Naphthalimide Dyes with Orthogonal Functional Groups for "Click" Chemistry: Attachment to Solid Supports and Applications in Drug Allergy Diagnosis

Abstract

The preparation and characterization of new functional materials for sensing have an important role in clinical diagnosis. Monitoring the surface functionalization of functional material is crucial because the final sensing properties are affected by how the (bio)molecules are immobilized on the surface of solid supports. Here, a new approach for the preparation of functional materials for biomedical diagnosis was developed. This method employs a fluorescent dye comprising 4-amino-1,8-naphthalimide with two orthogonal functional groups suitable for click chemistry. The orthogonal reactivity of these groups allows the sequential functionalization of the fluorophore, firstly with (bio)molecules, and then binding of the (bio)molecule-naphthalimide macrostructure onto the surface of a solid support. The fluorescent properties confirm the immobilization of the (bio)molecule on the surface of the solid support, without requiring other indirect methods to verify the immobilization. These functional materials were tested successfully with sera of patients, thus proving their potential application for allergic drug diagnosis.

Keywords: cellulose; click chemistry; dendrimers; drug allergy; dyes.