Photochemical Activation of Tertiary Amines for Applications in Studying Cell Physiology

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

Research output: Contribution to journalArticlepeer-review

Abstract

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.

Original languageEnglish (US)
Pages (from-to)12591-12600
Number of pages10
JournalJournal of the American Chemical Society
Volume139
Issue number36
DOIs
StatePublished - 2017

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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