Synthesis of photocaged molecules towards spatial and temporal control of gene expression

Date
2011
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University of Delaware
Abstract
Spatial and temporal control of gene expression can aid in the understanding of gene function and cellular processes. Photo-labile protecting groups are chemical moieties that can be installed on a biologically active compound, blocking its biological function. Upon irradiation of the "caged" compound, the protecting group is removed "releasing" the now biologically active molecule. In this work, a Tamoxifen aziridine derivative was synthesized and attempts were made to link it to a coumarin-based photolabile protecting group via a variety of synthetic strategies. However, none of the tamoxifen coumarin compounds were successfully synthesized. The failure of linking the tamoxifen core structure to a coumarin derivative can be attributed to two reasons: 1) instability of the coumarin in basic conditions for sufficient deprotonaton of the tamoxifen phenol; 2) tendency of the electron-rich tamoxifen olefin to be unstable in acidic conditions.
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