Improved synthesis and evaluation of 17-substituted aminoalkylgeldanamycin derivatives applicable to drug delivery systems

Bioorg Med Chem Lett. 2001 Aug 20;11(16):2089-91. doi: 10.1016/s0960-894x(01)00374-2.

Abstract

The 17-methoxy group of geldanamycin was substituted with 1,3-diaminopropane and 1,3-diamino-2-hydroxypropane to introduce a primary amino group useful for conjugation with targeting moieties and drug carriers. We have developed a procedure that has provided improved yield and reproducibility of the syntheses. Both geldanamycin derivatives demonstrated antiproliferative activity towards the human ovarian carcinoma cell line, A2780.

Publication types

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

MeSH terms

  • Antibiotics, Antineoplastic / chemical synthesis*
  • Antibiotics, Antineoplastic / chemistry
  • Antibiotics, Antineoplastic / pharmacology
  • Benzoquinones
  • Diamines / chemistry
  • Drug Carriers / chemistry
  • Drug Delivery Systems
  • Drug Screening Assays, Antitumor
  • Humans
  • Lactams, Macrocyclic
  • Quinones / chemical synthesis*
  • Quinones / chemistry
  • Quinones / pharmacology
  • Tumor Cells, Cultured

Substances

  • Antibiotics, Antineoplastic
  • Benzoquinones
  • Diamines
  • Drug Carriers
  • Lactams, Macrocyclic
  • Quinones
  • trimethylenediamine
  • geldanamycin