Amoxicillin (AX) is the penicillin currently regarded as the main culprit in eliciting allergic reactions. According to hapten hypothesis, AX immunogenicity can only be gained by forming covalent conjugates with proteins. The diagnosis of immediate allergic reactions (IRs) to AX in clinical practice is based mainly on in vivo and in vitro methods. Due to the non-optimal sensitivity of skin tests, drug provocation test is considered the gold standard to establish the diagnosis, which is risky to the patient and not recommended in patients with a history of life-threatening reactions. In vitro tests are based on the determination of specific IgE (sIgE) (immunoassays), with the commercial ImmunoCAP only detecting 20% of allergic patients, and on the quantification of basophil activation after stimulation with the culprit drug, showing sensitivity around 50%. Among the factors affecting such low sensitivity could be the fact that correct antigenic determinant and/or conjugates are not incorporated into in vitro tests. In this thesis we propose the use of structural activity approach to nano-engineer the structural properties of conjugates to be appropriate for the crosslinking of sIgE bound to high-affinity receptor on basophils or mast cells (MCs). To attain this, we made use of dendrimer-based structures to generate three different structures called: (1) Dendrimeric Antigens (DeAns); (2) Bidendron Antigens (BiAns); and (3) Bidendron Antigens of different generations (BiAn-dGn), to obtain a library of well-defined nanoarchitectures, with variation in the size and numbers of antigenic determinants. The DeAns were prepared by decoration of terminal amino groups of dendrimers with AX. The BiAns and BiAn-dGn were constructed based on AX-decorated dendrons spaced with polyethylene glycol (PEG) chains of distinct lengths (600 - 12000 Dalton).