DNA interaction analysis of fluorenylidene double bridged cyclotriphosphazene derivatives

Abstract

Abstract DNA is a target molecule for anticancer drug development, and investigation on DNA interactions with synthesized potential drugs has great importance in order to discover new drug candidates, hence in this study an electrochemical biosensor has been used to perform quantitative analysis of DNA/compound interactions. In this study, full paraben substituted fluorenylidene double bridged cyclotriphosphazene compounds (9–13) were synthesized for the first time and their effect on DNA were investigated using an automated biosensor device MiSens®. The reaction of fluorenylidene double bridged cyclotriphospazene (FDBC) compound (3) with parabens: methyl 4-hydroxybenzoate, (4); ethyl 4-hydroxybenzoate, (5); propyl 4-hydroxybenzoate, (6); butyl 4-hydroxybenzoate (7), benzyl paraben (8) were performed, respectively. Compounds 9–13 were obtained and fully characterizated by mass spectrometry, 31P NMR and 1H spectroscopy. Biosensor based screening tests were used to investigate DNA interaction properties of the newly synthesised compounds by measuring DNA hybridization efficiency on the biochip surface. The effect of the compounds to the plasmid DNA structure were analyzed by agarose gel electrophoresis, in addition the antimicrobial activities of the compounds have been investigated. The biosensor assay and the agarose gel electrophoresis investigation indicated DNA/compound interaction for the compounds 12 and 13 none of the compounds has shown antimicrobial activity.