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Effect of 1,4-Dioxane Solvent on β-Glucuronidation Using Methyl 1,2,3,4-Tetra-O-acetyl-β-D-glucuronate as the Glycosyl Donor Chem. Pharm. Bull. (IF 1.7) Pub Date : 2024-04-25 Tetsuya Kajimoto, Tianqi Du, Kimiyoshi Kaneko, Yasuyuki Matsushima, Tsuyoshi Miura
A facile and selective β-D-glucuronidation of alcohols, such as (−)-menthol, cholestanol, (+)- and (−)-borneols, and 2-adamantanol, using commercially available methyl 1,2,3,4-tetra-O-acetyl-β-D-glucuronate as the glycosyl donor and trimethylsilyl bis(trifluoromethanesulfonyl)imide (Tf2NTMS) (0.5 equivalent) as the activator in 1,4-dioxane at 60 °C gave products in moderate yields. The addition of
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Discovery and Structure–Activity Relationship of a Ryanodine Receptor 2 Inhibitor Chem. Pharm. Bull. (IF 1.7) Pub Date : 2024-04-22 Ryosuke Ishida, Xi Zeng, Nagomi Kurebayashi, Takashi Murayama, Shuichi Mori, Hiroyuki Kagechika
Ryanodine receptor 2 (RyR2) is a large Ca2+-release channel in the sarcoplasmic reticulum (SR) of cardiac muscle cells. It serves to release Ca2+ from the SR into the cytosol to initiate muscle contraction. RyR2 overactivation is associated with arrhythmogenic cardiac disease, but few specific inhibitors have been reported so far. Here, we identified an RyR2-selective inhibitor 1 from the chemical
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Exploring the Effectiveness of Carboxymethylated and Crosslinked Albizia Procera Gum in Diltiazem Hydrochloride Matrix Tablets: A Comparative Analysis Chem. Pharm. Bull. (IF 1.7) Pub Date : 2024-04-19 Sudipta Mukherjee, Jasmina Khanam
This study investigates the efficacy of modified Albizia procera gum as a release-retardant polymer in Diltiazem hydrochloride (DIL) matrix tablets. Carboxymethylated Albizia procera gum (CAP) and ionically crosslinked carboxymethylated Albizia procera gum (Ca-CAP) were utilized, with Ca-CAP synthesized via crosslinking CAP with calcium ions (Ca2+) using calcium chloride (CaCl2). FTIR analysis affirmed
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In Vitro and in Vivo Study of a Photostable Quinone Compound with Enhanced Therapeutic Efficacy against Chagas Disease Chem. Pharm. Bull. (IF 1.7) Pub Date : 2024-04-19 Yutaka Suto, Nagisa Inoue, Mohammed Suliman Omer Tagod, Yoko Onizuka, Tomoya Nobuta, Mayumi Ishii, Daniel Ken Inaoka, Kayoko Kanamitsu, Noriyuki Yamagiwa, Junko Nakajima-Shimada
Chagas disease, a neglected tropical disease caused by the protozoan Trypanosoma cruzi poses a significant health challenge in rural areas of Latin America. The current pharmacological options exhibit notable side effects, demand prolonged administration, and display limited efficacy. Consequently, there is an urgent need to develop drugs that are safe and clinically effective. Previously, we identified
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Discovery of a Novel Lidocaine Metabolite by Human Liver Microsome and Identification of Microbial Species Which Produces the Same Metabolite Chem. Pharm. Bull. (IF 1.7) Pub Date : 2024-04-19 Sho Hori, Hikari Taniguchi, Sota Yoshimura, Kanako Takeda, Ryusei Yamashita, Atsushi Kimishima, Kazuo Harada
Preparation of drug metabolites at the milligram scale is essential for determining the structure and toxicity of drug metabolites. However, their preparation using recombinant proteins and human liver microsomes (HLM) is often difficult because of technical and ethical issues. Reproducing human drug metabolism in food-derived microorganisms may be useful for overcoming these challenges. In this study
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Comparison of Non-ephedrine Constituents from Ephedra Plants Cultivated in Japan Chem. Pharm. Bull. (IF 1.7) Pub Date : 2024-04-17 Kengo Hayashi, Yuki Miyao, Hina Matsui, Takao Yamaura, Ken Tanaka, Mariko Baba, Hiroaki Hayashi
Ephedra plants, the main components of which are ephedrine alkaloids, are used as traditional medicines in Eastern Asian countries. In this study, we isolated non-ephedrine constituents from various Ephedra plant species cultivated in Japan. HPLC analysis suggested that kynurenic acid and its derivatives accumulated in a wide range of Ephedra plant species. Furthermore, a large amount of (2R,3S)-O-benzoyl
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Sustained Release Formulation of Hydroxypropyl-β-cyclodextrin Eye Drops Using Xanthan Gum Chem. Pharm. Bull. (IF 1.7) Pub Date : 2024-04-15 Taishi Higashi, Taito Goto, Risako Onodera, Tatsunori Hirotsu, Hanako Ohashi Ikeda, Keiichi Motoyama
