Tetrahedron Letters

Synthesis of a macrocyclic rhodamine 110 enzyme substrate as an intracellular probe for caspase 3 activity

AP Guzikowski, JJ Naleway, CT Shipp, RC Schutte

Index: Guzikowski, Anthony P.; Naleway, John J.; Shipp, Christina T.; Schutte, Rod C. Tetrahedron Letters, 2000 , vol. 41, # 24 p. 4733 - 4735

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Citation Number: 8

Abstract

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 ...