A CyHQ-linker for the controlled spatiotemporal study of gene expression in zebrafish
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Several hydroxyquinoline-protected acetates were synthesized to study how changes in substituents at C-8 affect their ground-state and excited-state chemistry and photoreactivity. Strong electron withdrawing groups form a greater proportion of the anionic form of the quinoline at neutral pH. A photoremovable protecting group for carbonyl compounds, Bhc-dithiol, should be more resistant to hydrolysis in the dark than Bhc-diol. The synthesis of a protected version of Bhc-dithiol is described. A CyHQ-based linker for the activation of morpholinos was synthesized for use in spatio-temporal studies of gene expression in developing zebrafish embryos. This cyano-based derivative of BHQ has a three-fold higher molar absorptivity than BHQ and higher sensitivity to one-photon excitation, which will enable more efficient photoactivation of the morpholino than a previous BHQ-based-linker analog.