Bietti’s crystalline dystrophy (BCD) is an autosomal recessive chorioretinal degeneration caused by mutations in the CYP4V2 gene. It is characterized by cholesterol accumulation and crystal-like deposits in the retinas. Hydroxypropyl-β-cyclodextrin (HP-β-CyD) exerts therapeutic effects against BCD by reducing lysosomal dysfunction and inhibiting cytotoxicity in induced pluripotent stem cell (iPSC)-RPE
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A Method for the Tensile Strength Prediction of Tablets with Differing Powder Plasticities Chem. Pharm. Bull. (IF 1.7) Pub Date : 2024-04-09 Takeru Yano, Atsushi Oshiro, Shuji Ohsaki, Hideya Nakamura, Satoru Watano
Tablets are the most commonly used dosage form in the pharmaceutical industry, and their properties such as disintegration, dissolution, and portability are influenced by their strength. However, in industry, the mixing fraction of powders to obtain a tablet compact with sufficient strength is determined based on empirical rules. Therefore, a method for predicting tablet strength based on the properties
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Unexpected Formation of 11(9→7)-abeo-Steroid Skeleton in Synthetic Studies toward Batrachotoxin Chem. Pharm. Bull. (IF 1.7) Pub Date : 2024-04-03 Hiroyuki Mutoh, Yuuki Watanabe, Daiki Kamakura, Koichi Hagiwara, Masayuki Inoue
Batrachotoxin (1) is a potent cardio- and neurotoxic steroid isolated from certain species of frogs, birds, and beetles. We previously disclosed two synthetic routes to 1. During our synthetic studies toward 1, we explored an alternative strategy for efficiently assembling its 6/6/6/5-membered steroidal skeleton (ABCD-ring). Here we report the application of intermolecular Weix and intramolecular pinacol
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Effects of Saikosaponin-A on Insulin Resistance in Obesity: Computational and Animal Experimental Study Chem. Pharm. Bull. (IF 1.7) Pub Date : 2024-04-04 Min-Seong Lee, Ji-won Noh, Byung-Cheol Lee
Obesity is known to be associated with increased inflammation and dysregulated autophagy, both of which contribute to insulin resistance. Saikosaponin-A (SSA) has been reported to exhibit anti-inflammatory and lipid-lowering properties. In this research, we employed a combination of computational modeling and animal experiments to explore the effects of SSA. Male C57BL/6 mice were categorized into
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Development of Methodologies toward the Unified Synthesis of Ellagitannins Chem. Pharm. Bull. (IF 1.7) Pub Date : 2024-04-01 Kazutada Ikeuchi
Ellagitannins, a class of polyphenols with divergent structures, have attracted considerable attention from synthetic organic chemists. The basic structures in ellagitannins contain esters of D-glucose with galloyl or hexahydroxyldiphenoyl groups, as well as diaryl ether structures. Thus, the synthesis methodologies of such components have been developed by various groups, including our group. This
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Eperisone Hydrochloride, a Muscle Relaxant, Is a Potent P2X7 Receptor Antagonist Chem. Pharm. Bull. (IF 1.7) Pub Date : 2024-03-30 Makoto Okada, Takashi Nose
Eperisone Hydrochloride was launched in Japan in 1983 and has been used to improve muscle tone and treat spastic paralysis (Originator: Eisai Co., Ltd.). However, its biochemical mechanism of action is unknown. SB Drug Discovery was used to evaluate purinergic P2X (P2X) receptor antagonism using fluorescence. In this study, we discovered that its target protein is the P2X7 receptor. Also, P2X receptor
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Magnetic Polystyrene Nanoparticles Prepared by Emulsion Solvent-Evaporation for the Chemiluminescent Immunoassay Chem. Pharm. Bull. (IF 1.7) Pub Date : 2024-03-28 Hiroaki Ichimaru, Masashi Kurimoto, Shigetoshi Kikuchi
In clinical diagnosis, magnetic polystyrene nanoparticles (MPS NPs) are commonly applied to, e.g., the chemiluminescent immunoassay (CLEIA). However, the conventional preparation method of MPS NPs requires a long duration of heating to form polymer particles, which is inefficient. In this study, we prepared MPS NPs by emulsion solvent-evaporation without heating. We evaluated the effect of the solvent
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Late-Stage Derivatization of Oleanolic Acid-Based Anti-HIV-1 Compounds Chem. Pharm. Bull. (IF 1.7) Pub Date : 2024-03-25 Reon Takeuchi, Junko Fujimoto, Yoshinori Taguchi, Ryuji Ide, Ryuji Kyan, Kohei Sato, Nobuyuki Mase, Masaru Yokoyama, Shigeyoshi Harada, Tetsuo Narumi
