Chemical & pharmaceutical bulletin最新文献_第10页

Syntheses and Cytotoxicities of Quinazolinone-Based Conjugates 喹唑啉酮类共轭物的合成与细胞毒性

IF 1.7 4区医学

Chemical & pharmaceutical bulletin Pub Date : 2024-01-12 DOI: 10.1248/cpb.c23-00674

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

{"title":"Syntheses and Cytotoxicities of Quinazolinone-Based Conjugates","authors":"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","doi":"10.1248/cpb.c23-00674","DOIUrl":"https://doi.org/10.1248/cpb.c23-00674","url":null,"abstract":"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 4-fluoro-phenyl moiety at the C-2 position of the quinazolinone ring displayed good cytotoxicities against the A549 and MCF-7 cell lines, while 8b–d with the thioether-linked benzimidazole moiety incorporated on the right side of the oxadiazole ring induced comparable stronger activities toward the MCF-7 cell line, relative to the simple two-heterocycle-containing hybrid 10i. These novel quinazolinone-based hybrids could be considered as lead compounds that merit further optimization and development as anti-cancer agents.\u0000\u0000<img alt=\"\" src=\"https://www.jstage.jst.go.jp/pub/cpb/72/1/72_c23-00674/figure/72_c23-00674.png\"/>\u0000Fullsize Image","PeriodicalId":9773,"journal":{"name":"Chemical & pharmaceutical bulletin","volume":"95 1","pages":""},"PeriodicalIF":1.7,"publicationDate":"2024-01-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139422319","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}

引用次数: 0

Elucidation of Degradation Behavior of Nitrazepam, a Benzodiazepine Drug, under Basic Conditions: Study on Degradability of Drugs in Stomach (IV) 阐明苯二氮卓类药物硝西泮在基本条件下的降解行为：药物在胃中的降解性研究（IV）

IF 1.7 4区医学

Chemical & pharmaceutical bulletin Pub Date : 2024-01-01 DOI: 10.1248/cpb.c23-00626

Koichi Saito, Mai Yokota, Rie Ito, Miho Sakamoto, Kimio Higashiyama

{"title":"Elucidation of Degradation Behavior of Nitrazepam, a Benzodiazepine Drug, under Basic Conditions: Study on Degradability of Drugs in Stomach (IV)","authors":"Koichi Saito, Mai Yokota, Rie Ito, Miho Sakamoto, Kimio Higashiyama","doi":"10.1248/cpb.c23-00626","DOIUrl":"https://doi.org/10.1248/cpb.c23-00626","url":null,"abstract":"This study investigates the stability of nitrazepam (NZP), a benzodiazepine drug, under basic conditions, since alkaline putrefactive amines and ammonia are produced once bodies are left to decompose for a long period postmortem after a murder involving NZP or an accidental overdose of NZP. The degradation of NZP in an aqueous alkaline solution was investigated by LC/photodiode array detector (PDA) where the NZP degradation product was isolated and purified by solid-phase extraction using Oasis® MCX, and its chemical structure was determined by LC/time-of-flight (TOF)-MS, NMR spectroscopy, and single-crystal X-ray crystallography. The results revealed that NZP was immediately degraded under basic conditions with 2-amino-5-nitrobenzophenone being an intermediate which further degraded to provide 2-hydroxy-5-nitrobenzophenone as the final degradation product. These results are expected to be useful in clinical chemistry and forensic science, such as the detection of drugs during postmortem examination and suspected addiction.\u0000\u0000<img alt=\"\" src=\"https://www.jstage.jst.go.jp/pub/cpb/72/1/72_c23-00626/figure/72_c23-00626.png\"/>\u0000Fullsize Image","PeriodicalId":9773,"journal":{"name":"Chemical & pharmaceutical bulletin","volume":"18 1","pages":""},"PeriodicalIF":1.7,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139063645","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}

引用次数: 0

Synthesis of 2,8-Dioxabicyclo[3.3.1]nonane Derivatives and Their Neuroprotective Activities 2,8-Dioxabicyclo[3.3.1]nonane 衍生物的合成及其神经保护活性

IF 1.7 4区医学

Chemical & pharmaceutical bulletin Pub Date : 2024-01-01 DOI: 10.1248/cpb.c23-00693

Hitoshi Kamauchi, Akifumi Takanashi, Mitsuaki Suzuki, Kouki Izumi, Koichi Takao, Yoshiaki Sugita

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Development of an Artificial Nucleic Acid Skeleton Allowing for Unnatural-Type Triplex DNA Formation with Duplex DNA Having a TA Inversion Site 开发人工核酸骨架，允许与具有 TA 反转位点的双链 DNA 形成非天然型三重 DNA

