Monoalkoxy BODIPYs--a fluorophore class for bioimaging

Bioconjug Chem. 2014 Jun 18;25(6):1043-51. doi: 10.1021/bc400575w. Epub 2014 May 14.


Small molecule fluorophores are indispensable tools for modern biomedical imaging techniques. In this report, we present the development of a new class of BODIPY dyes based on an alkoxy-fluoro-boron-dipyrromethene core. These novel fluorescent dyes, which we term MayaFluors, are characterized by good aqueous solubility and favorable in vitro physicochemical properties. MayaFluors are readily accessible in good yields in a one-pot, two-step approach starting from well-established BODIPY dyes, and allow for facile modification with functional groups of relevance to bioconjugate chemistry and bioorthogonal labeling. Biological profiling in living cells demonstrates excellent membrane permeability, low nonspecific binding, and lack of cytotoxicity.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Boron Compounds / analysis*
  • Boron Compounds / chemical synthesis
  • Boron Compounds / chemistry
  • Cell Membrane Permeability
  • Cell Survival
  • Female
  • Fluorescent Dyes / analysis*
  • Fluorescent Dyes / chemical synthesis
  • Fluorescent Dyes / chemistry
  • Humans
  • MCF-7 Cells
  • Molecular Imaging / methods*
  • Molecular Structure
  • Solubility
  • Tumor Cells, Cultured


  • 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
  • Boron Compounds
  • Fluorescent Dyes