Trichothecenes Hapten Design and Synthesis

Trichothecenes are a large family of structurally related toxins widely found in nature. They’re a series of mycotoxins with similar biological activity and chemical architecture. Trichothecenes are mainly derived from Fusarium, Myrothecium, Stachybotrys, Trichoderma, and several other molds. These mycotoxins can pollute wheat, barley, oats, corn, and other grains, resulting in serious illness, even death. A hapten is defined as a substance that is not immunogenic but can bind to specific antibodies. To specifically detect trichothecenes, many immunoassays have emerged and attracted plenty of attention such as antigen-antibody interaction. As a leading provider in the antibody industry, Creative Biolabs has abundant experience in developing antibodies for small molecular compounds and is particularly skilled at providing end-to-end solutions for trichothecene hapten design and synthesis projects.

Introduction to Trichothecenes

Trichothecenes are a group of tetracyclic sesquiterpenoid substances (C-12, C-13 epoxytrichothecenes) containing over 200 compounds of broadly varying toxicity. The epoxy group at C-12 and C-13 is considered important for its toxicity. Pure trichothecenes are stable colorless crystalline that can be soluble in polar solvent but hard to dissolve in water, without fluorescence under ultraviolet light. The basic structure of this kind of mycotoxins is the sesquiterpene with four rings. Based on different types of substituent, trichothecenes have been classified into four different types: A, B, C, and D. The symbols of type A are substituent of -H, -OH, -OAC, or -OCOCH2CH(CH3)2 on C-8 position and no big rings between C-4 and C-15 position, including T-2 toxin, HT-2 toxin, Diacetoxyscirpenol (DAS), Neosolaniol (NEO), etc. The symbols of type B is carbonyl group on C-8 position, including Deoxynivalenol (DON), 3-Acetyldeoxynivalenol (3 AcDON), Fusarenon X (FX), Nivalenol (NIV), etc. Trichothecenes can cause apoptosis and necrosis in the lymphoid, hematopoietic, and gastrointestinal tissues leading to vomiting, diarrhea, leukopenia, which could be lethal. The naturally contaminated trichothecenes are type A and B, and type B belongs to the most polluted and harmful one.

The general core structures for Type A, B, C, and D trichothecenes. Fig.1 The general core structures for Type A, B, C, and D trichothecenes. (Shank, 2011)

Hapten Design &Synthesis Services at Creative Biolabs

Trichothecene mycotoxins are also loosely categorized into two classes, macrocyclic and non-macrocyclic trichothecenes, by virtue of the presence or absence of a macrocyclic ring linking C-4 and C-15 with diesters or triesters. Field fungi of the genus Fusarium are major producers of non-macrocyclic groups, including T-2 toxin, the best-known trichothecene, and DON. To better understand the function of trichothecenes, prevent these toxin-related diseases, and explore the roles as a robust pharmaceutical agent, our experts take efforts to investigate the structure of this class of compounds and have developed a series of strategies and custom services to produce artificial antigens for trichothecenes. According to different types of trichothecenes, we are pleased to introduce cost-effective and time-saving hapten design platforms including but not limited to:

  • Design and Synthesis of Haptens for Deoxynivalenol (DON)
  • DON is the most frequently observed trichothecene in cereal grains around the world. For this toxin, there’re three active free hydroxyls in distinct sites, and the hydroxyl on C3 is generally selected for derivation. Therefore, the other hydroxyls are supposed to be blocked by butylboric acids (BBA) before the synthesis process. Then, the succinic anhydride is employed for hapten derivation. In another way, an antigen can be produced by the carbodiimide (CDI) method as the existence of hydroxyls.

  • Design and Synthesis of Haptens for T-2 toxin
  • T-2 toxin is another kind of trichothecenes that has a similar structure to HT-2 toxin. T-2 toxin only holds one hydroxyl, so that it may be derived directly by succinic anhydride without blocking operation.

The 1H NMR spectra of (A) T-2 toxin and (B) DON at 300 MHz in CDCl3. Fig.2 The 1H NMR spectra of (A) T-2 toxin and (B) DON at 300 MHz in CDCl3. (Shank, 2011)

Advantages

  • End-to-end solutions for hapten design and synthesis of trichothecenes
  • Trained technicians have extensive expertise in antigen preparation and rich experience in antibody production
  • Strict quality controls at the end of each phase, enabling high efficacy, low risk, and reasonable cost

Based on strong capacities and expertise in antibody production, Creative Biolabs has multiple rapid and sensitive strategies to design ideal haptens according to their accurate chemical structures. We offer the best solutions and excellent platforms for trichothecene hapten design and synthesis, accompany to generate high-affinity and -specificity antibodies for global clients. If you’re interested in our services, please don’t hesitate to contact us or directly send us an inquiry.

Reference

  1. Shank, R.A.; et al. Current and future experimental strategies for structural analysis of trichothecene mycotoxins--A prospectus. Toxins (Basel). 2011, 3(12): 1518-1553.
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