Near infrared active heptacyanine dyes with unique cancer-imaging and cytotoxic properties

Bioorg Med Chem Lett. 2012 Jan 15;22(2):1242-6. doi: 10.1016/j.bmcl.2011.11.070. Epub 2011 Nov 28.


Three near-infrared fluorescent heptacarbocyanine dyes have been synthesized using a facile one-pot synthetic approach. The reaction methodology afforded a mixture of three symmetric and unsymmetric heptacyanines containing various N-indolenine substituents, a dicarbocyclic acid (DA), a monoester (ME), and a diester (DE). These compounds were isolated, purified, characterized and biologically investigated for tumor cell cytotoxicity and uptake selectivity. Using cell viability and in vitro proliferation assays, we found that the esterified dyes (monoester, ME and diester, DE) were selectively cytotoxic to cancer cells and spared normal fibroblast cells. Additionally, confocal fluorescence imaging confirmed selective uptake of these dyes in cancer cells, thus suggesting tumor cell targeting.

MeSH terms

  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Carbocyanines / chemical synthesis
  • Carbocyanines / chemistry
  • Carbocyanines / pharmacology*
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Cell Survival / drug effects
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor
  • Fluorescent Dyes / chemical synthesis
  • Fluorescent Dyes / chemistry
  • Fluorescent Dyes / pharmacology*
  • HeLa Cells
  • Humans
  • Infrared Rays*
  • Microscopy, Confocal
  • Molecular Structure
  • Neoplasms / diagnosis*
  • Neoplasms / drug therapy*
  • Spectrometry, Fluorescence
  • Stereoisomerism
  • Structure-Activity Relationship


  • Antineoplastic Agents
  • Carbocyanines
  • Fluorescent Dyes