Peptide T-araC conjugates: solid-phase synthesis and biological activity of N4-(acylpeptidyl)-araC

Bioorg Med Chem. 2000 Mar;8(3):539-47. doi: 10.1016/s0968-0896(99)00317-x.

Abstract

Due to the capability of peptidyl derivatives of araC to behave as prodrugs of this antimetabolite, and because of the well known biological properties of peptide T and its analogues (in particular that of targeting CD4+ cells), new peptide T-araC conjugates were prepared and tested in vitro for antiproliferative activity. The aim was that of specifically delivering the antitumor drug to CD4+ cells. N4-(Acylpeptidyl)-derivatives of araC were synthesized by a new general approach involving solid-phase synthesis, which allows mild conditions, avoids the usually required protection of the glycoside portion of nucleosides and affords high yields of the final products. After the demonstration that peptide T-araC conjugates were able to activate chemotaxis by binding CD4 receptor on monocyte membranes, the antiproliferative activity was evaluated against a panel of leukemia lymphoma and carcinoma cell lines derived from human tumors, three CD4+ cell lines included. Title compounds resulted effective as antiproliferative agents at concentrations 4- to 10-fold higher than those of araC alone, did not preferentially inhibit CD4+ cells and proved stable not only in cell culture medium containing 20% FCS, but also in human plasma. All this suggests their potential utility in vivo.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antimetabolites, Antineoplastic / chemistry
  • Antimetabolites, Antineoplastic / pharmacology
  • CD4 Antigens
  • Cell Division / drug effects
  • Chemotaxis / drug effects
  • Cytarabine / chemical synthesis
  • Cytarabine / chemistry*
  • Cytarabine / pharmacology*
  • Dose-Response Relationship, Drug
  • Drug Carriers / chemical synthesis
  • Drug Carriers / chemistry
  • Drug Stability
  • Humans
  • Inhibitory Concentration 50
  • Monocytes / drug effects
  • Oligopeptides / chemical synthesis
  • Oligopeptides / metabolism
  • Peptide Hydrolases / metabolism
  • Peptide T / chemical synthesis
  • Peptide T / chemistry*
  • Peptide T / pharmacology*
  • Prodrugs / chemical synthesis
  • Prodrugs / pharmacology
  • Time Factors
  • Tumor Cells, Cultured / drug effects

Substances

  • Antimetabolites, Antineoplastic
  • CD4 Antigens
  • Drug Carriers
  • Oligopeptides
  • Prodrugs
  • Cytarabine
  • Peptide T
  • Peptide Hydrolases