Synthesis, characterization and Akt phosphorylation inhibitory activity of cyclopentanecarboxylate-substituted alkylphosphocholines

Bioorg Med Chem. 2013 Apr 1;21(7):2018-24. doi: 10.1016/j.bmc.2013.01.010. Epub 2013 Feb 4.

Abstract

Akt is activated in most human cancers and contributes to cell growth, proliferation and cellular survival pathway. Accordingly, it is an attractive target for anticancer therapy. A series of novel alkylphosphocholines, incorporating cyclopentanecarboxylate in the phospholipid head group with trans and cis orientations, were synthesized and evaluated for their Akt phosphorylation inhibitory activities and cytotoxicities against human cancer cell lines, A549, MCF-7 and KATO III. Among the synthesized compounds, 5a, 5b and 6c exhibited potent inhibitory Akt phosphorylation effects with IC50 value of 3.1, 2.0 and 3.0 μM, respectively, and their potencies were better than those of three reference compounds miltefosine, perifosine and edelfosine. All the new compounds, except 5d and 6e, displayed more potent growth inhibition against A549 cells than reference compounds. Specifically, compound 5b exhibited most remarkable cytotoxicities on A549 cells as well as MCF-7 and KATO III cells. Importantly, the cytotoxic effects of these compounds correlated with their Akt phosphorylation inhibitory activities.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / pharmacology*
  • Carboxylic Acids / chemical synthesis
  • Carboxylic Acids / chemistry
  • Carboxylic Acids / pharmacology
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Cyclopentanes / chemical synthesis
  • Cyclopentanes / chemistry
  • Cyclopentanes / pharmacology
  • Humans
  • Neoplasms / drug therapy
  • Neoplasms / metabolism
  • Phospholipid Ethers / pharmacology
  • Phosphorylation / drug effects*
  • Phosphorylcholine / analogs & derivatives
  • Phosphorylcholine / chemical synthesis
  • Phosphorylcholine / chemistry*
  • Phosphorylcholine / pharmacology*
  • Proto-Oncogene Proteins c-akt / metabolism*

Substances

  • Antineoplastic Agents
  • Carboxylic Acids
  • Cyclopentanes
  • Phospholipid Ethers
  • Phosphorylcholine
  • edelfosine
  • perifosine
  • miltefosine
  • Proto-Oncogene Proteins c-akt