Photoactivatable, biologically-relevant phenols with sensitivity toward 2-photon excitation

Duncan E. McLain, Adam C. Rea, Magnus B. Widegren, Timothy M. Dore

Research output: Contribution to journalArticle

Abstract

Spatio-temporal release of biologically relevant small molecules provides exquisite control over the activation of receptors and signaling pathways. This can be accomplished via a photochemical reaction that releases the desired small molecule in response to irradiation with light. A series of biologically-relevant signaling molecules (serotonin, octopamine, capsaicin, N-vanillyl-nonanoylamide, estradiol, and tyrosine) that contain a phenol moiety were conjugated to the 8-bromo-7-hydroxyquinolinyl (BHQ) or 8-cyano-7-hydroxyquinolinyl (CyHQ) photoremovable protecting groups (PPGs). The CyHQ caged compounds proved sensitive toward 1PE and 2PE processes with quantum efficiencies of 0.2-0.4 upon irradiation at 365 nm and two-photon action cross sections of 0.15-0.31 GM when irradiated at 740 nm. All but one BHQ caged compound, BHQ-estradiol, were found to be sensitive to photolysis through 1PE and 2PE with quantum efficiencies of 0.30-0.40 and two photon cross sections of 0.40-0.60 GM. Instead of releasing estradiol, BHQ-estradiol underwent debromination.

Original languageEnglish (US)
Pages (from-to)2151-2158
Number of pages8
JournalPhotochemical and Photobiological Sciences
Volume14
Issue number12
DOIs
StatePublished - 2015

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry

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