Photolabile precursors of cyclic nucleotides with high aqueous solubility and stability.
2002
Photolabile phosphotriester derivatives of cyclic AMP and cyclic GMP are described, where the additional group on the phosphate is a 2-nitrobenzyl that bears an electron-withdrawing and dianionic substituent. This confers high aqueous solubility and excellent resistance to hydrolysis of the phosphotriester (t1/2 for hydrolysis at pH 7, 22 °C, is >3 months for the axial isomers 3a and 4a and >1 month for the equatorial isomers 3b and 4b). The photolysis quantum yields are in the range 0.15−0.24, and the product release rate upon flash photolysis is 1.7 s-1 at pH 7.0, 20 °C.
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