Design and Synthesis of Compound-specific Haptens for Pyrethroid Insecticides

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Introduction of Pyrethroid Insecticides

Pyrethroids insecticides are widely used worldwide ranging from agriculture to public health due to their high insecticidal activity and low toxicity to mammals. Although pyrethroids are thought to be safe for humans, many pyrethroids are highly toxic to aquatic life, especially fish. It has been reported that high exposure to pyrethroids may cause lymph node suppression of the immune system, endocrine disruption and splenic damage, even carcinogenesis. At the same time, the problem of pyrethroid residues in agricultural products and foods has become more serious. Therefore, there is a need to develop a fast, sensitive and specific method to monitor residue levels of pyrethroids in food.

There are many analytical methods for detecting pyrethroid residues, such as high-performance liquid chromatography (HPLC) and gas chromatography with an electron capture detector (GC/ECD). Although these methods have good sensitivity and accuracy, they are time-consuming, laborious and expensive. Therefore, a more effective and cheaper method for detecting pesticide residues is needed. Immunoassays can be used for pesticide residue analysis and screening. Immunoassays are considered to be a valuable supplement to existing chromatography technologies because of their attractive features, including high sensitivity and selectivity, rapid detection, and ease of operation. Immunoassay is a lower cost, higher sample throughput, and more suitable for high-throughput screening methods, which can be used to detect pyrethroid residues in agriculture, environmental monitoring and food.

Structures of Pyrethroids Compounds

According to the chemical structure of pyrethroids and their mechanism of action on insect target sites, they can be divided into two types of compounds (Fig.1): The type I compounds are simple cyclic alcohol esters of 2,2-dimethyl-3-(2-methyl-1-propenyl)-cyclopropane carboxylic acid, and The type II compounds are esters of an aryl cyanohydrin.

Chemical structures of pyrethroids compounds. Fig.1 Chemical structures of pyrethroids compounds. (Lu, 2010)

Synthesis of Compound-specific Haptens for Pyrethroid Insecticides

Obtaining haptens with the appropriate chemical structure is key to developing novel antibodies and immunoassays. In order to generate antibodies that are specific for the pyrethroid compound, the entire pyrethroid molecule needs to be modified to attach a spacer arm containing functional groups to facilitate coupling to the carrier protein. One method is to attach a short handle on the aromatic rings of the deltamethrin molecule. Another method is to replace the α-cyano group with a carboxylic acid-terminated spacer.

With the increasing demand for chemical residue detection, people have gradually focused on immunoassays for total residues of complexes. Specific antibodies against type I or type II pyrethroid compounds have been reported. For example, the metabolite analogs of deltamethrin are modified to attach spacer arms to make haptens, which are then conjugated to carrier proteins to produce antibodies to specific complexes. To generate specific antibodies against type I and II pyrethroid compounds, Creative Biolabs provides comprehensive compound-specific haptens design and synthesis services for pyrethroid insecticides, including functional group modification, hapten-carrier coupling, immunogen characterization and identification, etc. Besides, we can also provide you with tailored services to meet your hapten synthesis needs according to the specific requirements of customers. If you want to know more, please feel free to contact us.

Reference

  1. Lu, Y.; et al. Development of general immunoassays for pyrethroids: a new approach for hapten synthesis using pyrethroid metabolite analogue and application to food samples. Food and agricultural immunology. 2010, 21(1): 27-45.
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