Viscosity-Induced Emission of 5-(Diarylmethylene)imidazolone with Extended Conjugation via Attachment of N-Methylpyrrole at the 2-Position

IF 1.5 4区 医学 Q4 CHEMISTRY, MEDICINAL Chemical & pharmaceutical bulletin Pub Date : 2024-05-31 DOI:10.1248/cpb.c24-00143
Masahiro Ikejiri, Aki Yoshimizu, Fumika Shiota, Ai Nagayama, Aki Fujisaka, Yuichi Kuboki, Kazuyuki Miyashita
{"title":"Viscosity-Induced Emission of 5-(Diarylmethylene)imidazolone with Extended Conjugation via Attachment of N-Methylpyrrole at the 2-Position","authors":"Masahiro Ikejiri, Aki Yoshimizu, Fumika Shiota, Ai Nagayama, Aki Fujisaka, Yuichi Kuboki, Kazuyuki Miyashita","doi":"10.1248/cpb.c24-00143","DOIUrl":null,"url":null,"abstract":"</p><p>We have developed a series of 2-monoaryl-5-diarylmethylene analogs of the green fluorescent protein chromophore to study their viscosity-induced emission (VIE) properties. The analogs were synthesized by a condensation with methyl imidate and <i>N</i>-(diarylmethylene)glycinate. Among the analogs, the <i>N</i>-methylpyrrol-2-yl-substituted analog <b>1h</b> induced the most remarkable VIE behavior in triglyceride and lipid bilayers probably due to the high π-electron-rich property of the pyrrole ring. The pyrrole substituent in imidazolone analogs can be expected to become a common template for introducing VIE behavior.</p>\n<p></p>\n<img alt=\"\" src=\"https://www.jstage.jst.go.jp/pub/cpb/72/5/72_c24-00143/figure/72_c24-00143.png\"/>\n<span style=\"padding-left:5px;\">Fullsize Image</span>","PeriodicalId":9773,"journal":{"name":"Chemical & pharmaceutical bulletin","volume":"76 1","pages":""},"PeriodicalIF":1.5000,"publicationDate":"2024-05-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Chemical & pharmaceutical bulletin","FirstCategoryId":"3","ListUrlMain":"https://doi.org/10.1248/cpb.c24-00143","RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"CHEMISTRY, MEDICINAL","Score":null,"Total":0}
引用次数: 0

Abstract

We have developed a series of 2-monoaryl-5-diarylmethylene analogs of the green fluorescent protein chromophore to study their viscosity-induced emission (VIE) properties. The analogs were synthesized by a condensation with methyl imidate and N-(diarylmethylene)glycinate. Among the analogs, the N-methylpyrrol-2-yl-substituted analog 1h induced the most remarkable VIE behavior in triglyceride and lipid bilayers probably due to the high π-electron-rich property of the pyrrole ring. The pyrrole substituent in imidazolone analogs can be expected to become a common template for introducing VIE behavior.

Abstract Image Fullsize Image
查看原文
分享 分享
微信好友 朋友圈 QQ好友 复制链接
本刊更多论文
通过在 2-位连接 N-甲基吡咯扩展共轭的 5-(二亚甲基)咪唑啉酮的粘度诱导发射
我们开发了一系列绿色荧光蛋白发色团的 2-单芳基-5-二亚甲基类似物,以研究它们的粘度诱导发射(VIE)特性。这些类似物是通过亚胺酸甲酯和 N-(二芳基亚甲基)甘氨酸缩合合成的。在这些类似物中,N-甲基吡咯-2-基取代的类似物 1h 在甘油三酯和脂质双分子层中具有最显著的 VIE 特性,这可能是由于吡咯环具有高π电子富集特性。咪唑啉酮类似物中的吡咯取代基有望成为引入 VIE 行为的常见模板。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
求助全文
约1分钟内获得全文 去求助
来源期刊
CiteScore
3.20
自引率
5.90%
发文量
132
审稿时长
1.7 months
期刊介绍: The CPB covers various chemical topics in the pharmaceutical and health sciences fields dealing with biologically active compounds, natural products, and medicines, while BPB deals with a wide range of biological topics in the pharmaceutical and health sciences fields including scientific research from basic to clinical studies. For details of their respective scopes, please refer to the submission topic categories below. Topics: Organic chemistry In silico science Inorganic chemistry Pharmacognosy Health statistics Forensic science Biochemistry Pharmacology Pharmaceutical care and science Medicinal chemistry Analytical chemistry Physical pharmacy Natural product chemistry Toxicology Environmental science Molecular and cellular biology Biopharmacy and pharmacokinetics Pharmaceutical education Chemical biology Physical chemistry Pharmaceutical engineering Epidemiology Hygiene Regulatory science Immunology and microbiology Clinical pharmacy Miscellaneous.
期刊最新文献
Theoretical Framework for Novel Catalytic Biomolecules Composed of Multiple Peptides Two Preparation Methods for Peptide Thioester Containing Tyr(SO3H) Residue(s) without the Use of Protecting Group for Sulfate Moiety Total Synthesis of Dinorsesquiterpenoid Oxyphyllin A/Belchinoid A Evaluation of STAT3 Inhibition by Cancer Chemopreventive Trichothecenes Derived from Metabolites of Trichothecium roseum Galangin Promotes Tendon Repair Mediated by Tendon-Derived Stem Cells through Activating the TGF-β1/Smad3 Signaling Pathway
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
现在去查看 取消
×
提示
确定
0
微信
客服QQ
Book学术公众号 扫码关注我们
反馈
×
意见反馈
请填写您的意见或建议
请填写您的手机或邮箱
已复制链接
已复制链接
快去分享给好友吧!
我知道了
×
扫码分享
扫码分享
Book学术官方微信
Book学术文献互助
Book学术文献互助群
群 号:481959085
Book学术
文献互助 智能选刊 最新文献 互助须知 联系我们:info@booksci.cn
Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。
Copyright © 2023 Book学术 All rights reserved.
ghs 京公网安备 11010802042870号 京ICP备2023020795号-1