Cell-permeable esters of diazeniumdiolate-based nitric oxide prodrugs

H Chakrapani, AE Maciag, ML Citro, LK Keefer…

Index: Chakrapani, Harinath; Maciag, Anna E.; Citro, Michael L.; Keefer, Larry K.; Saavedra, Joseph E. Organic Letters, 2008 , vol. 10, # 22 p. 5155 - 5158

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Citation Number: 19

Abstract

Although O 2-(2, 4-dinitrophenyl) derivatives of diazeniumdiolate-based nitric oxide (NO) prodrugs bearing a free carboxylic acid group were activated by glutathione to release NO, these compounds were poor sources of intracellular NO and showed diminished antiproliferative activity against human leukemia HL-60 cells. The carboxylic acid esters of these prodrugs, however, were found to be superior sources of intracellular NO and potent ...