Photochemical Properties of New Photolabile cAMP Derivatives in a Physiological Saline Solution

Article abstract of DOI:10.1021/jo00118a008

Three new photolabile esters of cAMP (2-anthraquinonyl)methyl (1a), (7-methoxycoumarinyl)methyl (2a), and 2-naphthylmethyl (3a), have been developed.The stability and photochemical properties of these derivatives were compared to the previously reported ones in a physiological saline solution (1percent DMSO in Ringer's solution, pH 7.4).We found that 2a had satisfactory stability (t_1/2 > 1000 h) in the dark and was photolyzed to release the parent cAMP on 340 nm irradiation (Φ_app = 0.10, Ε₃₄₀ = 6730) more efficiently than previously reported caged cAMPs.A biological test using the melanophores of the medaka (Oryzias latipes) revealed that 2a penetrated into the melanophores, inactive before irradiation and activated to release cAMP upon irradiation.We have developed a new caged cAMP which can be used in the investigation of biological responses regulated by intracellular cAMP concentrations using living cells.