A 12-keto-type oleanolic acid derivative (4) has been identified as a potent anti-human immunodeficiency virus type-1 (HIV-1) compound that demonstrates synergistic effects with several types of HIV-1 neutralizing antibodies. In the present study, we used a common key synthetic intermediate to carry out the late-stage derivatization of an anti-HIV compound based on the chemical structure of a 12-keto-type
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Synthesis of 2-Substituted Indoles via Migration Reaction of 3-Substituted Indoles with Triflic Acid Chem. Pharm. Bull. (IF 1.7) Pub Date : 2024-03-25 Kosuke Nakashima, Yuka Kudo, Yasuyuki Matsushima, Shin-ichi Hirashima, Tsuyoshi Miura
This study showcases the 1,2-migration reactions of alkyl and aryl groups on the indole molecule. Trifluoromethanesulfonic acid effectively facilitates the migration of the substituent from C3- to C2-position of the indole structure. The resulting C2-substituted indoles offer a valuable pathway for the synthesis of natural products and medicinal compounds. Fullsize Image
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Development of an Auraptene-Loaded Transdermal Formulation Using Non-ionic Sugar Ester Surfactants Chem. Pharm. Bull. (IF 1.7) Pub Date : 2024-03-20 Kathrine Anne Flores, Akie Okada, Florencio Arce Jr., Gerard Lee See, Shoko Itakura, Hiroaki Todo, Kenji Sugibayashi
Auraptene (Aur) is a naturally occurring monoterpene coumarin ether that exhibits numerous therapeutic properties. Its high lipophilicity and low skin penetration, however, limit its potential application for local and transdermal delivery. Biocompatible non-ionic sugar esters (SEs) possess beneficial properties for the development of transdermal formulations in delivering pharmaceutically challenging
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Controlled Release of Lysozyme Using Polyvinyl Alcohol-Based Polymeric Nanofibers Generated by Electrospinning Chem. Pharm. Bull. (IF 1.7) Pub Date : 2024-03-21 Riho Ogawa, Kouji Hara, Ayaka Kobayashi, Nobuyoshi Yoshimura, Yutaka Taniguchi, Eriko Yamazoe, Takaaki Ito, Kohei Tahara
Polymeric nanofibers generated via electrospinning offer a promising platform for drug delivery systems. This study examines the application of electrospun polyvinyl alcohol (PVA) nanofibers for controlled lysozyme (LZM) delivery. By using various PVA grades, such as the degree of polymerization/hydrolysis, this study investigates their influence on nanofiber morphology and drug-release characteristics
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Effect of Two-Photon Excitation to 8-Azacoumarin Derivatives as Photolabile Protecting Groups Chem. Pharm. Bull. (IF 1.7) Pub Date : 2024-03-16 Takuya Kobayakawa, Hikaru Takano, Takahiro Ishii, Peter Bolah, Kohei Tsuji, Nami Ohashi, Wataru Nomura, Toshiaki Furuta, Hirokazu Tamamura
An improvement of the two-photon excitation was achieved using 8-azacoumarin-type caged compounds, which showed large values of the two-photon uncaging action cross-section (δu >0.1 Goeppert–Mayer (GM)). In particular, the 7-hydroxy-6-iodo-8-azacoumarin (8-aza-Ihc)-caged compound showed an excellent uncaging action cross-section value (δu = 1.28 GM). Therefore, 8-azacoumarin-type photolabile protecting
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Systematic Studies of Functional Group Tolerance and Chemoselectivity in Carbene-Mediated Intramolecular Cyclopropanation and Intermolecular C–H Functionalization Chem. Pharm. Bull. (IF 1.7) Pub Date : 2024-03-16 Haruki Kanda, Ayaka Okabe, Shingo Harada, Tetsuhiro Nemoto
Generating reliable data on functional group compatibility and chemoselectivity is essential for evaluating the practicality of chemical reactions and predicting retrosynthetic routes. In this context, we performed systematic studies using a functional group evaluation kit including 26 kinds of additives to assess the functional group tolerance of carbene-mediated reactions. Our findings revealed that
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Evaluating a Retro-Inverso Type Inhibitor of HTLV-1 Protease as a Competitive Inhibitor Chem. Pharm. Bull. (IF 1.7) Pub Date : 2024-03-14 Chiyuki Awahara, Daiki Oku, Kazuya Kobayashi, Yasunao Hattori
The inhibition mode of a retro-inverso (RI) inhibitor containing a hydroxyethylamine dipeptide isostere against the human T-cell leukemia virus type-1 (HTLV-1) protease was examined. Enzymatic evaluation of the RI-modified inhibitor containing a D-allo-Ile residue revealed that HTLV-1 was competitively inhibited. IC50 values of the RI-modified inhibitor and pepstatin A, a standard inhibitor of aspartic
