Structural and functional relationship among diamines in terms of inhibition of cell growth

J Biochem. 2004 Oct;136(4):533-9. doi: 10.1093/jb/mvh150.

Abstract

Following the report that agmatine has an anti-proliferative effect on cell growth through induction of antizyme [Satriano et al. (1998) J. Biol. Chem. 273, 15313-15316], we examined the effects of 16 different diamines on cell growth. Many diamines had little or no effect on cell growth, but agmatine and 1,6-hexanediamine had anti-proliferative effects, with agmatine having the strongest effect. Inhibition of cell growth occurred after 2 days, and inhibitory effects paralleled the degree of antizyme induction. Decreased spermine levels indicated that induction of spermidine/spermine N(1)-acetyltransferase was also involved in the inhibition of cell growth by agmatine and 1,6-hexanediamine. The frameshift efficiency (ratio of antizyme synthesis with or without frameshift) measured in a rabbit reticulocyte cell-free system was also increased by 1,3-propanediamine and cis-1,4-cyclohexanediamine in addition to agmatine and 1,6-hexanediamine. However, the intracellular levels of 1,3-propanediamine and cis-1,4-cyclohexanediamine were low when these compounds were added to the cell-culture medium. Other diamines had no effect on cell growth or frameshift efficiency. The results suggest that the presence of two amino-groups separated by an appropriate distance is important for the enhancement of frameshifting by diamines.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetamides / pharmacology
  • Acetyltransferases / chemistry
  • Agmatine / pharmacology
  • Animals
  • Blotting, Western
  • Cell Proliferation*
  • Cell-Free System
  • Cells, Cultured
  • Cyclohexylamines / pharmacology
  • Diamines / pharmacology
  • Frameshift Mutation
  • Models, Chemical
  • Models, Molecular
  • Polyamines / chemistry
  • Putrescine / analogs & derivatives*
  • Putrescine / chemistry
  • Putrescine / pharmacology*
  • Rabbits
  • Stereoisomerism
  • Structure-Activity Relationship
  • Time Factors

Substances

  • Acetamides
  • Cyclohexylamines
  • Diamines
  • Polyamines
  • N-acetyl-1,6-diaminohexane
  • Agmatine
  • trimethylenediamine
  • Acetyltransferases
  • diamine N-acetyltransferase
  • Putrescine