IF 1.7 4区医学

Chemical & pharmaceutical bulletin Pub Date : 2024-01-01 DOI: 10.1248/cpb.c23-00666

Akihiro Ito, Lei Wang, Ryotaro Notomi, Shigeki Sasaki, Yosuke Taniguchi

{"title":"Development of an Artificial Nucleic Acid Skeleton Allowing for Unnatural-Type Triplex DNA Formation with Duplex DNA Having a TA Inversion Site","authors":"Akihiro Ito, Lei Wang, Ryotaro Notomi, Shigeki Sasaki, Yosuke Taniguchi","doi":"10.1248/cpb.c23-00666","DOIUrl":"https://doi.org/10.1248/cpb.c23-00666","url":null,"abstract":"Triplex DNA formation has generated much interest as a genomic targeting tool that directly targets duplex DNA. However, fundamental limitations in the base pairs of target duplex DNA sequences that can form stable triplex DNA have limited the application. Recently, we have reported on the recognition of CG and 5mCG base pairs by artificial nucleic acid derivatives with a 2′-deoxynebularine skeleton. Therefore, we attempted to explore the basic skeleton that is important for the development of new artificial nucleic acids allowing for the recognition of TA base pairs. In this study, we focused on a benzimidazole skeleton and introduced a hydroxyl group to enable one-point hydrogen bonding. We have synthesized artificial nucleoside analogues with hydroxyl group on the benzimidazole and incorporated their amidite derivatives into triplex forming oligonucleotides (TFOs). The gel shift assay was performed to evaluate the triplex DNA formation ability of synthesized TFOs, and TFOs containing hydroxybenzimidazole were successfully recognized TA base pairs for all four different sequences. Moreover, compared to the results for the TFOs containing benzimidazole, which suggested hydrogen bonding formation at the hydroxyl group. Therefore, hydroxybenzimidazole would be an important artificial nucleic acid skeleton for TA base pair recognition.\u0000\u0000<img alt=\"\" src=\"https://www.jstage.jst.go.jp/pub/cpb/72/1/72_c23-00666/figure/72_c23-00666.png\"/>\u0000Fullsize Image","PeriodicalId":9773,"journal":{"name":"Chemical & pharmaceutical bulletin","volume":"1 1","pages":""},"PeriodicalIF":1.7,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139072213","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}

引用次数: 0

Foreword. 前言

IF 1.7 4区医学

Chemical & pharmaceutical bulletin Pub Date : 2024-01-01 DOI: 10.1248/cpb.c24-ctf7203

Akira Kotani

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Development of a Fluorescence Probe for Detecting Nitroreductase Activity Based on Steric Repulsion-Induced Twisted Intramolecular Charge Transfer (sr-TICT). 基于立体斥力诱导的分子内扭转电荷转移（sr-TICT）的检测硝基还原酶活性的荧光探针的开发。

IF 1.5 4区医学

Chemical & pharmaceutical bulletin Pub Date : 2024-01-01 DOI: 10.1248/cpb.c24-00486

Mizuki Sugimoto, Eita Sasaki, Hisashi Ohno, Takayuki Ikeno, Sota Yamada, Kenjiro Hanaoka

{"title":"Development of a Fluorescence Probe for Detecting Nitroreductase Activity Based on Steric Repulsion-Induced Twisted Intramolecular Charge Transfer (sr-TICT).","authors":"Mizuki Sugimoto, Eita Sasaki, Hisashi Ohno, Takayuki Ikeno, Sota Yamada, Kenjiro Hanaoka","doi":"10.1248/cpb.c24-00486","DOIUrl":"10.1248/cpb.c24-00486","url":null,"abstract":"Twisted intramolecular charge transfer (TICT) is a phenomenon involving intramolecular charge transfer together with intramolecular rotation upon photoexcitation, and in general this excited state of fluorescent dyes undergoes non-radiative decay (producing no fluorescence). We recently discovered that the magnitude of TICT in rhodamine derivatives could be regulated by altering the size of the substituents on the xanthene moiety, generating differing degrees of intramolecular steric repulsion. To further illustrate the usefulness and generality of this strategy, we describe here an application of quinone methide chemistry, which is widely used as a fluorescence off/on switching reaction for fluorescence probes detecting enzymatic activity, to construct a steric repulsion-induced (sr)-TICT-based fluorescence probe targeting nitroreductase (NTR) activity. The developed probe was almost non-fluorescent in phosphate-buffered saline (PBS) due to strong induction of the TICT state. On the other hand, when the probe was incubated with NTR and nicotinamide adenine dinucleotide (NADH), a large fluorescence increase was observed over time. We confirmed that the enzymatic reaction proceeded as expected, i.e., the nitro group of the probe was reduced to the corresponding amino group, followed by spontaneous elimination of iminoquinone methide. These results suggest that our simple design strategy based on the sr-TICT mechanism, i.e., controlling intramolecular steric repulsion, would be applicable to the development of fluorescence probes for a variety of enzymes.","PeriodicalId":9773,"journal":{"name":"Chemical & pharmaceutical bulletin","volume":"72 9","pages":"810-816"},"PeriodicalIF":1.5,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142307185","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}

