8-Bromo-7-hydroxyquinoline as a photoremovable protecting group for physiological use: Mechanism and scope

Yue Zhu, Christopher M. Pavlos, John P. Toscano, Timothy Dore

Research output: Contribution to journalArticle

Abstract

Two-photon excitation (2PE) of "caged" biomolecules represents a powerful method to investigate the temporal and spatial relevance of physiological function in real time and on living tissue, because the excitation volume can be restricted to 1 fL. Additionally, low-energy IR light is used, which minimizes tissue destruction and enables deeper penetration into tissue preparations. Exploitation of this technology for studying cell physiology requires the further development of photoremovable protecting groups with sufficient sensitivity to 2PE for use in "caged" compounds. 8-Bromo-7-hydroxyquinoline (BHQ) is efficiently photolyzed by classic 1PE (365 nm) and 2PE (740 nm) under simulated physiological conditions (aqueous buffer of high ionic strength, pH 7.2) to release carboxylates, phosphates, and diols-functional groups commonly found on bioactive molecules such as neurotransmitters, nucleic acids, and drugs. It is stable in the dark, soluble in water, and exhibits low levels of fluorescence, which will enable use in conjunction with fluorescent indicators of biological function. BHQ-protected effectors are synthetically accessible. Stern-Volmer quenching, time-resolved infrared (TRIP), and 18O-labeling experiments suggest that the photolysis occurs through a solvent-assisted photoheterolysis (SN1) reaction mechanism on the sub-microsecond time scale. BHQ has the requisite photochemical and photophysical properties as a photoremovable protecting group to regulate the action of biological effectors in cell and tissue culture with light, especially 2PE.

Original languageEnglish (US)
Pages (from-to)4267-4276
Number of pages10
JournalJournal of the American Chemical Society
Volume128
Issue number13
DOIs
StatePublished - Apr 5 2006

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Tissue
Infrared radiation
Tissue culture
Nucleic acids
Physiology
Photolysis
Biomolecules
Ionic strength
Cell culture
Light
Cell Physiological Phenomena
Labeling
Nucleic Acids
Functional groups
Neurotransmitter Agents
Quenching
Buffers
Phosphates
Photons
Fluorescence

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

8-Bromo-7-hydroxyquinoline as a photoremovable protecting group for physiological use : Mechanism and scope. / Zhu, Yue; Pavlos, Christopher M.; Toscano, John P.; Dore, Timothy.

In: Journal of the American Chemical Society, Vol. 128, No. 13, 05.04.2006, p. 4267-4276.

Research output: Contribution to journalArticle

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