Chloramphenicols (CAPs) Hapten Design and Synthesis
A hapten is a small molecule that triggers an immune response only when attached to a large carrier such as a protein. Hapten is involved in the generation of many immune responses, making it a topic of interest to immunologists, and it is also used in laboratory research and certain types of immunoassays and diagnostic tests. Based on years of experience in hapten antibody development, Creative Biolabs provides high-quality hapten design and synthesis services to increase the specificity and sensitivity of immunogens.
Introduction of Chloramphenicols (CAPs)
CAPs, also known as amphenicols antibiotics (APs), mainly include chloramphenicol (CAP), thiamphenicol (TAP), florfenicol (FF), and the derivatives. As shown in Fig.1, the chemical structure of CAPs has special groups closely related to antibacterial activity, including the dichloroacetamide group, propylene glycol, and p-nitrobenzene group. The main function of CAPs is to inhibit the synthesis of bacterial proteins by acting on the 50s subunit of bacterial 70s ribosome, inhibiting the activity of transpeptidase to hinder the extension of the peptide chain.
Fig.1 Chemical structures of chloramphenicols antibiotics. (Xu, 2015)
CAPs Hapten Design and Synthesis Service
Substances with a molecular weight of less than 1000 are not immunogenic and usually cannot be recognized by the immune system. CAPs are small molecule substances, and only when coupled with a macromolecular carrier can they trigger an immune response and produce antibodies against small molecules. To make them immunogenic, Creative Biolabs provides a full range of small molecule hapten design and synthesis services, including 1) selecting the most suitable position on the hapten for the coupling carrier to improve the specificity, sensitivity, and immunogenicity of the immunogen; 2) according to the characteristics of the hapten and the carrier, we choose the best coupling method to achieve the best results; 3) precisely control the most appropriate ratio of drug to a carrier protein to enhance the performance of immunoassay. Our hapten design and synthesis services cover three antibiotics for CAPs, including:
CAP is an antibiotic first discovered by Ehrlich et al. The structure is shown in Fig.1. This antibiotic is unique in that it is the first natural product containing a nitro group and the first natural product which was a derivative of dichloroacetic acid. CAP is one of the effective broad-spectrum antibiotics that can be used to treat a variety of bacterial infections. It kills bacteria or prevents their growth by inhibiting the synthesis of bacterial proteins. Bacterial diseases that can be treated with CAP include Neisseria species, Staphylococcus and Streptococcus species, Rickettsia, and lymphogranuloma-psittacosis group of organisms.
TAP is a methyl-sulfonyl analog of CAP in which the nitro group has been substituted with a methylsulfonyl group. It is a broad-spectrum antibiotic that is active against Gram-positive and Gram-negative organisms. TAP functions by binding the 50s ribosomal subunit and inhibiting protein synthesis by preventing aminoacyl tRNA from attaching to the A site. Its mechanism of action is the same as that of CAP, but its effect is about three times that of CAP. Its main advantage over CAP is that it has never been associated with aplastic anemia. In Asia and Latin America, the drug is used to treat various infections, including sexually transmitted diseases. In Europe and the United States, the drug is used in veterinary practice.
FF, a fluorinated derivative of TP, is a broad-spectrum antibiotic that belongs to the class of aminophenol that inhibits protein synthesis through its bacteriostatic activity. It has a broad antibacterial spectrum similar to CAP and stronger than TP in vitro. Furthermore, FF showed activity against CAP-resistant strains, such as Escherichia coli, Klebsiella pneumonia, Proteus valgaris, Salmonella Typhimurium and Staphylococcus aureus. FF is a veterinary antibiotic used to treat bovine respiratory diseases and foot rot. It is also used in aquaculture. Although FF is not used in human medicine, it is speculated that the same advantages as veterinary medicine can be applied, including comparable efficacy to CAP, lower toxicity and less development of resistance.
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- Xu, N.; et al. Development and characterisation of an ultrasensitive monoclonal antibody for chloramphenicol. Food and agricultural immunology. 2015, 26(3): 440-450.