Benzimidazoles (BZs) Hapten Design and Synthesis
Benzimidazoles (BZs) are a class of drugs with activities against fungi, protozoa, and helminths and are widely employed in veterinary and human medicine, resulting in great selection pressure and the emergence of BZs resistance. In other words, monitoring the uses of BZs is necessary. Compared with the traditional ways to detect BZs, such as gas chromatography-mass spectrometry (GC-MS), liquid chromatography-mass spectrometry (LC-MS), or high-performance liquid chromatography-mass spectrometry (HPLC-MS), the immunoassay based on the antigen-antibody reaction can improve the efficiency and reduce the time and cost. The core of the immunoassay method is to obtain specific antibodies. Creative Biolabs offers comprehensive services on BZs hapten design and synthesis. We have extensive experience and expertise in designing, preparing haptens, and developing small molecule antibodies. Here, we provide the design and synthesis of class-specific and compound-specific haptens for BZs.
Benzimidazole is a heterocyclic aromatic organic compound. This bicyclic compound consists of the fusion of benzene and imidazole, shown in Fig.1. There are seven positions in BZ that can be substituted with a variety of chemical entities, but most of the bioactive BZs based compounds bear functional groups at 1, 2 and/or 5(or 6) positions. The major activities of Benzimidazole include antihypertensive, anti-inflammatory, antibacterial, antifungal, anthelmintic, antiviral, antioxidant, antiulcer, antitumor, pyschoactivity, shown in Fig.2.
Figure.1 Structure of BZ. (Prasad, 2016)
Haptens are small molecules that can stimulate the production of the antibody when conjugated to a carrier molecule. Due to the small size, a hapten itself cannot be presented to T cells because it is not able to bind to the major histocompatibility complex (MHC) independently and induce immune response significantly. However, haptens can be combined with the carriers, which are relatively larger molecules traveling through the circulation but do not induce the immune response by themselves, such as keyhole limpet haemocyanin (KLH) and bovine serum albumin(BSA). The resulting hapten-carrier conjugates will take advantage of the larger size and then elicit the immune response more efficiently. Creative Biolabs provides BZs hapten design and synthesis services to meet our clients’ antibody discovery needs.
Figure.2 Multifunction of BZs. (Bansal, 2012)
In terms of the design and synthesis of class-specific haptens for BZs, we mainly focus on some positions in BZs, including N1, C2, and R2, shown in Fig.3. At Creative Biolabs, we first select the most suitable position on the molecule to attach a linker based on customers’ requirements; and secondly, we design and synthesize the linker with the most suitable length.
Figure. 3 The positions in BZ for the class-specific haptens design and synthesis.
For the design and synthesis of compound-specific haptens for BZs, we mainly focus on the specific position in C5 of BZs, shown in Fig.4. The steps of this service are similar to the design and synthesis of class-specific haptens for BZs. It is necessarily noticed that the designed hapten should has a certain degree of complexity or rigidity and maintain the original molecular structure of the antibiotics itself and to make this hapten to be exposed on the surface of the carrier.
Figure. 4 The position in BZ for the compound-specific haptens design and synthesis.
At Creative Biolabs, we have the design, synthesis, modification, and characterization experience and expertise of haptens. Based on the clients' objectives, we can provide one-stop services such as class-specific and compound-specific hapten design and synthesis. For more specific details, please don't hesitate to contact us.
- Prasad, P. M. K.; et al. POTENT BIOLOGICAL AGENT BENZIMIDAZOLE–A REVIEW. International Journal of Pharmacy and Pharmaceutical Sciences. 2016, 8(12): 22.
- Bansal, Y.; Silakari, O. The therapeutic journey of benzimidazoles: A review. Bioorganic & Medicinal Chemistry. 2012, 20(21), 6208–6236.