引用次数: 0

Synthesis and Cytotoxicity of Cyclic Octapeptide Surugamides with Varied N-Acyl Moieties. 具有不同 N-酰基的环状八肽素酰胺的合成与细胞毒性

IF 1.5 4区医学

Chemical & pharmaceutical bulletin Pub Date : 2024-01-01 DOI: 10.1248/cpb.c24-00533

Kenichi Matsuda, Shinya Niikura, Rintaro Ichihara, Kei Fujita, Anna M Strasser, Rokusuke Yoshikawa, Jiro Yasuda, Yoshiki Hiramatsu, Hironori Hayashi, Eiichi N Kodama, Toshiyuki Wakimoto

引用次数: 0

Recyclable 2-Fluoropyridine Derivative as a Storage for Highly Electrophilic 1,1-Bis(triflyl)ethylene. 可回收的 2-氟吡啶衍生物作为高亲电性 1,1-双（三烯丙基）乙烯的储存剂。

IF 1.5 4区医学

Chemical & pharmaceutical bulletin Pub Date : 2024-01-01 DOI: 10.1248/cpb.c24-00499

Hikaru Yanai, Shoki Hoshikawa, Hiromu Watanabe, Hiroshi Kaneko, Hidemasa Nakaminami, Takashi Matsumoto

引用次数: 0

The Impact of Adding a Cationic Metal Salt and Curcumin to Monoammonium Glycyrrhizic Acid on Its Solubilizing Capacity and Gelation. 甘草酸单铵中添加阳离子金属盐和姜黄素对其增溶能力和凝胶化的影响

IF 1.5 4区医学

Chemical & pharmaceutical bulletin Pub Date : 2024-01-01 DOI: 10.1248/cpb.c24-00399

Kenta Ando, Hiromasa Uchiyama, Katsuhiko Minoura, Kazunori Kadota, Yuichi Tozuka

{"title":"The Impact of Adding a Cationic Metal Salt and Curcumin to Monoammonium Glycyrrhizic Acid on Its Solubilizing Capacity and Gelation.","authors":"Kenta Ando, Hiromasa Uchiyama, Katsuhiko Minoura, Kazunori Kadota, Yuichi Tozuka","doi":"10.1248/cpb.c24-00399","DOIUrl":"https://doi.org/10.1248/cpb.c24-00399","url":null,"abstract":"Monoammonium glycyrrhizic acid (MAG), a glycyrrhizic acid monoammonium salt, is a naturally derived low-molecular-weight gelling agent with surface-active properties. It has the capacity to individually facilitate the preparation of gel-solubilized drugs. As MAG is an anionic surfactant with carboxyl groups, the addition of counterions may affect micelle formation and gelation. In this study, the solubilization and gelling properties of MAG were investigated following the addition of metal salts (NaCl and KCl). The addition of metal salts resulted in a decrease in the critical micelle concentration and an increase in gel hardness. Supersaturation of curcumin (CUR) was maintained by the addition of metal salts because of increased micelle number and viscosity. When the gel hardness was compared between formulations with and without CUR, a significant reduction in hardness was observed with the solubilization of CUR. The addition of KCl prevented the decrease in the hardness of gels containing CUR compared to the addition of NaCl. Put together, the addition of metal salts had a noteworthy impact on micelle and gel formation of MAG. In particular, the addition of KCl was more effective in the preparation of gel-solubilized CUR.","PeriodicalId":9773,"journal":{"name":"Chemical & pharmaceutical bulletin","volume":"72 9","pages":"838-844"},"PeriodicalIF":1.5,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142342559","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}

引用次数: 0

Five New Analogs of Streptogramin Antibiotic Viridogrisein Isolated from Streptomyces niveoruber. 从尼沃鲁伯链霉菌（Streptomyces niveoruber）中分离出的五种新的链霉菌素抗生素类似物--Viridogrisein。

IF 1.7 4区医学

Chemical & pharmaceutical bulletin Pub Date : 2024-01-01 DOI: 10.1248/cpb.c23-00776

Aya Yoshimura, Takumi Honda, Toshiyuki Wakimoto

引用次数: 0