New synthetic aliphatic sulfonamido-quaternary ammonium salts as anticancer chemotherapeutic agents

Eur J Med Chem. 2013 Nov:69:670-7. doi: 10.1016/j.ejmech.2013.09.022. Epub 2013 Sep 21.

Abstract

RhoB is expressed during tumor cell proliferation, survival, invasion, and metastasis. In malignant progression, the expression levels of RhoB are commonly attenuated. RhoB is known to be linked to the regulation of the PI3K/Akt survival pathways. Based on aliphatic amido-quaternary ammonium salts that induce apoptosis via up-regulation of RhoB, we synthesized novel aliphatic sulfonamido-quaternary ammonium salts. These new synthetic compounds were evaluated for their biological activities using an in vitro RhoB promoter assay in HeLa cells, and in a growth inhibition assay using human cancer cell lines including PC-3, NUGC-3, MDA-MB-231, ACHN, HCT-15, and NCI-H23. Compound 5b (ethyl-dimethyl-{3-[methyl-(tetradecane-1-sulfonyl)-amino]-propyl}-ammonium; iodide) was the most promising anticancer agent in the series, based upon the potency of growth inhibition and RhoB promotion. These new aliphatic sulfonamido-quaternary ammonium salts could be a valuable series for development of new anticancer chemotherapeutic agents.

Keywords: Aliphatic sulfonamido-quaternary ammonium salts; Anticancer chemotherapeutic agents; NSC126188; Open-ring moiety of quaternary ammonium salts; Perifosine; RhoB.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor
  • HeLa Cells
  • Humans
  • Molecular Structure
  • Quaternary Ammonium Compounds / chemical synthesis
  • Quaternary Ammonium Compounds / chemistry
  • Quaternary Ammonium Compounds / pharmacology*
  • Salts / chemical synthesis
  • Salts / chemistry
  • Salts / pharmacology
  • Structure-Activity Relationship
  • Sulfonamides / chemistry*
  • rhoB GTP-Binding Protein / antagonists & inhibitors
  • rhoB GTP-Binding Protein / biosynthesis
  • rhoB GTP-Binding Protein / metabolism

Substances

  • Antineoplastic Agents
  • Quaternary Ammonium Compounds
  • Salts
  • Sulfonamides
  • rhoB GTP-Binding Protein