Novel 3-hydroxy vinylboronates influence sphingolipid metabolism, cause apoptosis in Jurkat cells and prevent tumor development in nude mice

Bioorg Med Chem Lett. 2013 Jan 15;23(2):507-12. doi: 10.1016/j.bmcl.2012.11.028. Epub 2012 Nov 22.

Abstract

A series of novel 3-hydroxy vinylboronates which share structural similarities with sphingolipids were synthesized and tested in vitro and in vivo as anticancer agents. The molecules reduced cancer cell survival in vitro by influencing their sphingolipid metabolism. In a cancer model in nude mice the lead compound E7 prevented the development of tumor as long as the treatment period continued. Moreover, it delayed tumor growth after the treatment was finished.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology
  • Apoptosis / drug effects*
  • Boronic Acids / chemical synthesis*
  • Boronic Acids / chemistry
  • Boronic Acids / pharmacology
  • Disease Models, Animal
  • Humans
  • Hydroxylation
  • Inhibitory Concentration 50
  • Jurkat Cells
  • Mice
  • Mice, Nude
  • Molecular Structure
  • Neoplasms / drug therapy*
  • Neoplasms / prevention & control
  • Sphingolipids* / metabolism
  • Vinyl Compounds / chemical synthesis*
  • Vinyl Compounds / chemistry
  • Vinyl Compounds / pharmacology*

Substances

  • Antineoplastic Agents
  • Boronic Acids
  • Sphingolipids
  • Vinyl Compounds