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Dissolution Profiles of Oral Disintegrating Tablet with Taste Masking Granule Polymer Coating in Biorelevant Bicarbonate Buffer Chem. Pharm. Bull. (IF 1.7) Pub Date : 2024-03-13 Masaki Higashino, Kiyohiko Sugano
The current study aimed to explore the impact of buffer species on the dissolution behavior of orally disintegrating tablets (ODT) containing a basic polymer and its influence on bioequivalence (BE) prediction. Fexofenadine hydrochloride ODT formulations were used as the model formulations, Allegra® as the reference formulation, and generic formulations A and B as the test formulations. Allegra®, generic
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Organocatalyzed Amine-Free O-Phosphorylation of Alcohols with 4-Methylpyridine N-Oxide Chem. Pharm. Bull. (IF 1.7) Pub Date : 2024-03-12 Keisuke Yoshida, Wataru Hirano, Ryuuki Ota, Shinji Kitagaki
Amine-free phosphorylation of various alcohols was developed with 4-methylpyridine N-oxide in the presence of 4 Å molecular sieves at room temperature. This mild method gave various phosphorylated products in high yield and could be applied to acid- or base-sensitive substrates. Furthermore, this method was also effective for the chemoselective phosphorylation of diols or polyols. Fullsize Image
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Synthesis of a Cyclic Hexaamide Consisting of a Brominated m-Phenylene Repeating Unit Chem. Pharm. Bull. (IF 1.7) Pub Date : 2024-03-08 Akihiro Yokoyama, Ayaka Chino, Kenta Rakumitsu
Aiming to synthesize a cyclic hexaamide, 4-bromo-3-(isobutylamino)benzoic acid was subjected to self-condensation reactions in the presence of either dichlorotriphenylphosphorane in 1,1,2,2-tetrachloroethane or tetrachlorosilane in pyridine. However, instead of the targeted cyclic hexaamide, the cyclic triamide and the cyclic tetraamide were obtained. The cyclic hexaamide was successfully synthesized
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Protective Mechanisms of Juncus effusus and Carbonized Juncus effusus against D-Galactosamine-Induced Acute Liver Injury in Mice Chem. Pharm. Bull. (IF 1.7) Pub Date : 2024-03-06 Xiangming Wang, Menghui Zhao, Chengguo Ju, Hui Gao, Wei Wang
This study investigated the hepatoprotective effects of Juncus effusus (J. effusus) and Carbonized J. effusus against liver injury caused by D-galactosamine (D-GalN) in mice. J. effusus and Carbonized J. effusus were administered by gavage once daily starting seven days before the D-GalN treatment. The results of the study indicated that J. effusus and Carbonized J. effusus suppressed the D-GalN-induced
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Effect of Concomitant Drugs on Sodium Zirconium Cyclosilicate Hydrate in Artificial Intestinal Juice Chem. Pharm. Bull. (IF 1.7) Pub Date : 2024-03-06 Yuri Mizuno, Fumihiko Ogata, Yugo Uematsu, Naohito Kawasaki
To explore drug interactions involving sodium zirconium cyclosilicate hydrate (SZC) and concomitant drugs like calcium antagonists (amlodipine and nifedipine) and β-blockers (carvedilol and bisoprolol), we investigate how these concomitant drugs influenced the administration of SZC in an artificial intestinal juice. Initially, we assessed the potassium ion adsorption capacity, ranking it as follows:
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Electrochemical Characterization of a Novel Organoelectrocatalyst, 7-Azabicyclo[2.2.1]heptan-7-ol (ABHOL), and Its Application to Electrochemical Sensors Chem. Pharm. Bull. (IF 1.7) Pub Date : 2024-03-01 Masaki Toda, Kyoko Sugiyama, Fumiya Sato, Yusuke Sasano, Tsutomu Fujimura, Yoshiharu Iwabuchi, Katsuhiko Sato
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
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Construction of Biosensing System for Glycated Albumin Using an Electron Transfer Peptide-Modified Protein Probe Chem. Pharm. Bull. (IF 1.7) Pub Date : 2024-03-01 Michiru Ito, Kazuharu Sugawara
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
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Development of a Potential-Modulated Electrochemiluminescence Measurement System for Selective and Sensitive Determination of the Controlled Drug Codeine Chem. Pharm. Bull. (IF 1.7) Pub Date : 2024-03-01 Fumiki Takahashi, Yuki Shimosaka, Shuki Mori, Mayu Kaneko, Yuta Harayama, Kanya Kobayashi, Taku Shoji, Yasuo Seto, Hirosuke Tatsumi, Jiye Jin
Codeine is a common analgesic drug that is a pro-drug of morphine. It also has a high risk of abuse as a recreational drug because of its extensive distribution as an OTC drug. Therefore, sensitive and selective screening methods for codeine are crucial in forensic analytical chemistry. To date, a commercial analytical kit has not been developed for dedicated codeine determination, and there is a need
