Avermectins (AVMs) Hapten Design and Synthesis

Macrocyclic lactones comprise several groups, including avermectins (AVMs), macrolides, and milbemycins. They belong to a class of antimicrobial agents that have been extensively used in food-producing animals. The antimicrobial activity of these compounds is attributed to the inhibition of protein synthesis. AVMs are one of the important antibacterial and antiparasitic classes that are applied in human and veterinary medicine, and crop protection. A hapten is a type of small molecule which cannot elicit an immune response, except coupled to a large molecular carrier. As a well-known expert and reliable provider in antibody production, Creative Biolabs is specialized in hapten design and synthesis projects and our scientists offer one-stop, custom services to rapidly prepare AVMs haptens for further antibody development.

Introduction to AVMs

AVMs belong to 16-membered ring macrolide antibiotics and are naturally occurring fermentation products derived from the soil actinomycete Streptomyces avermitilis. They are highly active against many nematodes, insects, and mites, as well as in animal husbandry to control arthropod pests. Furthermore, their toxicity for mammals has been proven relatively low. There’s five kind of AVMs, namely abamectin (ABM), ivermectin (IVM), doramectin (DOR), emamectin (EMA), and eprinomectin (EPR). The structural difference among EMA, IVM, and AVM is in C-25 and C-22-23. EMA and IVM have a saturated bond in that position, whereas AVM has a double bond. The toxicity of IVM is lower than that of AVM, indicating that the single bond in the C-22-23 site might be the better group in terms of safety. The AVM compounds are prevalently employed in farm animals and agriculture for the treatment of a broad spectrum of parasitic diseases. Nevertheless, the extensive usage of AVMs would result in residues in agricultural products including fruits.

The structure of AVM structural analogs: (A) AVM; (B) IVM; (C) DOR; (D) EP and (E) EMM. Fig.1 The structure of AVM structural analogs: (A) AVM; (B) IVM; (C) DOR; (D) EP and (E) EMM. (Xie, 2017)

Hapten Design &Synthesis Services at Creative Biolabs

Immunoassays are regarded as an effective and economical screening method by virtue of their high throughput, strong sensitivity, and fast analysis. In the last decades, several immunodetections have been developed to detect AVMs based on monoclonal or polyclonal antibodies. At Creative Biolabs, we have rich knowledge and experience in antibody production and are dedicated to providing speedy, simple, and sensitive methods for clients to prepare high-quality AVM haptens.

The UV–Vis spectra of different antigens. (A) UV–Vis spectra of AVM–BSA immunogens and (B) UV–Vis spectra of AVM–OVA coating antigens. Fig.2 The UV–Vis spectra of different antigens. (A) UV–Vis spectra of AVM–BSA immunogens and (B) UV–Vis spectra of AVM–OVA coating antigens. (Xie, 2017)

AVMs are a type of 16-membered ring macrolide antibiotics. The basic structural motif of the molecule is evident in the natural product AVM B1a, which is also the principal component of the insecticide abamectin. AVMs contain three hydroxyl groups and are selected for the preparation of artificial antigens. They can be combined with carrier proteins using different approaches, such as the chemical coupling method. Here, we have summarized two available approaches to synthesize ideal AVM haptens.

  • For hapten 1: AVMs are conjugated to carrier proteins, such as bovine serum albumin (BSA) or ovalbumin (OVA), with the N-hydroxysuccinimide (NHS)/1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC) method.
  • For hapten 2: AVMs are conjugated to carrier proteins, BSA or OVA, with the carbonyldiimidazole (CDI) method.

According to different types of AVMs, our technical teams have established a series of hapten design platforms for specific antiparasitics including but not limited to:

Advantages

  • End-to-end solutions for AVMs hapten design and synthesis, based on their structural characteristics
  • Experienced specialists with rich knowledge in antigen preparation and antibody development
  • Strict quality controls (QCs) enable super-low risk and reasonable costs
  • Full technical support and better services on pre- and after-sales

Natural AVMs and its derivatives are potent endectocide compounds, well-known for their unique mode of action against a wide range of nematode and arthropod animal parasites. Therefore, they play a very important role as bactericidal and antiparasitic agents, as well as Mycobacterium tuberculosis. With a high reputation and strong capacity in the biotechnology field, Creative Biolabs focuses on the chemical and pharmaceutical aspects of AVMs, including their stabilities, synthetic processes, impurities and degradation pathways. We provide hapten design and synthesis services against AVMs and other small molecular compounds as clients’ demands. If you’re interested in our services, please don’t hesitate to contact us or directly send us an inquiry.

Reference

  1. Xie, Z.; et al. Development of ic-ELISA and lateral-flow immunochromatographic assay strip for the simultaneous detection of avermectin and ivermectin. Food Agr Immunol. 2017, 28(3): 439-451.
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