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Cell-permeable esters of diazeniumdiolate-based nitric oxide prodrugs.

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 inhibitors of HL-60 cell proliferation.

SUBMITTER: Chakrapani H

PROVIDER: S-EPMC6939382 | biostudies-literature | 2008 Nov

REPOSITORIES: biostudies-literature

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Cell-permeable esters of diazeniumdiolate-based nitric oxide prodrugs.

Chakrapani Harinath H Maciag Anna E AE Citro Michael L ML Keefer Larry K LK Saavedra Joseph E JE

Organic letters 20081029 22

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 inhibitors of HL-60 cell proliferation. ...[more]

PMID: 18956868

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