anti-SARS-CoV-2 Activity of Amodiaquine Analogs.","authors":"Shin Aoki, Tomohiro Tanaka, Kenta Yokoi, Azusa Kanbe, Tomoe Morita, Mayuka Nii, Hidetoshi Satoh, Masaki Kakihana, Shotaro Otaki, Saki Sekiguchi, Koki Nakamura, Toshifumi Tojo, Masanori Baba, Mika Okamoto","doi":"10.1248/cpb.c24-00647","DOIUrl":"https://doi.org/10.1248/cpb.c24-00647","url":null,"abstract":"<p><p>The pandemic of coronavirus disease 2019, caused by the new coronavirus severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2), remains a serious concern worldwide. Although some effective vaccines have been developed, only a few anti-SARS-CoV-2 drugs have been approved for their clinical use. In this study, we designed and synthesized new anti-SARS-CoV-2 drugs based on the chemical structure of amodiaquine, which is known as an antimalarial drug. Consequently, we have identified amodiaquine analogs functionalized with dialkylamino-pendant aminophenol moieties that possess a high level of anti-SARS-CoV-2 activity with a low level of toxicity.</p>","PeriodicalId":9773,"journal":{"name":"Chemical & pharmaceutical bulletin","volume":"73 4","pages":"355-368"},"PeriodicalIF":1.5,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143984425","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":"Asymmetric Synthesis of 3-Spiro-Fused 2-Oxindoles via Organocatalyst/N-Iodosuccinimide/Hydrogen Peroxide-Mediated Oxidative Cyclization.","authors":"Kosuke Nakashima, Yuichi Okuaki, Misaki Deguchi, Yasuyuki Matsushima, Shin-Ichi Hirashima, Tsuyoshi Miura","doi":"10.1248/cpb.c24-00839","DOIUrl":"https://doi.org/10.1248/cpb.c24-00839","url":null,"abstract":"<p><p>A squaramide organocatalyst was employed to efficiently promote asymmetric oxidative lactonization to construct spiro-fused 2-oxindoles in moderate-to-good yield and enantioselectivity (up to 81% enantiomeric excess (ee)). Herein, we report the first study accomplishing stereoselective oxidative cyclization from indole propionic acid using an organocatalyst, N-iodosuccinimide (NIS), and hydrogen peroxide under metal-free and mild reaction conditions.</p>","PeriodicalId":9773,"journal":{"name":"Chemical & pharmaceutical bulletin","volume":"73 4","pages":"382-387"},"PeriodicalIF":1.5,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143967767","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":"Potential of Waste Basil Seeds for Gadolinium Ion Removal from Aqueous Solutions.","authors":"Fumihiko Ogata, Noriaki Nagai, Yugo Uematsu, Nanami Matsumoto, Chalermpong Saenjum, Naohito Kawasaki","doi":"10.1248/cpb.c25-00085","DOIUrl":"https://doi.org/10.1248/cpb.c25-00085","url":null,"abstract":"<p><p>This study examined the potential of waste basil seeds (BSs) calcined at 500°C or 1000°C (BS500 or BS1000, respectively) for gadolinium removal from aqueous solutions. Gadolinium ion adsorption onto the produced adsorbents was also assessed in relation to a number of parameters, including initial concentration, adsorption temperature, exposure time, and pH. Higher initial concentrations, adsorption temperatures, and exposure times (BS, BS500 ≒ BS1000) resulted in an increase in the quantity of adsorbed gadolinium ions; To further understand the adsorption mechanism, detailed analyses of elemental distribution and binding energy were conducted. According to the proposed mechanism, gadolinium adsorption onto BS1000 may involve an ion exchange process, wherein hydrogen ions from functional groups such carboxyl and hydroxyl groups on the surface of BS1000 are replaced by gadolinium ions. Additionally, the effects of coexisting ions on gadolinium adsorption were investigated, revealing that while monovalent cations did not impact gadolinium ion adsorption capacity, divalent and trivalent cations significantly reduced it. Finally, the desorption of gadolinium ions was tested using desorption agents such as distilled water, hydrochloric acid, and sodium hydroxide. The results revealed that a 100 mmol/L hydrochloric acid solution was particularly effective for desorbing gadolinium ions. Overall, BS1000 demonstrates promising properties as an adsorbent for gadolinium ion removal from aqueous solutions.</p>","PeriodicalId":9773,"journal":{"name":"Chemical & pharmaceutical bulletin","volume":"73 5","pages":"427-433"},"PeriodicalIF":1.5,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143974605","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}
Sana Ohashi, Sumie Ishiguro, Tsukasa Fukunaga, Akinobu Matsumoto, Mina Hirata, Masahito Inagaki, Naoko Abe, Fumitaka Hashiya, Hiroshi Abe
