A Highly Selective and Strong Anti-Interference Host-Guest Complex as Fluorescent Probe for Detection of Amantadine by Indicator Displacement Assay.

Linzhao Zhu,Zhiyong Zhao,Xiongzhi Zhang,Feng Liang,Simin Liu,Haijun Zhang

doi:10.3390/molecules23040947

Linzhao Zhu, Zhiyong Zhao + Show 4 more

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https://doi.org/10.3390/molecules23040947

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Abstract

Amantadine (AMA) and its derivatives are illicit veterinary drugs that are hard to detect at very low concentrations. Developing a fast, simple and highly sensitive method for the detection of AMA is highly in demand. Here, we designed an anthracyclic compound (ABAM) that binds to a cucurbit[7]uril (CB[7]) host with a high association constant of up to 8.7 × 108 M−1. The host-guest complex was then used as a fluorescent probe for the detection of AMA. Competition by AMA for occupying the cavity of CB[7] allows ABAM to release from the CB[7]-ABAM complex, causing significant fluorescence quenching of ABAM (indicator displacement assay, IDA). The linear range of the method is from 0.000188 to 0.375 μg/mL, and the detection limit can be as low as 6.5 × 10−5 μg/mL (0.35 nM). Most importantly, due to the high binding affinity between CB[7] and ABAM, this fluorescence host-guest system shows great anti-interference capacity. Thus, we are able to accurately determine the concentration of AMA in various samples, including pharmaceutical formulations.

Highlights

Amantadine (AMA, Figure 1) was first found by Davies in 1964, and was used to treat influenza virus [1]
Because of its effective treatment and low cost, AMA was recognized as the first anti-influenza drug by the U.S Food and Drug Administration (FDA) in 1966 [2,3]
The slight downfield shifts of H1 -4 proton signals is caused by weakened π−π stacking interactions between anthracene moieties upon the encapsulation of ABAM

Summary

Introduction

Amantadine (AMA, Figure 1) was first found by Davies in 1964, and was used to treat influenza virus [1]. AMA has been mixed with fodder, aiming to prevent and treat animal diseases, especially in chicken farming [4]. This kind of drug abuse results in the accumulation of AMA in the human body, causing various kinds of poisonous effects. The abuse of AMA may cause virus resistance and virus variation, which have bad effects on human treatment [5]. Because of these potential risks, AMA has been banned in livestock farming by USA and China since

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