Ncm, a photolabile group for preparation of caged molecules: Synthesis and biological application

Sukumaran Muralidharan, Nathaniel D.A. Dirda, Elizabeth J. Katz, Cha Min Tang, Sharba Bandyopadhyay, Patrick Kanold, Joseph P.Y. Kao

Research output: Contribution to journalArticle

Abstract

Ncm, 6-nitrocoumarin-7-ylmethyl, is a photolabile protective group useful for making "caged" molecules. Ncm marries the reliable photochemistry of 2-nitrobenzyl systems with the excellent stability and spectroscopic properties of the coumarin chromophore. From simple, commercially available starting materials, preparation of Ncm and its caged derivatives is both quick and easy. Photorelease of Ncm-caged molecules occurs on the microsecond time scale, with quantum efficiencies of 0.05-0.08. We report the synthesis and physical properties of Ncm and its caged derivatives. The utility of Ncm-caged glutamate for neuronal photostimulation is demonstrated in cultured hippocampal neurons and in brain slice preparations.

Original languageEnglish (US)
Article numbere0163937
JournalPloS one
Volume11
Issue number10
DOIs
StatePublished - Oct 1 2016
Externally publishedYes

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Photochemistry
Glutamic Acid
chemical derivatives
Derivatives
Neurons
Molecules
synthesis
coumarin
photochemistry
Photochemical reactions
Brain
Chromophores
Quantum efficiency
glutamates
physical properties
Physical properties
neurons
brain

ASJC Scopus subject areas

  • Biochemistry, Genetics and Molecular Biology(all)
  • Agricultural and Biological Sciences(all)

Cite this

Muralidharan, S., Dirda, N. D. A., Katz, E. J., Tang, C. M., Bandyopadhyay, S., Kanold, P., & Kao, J. P. Y. (2016). Ncm, a photolabile group for preparation of caged molecules: Synthesis and biological application. PloS one, 11(10), [e0163937]. https://doi.org/10.1371/journal.pone.0163937

Ncm, a photolabile group for preparation of caged molecules : Synthesis and biological application. / Muralidharan, Sukumaran; Dirda, Nathaniel D.A.; Katz, Elizabeth J.; Tang, Cha Min; Bandyopadhyay, Sharba; Kanold, Patrick; Kao, Joseph P.Y.

In: PloS one, Vol. 11, No. 10, e0163937, 01.10.2016.

Research output: Contribution to journalArticle

Muralidharan, S, Dirda, NDA, Katz, EJ, Tang, CM, Bandyopadhyay, S, Kanold, P & Kao, JPY 2016, 'Ncm, a photolabile group for preparation of caged molecules: Synthesis and biological application', PloS one, vol. 11, no. 10, e0163937. https://doi.org/10.1371/journal.pone.0163937
Muralidharan, Sukumaran ; Dirda, Nathaniel D.A. ; Katz, Elizabeth J. ; Tang, Cha Min ; Bandyopadhyay, Sharba ; Kanold, Patrick ; Kao, Joseph P.Y. / Ncm, a photolabile group for preparation of caged molecules : Synthesis and biological application. In: PloS one. 2016 ; Vol. 11, No. 10.
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