Studies on an immunosuppressive macrolactam, ascomycin: synthesis of a C-33 hydroxyl derivative

Bioorg Med Chem Lett. 1998 Apr 21;8(8):935-8. doi: 10.1016/s0960-894x(98)00145-0.

Abstract

Ascomycin 2, a close analogue of the immunosuppressant FK506 1, was modified to incorporate a hydroxyl group at the C-33 position. This increased the aqueous solubility of ascomycin by a hundred-fold at pH 7.4 and by approximately 300-fold at pH 6.5. Ascomycin 3 also exhibited an excellent immunosuppressive activity in vitro, as tested in a human mixed lymphocyte proliferation (HuMLR) assay, and in vivo using a rat popliteal lymph node (rPLN) hyperplasia assay.

MeSH terms

  • Animals
  • Humans
  • Hydrogen-Ion Concentration
  • Hyperplasia
  • Immunosuppressive Agents / chemical synthesis*
  • Immunosuppressive Agents / chemistry
  • Immunosuppressive Agents / pharmacology
  • Indicators and Reagents
  • Lymph Nodes / drug effects
  • Lymph Nodes / pathology
  • Lymphocyte Activation / drug effects*
  • Lymphocyte Culture Test, Mixed
  • Molecular Conformation
  • Molecular Structure
  • Rats
  • Solubility
  • Structure-Activity Relationship
  • Tacrolimus / analogs & derivatives*
  • Tacrolimus / chemical synthesis
  • Tacrolimus / chemistry
  • Tacrolimus / pharmacology

Substances

  • Immunosuppressive Agents
  • Indicators and Reagents
  • immunomycin
  • Tacrolimus