Synthesis and spectral characterization of environmentally responsive fluorescent deoxycytidine analogs.

Adam A H Elmehriki, Mojmír Suchý, Kirby J Chicas, Filip Wojciechowski, Robert H E Hudson
{"title":"Synthesis and spectral characterization of environmentally responsive fluorescent deoxycytidine analogs.","authors":"Adam A H Elmehriki,&nbsp;Mojmír Suchý,&nbsp;Kirby J Chicas,&nbsp;Filip Wojciechowski,&nbsp;Robert H E Hudson","doi":"10.4161/adna.29174","DOIUrl":null,"url":null,"abstract":"<p><p>Herein, we describe the synthesis and spectroscopic properties of five novel pyrrolodeoxycytidine analogs, and the related 5-(1-pyrenylethynyl)-2'-deoxycytidine analog; as well as fluorescence characterization of 5-(p-methoxyphenylethynyl)-2'-deoxyuridine. Within this series of compounds, rigidification of the structure from 6-phenylpyrrolodeoxycytidine to 5,6-benzopyrroldeoxycytidine made remarkable improvement of the fluorescence quantum yield (Φ ~1, EtOH) and substantially increased the Stokes shift. Exchange of the phenyl group of 6-phenylpyrrolodeoxycytidine for other heterocycles (benzofuryl or indolyl) produced an increase in the extinction coefficient at the excitation wavelength while preserving high quantum yields. The steady-state fluorescence response to the environment was determined by sensitivity of Stokes shift to solvent polarity. The effect of solvent polarity on fluorescence emission intensity was concurrently examined and showed that 5,6-benzopyrrolodeoxycytidine is highly sensitive to the presence of water. On the other hand, the previously synthesized 5-(p-methoxyphenylethynyl)-2'-deoxyuridine was found to be sensitive to solvent viscosity indicating molecular rotor behavior. </p>","PeriodicalId":8444,"journal":{"name":"Artificial DNA: PNA & XNA","volume":null,"pages":null},"PeriodicalIF":0.0000,"publicationDate":"2014-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.4161/adna.29174","citationCount":"7","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Artificial DNA: PNA & XNA","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.4161/adna.29174","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 7

Abstract

Herein, we describe the synthesis and spectroscopic properties of five novel pyrrolodeoxycytidine analogs, and the related 5-(1-pyrenylethynyl)-2'-deoxycytidine analog; as well as fluorescence characterization of 5-(p-methoxyphenylethynyl)-2'-deoxyuridine. Within this series of compounds, rigidification of the structure from 6-phenylpyrrolodeoxycytidine to 5,6-benzopyrroldeoxycytidine made remarkable improvement of the fluorescence quantum yield (Φ ~1, EtOH) and substantially increased the Stokes shift. Exchange of the phenyl group of 6-phenylpyrrolodeoxycytidine for other heterocycles (benzofuryl or indolyl) produced an increase in the extinction coefficient at the excitation wavelength while preserving high quantum yields. The steady-state fluorescence response to the environment was determined by sensitivity of Stokes shift to solvent polarity. The effect of solvent polarity on fluorescence emission intensity was concurrently examined and showed that 5,6-benzopyrrolodeoxycytidine is highly sensitive to the presence of water. On the other hand, the previously synthesized 5-(p-methoxyphenylethynyl)-2'-deoxyuridine was found to be sensitive to solvent viscosity indicating molecular rotor behavior.

Abstract Image

Abstract Image

Abstract Image

环境响应型荧光脱氧胞苷类似物的合成与光谱表征。
本文描述了五种新型吡咯脱氧胞苷类似物的合成和光谱性质,以及相关的5-(1-芘乙炔基)-2'-脱氧胞苷类似物;以及5-(对甲氧基苯乙基)-2'-脱氧尿苷的荧光表征。在这一系列化合物中,从6-苯基吡咯烷脱氧胞苷结构固化为5,6-苯并吡咯烷脱氧胞苷,荧光量子产率显著提高(Φ ~1, EtOH), Stokes位移显著增加。6-苯基吡咯脱氧胞苷的苯基与其他杂环(苯并呋喃基或吲哚基)交换,在保持高量子产率的同时,增加了激发波长处的消光系数。稳态荧光对环境的响应由Stokes位移对溶剂极性的敏感性决定。同时考察了溶剂极性对荧光发射强度的影响,结果表明,5,6-苯并吡咯脱氧胞苷对水的存在高度敏感。另一方面,先前合成的5-(对甲氧基苯乙基)-2'-脱氧尿嘧啶对溶剂粘度敏感,表明分子转子行为。
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 求助全文
来源期刊
自引率
0.00%
发文量
0
×
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
确定
请完成安全验证×
copy
已复制链接
快去分享给好友吧!
我知道了
右上角分享
点击右上角分享
0
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 布克学术 All rights reserved.
京ICP备2023020795号-1
ghs 京公网安备 11010802042870号
Book学术文献互助
Book学术文献互助群
群 号:481959085
Book学术官方微信