Synthesis and characterization of BODIPY-alpha-tocopherol: a fluorescent form of vitamin E.

ABSTRACT: Fluorescent nitrobenzoxadiazole analogues of alpha-tocopherol (NBD-alpha-Tocs; lambda(ex) = 468 nm, lambda(em) = 527 nm) have been made previously to aid study of the intracellular location and transfer of vitamin E. However, these analogues are susceptible to photobleaching while under illumination for confocal microscopy as well as in in vitro FRET transfer assays. Here we report the synthesis of three fluorescent analogues of alpha-tocopherol incorporating the more robust dipyrrometheneboron difluoride (BODIPY) fluorophore. A BODIPY-linked chromanol should have no intervening polar functional groups that might interfere with binding to the hydrophobic binding site of the tocopherol transfer protein (alpha-TTP). A key step in bringing the two ring systems together was a metathesis reacti

SUBMITTER: West R 

PROVIDER: S-EPMC2891523 | biostudies-literature | 2010 May

REPOSITORIES: biostudies-literature