Synthesis of Piperazine Functionalized Calix[4]Arene-1,8-Naphthalimidine Derivatives and Preparation of Antimicrobial Transparent Biofilms

Abstract

In supramolecular chemistry, calix[n]arenes, known as the “third generation” host molecules after crown ethers and cyclodextrins, are important macrocyclic compounds (Neri et al., 2016). Calix[n]arenes are macrocyclic molecules containing phenolic rings bridged by methylene groups and are known for their ability to form inclusion complexes or act as molecular scaffolds (Fateh et al., 2021; Migliore et al., 2021). In recent years, it has been proven by various studies that some calix[n]arene derivatives are suitable for bioactivity studies. In this study, three new fluorescent calix[4]arene derivatives were formed and characterized by reacting calix[4]arene with 4-bromo-1,8-naphthalanhydride and then replacing the bromine in the naphthyl groups with piperase derivatives. These synthesized fluorescent compounds were reacted with hyaluronic acid to form transparent biofilm, and FE-SEM and EDX analyses were performed to determine the surface profiles of these prepared antimicrobial transparent biofilms. Among the synthesized compounds, compound number 7 showed significant antimicrobial activity on Sarcian lutea at a dose of 0.097 mg/ml and also, this MIC value was reported as the lowest value recorded in the entire study.