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

Duncan E. McLain, Adam C. Rea, Magnus B. Widegren, Timothy 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 - Jan 1 2015

    Fingerprint

    Phenols
    phenols
    Estradiol
    Photons
    quantum efficiency
    sensitivity
    photons
    Quantum efficiency
    serotonin
    Molecules
    excitation
    molecules
    irradiation
    tyrosine
    cross sections
    Irradiation
    releasing
    Octopamine
    photochemical reactions
    photolysis

    ASJC Scopus subject areas

    • Physical and Theoretical Chemistry

    Cite this

    Photoactivatable, biologically-relevant phenols with sensitivity toward 2-photon excitation. / McLain, Duncan E.; Rea, Adam C.; Widegren, Magnus B.; Dore, Timothy.

    In: Photochemical and Photobiological Sciences, Vol. 14, No. 12, 01.01.2015, p. 2151-2158.

    Research output: Contribution to journalArticle

    McLain, Duncan E. ; Rea, Adam C. ; Widegren, Magnus B. ; Dore, Timothy. / Photoactivatable, biologically-relevant phenols with sensitivity toward 2-photon excitation. In: Photochemical and Photobiological Sciences. 2015 ; Vol. 14, No. 12. pp. 2151-2158.
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