The synthesis of amphiphilic pillar[5]arene functionalized reduced graphene oxide and its application as novel fluorescence sensing platform for the determination of acetaminophen

A sensitive and selective fluorescence approach based on a competitive host–guest interaction between amphiphilic pillar[5]arene (amPA5) and signal probe (acridine orange, AO)/target molecule (acetaminophen, AP) was developed by using amPA5 functionalized reduced graphene oxide (amPA5-RGO) as a rece...

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Published in:	Biosensors & bioelectronics Vol. 91; pp. 863 - 869
Main Authors:	Zhao, Genfu, Yang, Long, Wu, Shilian, Zhao, Hui, Tang, E, Li, Can-Peng
Format:	Journal Article
Language:	English
Published:	England Elsevier B.V 15.05.2017
Subjects:	Acetaminophen Acetaminophen - blood acridine orange Amphiphilic pillararene Analgesics, Non-Narcotic - blood biosensors blood serum detection limit fluorescence Fluorescence sensing graphene oxide Graphite - chemistry Host–guest interaction Humans hydrogen bonding hydrophobic bonding hydrophobicity Limit of Detection Molecular Docking Simulation molecular models Oxidation-Reduction Oxides - chemistry Quaternary Ammonium Compounds - chemistry Reduced graphene oxide Spectrometry, Fluorescence - methods Surface-Active Agents - chemistry Fluorescence sensing Amphiphilic pillararene Reduced graphene oxide Acetaminophen Host–guest interaction
ISSN:	0956-5663, 1873-4235
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Abstract	A sensitive and selective fluorescence approach based on a competitive host–guest interaction between amphiphilic pillar[5]arene (amPA5) and signal probe (acridine orange, AO)/target molecule (acetaminophen, AP) was developed by using amPA5 functionalized reduced graphene oxide (amPA5-RGO) as a receptor. Due to the host–guest interaction, AO and AP molecules both can enter into the hydrophobic inner cavity of amPA5 that could form a complex of 1:1 guest–host with amPA5 according to the size of molecules and the cavity of amPA5, but the AP interacts more strongly with amPA5 than with AO, so it can detect AP by the host-guest competition. The low detection limit of 0.05μM (S/N=3) and a linear response range of 0.1–4.0μM and 4.0–32μM for AP was obtained by using this method. It had lower detection limit and wider linear range than other methods, therefore, it was successfully utilized to detect AP in serum samples, and exhibited a promising application in practice. The molecular docking studies indicated that the major driving forces for the formation of the inclusion complex of AP and amPA5 are hydrogen bonding, π-π interactions, and hydrophobic interactions. Fluorescent approach for AP sensing using AO·amPA5-RGO as receptor. [Display omitted] •A novel fluorescent approach for acetaminophen sensing platform was constructed.•The determination of acetaminophen is based on a competitive host–guest interaction.•The method showed lower detection limit and wider linear range than other methods.•The interaction of competitive recognition was clarified by molecular docking study.
AbstractList	A sensitive and selective fluorescence approach based on a competitive host–guest interaction between amphiphilic pillar[5]arene (amPA5) and signal probe (acridine orange, AO)/target molecule (acetaminophen, AP) was developed by using amPA5 functionalized reduced graphene oxide (amPA5-RGO) as a receptor. Due to the host–guest interaction, AO and AP molecules both can enter into the hydrophobic inner cavity of amPA5 that could form a complex of 1:1 guest–host with amPA5 according to the size of molecules and the cavity of amPA5, but the AP interacts more strongly with amPA5 than with AO, so it can detect AP by the host-guest competition. The low detection limit of 0.05μM (S/N=3) and a linear response range of 0.1–4.0μM and 4.0–32μM for AP was obtained by using this method. It had lower detection limit and wider linear range than other methods, therefore, it was successfully utilized to detect AP in serum samples, and exhibited a promising application in practice. The molecular docking studies indicated that the major driving forces for the formation of the inclusion complex of AP and amPA5 are hydrogen bonding, π-π interactions, and hydrophobic interactions. A sensitive and selective fluorescence approach based on a competitive host–guest interaction between amphiphilic pillar[5]arene (amPA5) and signal probe (acridine orange, AO)/target molecule (acetaminophen, AP) was developed by using amPA5 functionalized reduced graphene oxide (amPA5-RGO) as a receptor. Due to the host–guest interaction, AO and AP molecules both can enter into the hydrophobic inner cavity of amPA5 that could form a complex of 1:1 guest–host with amPA5 according to the size of molecules and the cavity of amPA5, but the AP interacts more strongly with amPA5 than with AO, so it can detect AP by the host-guest competition. The low detection limit of 0.05μM (S/N=3) and a linear response range of 0.1–4.0μM and 4.0–32μM for AP was obtained by using this method. It had lower detection limit and wider linear range than other methods, therefore, it was successfully utilized to detect AP in serum samples, and exhibited a promising application in practice. The molecular docking studies indicated that the major driving forces for the formation of the inclusion complex of AP and amPA5 are hydrogen bonding, π-π interactions, and hydrophobic interactions. Fluorescent approach for AP sensing using AO·amPA5-RGO as receptor. [Display omitted] •A novel fluorescent approach for acetaminophen sensing platform was constructed.•The determination of acetaminophen is based on a competitive host–guest interaction.•The method showed lower detection limit and wider linear range than other methods.•The interaction of competitive recognition was clarified by molecular docking study.
Author	Yang, Long Tang, E Li, Can-Peng Wu, Shilian Zhao, Genfu Zhao, Hui
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Keywords	Fluorescence sensing Amphiphilic pillararene Reduced graphene oxide Acetaminophen Host–guest interaction
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Snippet	A sensitive and selective fluorescence approach based on a competitive host–guest interaction between amphiphilic pillar[5]arene (amPA5) and signal probe... A sensitive and selective fluorescence approach based on a competitive host-guest interaction between amphiphilic pillar[5]arene (amPA5) and signal probe...
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SubjectTerms	Acetaminophen Acetaminophen - blood acridine orange Amphiphilic pillararene Analgesics, Non-Narcotic - blood biosensors blood serum detection limit fluorescence Fluorescence sensing graphene oxide Graphite - chemistry Host–guest interaction Humans hydrogen bonding hydrophobic bonding hydrophobicity Limit of Detection Molecular Docking Simulation molecular models Oxidation-Reduction Oxides - chemistry Quaternary Ammonium Compounds - chemistry Reduced graphene oxide Spectrometry, Fluorescence - methods Surface-Active Agents - chemistry
Title	The synthesis of amphiphilic pillar[5]arene functionalized reduced graphene oxide and its application as novel fluorescence sensing platform for the determination of acetaminophen
URI	https://dx.doi.org/10.1016/j.bios.2017.01.053 https://www.ncbi.nlm.nih.gov/pubmed/28160654 https://www.proquest.com/docview/1865535577 https://www.proquest.com/docview/2000323140
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