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Proceedings Paper

Design and synthesis of a new class of fluorescent photoaffinity label with specific reference to 4-benzoyl-1-benzamidofluorescein: a new photolabel for adenine nucleotide binding domains on enzymes
Author(s): Jane E. Rosen
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Paper Abstract

Benzophenone was used as the photoreactive moiety in the synthesis of several water soluble, fluorescent photoaffinity labels. The following compounds were synthesized: 5-(2-(p- benzoylbenzamido)ethylamino-1-napthalenesulfonate (BzEDANS); 5-(2-(p- benzoylbenzamido)hexylamino-1-napthalenesulfonate (BzHDANS); and 4-benzoyl-1- benzamidofluorescein (BzAF). BzEDANS and BzHDANS were found to be unsuitable for use as photochemical probes. They were incapable of photoinduced covalent binding to methylene carbon due to intramolecular triplet-triplet energy transfer. BzAF was synthesized because its fluorescent moiety, fluorescein, is an inefficient acceptor for intramolecular quenching of the benzophenone triplet state diradical intermediate. BzAF was found to be a suitable and efficient photolabel and is presently a prototype for a new class of fluorescent photolabel.

Paper Details

Date Published: 18 May 1993
PDF: 27 pages
Proc. SPIE 1885, Advances in Fluorescence Sensing Technology, (18 May 1993); doi: 10.1117/12.144723
Show Author Affiliations
Jane E. Rosen, New York Univ. (United States)


Published in SPIE Proceedings Vol. 1885:
Advances in Fluorescence Sensing Technology
Joseph R. Lakowicz; Richard B. Thompson, Editor(s)

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