Fluorescence Polarization Immunoassay for Alternaria Mycotoxin Tenuazonic Acid Detection and Molecular Modeling Studies
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Fluorescence Polarization Immunoassay for Alternaria Mycotoxin Tenuazonic Acid Detection and Molecular Modeling Studies of Antibody Recognition Feng Wang 1 & Jun Cai 1 & Sergei A. Eremin 2 & Zhi-Li Xiao 1 & Yu-Dong Shen 1 & Yuan-Xin Tian 3 & Zhen-Lin Xu 1 & Jin-Yi Yang 1 & Hong-Tao Lei 1 & Yuan-Ming Sun 1 & Hong Wang 1 Received: 17 December 2017 / Accepted: 13 March 2018 # Springer Science+Business Media, LLC, part of Springer Nature 2018
Abstract A simple and rapid method of fluorescence polarization immunoassay (FPIA) for detection of Alternaria mycotoxin tenuazonic acid (TeA) was described. In this study, the tracers TeAH-FITC and TeAH-DTAF were synthesized from hapten 5-(sec-butyl)-3-(1-hydrazonoethyl)-4-hydroxy-1H-pyrrol-2(5H)-one (TeAH) and different fluoresceins isothiocyanate isomer I (FITC) or 5-([4,6-dichlorotriazin-2-yl]amino)fluorescein hydrochloride (DTAF), respectively. The established FPIA showed an IC50 value of 3.0 μg/mL with a detection limit of 0.13 μg/mL for TeAH based on the tracer of TeAH-FITC, and with the same properties of 7.3 and 0.93 μg/mL based on TeAH-DTAF. The former gave better assay sensitivity than the latter, that the 2,4-dichloro-s-triazine group of TeAH-DTAF may affect the specific recognition of tracer and antibody. Models of the lowest energy conformation and the molecular electrostatic potential isosurface studies revealed that the –C=N–N– and –CHCH3(CH2CH3) groups were the characteristic chemical groups in anti-TeAH antibody-analyte recognition via molecular modeling, which could create a theoretical guide for hapten design of small molecules and provide the traditional theory with empirical proof. Keywords Tenuazonic acid . Fluorescence polarization immunoassay . Molecular modeling . Antibody recognition
Introduction Tenuazonic acid (3-acetyl-5-s-butyl-4-hydroxy-3-pyrrolin-2one, TeA) is a natural phytotoxin produced by species of Pyricularia, Phoma, and Alternaria alternate. Species of Alternaria are known to produce at least 70 secondary toxic metabolites. TeA was identified as having the highest toxicity in the family, which was the only one among Alternaria toxins that belongs to the list of toxic chemicals of the US Food and
* Hong Wang [email protected] 1
College of Food Science, South China Agricultural University, Guangdong Provincial Key Laboratory of Food Quality and Safety, National-Local Joint Engineering Research Center for Processing and Safety Control of Livestock and Poultry Products, Guangzhou 510642, People’s Republic of China
2
Faculty of Chemistry, M.V. Lomonosov Moscow State University, Leninskie gory 1, Building 3, Moscow 119991, Russia
3
School of Pharmaceutical Sciences, Southern Medical University, Guangzhou 510515, People’s Republic of China
Drug Administration (Ostry 2008; Mikula et al. 2013). Firstly, it and its derivatives were used as a kind of commercial herbicide in fields (Sinning 1992). However, it was reported that TeA was acutely or subacutely toxic to mice, dogs, and shrimps (Yekeler et al. 2001; Rychlik et al. 2016; Patriarca 2016
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