title: 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.
authors.affiliation: New York University Abu Dhabi, PO Box 129188, Abu Dhabi, United Arab Emirates. timothy.dore@nyu.edu and Department of Chemistry, University of Georgia, Athens, Georgia30602, USA.
authors.forename: Duncan E
authors.initials: DE
authors.lastname: McLain
authors.affiliation: Department of Chemistry, University of Georgia, Athens, Georgia30602, USA.
authors.forename: Adam C
authors.initials: AC
authors.lastname: Rea
authors.affiliation: New York University Abu Dhabi, PO Box 129188, Abu Dhabi, United Arab Emirates. timothy.dore@nyu.edu.
authors.forename: Magnus B
authors.initials: MB
authors.lastname: Widegren
authors.affiliation: New York University Abu Dhabi, PO Box 129188, Abu Dhabi, United Arab Emirates. timothy.dore@nyu.edu and Department of Chemistry, University of Georgia, Athens, Georgia30602, USA.
authors.forename: Timothy M
authors.initials: TM
authors.lastname: Dore
mesh_terms: D006912:Hydroxyquinolines / Q000737:chemistry*; D008027:Light; D009570:Nitriles / Q000737:chemistry*; D010636:Phenols / Q000737:chemistry*; D010782:Photolysis; D017785:Photons
chemical_list: C575767:8-bromo-7-hydroxyquinoline; D006912:Hydroxyquinolines; D009570:Nitriles; D010636:Phenols