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Issue 12, 2015
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Photoactivatable, biologically-relevant phenols with sensitivity toward 2-photon excitation

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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.

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

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Supplementary files

Article information


Submitted
06 Sep 2015
Accepted
01 Oct 2015
First published
07 Oct 2015

Photochem. Photobiol. Sci., 2015,14, 2151-2158
Article type
Paper
Author version available

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

D. E. McLain, Adam. C. Rea, M. B. Widegren and T. M. Dore, Photochem. Photobiol. Sci., 2015, 14, 2151
DOI: 10.1039/C5PP00334B

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