Synthesis and development of biologically active fluorescent-labeled vitamin K analogues and monitoring of their subcellular distribution

New fluorescent analogues of menaquinone-4 and phylloquinone were prepared and their subcellular distribution monitored using a confocal laser scanning microscope. These analogues incorporate an FITC group anchored to the naphthoquinone skeleton through an amide bond expected to be resistant to metabolism. On their addition to the culture medium, fluorescence was readily observed inside a human osteosarcoma cell line. This result indicates that the fluorescent analogues penetrate into cells the same as vitamin K, and therefore, would be useful for achieving insight into the action mechanism of vitamin K.