Inclusion complexation of 4′,6-diamidino-2-phenylindole (DAPI) with cucurbit[7]uril and cyclodextrins (native β-, 2,6-di-O-methylated β-, and γ-cyclodextrin): characteristic inclusion behaviour and fluorescence enhancement

IF 1.7 4区 化学 Q3 CHEMISTRY, MULTIDISCIPLINARY
Yoshimi Sueishi, Seiya Hagiwara, Naoya Inazumi, Tadashi Hanaya
{"title":"Inclusion complexation of 4′,6-diamidino-2-phenylindole (DAPI) with cucurbit[7]uril and cyclodextrins (native β-, 2,6-di-O-methylated β-, and γ-cyclodextrin): characteristic inclusion behaviour and fluorescence enhancement","authors":"Yoshimi Sueishi,&nbsp;Seiya Hagiwara,&nbsp;Naoya Inazumi,&nbsp;Tadashi Hanaya","doi":"10.1007/s10847-020-01042-6","DOIUrl":null,"url":null,"abstract":"<p>Herein, we investigated the inclusion complexation of a fluorescent probe [4′,6-diamidino-2-phenylindole (DAPI)]?using various cyclodextrins (CDs) and cucurbit[7]uril (CB7). Using the?continuous variation method, DAPI was found to form a 1:1 inclusion complex with CDs and CB7. <sup>1</sup>H-NMR and 2D ROESY (<sup>1</sup>H-<sup>1</sup>H rotating frame nuclear Overhauser effect) spectroscopy indicated that the inclusion of DAPI by the CDs and CB7 occurs via the encapsulation of the phenyl group and indole moiety of DAPI. The stability of the CB7?inclusion complex was higher than?that of the CDs: the stability was attributed to the extra interaction formed between the dicationic dye (DAPI) and polar carbonyl groups at the portals of CB7. Furthermore, we determined the fluorescence quantum yield (Φ) of the inclusion complexes. The Φ values of DAPI were significantly enhanced upon its inclusion by CB7 and increased as the empirical solvent polarity parameter (E<sub>T</sub>(30)) decreased. Based on these results, we concluded that the polarity of the microenvironment and protonation ability of the excited state of DAPI play important roles in emission efficiency.</p>","PeriodicalId":54324,"journal":{"name":"Journal of Inclusion Phenomena and Macrocyclic Chemistry","volume":null,"pages":null},"PeriodicalIF":1.7000,"publicationDate":"2021-01-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1007/s10847-020-01042-6","citationCount":"3","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Inclusion Phenomena and Macrocyclic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://link.springer.com/article/10.1007/s10847-020-01042-6","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 3

Abstract

Herein, we investigated the inclusion complexation of a fluorescent probe [4′,6-diamidino-2-phenylindole (DAPI)]?using various cyclodextrins (CDs) and cucurbit[7]uril (CB7). Using the?continuous variation method, DAPI was found to form a 1:1 inclusion complex with CDs and CB7. 1H-NMR and 2D ROESY (1H-1H rotating frame nuclear Overhauser effect) spectroscopy indicated that the inclusion of DAPI by the CDs and CB7 occurs via the encapsulation of the phenyl group and indole moiety of DAPI. The stability of the CB7?inclusion complex was higher than?that of the CDs: the stability was attributed to the extra interaction formed between the dicationic dye (DAPI) and polar carbonyl groups at the portals of CB7. Furthermore, we determined the fluorescence quantum yield (Φ) of the inclusion complexes. The Φ values of DAPI were significantly enhanced upon its inclusion by CB7 and increased as the empirical solvent polarity parameter (ET(30)) decreased. Based on these results, we concluded that the polarity of the microenvironment and protonation ability of the excited state of DAPI play important roles in emission efficiency.

Abstract Image

4′,6-二氨基-2-苯基吲哚(DAPI)与葫芦[7]脲和环糊精(天然β-、2,6-二o-甲基化β-和γ-环糊精)的包合:特征包合行为和荧光增强
本文中,我们研究了荧光探针[4 ',6-二氨基-2-苯基吲哚(DAPI)]?使用各种环糊精(CDs)和葫芦[7]脲(CB7)。使用?连续变分法,发现DAPI与CDs和CB7形成1:1的包合物。1H-NMR和2D ROESY (1H-1H旋转框架核Overhauser效应)谱分析表明,CDs和CB7包合DAPI是通过包封DAPI的苯基和吲哚部分实现的。CB7的稳定性?包合络合物高于?CDs的稳定性是由于在CB7的入口处,指示染料(DAPI)和极性羰基之间形成了额外的相互作用。此外,我们测定了包合物的荧光量子产率(Φ)。DAPI的Φ值在CB7包合后显著增强,并随着经验溶剂极性参数ET(30)的减小而增大。基于这些结果,我们得出微环境的极性和DAPI激发态的质子化能力对发射效率有重要影响。
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
Journal of Inclusion Phenomena and Macrocyclic Chemistry
Journal of Inclusion Phenomena and Macrocyclic Chemistry Agricultural and Biological Sciences-Food Science
CiteScore
4.10
自引率
8.70%
发文量
54
期刊介绍: The Journal of Inclusion Phenomena and Macrocyclic Chemistry is the premier interdisciplinary publication reporting on original research into all aspects of host-guest systems. Examples of specific areas of interest are: the preparation and characterization of new hosts and new host-guest systems, especially those involving macrocyclic ligands; crystallographic, spectroscopic, thermodynamic and theoretical studies; applications in chromatography and inclusion polymerization; enzyme modelling; molecular recognition and catalysis by inclusion compounds; intercalates in biological and non-biological systems, cyclodextrin complexes and their applications in the agriculture, flavoring, food and pharmaceutical industries; synthesis, characterization and applications of zeolites. The journal publishes primarily reports of original research and preliminary communications, provided the latter represent a significant advance in the understanding of inclusion science. Critical reviews dealing with recent advances in the field are a periodic feature of the journal.
×
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