Abstract
This article summarizes the methods used in laboratory for the preparation and characterization of 4-coumarinylmethyl-caged phosphate esters and their application in studies of the role of cAMP on the dispersion and aggregation of pigment granules in live cells. The coumarin-caged cAMP compounds, MCM-cAMP, 4-(7-acetoxycoumarinyl) methyladenosine (ACM)-cAMP, 4-(7-propionyloxycoumarinyl) methyladenosine (PCM)-cAMP and 4-(7-hydroxycoumarinyl)methyladenosine (HCM)-cAMP cyclic 3',5'-monophosphates that differ from each other only by the substituent at the 7-position of the coumarin ring, have been prepared from reactions of the corresponding 4- coumarinylmethyl bromide with cAMP using the silver(I) oxide promoted method. These caged cAMP compounds exhibit similar photocleavage properties and efficiently release cAMP in Ringer's solution on irradiation with near-ultraviolet light. Another significant feature of these caged cAMPs is their long half-life in the dark in physiological salt solutions compared to those of o-nitrobenzyl- or onitrophenethyl-caged cAMPs, which in the experience readily hydrolyze in aqueous solution.
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