Synthesis and biological activity of spergualin analogues. I

J Antibiot (Tokyo). 1988 Nov;41(11):1629-43. doi: 10.7164/antibiotics.41.1629.

Abstract

Stable spergualin analogues were synthesized by substitutions of the alpha-hydroxyglycine residue of spergualin with various alpha- or omega-amino acids. The antitumor activity of these analogues against L1210 and their immunosuppressive effects on delayed-type hypersensitivity and antibody formation was then examined. Analogues substituted with glycine and L-serine showed significant biological activity but were less potent than 15-deoxyspergualin. Among the analogues synthesized so far, 10-[N-4-(4-guanidinophenyl)butyryl-L-seryl]-1,5,10-triazadecane has possessed the strongest antitumor and immunosuppressive activities.

MeSH terms

  • Animals
  • Antibiotics, Antineoplastic / chemical synthesis*
  • Antibiotics, Antineoplastic / pharmacology
  • Guanidines / chemical synthesis
  • Guanidines / pharmacology
  • Immunosuppressive Agents / pharmacology
  • Leukemia L1210 / drug therapy
  • Mice
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Antibiotics, Antineoplastic
  • Guanidines
  • Immunosuppressive Agents
  • spergualin