Development of a pH sensitive coumarin based chemosensor
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Fluorescent probes have found several uses in monitoring the physiological state of cells. Recently, the Glass lab has developed a fluorescent sensor capable of binding norepinephrine in chromaffin cell vesicles. This sensor is based on coumarin aldehyde compounds which have been shown to reversibly bind primary amines such as those found in neurotransmitters. The synthesis and evaluation of a coumarin based pH sensitive fluorescent chemosensor is described. The sensor would overcome two major challenges caused by the previous catecholamine sensor. The first is in the rate of binding of the sensor to the catecholamine; a slow rate of binding makes synaptic measurements difficult. To circumvent this impediment, a pH sensitive sensor is proposed since, it remains off upon binding to the neurotransmitter in the vesicle (pH=5.5). When the cell is stimulated and the neurotransmitters released into the synapse (pH=7.4) the sensor will fluoresce. The second challenge that is overcome is the lengthy synthesis of the coumain sensor. A short synthetic route is designed.