Synthesis of (aminoalkylamine)-N-aminoalkyl)azanonaborane(11) derivatives for boron neutron capture therapy

J Med Chem. 2002 Dec 19;45(26):5817-9. doi: 10.1021/jm020971k.

Abstract

New boron-containing polyamine have been synthesized: (aminoalkylamine)-N-(aminoalkyl)azanonaborane(11) derivatives [H(2)N(CH(2))(n)H(2)NB(8)H(11)NH(CH(2))(n)NH(2)], where n = 4-6 and 12, and [H(2)N(CH(2))(3)H(2)NB(8)H(11)NH(CH(2))(4)NH(2)]. (4-Aminobutylamine)-N-(4-aminobutyl)azanonaborane and (3-aminopropylamine)-N-(4-aminobutyl)azanonaborane were less toxic in vitro (LD(50) of approximately 700 and approximately 1100 microM, respectively) than spermine, while (4-aminobutylamine)-N-isopropylazanonaborane with its hydrophobic isopropyl group and those with n = 5, 6, and 12 were already toxic under similar conditions (LD(50) << 500 microM). These compounds may be useful as delivery agents for boron neutron capture therapy.

MeSH terms

  • Animals
  • Boranes / chemical synthesis*
  • Boranes / chemistry
  • Boranes / toxicity
  • Boron Neutron Capture Therapy
  • CHO Cells
  • Cell Survival / drug effects
  • Cricetinae
  • Lethal Dose 50
  • Polyamines / chemical synthesis*
  • Polyamines / chemistry
  • Polyamines / toxicity
  • Solubility
  • Structure-Activity Relationship

Substances

  • Boranes
  • Polyamines