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Unusual Enzymatic C–C Bond Formation and Cleavage Reactions during Natural Product Biosynthesis Chem. Pharm. Bull. (IF 1.7) Pub Date : 2024-03-01 Richiro Ushimaru
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
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Evaluation of Antibiotic Penicillin G Activities Based on Electrochemical Measurement of a Tetrazolium Salt Chem. Pharm. Bull. (IF 1.7) Pub Date : 2024-03-01 Hikaru Ikeda, Akira Tokonami, Shigeki Nishii, Masashi Fujita, Yojiro Yamamoto, Yasuhiro Sadanaga, Hiroshi Shiigi
This study focused on the electrochemical properties of tetrazolium salts to develop a simple method for evaluating viable bacterial counts, which are indicators of drug susceptibility. Considering that the oxidized form of tetrazolium, which has excellent cell membrane permeability, changes to the insoluble reduced form formazan inside the cell, the number of viable cells was estimated based on the
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Electrochemical Analysis for Total Alkalinity of Water by the Measurement of Cathodic Prepeak of Quinone Caused by Surplus Acid Chem. Pharm. Bull. (IF 1.7) Pub Date : 2024-03-01 Akira Kotani, Miyu Sakazume, Koichi Machida, Kazuhiro Yamamoto, Hideki Hakamata
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-tert-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
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Development of a Water Soluble Self-assembling Analogue of Vizantin Chem. Pharm. Bull. (IF 1.7) Pub Date : 2024-02-27 Mayo Nakano, Kyohei Sakamoto, Naoto Yamasaki, Yui Asano, Masataka Oda, Hironobu Takahashi, Takashige Kawakami, Masahisa Inoue, Hirofumi Yamamoto
Vizantin, 6,6′-bis-O-(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
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Nucleophilic Deprotection of p-Methoxybenzyl Ethers Using Heterogeneous Oxovanadium Catalyst Chem. Pharm. Bull. (IF 1.7) Pub Date : 2024-02-21 Rei Ikeda, Tomoya Nishio, Kyohei Kanomata, Shuji Akai
Nucleophilic deprotection of p-methoxybenzyl (PMB) [p-methoxyphenylmethyl (MPM)] ethers was developed using a heterogeneous oxovanadium catalyst V-MPS4 and a thiol nucleophile. The deprotection method had a wide reaction scope, including PMB ethers of primary, secondary, and tertiary alcohols bearing various functional groups. In addition, the PMB ether of an oxidation-labile natural product was successfully
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Antiproliferative Activities of Cynaropicrin and Related Compounds against Cancer Stem Cells Chem. Pharm. Bull. (IF 1.7) Pub Date : 2024-02-20 Kousuke Araki, Minami Hara, Shohei Hamada, Takahiro Matsumoto, Seikou Nakamura
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
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Enhanced Physical Stability of L-Ascorbic Acid in an Ionic Liquid Chem. Pharm. Bull. (IF 1.7) Pub Date : 2024-02-21 Takeshi Oshizaka, Issei Takeuchi, Katsuya Mukae, Kenji Mori, Kenji Sugibayashi
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
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Effect of Ag and Ni-Doped Cerium Oxide Nanoparticles on the Formation of ROS and Evaluation as an Alternative Physical Sunscreen Material Chem. Pharm. Bull. (IF 1.7) Pub Date : 2024-02-21 Agnes Giovanni Marsius, Satria Hidayat, Damar Rastri Adhika, Akhmad Zein Eko Mustofa, Veinardi Suendo, Heni Rachmawati
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
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Improved Dissolution Properties of Co-amorphous Probucol with Atorvastatin Calcium Trihydrate Prepared by Spray-Drying Chem. Pharm. Bull. (IF 1.7) Pub Date : 2024-02-16 Shinji Oyama, Noriko Ogawa, Kaori Kawai, Kanako Iwai, Toshiya Yasunaga, Hiromitsu Yamamoto
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
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Sulfonate Derivatives Containing a Kakuol Moiety as Potential Fungicidal Candidates: Design, Synthesis and Antifungal Activity Evaluation Chem. Pharm. Bull. (IF 1.7) Pub Date : 2024-02-09 Guoqing Sui, Lili Shu, Ailing Zhang, Dan Li, Shuhua Cao
As a part of our continuing exploration to discover new potential promising fungicide candidates, eighteen sulfonate derivatives (3a–3r) containing a kakuol moiety were designed and synthesized. Synthetic sulfonate derivatives were tested comprehensively for antifungal activities against four plant pathogenic fungi (Botrytis (B.) cinerea, Valsa (V.) mali, Fusarium (F.) graminearum, Sclerotinia (S.)
