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基于鼓形传感机制的荧光环蕃比率型检测 ATP。

Ratiometric Detection of ATP by Fluorescent Cyclophanes with Bellows-Type Sensing Mechanism.

机构信息

N. N. Vorozhtsov Institute of Organic Chemistry SB RAS, 9th Lavrentiev Avenue, 630090, Novosibirsk, Russian Federation.

Institute of Chemistry, Technische Universität Chemnitz, 09107, Chemnitz, Germany.

出版信息

Chemistry. 2020 Aug 6;26(44):9991-9997. doi: 10.1002/chem.202001523. Epub 2020 Jul 16.

DOI:10.1002/chem.202001523
PMID:32497327
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7496914/
Abstract

Pyrene-based cyclophanes have been synthesized with the aim to realize a bellows-type sensing mechanism for the ratiometric detection of nucleotide concentrations in a buffered aqueous solution. The sensing mechanism involves the encapsulation of a nucleobase between two pyrene rings, which affects the monomer-excimer equilibrium of the receptor in the excited state. The nature of the spacer and its connection pattern to pyrene rings have been varied to achieve high selectivity for ATP. The 1,8-substituted pyrene-based cyclophane with the 2,2'-diaminodiethylamine spacer demonstrates the best selectivity for ATP showing a 50-fold increase in the monomer-excimer emission ratio upon saturation with the nucleotide. The receptor can detect ATP within the biological concentrations range over a wide pH range. NMR and spectroscopic studies have revealed the importance of hydrogen bonding and stacking interactions for achieving a required receptor selectivity. The probe has been successfully applied for the real-time monitoring of creatine kinase activity.

摘要

基于芘的环芳烃已被合成，目的是实现一种波纹管型传感机制，用于在缓冲水溶液中对核苷酸浓度进行比率检测。传感机制涉及核苷碱基在两个芘环之间的封装，这会影响受体在激发态下的单体-激基复合物平衡。已经改变了间隔物的性质及其与芘环的连接模式，以实现对 ATP 的高选择性。带有 2,2'-二氨基二乙胺间隔物的 1,8-取代芘基环芳烃对 ATP 表现出最佳的选择性，在与核苷酸饱和时，单体-激基复合物发射比增加了 50 倍。该受体可以在宽 pH 范围内检测到生物浓度范围内的 ATP。NMR 和光谱研究表明，氢键和堆积相互作用对于实现所需的受体选择性非常重要。该探针已成功应用于实时监测肌酸激酶活性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/939e/7496914/3ed0e3f7d65c/CHEM-26-9991-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/939e/7496914/5de5c42cf045/CHEM-26-9991-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/939e/7496914/fbdfa9ae4d75/CHEM-26-9991-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/939e/7496914/60b1f3bbfa0b/CHEM-26-9991-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/939e/7496914/a20726de6483/CHEM-26-9991-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/939e/7496914/0dd713bf7aab/CHEM-26-9991-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/939e/7496914/3ed0e3f7d65c/CHEM-26-9991-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/939e/7496914/5de5c42cf045/CHEM-26-9991-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/939e/7496914/fbdfa9ae4d75/CHEM-26-9991-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/939e/7496914/60b1f3bbfa0b/CHEM-26-9991-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/939e/7496914/a20726de6483/CHEM-26-9991-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/939e/7496914/0dd713bf7aab/CHEM-26-9991-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/939e/7496914/3ed0e3f7d65c/CHEM-26-9991-g007.jpg

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