Synthesis and applications of Bhc-diol
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Photoremovable protecting groups have been used to study cell physiology. When covalently linked to biologically active molecules, they inactivate or “cage” these messengers. Reactivation or “uncaging” of physiological activity can be achieved with a flash of light. By multiphoton photolysis, the release of the messenger can be controlled in time, location, and amplitude. Caged compounds could be used in drug delivery. Because of a lack of physiologically useful caging groups for ketones and aldehydes, functional groups that are found in many biologically active molecules, such as steroids, a new photolabile protecting group based on a coumarin derivative, 6-bromo-4-(1,2-dihydroxyethyl)-7-hydroxycoumarin (Bhc-diol), was synthesized, and its photochemistry analyzed. Bhc-diol possesses sufficient one-photon quantum efficiency and two-photon uncaging cross-section for biological use. When conjugated to mifepristone, Bhc-diol has the promise to be a good photo-mediator of gene expression. Bhcdiol- mifepristone has been synthesized and its photochemical properties tested.