L-N6-(1-iminoethyl)lysine: a selective inhibitor of inducible nitric oxide synthase

J Med Chem. 1994 Nov 11;37(23):3886-8. doi: 10.1021/jm00049a007.


L-N6-(1-Iminoethyl)lysine (L-NIL) has been synthesized and is shown to be both a potent and selective inhibitor of mouse inducible nitric oxide synthase (miNOS). L-NIL has an IC50 of 3.3 microM for miNOS compared to an IC50 of 92 microM for rat brain constitutive NOS indicating that L-NIL is 28-fold more selective for inducible NOS. L-N5-(1-Iminoethyl)ornithine (L-NIO), which differs from L-NIL by having one less methylene group, has very similar potency for inducible NOS, but lacks selectivity. DL-N7-(1-Iminoethyl)homolysine was also synthesized and found to be substantially less potent than L-NIL or L-NIO, with intermediate selectivity for inducible NOS. These data suggest that L-NIL may be useful as a selective inhibitor of inducible NOS for determining the role of this enzyme in disease models.

MeSH terms

  • Amino Acid Oxidoreductases / antagonists & inhibitors*
  • Animals
  • Brain / enzymology
  • Lysine / analogs & derivatives*
  • Lysine / pharmacology
  • Mice
  • Nitric Oxide Synthase
  • Rats


  • N(6)-(1-iminoethyl)lysine
  • Nitric Oxide Synthase
  • Amino Acid Oxidoreductases
  • Lysine