Issue 12, 2015

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

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

Supplementary files

Article information

Article type
Paper
Submitted
06 Sep 2015
Accepted
01 Oct 2015
First published
07 Oct 2015

Photochem. Photobiol. Sci., 2015,14, 2151-2158

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Spotlight

Advertisements