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Targeted Therapy for Prostate Cancer by Prostate-Specific Membrane Antigen-Targeted Small-Molecule Drug Conjugates Chem. Pharm. Bull. (IF 1.7) Pub Date : 2024-02-01 Ryo Nakajima
In the aging global population, prostate cancer is a worldwide health problem because the incidence rate of this disease increases at advanced ages. Although early-stage prostate cancer can be treated by total prostatectomy, the surgery causes side effects, such as incontinence and dysuria, that lower QOL. Once the disease progresses to metastatic castration-resistant prostate cancer (mCRPC), there
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Total Synthesis of Marine Polyketide Plakortone Q Chem. Pharm. Bull. (IF 1.7) Pub Date : 2024-02-03 Shinnosuke Okazaki, Kaho Senda, Ayaka Tokuta, Misa Inagaki, Kazuo Kamaike, Koichiro Ota, Hiroaki Miyaoka
The total synthesis of the natural bicyclo[3.3.0]furanolactone polyketide, plakortone Q, was achieved in 24 steps from (R)-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-endo-tet cyclization
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A Structure–Activity Relationship Study of SNAIL1 Peptides as Inhibitors of Lysine-Specific Demethylase 1 Chem. Pharm. Bull. (IF 1.7) Pub Date : 2024-02-01 Yuri Takada, Kyohei Adachi, Yuka Fujinaga, Yasunobu Yamashita, Yukihiro Itoh, Takayoshi Suzuki
Peptides have recently garnered attention as middle-molecular-weight drugs with the characteristics of small molecules and macromolecules. Lysine-specific demethylase 1 (LSD1) is a potential therapeutic target for lung cancer, neuroblastoma, and leukemia, and some peptide-based LSD1 inhibitors designed based on the N-terminus of SNAIL1, a member of the SNAIL/SCRATCH family of transcription factors
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Synthesis of Coumarin-Conjugated Oligonucleotides via Knoevenagel Condensation to Prepare an Oligonucleotide Library Chem. Pharm. Bull. (IF 1.7) Pub Date : 2024-02-01 Takashi Osawa, Satoshi Obika
DNA-encoded libraries (DELs) are attracting attention as a screening tool in the early stages of drug discovery. In the development of DELs, drug candidate compounds are chemically synthesized on barcode DNA. Therefore, it is important to perform the synthesis under mild conditions so as to not damage the DNA. On the other hand, coumarins are gaining increasing research focus not only because they
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Rational Design of Amphipathic Antimicrobial Peptides with Alternating L-/D-Amino Acids That Form Helical Structures Chem. Pharm. Bull. (IF 1.7) Pub Date : 2024-02-01 Motoharu Hirano, Hidetomo Yokoo, Nobumichi Ohoka, Takahito Ito, Takashi Misawa, Makoto Oba, Takao Inoue, Yosuke Demizu
Antimicrobial peptides (AMPs) are promising therapeutic agents against bacteria. We have previously reported an amphipathic AMP Stripe composed of cationic L-Lys and hydrophobic L-Leu/L-Ala residues, and Stripe exhibited potent antimicrobial activity against Gram-positive and Gram-negative bacteria. Gramicidin A (GA), composed of repeating sequences of L- and D-amino acids, has a unique β6.3-helix
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Allosteric Hsp70 Modulator YM-1 Induces Degradation of BRD4 Chem. Pharm. Bull. (IF 1.7) Pub Date : 2024-02-01 Yugo Mishima, Shusuke Tomoshige, Shinichi Sato, Minoru Ishikawa
YM-1, an allosteric modulator of heat-shock 70 kDa protein (Hsp70), inhibits cancer cell growth, but the mechanism is not yet fully understood. Here, we show that YM-1 induces the degradation of bromodomain containing 4 (BRD4), which mediates oncogene expression. Overall, our results indicate that YM-1 promotes the binding of HSP70 to BRD4, and this in turn promotes the ubiquitination of BRD4 by C-terminus
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In Silico Prediction of N-Nitrosamine Formation Pathways of Pharmaceutical Products Chem. Pharm. Bull. (IF 1.7) Pub Date : 2024-02-01 Genichiro Tsuji, Takashi Kurohara, Takuji Shoda, Hidetomo Yokoo, Takahito Ito, Sayaka Masada, Nahoko Uchiyama, Eiichi Yamamoto, Yosuke Demizu
The recent discovery of N-nitrosodimethylamine (NDMA), a mutagenic N-nitrosamine, in pharmaceuticals has adversely impacted the global supply of relevant pharmaceutical products. Contamination by N-nitrosamines diverts resources and time from research and development or pharmaceutical production, representing a bottleneck in drug development. Therefore, predicting the risk of N-nitrosamine contamination
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Identification of a Histone Deacetylase 8 Inhibitor through Drug Screenings Based on Machine Learning Chem. Pharm. Bull. (IF 1.7) Pub Date : 2024-02-01 Atika Nurani, Yasunobu Yamashita, Yuuki Taki, Yuri Takada, Yukihiro Itoh, Takayoshi Suzuki
Histone deacetylase 8 (HDAC8) is a zinc-dependent HDAC that catalyzes the deacetylation of nonhistone proteins. It is involved in cancer development and HDAC8 inhibitors are promising candidates as anticancer agents. However, most reported HDAC8 inhibitors contain a hydroxamic acid moiety, which often causes mutagenicity. Therefore, we used machine learning for drug screening and attempted to identify
