Multifunctionalization of cyanuric chloride for the stepwise synthesis of potential multimodal imaging chemical entities

Abstract

We report a synthetic strategy to combine different moieties in a single structure using cyanuric chloride (2,4,6-trichlorotriazine) as a starting platform for preparing potential bioimaging agents. This reacted with macrocycles of the porphyrin family and DOTA type metal chelators through mono-, di- and tri- substitution of its chlorine atoms by appropriate nucleophiles, controlling the stepwise by temperature, to produce a system that opens the potential for biomedicinal applications. Porphyrins were chosen as one of the sensing arms, based on their rich structural chemistry, and excellent photophysical properties, while DO3A was used since it can form a versatile aminopropionate functionalized metal ion chelator. All new compounds were fully characterized, both spectroscopically and photophysically. Keywords: Porphyrins, Aza-chelates, Sulfonation, Fluorescence, Biomedicinal applications, Cyanuric chloride