Novel N-acetyl-Glycol-split heparin biotin-conjugates endowed with anti-heparanase activity

Eur J Med Chem. 2020 Jan 15:186:111831. doi: 10.1016/j.ejmech.2019.111831. Epub 2019 Oct 30.

Abstract

Heparanase is regarded as a promising target for anticancer drugs and Ronepastat is one of the most promising heparanase inhibitors insert in clinical study for Multiple Myeloma Therapy. To improve its pharmacokinetic/pharmacodynamic profile, as well to have an antidote able to neutralize its activity in case of over dosages or intolerance, a new class of its derivatives was obtained inserting non-carbohydrate moieties of different length between the polysaccharide chain and biotin or its derivatives. In vitro these novel derivatives maintain the anti-heparanase activity without induced toxicity. The newly synthesized compounds retained the ability to attenuate the growth of CAG myeloma tumors in mice with potency similar, or in one case even higher than that of the reference compound Roneparstat as well as inhibited metastatic dissemination (lung colonization) of murine B16-F10 melanoma cells in vivo.

Keywords: Anticancer agents; Antimetastatic agents; Biotinylated agents; Heparanase inhibitors; Roneparstat.

MeSH terms

  • Animals
  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Biotin / chemistry*
  • Cell Proliferation / drug effects
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor
  • Female
  • Glucuronidase / antagonists & inhibitors*
  • Glucuronidase / metabolism
  • Glycols / chemical synthesis
  • Glycols / chemistry
  • Glycols / pharmacology*
  • Glycoside Hydrolase Inhibitors / chemical synthesis
  • Glycoside Hydrolase Inhibitors / chemistry
  • Glycoside Hydrolase Inhibitors / pharmacology*
  • Heparin / chemistry*
  • Melanoma, Experimental / drug therapy
  • Melanoma, Experimental / metabolism
  • Melanoma, Experimental / pathology
  • Mice
  • Mice, Inbred C57BL
  • Molecular Structure
  • Optical Imaging
  • Structure-Activity Relationship

Substances

  • Antineoplastic Agents
  • Glycols
  • Glycoside Hydrolase Inhibitors
  • Biotin
  • Heparin
  • heparanase
  • Glucuronidase