Design and Synthesis of Haptens for Streptomycins

Aminoglycoside (AG) antibiotics are a class of antibiotics defined from the molecular structure of multiple amino and hydroxyl, and they’re attached to amino alcohol ring and amino sugar molecule by glycosidic linkages. Historically, streptomycin was the first class of AG antibiotics which has been discovered by Selman Waksman in 1943. As a well-recognized specialist in antibody construction, Creative Biolabs has rich experience and abundant records of successfully developing anti-hapten antibodies with high affinity and high specificity for small-molecule antigens. Particularly, we’d like to offer custom immunogen design and synthesis services for streptomycins and other AG antibiotics for worldwide customers.

Introduction to Streptomycin

Fig.1 Chemical structure of streptomycin.

Streptomycin is produced by the soil organism Streptomyces griseus with antibacterial activity. This antibiotic irreversibly binds to the 16S rRNA and S12 protein within the bacterial 30S ribosomal subunit. Consequently, the agent interferes with the assembly of initiation complex between the mRNA and bacterial ribosome, thereby blocking the initiation of protein synthesis. Furthermore, streptomycin triggers misreading of mRNA templates and induces translational frameshift, subsequently resulting in premature termination. This process eventually causes bacterial cell death. Today, streptomycin has been known as an amino cyclitol glycoside that consists of streptidine containing a disaccharyl moiety attached at the 4-position. It comprises three components linked glycosidically (by ether bonds):

• streptidine (inositol with two guanido groups);
• streptose (methyl pentose);
• streptoscamine (N-methyl-L-glycosamine).

To be noticed, two guanido groups of streptidine are significant for the antibiotic activity and removal of either group would reduce its antibiotic activity up to 90%.

Rational Hapten Design Services at Creative Biolabs

Haptens are a type of small molecular weight compounds that stimulate the immune system when they’re linked to carrier proteins. In vivo, haptens easily bind to serum proteins and the combined molecular weights (MW) of the protein and the hapten need to exceed 3000 MW to induce an immune response. The immune response is targeted at both the carrier protein and the hapten. And the carrier protein has a distinct and unique antigenic structure after attached to the hapten.

Streptomycin is a pseudotrisaccharide with a monosubstituted aminocyclitol to which a disaccharide is coupled. It is a broad-spectrum antibiotic generally used for the treatment of active tuberculosis, often in combination with other antituberculosis agents. It was the first developed antimicrobial agent after penicillin and also the first antibiotic effective in administrating tuberculosis. In contrast to penicillin, streptomycin can inhibit Mycobacterium tuberculosis, as well as Gram-positive and Gram-negative bacteria. At Creative Biolabs, our scientists focus on the application and preparation methods of streptomycin and other small molecular haptens. Notably, haptens are valuable but difficult to solve targets. As such, we have developed technical platforms equipped with the best solution to design and synthesize haptens for streptomycin. Our design strategies are convenient to use, low in detection cost, and promote quick, accurate, and efficient in anti-hapten antibody production. The details are as follows.

Advantages

• One-stop, customized services for hapten design and synthesis to streptomycin and other antibiotics
• Time-saving, cost-effective projects monitored by technical directors with rich knowledge in hapten design
• Full deliverables including purified products, a final report with detailed diagrams and protocols

Haptens are increasingly essential to antibody-based immunoassays. Anti-hapten antibodies allow the detection of small molecules using rapid and potent immunological technologies, such as ELISA and IHC/IF. Either raised against endogenous small molecules or exogenous compounds, anti-hapten antibodies have become attractive detecting tools in the field of human health for diagnostic and therapeutic applications. Streptomycin is featured chemically as an AG antibiotic, having a role as a bacterial metabolite, an antimicrobial agent, an antibacterial drug, and an antifungal agrochemical.

Combining more than 10 years of experience in the development of small molecular haptens, Creative Biolabs has built simple and useful workflows to accomplish hapten design and synthesis for streptomycin and also provides further anti-hapten antibody preparation for clients’ specific projects. If you’re interested in our services, please don’t hesitate to contact us or directly send us an inquiry.