Synthesis and characterization of photolabeling probes of miltefosine

Miltefosine is an ether-phospholipid analogue showing remarkable anti-cancer and anti-leishmanial activity thanks to its cell membrane-targeting properties. In order to study the mechanisms responsible for the biological effects of miltefosine using a photolabeling approach, we designed, synthesized and characterized photolabeling probes for studying the effects of miltefosine. In these probes, the photoactivatable tetrafluorophenylazido group is incorporated either at the polar head or in the alkyl chain of miltefosine. The probes showed fast, clear-cut photochemical reactions, which suggests that they are promising tools for use in photolabeling studies.