Sialated diazeniumdiolate: a new sialidase-activated nitric oxide donor

Org Lett. 2004 Nov 11;6(23):4203-5. doi: 10.1021/ol048397p.

Abstract

A new sialated diazeniumdiolate has been synthesized, and the glycosylation product was exclusively an alpha anomer. This new nitric oxide donor exhibited significantly improved stability as compared to its parent diazeniumdiolate salts, and it could be efficiently hydrolyzed by neuraminidase to release nitric oxide with a K(m) of 0.14 mM. The sialic acid-NO conjugate would be a valuable prodrug that targets NO to influenza viruses.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Azo Compounds / chemistry*
  • Azo Compounds / pharmacology*
  • Hydrogen-Ion Concentration
  • N-Acetylneuraminic Acid / chemistry*
  • Nitric Oxide Donors / chemistry*
  • Nitric Oxide Donors / pharmacology*
  • Spectrophotometry, Ultraviolet

Substances

  • Azo Compounds
  • Nitric Oxide Donors
  • diazeniumdiolate
  • N-Acetylneuraminic Acid