Design and Synthesis of Haptens for Acetamiprid

Food safety problems about pesticides have attracted increasing concerns around the world. Acetamiprid (C10H11ClN4), also known as mospilan, is one of the most potent neonicotinoid insecticides that has been broadly used to prevent multiple sucking insects in agricultural products. To specifically identify acetamiprid, a number of immunological technologies have emerged and gained more attention such as antigen-antibody response. As a famous expert in the antibody development market, Creative Biolabs is specialized in challenging hapten design and synthesis projects, especially for small molecular compounds. We’d like to assist clients in developing rapid and sensitive artificial antigens and further manufacturing hapten-based antibodies or immunoassays.

Introduction to Acetamiprid

Based on pharmacophore structures, neonicotinoid insecticides have been categorized into three types: a. nitrosamines (e.g. nitenpyram); b. the nitro pulse type (e.g. imidacloprid), and c. the cyano amidine type (e.g. acetamiprid). Acetamiprid is a nitro methylene heterocyclic compound that has a role as a neonicotinoid insecticide, a contaminant, and a xenobiotic. It is a carboxamidine that is acetamidine where the amino hydrogen is replaced by a (6-chloropyridin-3-yl) methyl and a methyl group while the hydrogen linked to the imino nitrogen is substituted by a cyano group. Although it belongs to neonicotinoids, acetamiprid holds insecticidal characteristics different from others in the same category of chemical structure. As an efficient pesticide, this compound has excellent activities and is widely applied to control various insect pests, of the orders Hemiptera, Thysanoptera, and Lepidoptera on fruits and vegetables. Because of its relatively low toxicity and chronic effect in mammals, acetamiprid has been regarded as a replacement insecticide for organophosphorus and conventional insecticides.

Chemical structure of acetamiprid. Fig.1 Chemical structure of acetamiprid.

Hapten Design &Synthesis Services at Creative Biolabs

Pesticide residues are a key factor in food safety and environmental contamination. Acetamiprid is a monochloropyridine, a nitrile, and a carboxamidine, and derives from a 2-chloropyridine. As a neonicotinoid insecticide, it is employed for the treatment of agricultural pests and represents the fastest-growing class of insecticides transported to the market. Traditional methods such as high-performance liquid chromatography (HPLC), gas chromatography (GC), mass spectrometry (MS), liquid chromatography-MS (LC-MS), and GC-MS have been found preferred in acetamiprid residue analysis. These techniques provide both qualitative and quantitative data, however, the thermolability and high polarity of acetamiprid make it hard to be analyzed by chromatography. Nowadays, antibody-based immunoassay favors the determination in a variety of matrices through the highly specific recognition interaction of antibody-antigen, together with integrating highly competitive performance including specificity, sensitivity, fast measurement, and easy-to-operate capabilities.

The UV spectra characterization for acetamiprid-BSA, acetamiprid, and BSA. Fig.2 The UV spectra characterization for acetamiprid-BSA, acetamiprid, and BSA. (Liu, 2017)

A previous study has demonstrated that antibody against acetamiprid displayed high cross-reactivity to thiacloprid (43.8%) and negligible cross-reaction to IM-1-2 (a metabolite of acetamiprid), imidacloprid, and many others. Because these analogs possess no =N–CN group in the molecules, this group seems to make a significant contribution to the antibody recognition. Moreover, the presence of N-methyl or N-methylene moiety in thiacloprid may be essential for the interaction in view of the result of the cross-reactivity to IM-2-1. Therefore, the group far away from the space armer is best recognized by antibodies. At Creative Biolabs, our experts are committed to developing the most suitable haptens according to our clients’ special requirements.

Advantages

  • Optimized solutions for hapten design and synthesis
  • Practiced technicians have rich experience in artificial antigen preparation and anti-hapten antibody production
  • Strict quality controls for highly sensitive hapten-carrier conjugates, and charge step by step for better service

Owing to its frequent and extensive usage, acetamiprid in crops and in water will result in a potential risk to human health. For this reason, the concentration of pesticide residue in agricultural products should be measured and monitored. Before detecting acetamiprid based on immunoassays, the synthesis of an ideal neonicotinoid hapten is required. In general, hapten design and synthesis involve the most time-consuming and complex processes of immunoreagent development. As a top-ranking provider in the field of hapten preparation, Creative Biolabs offers multiple design strategies for small molecular compounds and has generated several acetamiprid functionalized derivatives (haptens) to be immunogenic for the following immunization. If you’re interested in our services, please don’t hesitate to contact us or directly send us an inquiry.

References

  1. Liu, L.Q.; et al. Development of an immunochromatographic strip for detection of acetamiprid in cucumber and apple samples. Food and Agricultural Immunology. 2017, 1465-3443.
  2. Xu, C.L.; et al. Food Immunoassay. FOOD SCI NUTR. 2019.
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