Journal of the American Chemical Society
Journal of the American Chemical Society
5 years ago

Photochemical Activation of Tertiary Amines for Applications in Studying Cell Physiology

Photochemical Activation of Tertiary Amines for Applications in Studying Cell Physiology
Lili Du, Magnus B. Widegren, Naeem Asad, Xin Lan, David Lee Phillips, Davide Deodato, Timothy M. Dore
Representative tertiary amines were linked to the 8-cyano-7-hydroxyquinolinyl (CyHQ) photoremovable protecting group (PPG) to create photoactivatable forms suitable for use in studying cell physiology. The photoactivation of tamoxifen and 4-hydroxytamoxifen, which can be used to activate Cre recombinase and CRISPR-Cas9 gene editing, demonstrated that highly efficient release of bioactive molecules could be achieved through one- and two-photon excitation (1PE and 2PE). CyHQ-protected anilines underwent a photoaza-Claisen rearrangement instead of releasing amines. Time-resolved spectroscopic studies revealed that photorelease of the tertiary amines was extremely fast, occurring from a singlet excited state of CyHQ on the 70 ps time scale.

Publisher URL: http://dx.doi.org/10.1021/jacs.7b06363

DOI: 10.1021/jacs.7b06363

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