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Near-Infrared Fluorescent Silica Nanoparticles Based on Gold–Silver Alloy Nanoclusters for Clinical Diagnosis Chem. Pharm. Bull. (IF 1.7) Pub Date : 2024-01-30 Hiroaki Ichimaru, Shigetoshi Kikuchi
In clinical diagnosis, fluorescent particles are applied to detect analytes in biofluids, such as blood and saliva. However, current fluorescence detection methods have not been optimized to account for the overlapping autofluorescence peaks of biological substances. Gold and silver nanoclusters are known to the novel fluorescent materials and their emission wavelengths depend on cluster size. In this
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Design, Synthesis, and Biological Evaluation of Water-Soluble Prodrugs of C5-Curcuminoid GO-Y030 Based on Reversible Thia-Michael Reaction Chem. Pharm. Bull. (IF 1.7) Pub Date : 2024-01-30 Hiroyuki Yamakoshi, Michihiro Fukuda, Hiro Ikeda, Shogo Fujiki, Aki Kohyama, Shota Nagasawa, Hanae Shinozaki, Hiroyuki Shibata, Yoshiharu Iwabuchi
Although curcumin and its analogs exhibit anticancer activity, they are still not used as anticancer drugs because of their water insolubility and extremely poor bioavailability. This study describes the development of water-soluble prodrugs of GO-Y030, a potent antitumor C5-curcuminoid, in an attempt to enhance its bioavailability. These prodrugs release the parent compound via a retro-thia-Michael
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Development of Ethylcellulose Microparticles for Taste Masking of Fexofenadine Chem. Pharm. Bull. (IF 1.7) Pub Date : 2024-01-23 Yuri Ikeuchi-Takahashi, Machi Morii, Kurumi Yamazaki, Aoi Shimana, Ikki Shibazaki, Yasuko Obata
For taste masking of fexofenadine hydrochloride (FXD), ethylcellulose (EC) microparticles with FXD were developed. The amounts of EC, Tween 80, and polyvinyl alcohol (PVA) in the composition had little effect on initial drug release properties. Based on the results of the drug recovery and the drug release properties, FXD(EC200) was the optimal FXD microparticle formulation. From the results of Fourier
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Synthesis and Biological Evaluation of 2-Azolylmethylene-3-(2H)-benzofuranone Derivatives as Potent Monoamine Oxidases Inhibitors Chem. Pharm. Bull. (IF 1.7) Pub Date : 2024-01-23 Koichi Takao, Yuka Kubota, Kota Kurosaki, Hitoshi Kamauchi, Yoshihiro Uesawa, Yoshiaki Sugita
A series of 2-azolylmethylene-3-(2H)-benzofuranone derivatives, 2-indolylmethylene-3-(2H)-benzofuranone and 2-pyrrolylmethylene-3-(2H)-benzofuranone derivatives, were synthesized, and their monoamine oxidase (MAO) A and B inhibitory activities were evaluated. Compounds 1b, 3b, 6b, 7b, and 10b showed strong inhibitory activity against MAO-A, and compound 3b showed the highest potency and selectivity
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Chromatographic Evaluation and Characterization of Constituents of Sunflower Seed Extract Used as Food Additives Chem. Pharm. Bull. (IF 1.7) Pub Date : 2024-01-18 Yoshiaki Amakura, Takashi Uchikura, Morio Yoshimura, Naoko Masumoto, Yuzo Nishizaki, Naoki Sugimoto
Sunflower seed extract, an antioxidant agent registered on the List of Existing Food Additives in Japan, was evaluated using HPLC, and three common constituents were detected. These peaks were identified as monocaffeoylquinic acids (3-O-caffeoylquinic acid, 4-O-caffeoylquinic acid, and 5-O-caffeoylquinic acid [chlorogenic acid]). Upon scrutinizing other components, dicaffeoylquinic acids (isochlorogenic
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Bioinspired Total Synthesis of (+)-Kopsiyunnanine B Chem. Pharm. Bull. (IF 1.7) Pub Date : 2024-01-17 Sho Imaoka, Yuta Nakashima, Mariko Kitajima, Hayato Ishikawa
The first enantioselective total synthesis of kopsiyunnanine B, which has a unique folded and complex pentacyclic structure containing six contiguous chiral centers, has been achieved along our originally proposed biosynthetic pathway. The key reaction of this synthesis includes a bioinspired cascade that builds three ring structures and three chiral centers in one step and features the stereoselective
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Five New Analogs of Streptogramin Antibiotic Viridogrisein Isolated from Streptomyces niveoruber Chem. Pharm. Bull. (IF 1.7) Pub Date : 2024-01-18 Aya Yoshimura, Takumi Honda, Toshiyuki Wakimoto
Five new viridogriseins B–F were isolated from Streptomyces niveoruber, along with viridogrisein and griseoviridin which belong to streptogramin family antibiotics. A combination of liquid chromatography-tandem mass spectrometry (LC-MS/MS) analysis and the advanced Marfey’s method elucidated the structures of viridogriseins B–F, each featuring distinct constituent amino acids. Consistent with other