{"title":"Selection of Short 5'-UTR of Chemically Synthesized mRNA to Improve Translation Efficiency.","authors":"Sana Ohashi, Sumie Ishiguro, Tsukasa Fukunaga, Akinobu Matsumoto, Mina Hirata, Masahito Inagaki, Naoko Abe, Fumitaka Hashiya, Hiroshi Abe","doi":"10.1248/cpb.c25-00048","DOIUrl":"https://doi.org/10.1248/cpb.c25-00048","url":null,"abstract":"<p><p>The advent of mRNA medicine, initially implemented as a vaccine during the coronavirus disease 2019 (COVID-19) pandemic, has attracted interest in diverse therapeutic applications, including cancer vaccines and protein replacement therapies. Our group recently established a method for the complete chemical synthesis of mRNA. Although this approach has some advantages, chemically synthesized mRNA is limited to approximately 150 nucleotides in length and necessitates optimized designs for untranslated regions (UTRs) and coding sequences. To address this challenge, we investigated whether the non-reporter-based selection methods, including ribosome profiling and polysome profiling, which were often used for UTR optimization in long mRNA, could be adapted for short mRNA to identify highly translated UTR sequences. Using these methods, we collected mRNAs that interacted with ribosomes and analyzed their 5'-UTR sequences. We successfully identified a 9-nucleotide 5'-UTR that demonstrated approximately double the translation efficiency of the Kozak sequence, a widely used positive control. This work highlights the adaptability of ribosome-focused selection techniques for short, chemically synthesized mRNA and provides a foundation for effective sequence design. These findings advance the development of chemically synthesized mRNA as a viable alternative to in vitro-transcribed mRNA, paving the way for innovative therapeutic applications.</p>","PeriodicalId":9773,"journal":{"name":"Chemical & pharmaceutical bulletin","volume":"73 5","pages":"449-456"},"PeriodicalIF":1.5,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144092974","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":"Teleocidin Analogs Isolated from Streptomyces eurocidicus as Membrane-Vesicle-Regulated Natural Products.","authors":"Aya Yoshimura, Ryusuke Nakada, Toshiyuki Wakimoto","doi":"10.1248/cpb.c25-00197","DOIUrl":"https://doi.org/10.1248/cpb.c25-00197","url":null,"abstract":"<p><p>Four teleocidin analogs were isolated from Streptomyces eurocidicus, along with teleocidin B3. A combination of MS and NMR analyses elucidated their structures, revealing teleocidin A2 acetate and teleocidin B3 acetate as newly isolated metabolites. Teleocidins A2 and B3, known metabolites, exhibited weak antibacterial activities against Kocuria rhizophila and Bacillus subtilis. Notably, membrane vesicles of Burkholderia multivorans modulated the production levels of teleocidin analogs in S. eurocidicus, upregulating teleocidin biosynthesis but downregulating the subsequent acetylation step.</p>","PeriodicalId":9773,"journal":{"name":"Chemical & pharmaceutical bulletin","volume":"73 5","pages":"478-483"},"PeriodicalIF":1.5,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144118942","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":"Isolation of Compounds Including Two New Compounds from Asiasarum Root and Their Anti-glycation Activity.","authors":"Aiko Sano, Ryuichiro Suzuki","doi":"10.1248/cpb.c25-00034","DOIUrl":"https://doi.org/10.1248/cpb.c25-00034","url":null,"abstract":"<p><p>Two new glycosides, named 3-methoxy-5-methylphenol-6-O-β-glucopyranosyl-(1→6)-β-glucopyranoside (compound 1) and 1-O-feruloyl-α-arabinofuranosyl-(1→6)-β-glucopyranoside (compound 2), were isolated from Asiasarum root, together with eight known compounds. Asiasarum root (crude drug name in Latin: ASIASARI RADIX) is well known for its anti-inflammation and antitussive properties and is commonly found in Kampo formula in Japan. The structures of new compounds 1 and 2 were characterized using one- and two-dimensional (1D and 2D) NMR spectroscopy and MS. In addition, the anti-glycation activity of the isolates was evaluated. Glycation is particularly advanced in patients with diabetes and is suspected to be associated with diabetic complications such as nephropathy, osteoporosis, and Alzheimer's disease. The inhibition of this reaction is thought to be linked to the prevention and treatment of these diseases. Compounds 2 (79.4%), 4 (82.4%), 5 (79.8%), 6 (86.5%), 7 (90.1%), 9 (61.4%), and 10 (82.2%) showed activities comparable to that of aminoguanidine (45.3%) used as a positive control.</p>","PeriodicalId":9773,"journal":{"name":"Chemical & pharmaceutical bulletin","volume":"73 6","pages":"515-519"},"PeriodicalIF":1.5,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144246660","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}