Alcohol
Volume 20, Issue 1 , Pages 55-59 , January 2000

Reaction of Nitroxyl, an Aldehyde Dehydrogenase Inhibitor, with N-Acetyl-L-Cysteine

  • Don W. Shoeman

      Affiliations

    • Medical Research Laboratories (151), VA Medical Center, Minneapolis, MN 55417 USA
    • ,
  • Frances N. Shirota

      Affiliations

    • Medical Research Laboratories (151), VA Medical Center, Minneapolis, MN 55417 USA
    • ,
  • Eugene G. DeMaster

      Affiliations

    • Medical Research Laboratories (151), VA Medical Center, Minneapolis, MN 55417 USA
    • ,
  • Herbert T. Nagasawa

      Affiliations

    • Medical Research Laboratories (151), VA Medical Center, Minneapolis, MN 55417 USA
    • Department of Medicinal Chemistry, University of Minnesota, Minneapolis, MN 55455, USA
    • Corresponding Author InformationCorresponding author. Tel.: 612-725-2000 ext. 4578; Fax: 612-725-2255

Received 30 April 1999 ,Revised 1 July 1999 ,Accepted 3 July 1999.

References 

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  2. Brenner M, Niederweiser A, Pataki G. Amino acids and derivatives. In:  Stahl E editors. Thin Layer Chromatography. A Laboratory Handbook. New York: Academic Press; 1965;p. 497–553
  3. Conway TT, DeMaster EG, Lee MJC, Nagasawa HT. Prodrugs of nitroxyl and nitrosobenzene as cascade latentiated inhibitors of aldehyde dehydrogenase. J Med Chem. 1998;41:2903–2909
  4. DeMaster EG, Redfern B, Quast BJ, Dahlsteid T, Nagasawa HT. Mechanism for the inhibition of aldehyde dehydrogenase by nitric oxide. Alcohol. 1997;14:181–189
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  8. Greenstein JP, Wintz M. Chemistry of the Amino Acids, Vol. 3. New York: John Wiley & Sons, Inc; 1961;
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  10. Kitson TM. Mechanism of inactivation of sheep liver aldehyde dehydrogenase by disulfiram. Biochem J. 1983;213:551–554
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  12. Lee MJC, Nagasawa HT, Elberling JA, DeMaster EG. Prodrugs of nitroxyl as inhibitors of aldehyde dehydrogenase. J Med Chem. 1992;35:3648–3652b
  13. Moree WJ, van der Marel GA, Liskamp RMJ. Synthesis of peptides containing β-substituted aminoethane sulfinamide of sulfonamide transition-state isostere derived from amino acids. Tetrahedron Lett. 1992;33:6389–6392
  14. Nagasawa HT, DeMaster EG, Redfern B, Shirota FN, Goon DJW. Evidence for nitroxyl in the catalase-mediated bioactivation of the alcohol deterrent agent, cyanamide. J Med Chem. 1990;33:3120–3122
  15. Nagasawa HT, Kawle SP, Elberling JA, DeMaster EG, Fukuto JM. Prodrugs of nitroxyl as potential aldehyde dehydrogenase inhibitors vis-a-vis vascular smooth muscle relaxants. J Med Chem. 1995;38:1865–1871
  16. Vallari RC, Pietruszko R. Human aldehyde dehydrogenase (mechanism of inhibition by disulfiram). Science. 1982;216:637–639
  17. Weiner, H., Farres, J., Wang, T. T. Y., Cunningham, S. J., Zheng, C.-F., & Ghenbot, G. (1991). In H. Weiner, B. Wermuth, & D. W. Crabb (Eds.), Enzymology and Molecular Biology of Carbonyl Metabolism, Vol. 3 (pp. 13–17). New York: Plenum Press.
  18. Wong PS, Hyun J, Fukuto JM, Shirota FN, DeMaster EG, Shoeman DW, et al. The reaction between S-nitrosothiols and thiols (generation of nitroxyl and subsequent chemistry). Biochemistry. 1998;37:5362–5371

PII: S0741-8329(99)00056-7

Alcohol
Volume 20, Issue 1 , Pages 55-59 , January 2000

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