Journal
TETRAHEDRON LETTERS
Volume 41, Issue 24, Pages 4733-4735Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4039(00)00708-5
Keywords
cyclization; enzymes and enzyme reactions; fluorescence; macrocycle
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The synthesis of the macrocyclic rhodamine 110 caspase 3 substrate 8 is described. The key step is a high dilution intramolecular cyclization reaction of an in situ generated primary amine with a 4-nitrophenyl ester. Substrate 8 reacts with recombinant caspase 3 to yield a fluorescent signal but virtually no signal is detected in the absence of caspase 3 or in the presence of the caspase 3 inhibitor Ac-DEVD-CHO. Notably, 8 selectively stains live cells that have been induced to undergo apoptosis with etoposide. (C) 2000 Elsevier Science Ltd. All rights reserved.
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