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

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

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引用次数: 0

摘要

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。

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

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.

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来源期刊

Chemical & pharmaceutical bulletin 医学-化学综合

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.