Synthesis of conjugated spermine derivatives with 7-nitrobenzoxadiazole (NBD), rhodamine and bodipy as new fluorescent probes for the polyamine transport system

The synthesis of a series of conjugated spermine derivatives with benzoxadiazole, phenylxanthene or bodipy fluorophores is described. These fluorescent probes were used to identify the activity of the polyamine transport system (PTS). N1-Methylspermine NBD conjugate 5 proved to have the optimal fluorescence characteristics and was used to show a selectivity for PTS-proficient CHO versus PTS-deficient CHO-MG cells. It can therefore be used as a tool for the selection of cells sensitive to cytotoxic compounds vectored through the PTS.

Graphical abstractN1-Methylspermine NBD 5 was synthesized from 4-chloro-7-nitrobenzo[1,2,5]oxadiazole (NBD) 2 and protected spermine 1. 5 was used as a fluorescent probe to select polyamine transport system (PTS) expressing cells, sensitive to cytotoxic compounds vectored through the PTS.Figure optionsDownload full-size imageDownload as PowerPoint slide