Novel paraben derivatives of tetracyclic spermine cyclotriphosphazenes: synthesis, characterization and biosensor based DNA interaction analysis

Abstract

Biogenic polyamines such as spermine have long been known to play an important role in many biological processes, such as cellular growth regulation, stabilization of lipids, transcription and synthesis of proteins, and synthesis of nucleic acids and neurotransmitters. However, the efficacy of parabens, which are widely used as preservatives in many areas, has attracted attention in recent years. In this study, a new series of paraben-substituted dispiroansa (tetracyclic) spermine derivatives of cyclotriphosphazenes likely to be biologically active were synthesized for the first time. The structures of the well-purified compounds were illuminated by spectroscopic techniques such as NMR and mass analysis. In addition, the structures of compounds 2, 4 and 5 were assigned by an X-ray crystallographic technique. Also, it was observed that the compounds 1–6 showed high thermal stability according to thermogravimetric analysis curves. The results obtained from an automated electrochemical biosensor device were compared and it was seen that the effect on DNA of the synthesized novel compounds was much higher than that of the starting compounds. Biosensor results showed that especially compounds 2, 5 and 6 showed 75%, 67% and 78% activity at the highest concentration studied, respectively.