Photochemical Activation of Tertiary Amines for Applications in Studying Cell Physiology | Zendy

Naeem Asad | Zendy; Davide Deodato | Zendy; Xin Lan | Zendy; Magnus B. Widegren | Zendy; David Lee Phillips | Zendy; Lili Du | Zendy; Timothy M. Dore | Zendy

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Photochemical Activation of Tertiary Amines for Applications in Studying Cell Physiology

Author(s) -

Naeem Asad,

Davide Deodato,

Xin Lan,

Magnus B. Widegren,

David Lee Phillips,

Lili Du,

Timothy M. Dore

Publication year - 2017

Publication title -

journal of the american chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/jacs.7b06363

Subject(s) - chemistry , tertiary amine , recombinase , chemical biology , photochemistry , intracellular , combinatorial chemistry , biophysics , biochemistry , gene , organic chemistry , recombination , biology

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.

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