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 Dore

Research output: Contribution to journalArticle

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 - Jan 1 2017

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Cell Physiological Phenomena
Physiology
Amines
Chemical activation
Photons
Aniline Compounds
Clustered Regularly Interspaced Short Palindromic Repeats
Tamoxifen
Aniline
Excited states
Genes
Molecules

ASJC Scopus subject areas

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

Cite this

Photochemical Activation of Tertiary Amines for Applications in Studying Cell Physiology. / Asad, Naeem; Deodato, Davide; Lan, Xin; Widegren, Magnus B.; Phillips, David Lee; Du, Lili; Dore, Timothy.

In: Journal of the American Chemical Society, Vol. 139, No. 36, 01.01.2017, p. 12591-12600.

Research output: Contribution to journalArticle

Asad, Naeem ; Deodato, Davide ; Lan, Xin ; Widegren, Magnus B. ; Phillips, David Lee ; Du, Lili ; Dore, Timothy. / Photochemical Activation of Tertiary Amines for Applications in Studying Cell Physiology. In: Journal of the American Chemical Society. 2017 ; Vol. 139, No. 36. pp. 12591-12600.
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