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Efficient and Environmentally Benign Oxidative Cleavage of Pyrrolidine-2-methanols to γ-Lactams Using 2-Iodobenzamide as a Catalyst and Oxone Chem. Pharm. Bull. (IF 1.7) Pub Date : 2024-01-17 Hema Naga Lakshmi Perumalla, Tomoya Fujiwara, Maki Okada, Kanna Asakubo, Takashi Okitsu, Kengo Kasama, Hisanori Nambu, Takayuki Yakura
The oxidative cleavage reaction of pyrrolidine-2-methanols to γ-lactams has been described. In this reaction, [4-iodo-3-(isopropylcarbamoyl)phenoxy]acetic acid and powdered Oxone (2KHSO5·KHSO4·K2SO4) were employed as the catalyst and co-oxidant, respectively. The reaction is efficient and environmentally benign because it produces various lactams from readily available substrates in moderate to excellent
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Derivation of the Extended Kawakita Equation for Estimating the Yield State of Powder in Die Chem. Pharm. Bull. (IF 1.7) Pub Date : 2024-01-18 Tsubasa Sato, Naoto Morita, Etsuo Yonemochi, Kozo Takayama
For powder compaction, the Kawakita equation has been used to estimate the powder behavior inside the die. The compression pressure exerted on powders is not homogeneous because of the friction on the die wall. However, the yield pressure and porosity estimated using the Kawakita equation are defined based on the assumption that homogeneous voids and compression pressure are distributed throughout
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A Tricyclic Aromatic Polyketide Isolated from the Marine-Derived Fungus Curvularia aeria Chem. Pharm. Bull. (IF 1.7) Pub Date : 2024-01-18 Hitoshi Kamauchi, Mayu Tanaka, Mitsuaki Suzuki, Miho Furukawa, Atsushi Ikeda, Chihiro Sasho, Yuka Kiba, Masashi Kitamura, Koichi Takao, Yoshiaki Sugita
A novel tricyclic polyketide, curvulanone (1), was isolated from the marine-derived fungus Curvularia aeria. The structure of 1 was determined by NMR and single-crystal X-ray crystallography. 1 had a cyclopentabenzopyranone with 3-acetic acid structure that is rarely found in natural compounds. Monoamine oxidase and sirtuin 1 inhibitory test was exhibited and 1 showed their inhibitory activity. Fullsize
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Syntheses and Cytotoxicities of Quinazolinone-Based Conjugates Chem. Pharm. Bull. (IF 1.7) Pub Date : 2024-01-12 Hieu Trong Le, Kiep Minh Do, Quy Phu Nguyen, Chau Nguyen Minh Doan, Nhi Ai Nguyen, Tai Thi Phan, Xuyen Thi Cam Tran, Quy Thi Kim Ha, De Quang Tran, Hiroyuki Morita, Hue Thi Buu Bui
Two novel series of quinazolinone-based hybrids, including quinazolinone-1,3,4-oxadiazoles (10a–l) and quinazolinone-1,3,4-oxadiazole-benzimidazoles (8a–e), were designed and synthesized and their cytotoxic activities against three human cancer cell lines, lung cancer (A549), cervical cancer (HeLa), and breast cancer (MCF-7), were evaluated. The cytotoxic assays revealed that 10i with a lipophilic
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Development of Small-Molecule Anti-HIV-1 Agents Targeting HIV-1 Capsid Proteins Chem. Pharm. Bull. (IF 1.7) Pub Date : 2024-01-01 Takuya Kobayakawa, Masaru Yokoyama, Kohei Tsuji, Sayaka Boku, Masaki Kurakami, Masayuki Fujino, Takahiro Ishii, Yutaro Miura, Soshi Nishimura, Kouki Shinohara, Kenichi Yamamoto, Peter Bolah, Osamu Kotani, Tsutomu Murakami, Hironori Sato, Hirokazu Tamamura
The capsid of human immunodeficiency virus type 1 (HIV-1) forms a conical structure by assembling oligomers of capsid (CA) proteins and is a virion shell that encapsulates viral RNA. The inhibition of the CA function could be an appropriate target for suppression of HIV-1 replication because the CA proteins are highly conserved among many strains of HIV-1, and the drug targeting CA, lenacapavir, has
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Development of Fast Disintegrating Tablets Containing Loxoprofen Sodium by HYDROFLASH Manufacturing Method Chem. Pharm. Bull. (IF 1.7) Pub Date : 2024-01-01 Aya Kuwata, Tetsuo Ono, Yuri Tsuchiya, Etsuo Yonemochi
In order to create and offer superior pharmaceuticals for consumers who wish to be relieved of headache and fever as soon as possible, we established HYDROFLASH manufacturing method that enables us to offer fast disintegration tablets containing loxoprofen sodium (LX), which are difficult to disintegrate. As a result of screening excipients, tablets using mannitol showed the fastest disintegration
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Dual Engineering of Olivetolic Acid Cyclase and Tetraketide Synthase for the Formation of Longer Alkyl-Chain Olivetolic Acid Analogs and Their Antibacterial Activities Chem. Pharm. Bull. (IF 1.7) Pub Date : 2024-01-01 Hiroyuki Morita
Among presently used pharmaceuticals, about 60% were developed from natural products with unique chemical diversity and biological activities. Hence, the discovery of new bioactive compounds from natural products is still important for further drug development. In addition, breakthroughs in synthetic biology have also begun to produce many useful compounds through manipulations of the biosynthetic