Synthesis of novel ciprofloxacin analogues and evaluation of their anti-proliferative effect on human cancer cell lines

Bioorg Med Chem Lett. 2013 Dec 1;23(23):6292-5. doi: 10.1016/j.bmcl.2013.09.077. Epub 2013 Oct 1.

Abstract

A series of twenty two novel 1-cyclopropyl-6-fluoro-4-oxo-7-(4-substituted piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid analogues have been synthesized, characterized ((1)H NMR, (13)C NMR and LCMS) and evaluated for their inhibitory activity on the proliferation of human caucasian acute lymphoblastic leukemia cells (CCRF-CEM), breast adenocarcinoma cells (MDA-MB-468) and human colon carcinoma cells (HCT-116). Among all the synthesized ciprofloxacin analogues 3t at 50 μM showed comparable potency to doxorubicin (10 μM) in all three cell lines and 3j inhibited proliferation of MDA-MB-468 up to 35% selectively over other two cell lines.

Keywords: Anti-cancer; Anti-proliferative; Ciprofloxacin; Fluoroquinolones; Substituted piperazines.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology
  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Cell Line, Tumor
  • Ciprofloxacin / analogs & derivatives*
  • Ciprofloxacin / chemical synthesis
  • Ciprofloxacin / chemistry
  • Ciprofloxacin / pharmacology*
  • Drug Screening Assays, Antitumor
  • Fluoroquinolones / chemical synthesis*
  • Fluoroquinolones / chemistry
  • Fluoroquinolones / pharmacology*
  • Humans
  • Molecular Structure
  • Structure-Activity Relationship

Substances

  • Anti-Bacterial Agents
  • Antineoplastic Agents
  • Fluoroquinolones
  • Ciprofloxacin