Ncm, a Photolabile Group for Preparation of Caged Molecules: Synthesis and Biological Application.
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.
Center for Biomedical Engineering and Technology, University of Maryland School of Medicine, Baltimore, Maryland, United States of America.|Department of Physiology, University of Maryland School of Medicine, Baltimore, Maryland, United States of America.
Sukumaran
S
Muralidharan
Center for Biomedical Engineering and Technology, University of Maryland School of Medicine, Baltimore, Maryland, United States of America.|Department of Physiology, University of Maryland School of Medicine, Baltimore, Maryland, United States of America.
Nathaniel D A
ND
Dirda
Program in Neuroscience, University of Maryland, Baltimore, Baltimore, Maryland, United States of America.|Department of Neurology, University of Maryland School of Medicine, Baltimore, Maryland, United States of America.
Elizabeth J
EJ
Katz
Program in Neuroscience, University of Maryland, Baltimore, Baltimore, Maryland, United States of America.|Department of Neurology, University of Maryland School of Medicine, Baltimore, Maryland, United States of America.
Cha-Min
CM
Tang
Department of Biology, University of Maryland, College Park, Maryland, United States of America.
Sharba
S
Bandyopadhyay
Department of Biology, University of Maryland, College Park, Maryland, United States of America.
Patrick O
PO
Kanold
Center for Biomedical Engineering and Technology, University of Maryland School of Medicine, Baltimore, Maryland, United States of America.|Department of Physiology, University of Maryland School of Medicine, Baltimore, Maryland, United States of America.|Program in Neuroscience, University of Maryland, Baltimore, Baltimore, Maryland, United States of America.
Joseph P Y
http://orcid.org/0000-0002-8875-2180
JP
Kao
D000596:Amino Acids / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D000818:Animals; D001303:Auditory Cortex / Q000187:drug effects / Q000502:physiology / Q000528:radiation effects; D002478:Cells, Cultured; D003374:Coumarins / Q000138:chemical synthesis* / Q000494:pharmacology*; D005071:Evoked Potentials / Q000187:drug effects / Q000528:radiation effects; D005971:Glutamates / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D006863:Hydrogen-Ion Concentration; D008027:Light; D051379:Mice; D010782:Photolysis; D017966:Pyramidal Cells / Q000187:drug effects / Q000378:metabolism / Q000528:radiation effects
D000596:Amino Acids; D003374:Coumarins; D005971:Glutamates; C030123:coumarin
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