The synthesis and characterization of a variety of biologically relevant caged phenols and catechols
|dc.description.abstract||Spatio-temporal release of biologically relevant small molecules provides exquisite control over the activation of receptors and signaling pathways. This can be accomplished via a photochemical reaction that releases the desired small molecule in response to irradiation of light. A series of small molecules (serotonin, capsaicin, VNA, octopamine, tyrosine, dopamine, epinephrine, and norepinephrine) that contain either a phenol or catechol moiety were caged using either BHQ or CyHQ. In all cases the CyHQ caged compounds proved sensitive toward 1PE and 2PE processes with quantum efficiencies of 0.2 – 0.4 upon irradiation at 365 nm and two photon cross sections of 0.15 – 0.31 GM when irradiated at 740 nm. All but two compounds, BHQ-dopamine and BHQ-estradiol were found to be sensitive to both 1PE and 2PE with quantum efficiencies of 0.30 – 0.40 and two photon cross sections of 0.40 – 0.60 GM. CyHQ-epinephrine and CyHQ-norepinephrine possessed a novel photodegradation pathway that was analyzed through radical trapping experiments and product studies|
|dc.subject||two photon excitation|
|dc.title||The synthesis and characterization of a variety of biologically relevant caged phenols and catechols|
|dc.description.committee||Robert S Phillips|
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