Synthesis and biological evaluation of aminopolyamines

J Med Chem. 2005 May 5;48(9):3099-102. doi: 10.1021/jm050024m.

Abstract

Exploitation of the polyamine backbone as a vector for intracellular transport of various pharmacophores has focused largely on fixing the cargo molecule to one of the nitrogens in the linear chain. This communication describes the assembly of a model aminopolyamine analogue, 6-amino-N(1),N(12)-diethylspermine, and its biological properties. This amino polyamine presents an additional site of attachment for cargo molecules, reduces cell growth, and achieves cellular concentrations that are higher than those of N(1),N(12)-diethylspermine.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Acetyltransferases / metabolism
  • Adenosylmethionine Decarboxylase / metabolism
  • Animals
  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / pharmacokinetics
  • Antineoplastic Agents / pharmacology
  • Biological Transport
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Ornithine Decarboxylase / metabolism
  • Spermine / analogs & derivatives*
  • Spermine / chemical synthesis*
  • Spermine / pharmacokinetics
  • Spermine / pharmacology
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Antineoplastic Agents
  • Spermine
  • Acetyltransferases
  • diamine N-acetyltransferase
  • Ornithine Decarboxylase
  • Adenosylmethionine Decarboxylase